DGMG Radio

#321 | Jess Cook, VP of Marketing at Vector, joins Dave to break down what's actually working in early-stage B2B marketing. They dig into how she thinks about attribution for brand channels, how Vector's podcast became a top marketing channel, why they created a brand mascot, and details on what content strategy is working on LinkedIn right now. They also cover shift from content leader to VP of Marketing and how to drive demand without a massive team or budget.Timestamps(03:06) - — Meet Jess Cook & What is Vector? (07:39) - — B2B Influencer pilot setup: why this channel, why now (14:57) - — The result: 45 demos, ~$1.1M pipeline, and how she tracked it (16:55) - — How to run influencers (22:20) - — Scaling idea: retainer-style influencer partnerships (26:00) - — Vector's podcast: “awareness magnet” and the format that works (28:24) - — The production system: in-person batch recording a full season in 2 days (42:10) - — Jess's LinkedIn strategy: why she started posting and what she optimizes for (53:58) - — Content → VP shift: the two muscles she's building (metrics + leadership) Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five's first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#320 | Matt Carnevale, Head of Community at Exit Five, joins Dave for a discussion about community building. They dive into a bunch of the lessons learned from building the Exit Five community over the last few years, including specific plays like onboarding, matchmaking, and moderation. If you're thinking about community building in 2026, this is a good primer; plus the guys give their opinion on what “community” actually means and whether you should build a private community like Exit Five or focus more broadly on community building.Timestamps(00:02) - – Matt's path from BDR to Head of Community at Exit Five (08:29) - – What “community” actually means (and what it definitely isn't) (13:14) - – Why most B2B communities fail before they ever get traction (17:54) - – Community vs. content: what gets people in vs. what makes them stay (22:29) - – Why Slack groups aren't a strategy (27:14) - – Treating community like a product, not a marketing channel (34:48) - – The role of trust, curation, and saying no to the wrong people (40:23) - – What community managers actually do behind the scenes (47:18) - – How in-person events changed the Exit Five community (53:28) - – The biggest lessons Matt's learned after two years building Exit Five Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five's first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#319 | Dave sits down with Jess Lytle, Head of Marketing at Exit Five, to talk about how AI is changing the job of B2B marketers and the reality of how AI is actually being adopted internally. They also cover how AI even helped Jess get her job at Exit Five and why she's become obsessed about deploying AI in marketing and really believes this is the most important martech wave yet. Timestamps(00:00) - – Goals, manifestation, and reverse-engineering outcomes (06:14) - – Meet Jess Lytle, Head of Marketing at Exit Five (08:28) - – How Jess got hired at Exit Five (webinar → DMs → job) (10:28) - – From demand gen to AI: early adoption, teaching, and Lovable (15:58) - – Why AI feels different than traditional martech (18:28) - – Content in 2026: originality, human insight, and AI distribution (29:16) - – NotebookLM: real marketing workflows and internal use cases (35:16) - – AI tools, team structure, and hybrid marketer roles (45:56) - – Working at Exit Five, founder-led marketing, and brand bets Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five's first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#318 | Dave is joined by Kieran Flanagan, SVP of Marketing at HubSpot and former CMO at Zapier. They break down how AI is reshaping B2B marketing workflows, content creation, and team structure, plus Kieran's leadership philosophy for managing a 300+ person team while staying deeply involved in creative execution. This episode offers a clear look at how AI is changing the game and how B2B marketers can stay creative, strategic, and indispensable in the process.Timestamps(00:00) - – Intro + why AI matters now (04:28) - – Kieran's career + the 2-year mission framework (09:58) - – The grind, early-career advice, and earning your stripes (12:28) - – Operator vs. manager + strong opinions in leadership (20:28) - – Why collaborative brainstorms fail (25:28) - – ChatGPT vs. Claude + how Kieran actually uses AI (33:16) - – Where AI is taking B2B marketing (answers → actions) (44:46) - – Picking a lane: technical vs. creative marketers (52:16) - – The future CMO + agencies, in-person, and what still matters Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five's first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#317 | Dave hosts a live session with Dasha Shakov (Head of Marketing, Proton.ai), Emeric Ernoult (Founder, CEO, Agorapulse), and Finn Thormeier (Founder, Project 33) to break down what's working on LinkedIn right now. They discuss why LinkedIn is the most important channel for B2B, why social media is the best marketing channel available today, how founder-led and employee content drives growth, and what's changed about how people use the platform over the last five years. The group also gets into LinkedIn's thought leader ads, thoughts on measuring results when attribution is messy, and how to sell LinkedIn's value to leadership and convince them to spend time there. It's a look into how B2B teams can earn attention, build credibility, and make LinkedIn a massive growth channel in 2026.Timestamps(00:56) - – Why LinkedIn is still Dave's favorite B2B channel (05:01) - – Panel intros: Dasha, Finn, Emeric (07:25) - – Why LinkedIn changed and why it matters now (09:34) - – “Our buyers aren't on LinkedIn” is mostly wrong (12:26) - – Who should post: CEO, team, or company page (16:47) - – Why promo posts flop (and why that's okay) (21:44) - – What to actually post when starting from zero (38:13) - – Why thought leader ads outperform everything else Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five's first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

316 | In this episode, Dave breaks down how the best companies win by standing out through smart ideas, creative execution, and consistent attention. He pulls lessons from Drift, Savannah Bananas, and his own wins to show why ideas matter, why brand is a durable long-term advantage, and how strong content can still break through today. Plus: thoughts on AI slop, why LinkedIn can be a powerful channel when used well, leadership lessons from The Hard Thing About Hard Things, and rapid-fire listener questions on playbooks, thought leadership, and building something bigger than Exit Five.Timestamps(00:00) - – Why attention became a dirty word in marketing (03:08) - – Personal update: hip surgery, burnout, and getting back in rhythm (05:08) - – The LinkedIn algorithm isn't broken. Your content probably is (06:18) - – The big idea: attention is the real game in marketing (07:38) - – Lessons from Savannah Bananas and stealing ideas outside B2B (09:58) - – How Drift won by sucking the oxygen out of the market (12:18) - – Scrappy attention plays: billboards, protests, and founder brand (15:08) - – Why brand comes before product messaging (19:35) - – Listener Qs: playbooks, AI slop, and building real leverage (27:20) - – Final takeaway: stop being boring, earn attention first Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

315 | Jess Lytle (Head of Marketing at Exit Five) hosts a live roundtable with Morgan Cole (VP of Demand Gen at Red Canary), Lisa Cole (CMO at 2X), and Jean Cameron (Sr. Director of Field & Partner Marketing at Demandbase) on how B2B teams are using AI to drive pipeline and revenue. They share real examples of how marketers are identifying in-market buyers earlier, moving deals faster, replacing outdated lead scoring, and keeping marketing, sales, and ops aligned around revenue. The conversation goes deep on intent signals, buying groups, predictive analytics, brand vs demand, and what's changing in the new era of pipeline accountability. Timestamps(00:00) - AI hype vs real revenue impact (06:16) - Panel intros and GTM perspectives (08:46) - The real pipeline problem: growth without more headcount (11:16) - How teams use AI to identify in-market buyers earlier (16:46) - Buying groups, not leads: why account signals matter (20:46) - Predictive analytics, pipeline forecasting, and deal analysis (27:36) - Why traditional lead scoring is breaking (37:28) - How teams “swarm” accounts with marketing + sales (43:48) - Brand and demand together: building future pipeline Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

314 | In this episode, Dmitry Shamis sits down with Dave to break down how Dave writes—the process behind emails, newsletters, landing pages, and posts that get attention. They talk about why Dave starts with the hook, why editing matters more than writing, and why most B2B marketing fails by trying to say too much. Dave also shares how podcasting shaped his thinking, why formatting is underrated, how he decides when something is “done,” and why shipping beats waiting for perfection. If you want to learn more behind Dave's writing, creation, and marketing this episode is a great one for you; Dave shares a bunch of his behind the scenes style that he's not shared on the podcast before.What's Your Process? is hosted by Dmitry Shamis—co-founder of OhSnap!, former Head of Brand and Creative at HubSpot, and one of the early pioneers of self-service brand systems for B2B tech. The show is an in-depth look at the processes behind top marketers, with past guests including Jess Cook, Ross Simmonds, Eddie Shleyner, Lashay Lewis, and Melissa Rosenthal.Timestamps(00:00) - – Why this conversation matters (05:38) - – Dave's background and path into marketing (09:53) - – What Dave is world-class at (and why copy is the leverage) (14:28) - – Why hooks come first and editing beats writing (19:48) - – How podcasting sharpened Dave's instincts (25:18) - – Formatting, focus, and making writing easier to read (32:35) - – Deciding when something is “done” and when to ship (39:05) - – Why most B2B marketing fails by trying to say too much (45:50) - – Raising the bar, big bets, and making hard leadership calls Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#312 | In this episode, Udi Ledergor joins Dave to break down the ideas behind his new book, Courageous Marketing, and why most B2B marketing fails because it plays it safe. He also shares his journey from marketer #1 to CMO to Chief Evangelist at Gong, where he led category creation, brand, and marketing through massive scale. They unpack how Gong built a brand that actually stood out, what it means to punch above your weight as a B2B marketer, and how to think about brand ROI without fake dashboards.Timestamps(00:00) - – Meet Udi and his path into marketing (08:16) - – Early career lessons and building marketing from zero (15:16) - – How Gong found product-market fit and nailed positioning early (19:26) - – Courageous Marketing: why Udi wrote it and what it really means (23:16) - – Brand first: personality, positioning, then visuals (28:20) - – Campaigns that punched above their weight (billboards, experiments, perception hacks) (35:10) - – Proving brand impact: soft ROI, pipeline, and exec buy-in (47:40) - – The future: product-led marketing, AI, and courageous teams Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#312 | Jess Lytle (Head of Marketing at Exit Five) hosts a roundtable with a group of email experts on what's actually working in email, SMS, and in-app messaging right now. They dig into AI's impact on the inbox, how to sound human when everyone's using the same tools, and why relevance beats volume. The group also breaks down how to personalize without being creepy, what to do with “lurkers” who never click but still convert, and how to build messaging that survives the AI slop era. It's a sharp look at how B2B marketers can cut through the noise, earn attention, and actually get people to respond.Timestamps(00:17) - — Jess welcomes everyone (02:30) - — Why email and messaging aren't dead… bad messaging is (05:58) - — How AI changed the inbox and why standing out is harder than ever (06:34) - — Why human senders beat brand senders in email (10:03) - — Writing emails like you were invited into someone's personal space (12:18) - — Balancing stakeholder requests vs. what your audience actually wants (15:28) - — Real talk on AI personalization, enrichment, and where it actually works (21:33) - — Subject lines, preview text, and how people really decide what to open (23:08) - — Email stories and empathy-driven content that outperform (29:03) - — SMS, in-app, and email orchestration: what to use when (36:20) - — Measuring impact when email is assist, not hero (44:20) - — The future: AI-driven workflows, data challenges, and what's coming (53:00) - — Favorite tools (Claude, NotebookLM, etc.) and how people use them Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#311: Dave goes solo this week (his decision, he said give me the mic; but Dan is also on him about podcast downloads around the holidays) with a quick November breakdown from real life - recapping the Exit Five team trip to Arizona, a big leadership update at the company, and covering five timeless marketing principles that matter more than ever (if you care about fighting AI slop). He also talks about recovering from hip surgery (everyone's been asking how old he is), what he's been reading, and a Thanksgiving food debate.Timestamps(00:00) - - Intro + the sunglasses bit (04:08) - - Getting back into podcasting + November setup (05:38) - - The 5 timeless marketing principles (14:28) - - How to apply those principles in real marketing (15:38) - - Exit Five team trip to Arizona (17:28) - - Why in-person time matters (21:20) - - Dave's hip surgery and recovery (23:50) - - What he read and watched in November (27:20) - - The Thanksgiving overrated/underrated debate (29:40) - - Big news: Dan promoted to CEO and what's next for Exit Five Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#310 Category Creation | In this episode, Dave Gerhardt digs in with Josh Lowman, Founder & CEO of Gold Front, to unpack what “category creation” actually takes, why most companies get it wrong, and how the best brands win by owning a spot in the customer's mind. They get into the four real paths to category leadership, the trap of “fake” category design, why vibe and soul still beat spreadsheets, and how personal development quietly powers great marketing. If you're building a B2B brand and trying to stand out in a market that feels painfully same-same, this one hits exactly where you're stuck.Timestamps(00:00) - – Dave's Intro (03:22) - – Why Category Creation Got So Noisy (07:40) - – The Real Goal: Becoming Irreplaceable (12:26) - – How Customers Actually Form Categories (16:55) - – The Four Paths to Category Leadership (23:13) - – The Trap of “Fake” Category Design (28:56) - – Product Reality vs. Marketing Narrative (35:32) - – Why Vibe, Soul, and Taste Still Win (41:46) - – Community as a Differentiator (46:23) - – Josh on Therapy, Mindset, and Creative Clarity (52:15) - – Final Takeaways for B2B Marketers Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#309 Product Positioning | This episode is from a Drive 2025 (our annual Exit Five event) session with April Dunford (Founder, Ambient Strategy). April pulls from working with 300+ tech companies to unpack the real patterns behind winning positioning from calling out competitors' nonsense to teaching buyers what actually matters, avoiding category-creation traps, and fixing the sales messes that weak positioning creates. It's sharp, funny, brutally honest, and basically a crash course in how to make your product unmistakably different in a market full of noise.PS. Want to join us at Drive 2026?Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.Timestamps(00:00) - – Why Positioning Breaks (03:20) - – Teaching Buyers to Spot Competitor BS (06:48) - – Turning Differentiators into Real Value (10:26) - – The Trap of Overthinking Categories (14:13) - – Choosing Your Go-To-Market Before Your Positioning (18:50) - – Building a Story Only You Can Tell (23:18) - – When Great Storytelling Backfires (28:53) - – Positioning Multi-Product Companies (32:34) - – When and Why to Reposition (36:22) - – Bringing It All Together in Sales Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#308 Sales Alignment | In this session from Drive 2025 titled “Building Pipeline in the Shiny Object Era”, Jen Allen Knuth unpacks why deals stall even when your product is objectively better, how the explosion of shiny tools and AI noise is making it worse, and why most teams are unintentionally fueling the problem with me-centric messaging. Jen shares the two zero-dollar exercises every team should run to quantify how much pipeline they're losing today, align sales and marketing around the true blocker, and rebuild outbound messaging that creates curiosity.PS. Want to join us at Drive 2026? Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale. Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#307 Building Community | In this episode Dave joined Ali Orlando Wert (Director of Content Marketing & Brand at Databox) on their podcast called Move the Needle. She did an interview with Dave focused on community building. They cover how Exit Five grew 80 percent by operating more like a startup than a Slack group. Dave gets into the truth of building community, why most companies should not launch one, how to measure brand without losing your mind, and why AI has everyone simultaneously energized and spiraling. Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#306 Executive Insights | This episode was recorded live at our annual event, Drive 2025. I hosted Sylvia LePoidevin (CMO, Kandji), Trinity Nguyen (CMO, UserGems), and Natalie Taylor (Head of Marketing, Capsule) for a leadership panel breaking down what's working in B2B marketing. They get into events that reliably create pipeline, outbound that still converts, media plays LLMs keep citing, and the tactics they've stopped running (like generic webinars that no one shows up for).Want to come to Drive next year? Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.Timestamps(00:00) - – Intro + Drive 2025 context (02:47) - – Meet the speakers: Sylvia, Trinity, Natalie (04:39) - – The one thing each leader refuses to give up (04:50) - – How Capsule turns events into their #1 pipeline channel (08:53) - – Why outbound still works (and how UserGems does it) (13:46) - – How Kandji built a media property that LLMs actually cite (18:12) - – Plays they stopped doing (blogs, generic content, virtual thought leadership) (25:56) - – Playing offense: Shark Tank Day and GTM alignment (31:20) - – Team wide alignment strategies that drive revenue Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#305 Influencer Marketing | This episode is a live session from Drive 2025 with Brianna Doe, where she breaks down why influence is now shaping every step of the buying journey, how smart B2B brands are borrowing plays from B2C, and what it really takes to build a creator program that doesn't flame out on day one. She gets into the messy reality of picking the right creators and measuring impact without deluding yourself with vanity numbers. Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.Timestamps(00:00) - – Intro (03:22) - – Why Influence Drives Modern B2B Buying (06:17) - – What B2B Can Steal From B2C Playbooks (09:12) - – The Creator Engine Framework (12:29) - – Picking the Right Creators (Without Getting Burned) (15:47) - – Building Campaigns That Don't Feel Like Ads (19:02) - – How to Measure Real Impact (Not Vanity Metrics) (23:38) - – Running a 90-Day Pilot That Actually Works (26:23) - – Scaling From One-Off Posts to a Full Program Join 50,000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Paramark.It's November. 2026 planning is already here. And the stuff you're doing right now will decide how next year plays out. But here's the problem: most teams are still planning next year's marketing strategy based on the WRONG DATA because of broken attribution and a misleading gut feel.  And you can't make smart budget calls if you're just guessing what's working, what's not, and where to put your next dollar.That's where Paramark comes in. They help you replace the guesswork with actual insight backed by $2 billion in analyzed marketing data. They've figured out what actually drives incremental growth across every channel including LinkedIn, Meta, TikTok, Google, CTV, even OOH.And right now, they're offering a private 1:1 consultation with their CEO and CMO, Pranav and Sam, who have led marketing teams at companies like Dropbox, Adobe, Microsoft, and Shutterfly. In this 45-minute strategy session, they'll help you measure the real impact of every marketing dollar, pull insights from your current media mix, and design a 2026 roadmap that's rooted in data, not gut.This is a heck of an offer. And it's real. And will go fast. So if you want to future-proof your marketing strategy for 2026, don't miss out on this offer.Grab your spot at paramark.com/brand-consult.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#304 | AI Buying Shift | This episode is from a recent Exit Five live session where I pulled together Lindsay O'Brien (Head of Marketing & Operations, Predictiv), Tom Wentworth (CMO, incident.io), and Aditya Vempaty (VP of Marketing, MoEngage) for a real talk on how AI is completely rewiring the B2B buying journey. We got into why buyers no longer need your pretty funnel, how AI-powered research changes the sales call, and what that means for your GTM strategy.Timestamps(00:00) - – Intro + Dave Sets the Stage (04:07) - – How AI Is Changing B2B Buying (11:07) - – The Big Shift: Taste, Unscalable Work, and Distribution (16:07) - – Getting Exec Buy-In for “Unmeasurable” Marketing (20:07) - – Does the Funnel Still Matter? (24:07) - – Dead Tactics: Gating, A/B Testing, Lead Score Theater (30:53) - – AI That Actually Works (Real Use Cases) (37:53) - – Team Size, Skills, and the New CMO (43:53) - – Authenticity vs AI: Creative, Video, and Brand (58:53) - – Content Attribution + Final Takeaways Join 50,000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Paramark.It's November. 2026 planning is already here. And the stuff you're doing right now will decide how next year plays out. But here's the problem: most teams are still planning next year's marketing strategy based on the WRONG DATA because of broken attribution and a misleading gut feel.  And you can't make smart budget calls if you're just guessing what's working, what's not, and where to put your next dollar.That's where Paramark comes in. They help you replace the guesswork with actual insight backed by $2 billion in analyzed marketing data. They've figured out what actually drives incremental growth across every channel including LinkedIn, Meta, TikTok, Google, CTV, even OOH.And right now, they're offering a private 1:1 consultation with their CEO and CMO, Pranav and Sam, who have led marketing teams at companies like Dropbox, Adobe, Microsoft, and Shutterfly. In this 45-minute strategy session, they'll help you measure the real impact of every marketing dollar, pull insights from your current media mix, and design a 2026 roadmap that's rooted in data, not gut.This is a heck of an offer. And it's real. And will go fast. So if you want to future-proof your marketing strategy for 2026, don't miss out on this offer.Grab your spot at paramark.com/brand-consult.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#303 Storytelling | This episode is from Drive 2025, our 2-day in-person event for B2B marketers in Burlington, VT. Harry Dry, creator of Marketing Examples and one of the best copywriters on the internet, shared a masterclass on storytelling, creativity, and writing marketing that actually connects—showing how to find great ideas, turn real stories into memorable campaigns, and make people feel something in the process.Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.Timestamps(00:00) - – Intro from Dave (02:47) - – Harry's background + Marketing Examples origin (05:07) - – What makes good marketing storytelling (08:27) - – How to find and collect great ideas (12:52) - – The power of emotion in copy (17:37) - – Why simple writing wins (22:12) - – Turning real stories into campaigns (29:08) - – The role of curiosity in great marketing (33:53) - – How to write like you talk (39:03) - – Examples of high-performing campaigns (44:13) - – Q&A: writing habits, inspiration, and burnout Join 50,000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Paramark.It's November. 2026 planning is already here. And the stuff you're doing right now will decide how next year plays out. But here's the problem: most teams are still planning next year's marketing strategy based on the WRONG DATA because of broken attribution and a misleading gut feel.  And you can't make smart budget calls if you're just guessing what's working, what's not, and where to put your next dollar.That's where Paramark comes in. They help you replace the guesswork with actual insight backed by $2 billion in analyzed marketing data. They've figured out what actually drives incremental growth across every channel including LinkedIn, Meta, TikTok, Google, CTV, even OOH.And right now, they're offering a private 1:1 consultation with their CEO and CMO, Pranav and Sam, who have led marketing teams at companies like Dropbox, Adobe, Microsoft, and Shutterfly. In this 45-minute strategy session, they'll help you measure the real impact of every marketing dollar, pull insights from your current media mix, and design a 2026 roadmap that's rooted in data, not gut.This is a heck of an offer. And it's real. And will go fast. So if you want to future-proof your marketing strategy for 2026, don't miss out on this offer.Grab your spot at paramark.com/brand-consult.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#302 Growth | Dave is joined by Priscilla Barolo, former head of comms at Zoom (for nearly 10 years, including the pandemic) and current VP of Marketing at Neat, an Oslo-based video tech company. Neat's tech is used around the world from major enterprises like Atlassian to the White House. With a decade-long career at Zoom, including during its hypergrowth through the pandemic, Priscilla is a master in communications and B2B marketing leadership.Dave and Priscilla cover:The path from communications to marketing leadershipUnique challenges of marketing a physical product in the B2B tech spaceBuilding and scaling a global marketing team at a high-growth, remote-first company Join 50,000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Paramark.It's November. 2026 planning is already here. And the stuff you're doing right now will decide how next year plays out. But here's the problem: most teams are still planning next year's marketing strategy based on the WRONG DATA because of broken attribution and a misleading gut feel.  And you can't make smart budget calls if you're just guessing what's working, what's not, and where to put your next dollar.That's where Paramark comes in. They help you replace the guesswork with actual insight backed by $2 billion in analyzed marketing data. They've figured out what actually drives incremental growth across every channel including LinkedIn, Meta, TikTok, Google, CTV, even OOH.And right now, they're offering a private 1:1 consultation with their CEO and CMO, Pranav and Sam, who have led marketing teams at companies like Dropbox, Adobe, Microsoft, and Shutterfly. In this 45-minute strategy session, they'll help you measure the real impact of every marketing dollar, pull insights from your current media mix, and design a 2026 roadmap that's rooted in data, not gut.This is a heck of an offer. And it's real. And will go fast. So if you want to future-proof your marketing strategy for 2026, don't miss out on this offer.Grab your spot at paramark.com/brand-consult.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#310 Leadership & Strategy | I sat down with Maura Rivera, CMO at Qualified, to talk about what it's like leading marketing at one company for six years (and why most of her team has been there just as long). We got into how product launches are the glue that hold their marketing together, what agentic marketing really means for the future, why outbound is actually working for them right now, and how events have become a huge part of their strategy. Plus, plenty of good banter along the way.Watch this episode on YouTube on my channel: https://youtu.be/4tew-Q89FmsTimestamps(00:00) - — Intro & setup: Marketing's back in the driver seat (03:32) - — Work, life, and moving from Boston to Vermont (07:07) - — Competitors, community, and the small-world CMO circle (12:37) - — How Maura's Salesforce roots shaped Qualified (15:07) - — Working for a CEO who actually gets marketing (19:07) - — Lessons from startup life & learning every part of marketing (22:07) - — Building the right team and hiring people smarter than you (29:07) - — Why product launches are the heartbeat of marketing (43:53) - — Agentic marketing, events, and AI at Qualified (55:53) - — The future of marketing and why it's back on top Join 50,000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Paramark.It's November. 2026 planning is already here. And the stuff you're doing right now will decide how next year plays out. But here's the problem: most teams are still planning next year's marketing strategy based on the WRONG DATA because of broken attribution and a misleading gut feel.  And you can't make smart budget calls if you're just guessing what's working, what's not, and where to put your next dollar.That's where Paramark comes in. They help you replace the guesswork with actual insight backed by $2 billion in analyzed marketing data. They've figured out what actually drives incremental growth across every channel including LinkedIn, Meta, TikTok, Google, CTV, even OOH.And right now, they're offering a private 1:1 consultation with their CEO and CMO, Pranav and Sam, who have led marketing teams at companies like Dropbox, Adobe, Microsoft, and Shutterfly. In this 45-minute strategy session, they'll help you measure the real impact of every marketing dollar, pull insights from your current media mix, and design a 2026 roadmap that's rooted in data, not gut.This is a heck of an offer. And it's real. And will go fast. So if you want to future-proof your marketing strategy for 2026, don't miss out on this offer.Grab your spot at paramark.com/brand-consult.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#300 Drive | This episode is from Drive 2025, our 2-day in-person event for B2B marketers in Burlington, VT. It features Diane Wiredu, Founder of Lion Words and expert in B2B messaging and positioning. She shared a killer talk on “What Your Messaging Is Missing,” breaking down why most B2B copy sounds the same and how to close the meaning gap by focusing on clarity, balance, and buyer context.Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.Timestamps(00:00) - – Intro from Dave (02:52) - – What “message-market fit” actually means (05:22) - – Why most B2B messaging misses (09:27) - – The “meaning gap” and why it happens (14:12) - – Balancing clarity, emotion, and differentiation (19:37) - – How to simplify complex products (26:33) - – Examples of messaging that actually resonates (32:03) - – How to pressure-test your messaging (38:18) - – Aligning teams around a clear message (44:03) - – Turning insights into copy that converts (49:13) - – Q&A: internal buy-in, testing, next steps Join 50,000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Today's episode is brought to you by Paramark.It's November. 2026 planning is already here. And the stuff you're doing right now will decide how next year plays out. But here's the problem: most teams are still planning next year's marketing strategy based on the WRONG DATA because of broken attribution and a misleading gut feel.  And you can't make smart budget calls if you're just guessing what's working, what's not, and where to put your next dollar.That's where Paramark comes in. They help you replace the guesswork with actual insight backed by $2 billion in analyzed marketing data. They've figured out what actually drives incremental growth across every channel including LinkedIn, Meta, TikTok, Google, CTV, even OOH.And right now, they're offering a private 1:1 consultation with their CEO and CMO, Pranav and Sam, who have led marketing teams at companies like Dropbox, Adobe, Microsoft, and Shutterfly. In this 45-minute strategy session, they'll help you measure the real impact of every marketing dollar, pull insights from your current media mix, and design a 2026 roadmap that's rooted in data, not gut.This is a heck of an offer. And it's real. And will go fast. So if you want to future-proof your marketing strategy for 2026, don't miss out on this offer.Grab your spot at paramark.com/brand-consult.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#299 Drive | This episode is from Drive 2025, our 2 day in-person event for B2B marketers in Burlington, VT. Our first speaker was Sangram Vajre, Co-founder and CEO of GTM Partners and expert in GTM strategy. He shared a great session on building a repeatable GTM Operating System for sustainable growth, offering insight from 100 companies on what separates teams that scale from those that stall.Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.Timestamps(00:00) - – Intro from Dave (02:51) - – Sangram's background + setup (04:51) - – What GTM really means (11:46) - – The 3 stages of GTM maturity (12:11) - – Why NRR is the key metric (20:51) - – The “boring marketing” advantage (27:42) - – How to say no and prioritize (29:42) - – Why GTM alignment beats tactics (33:42) - – Building your GTM Operating System (36:02) - – Q&A: GTM alignment, discovery, growth Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by our friends at Paramark. You've heard it before – every B2B marketer's top pain point is marketing attribution. It's complicated, messy, and too often leads to fights with your CRO over whose lead deserves credit.That's where Paramark steps in. Their platform makes it simple to understand what's driving results (and what isn't) with tools like marketing mix modeling and incremental testing. No more relying on outdated click attribution or chasing UTM links. Instead, Paramark gives you actionable insights across channels, campaigns, and geographies to help you grow.Paramark's founder & CEO Pranav has been in your shoes as a B2B marketer. He's so passionate about solving this problem, he's offering listeners a free brand assessment. Pranav will personally analyze your brand's performance and share his insights—an opportunity you don't want to miss.Slots are limited, so act fast. Head to paramark.com/brand-consult to claim your spot. Trust us, this is worth your time.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#298 Q&A | OK I asked my team for some questions; a bit of a mailbag type of episode. So I sat down solo for this one and answered 15 questions from the Exit Five team about work, life, marketing, and everything in between. We got into everything from my daily routine and how I think about LinkedIn, to the best career advice I've ever gotten, what I'm reading, and a few personal stories I've never shared before.Watch this episode on YouTube on my channel: https://www.youtube.com/watch?v=EyagkJf6xHw&t=508sTimestamps(00:00) - – Intro (02:08) - – What's your LinkedIn content creation process? (04:53) - – How often do you check Slack and email? (05:53) - – What are you reading or listening to right now? (09:23) - – What does a perfect day look like for you? (11:23) - – Tell your life story in four minutes. (12:08) - – If you could gain any quality or ability, what would it be? (16:08) - – What's your most embarrassing work moment? (18:43) - – What's your favorite all-time book and why? (19:43) - – What's the best career advice you've ever received? (22:03) - – What motivates you when you're feeling unmotivated? (23:08) - – If you could transform into any animal, what would you choose? (23:43) - – What are your biggest pet peeves? (25:33) - – Which team member would you swap lives with for a day? (26:43) - – What's your go-to karaoke song? (27:18) - – If you weren't running Exit Five, what job would you have? (28:58) - – Wrap-up & closing Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/ ***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#297 Leadership | I sat down with Kelly Cheng, CMO at Goldcast, to talk about her path from growth marketer to marketing leader, how she's built and scaled Goldcast's marketing org, the shift from PLG to sales-led, and why she believes great CMOs play the long game.Timestamps(00:00) - – Intro (03:08) - – Kelly's path from Hong Kong to Boston (06:08) - – Joining Goldcast and the PLG pivot (09:08) - – Moving from growth marketer to CMO (12:08) - – The role of mentors in her career (20:08) - – Questions to ask before taking a CMO role (27:43) - – Inside Goldcast's marketing org structure (33:43) - – How Kelly measures brand and mindshare (40:43) - – Why the BDR team reports to marketing (46:43) - – The link between brand, content, and pipeline (51:43) - – Leading with vulnerability and the “long game” Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/ ***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

Hey it's me live from the airport, LGA to be exact. Sorry for the poor audio, my AirPods make it way worse than just talking into the phone, now I know. But we cleaned it up a bit. Recapping our NYC event if you missed it, talking about the ROI of hanging out in person and what's next. Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/ ***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#295 Messaging | Dave is joined by Emma Stratton, founder of Punchy, where she helps B2B tech companies sharpen their positioning and write messaging that actually connects. Emma's worked with hundreds of teams to cut through vague, abstract copy and turn it into language buyers instantly get.Dave and Emma cover:How to go from vague to punchy using specificity and buyer empathyWhy most B2B messaging blends into the “sea of sameness” (and how to stand out)How customer research and real conversations create message–market fitThey wrap with a candid chat on journaling, focus, and how managing your mental energy can make you a better marketer and human.Timestamps(00:00) - – Intro to Emma (04:13) - – What makes B2B messaging actually good (07:55) - – Common messaging mistakes (and why “clarity > clever”) (10:53) - – Positioning vs. messaging: what's the difference? (15:06) - – Why it's hard to name great B2B marketing examples (17:30) - – How to sharpen weak messaging and fix vague positioning statements (20:38) - – Simplifying complex products without dumbing it down (23:48) - – How to write for buyers (not just execs) (28:55) - – Using customer interviews and research to build strong messaging (33:33) - – Standing out in a crowded, buzzword-filled market (36:17) - – How storytelling fits into B2B messaging (39:23) - – Messaging advice for early-stage founders and startups (42:38) - – How often should you revisit and update messaging? (44:48) - – Productivity, managing your energy, and staying focused (48:03) - – Journaling, mindfulness, and being intentional with your time (51:58) - – Final takeaways Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/ ***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#294 Event Strategy | First time podcast guest alert! I invited Allison and Anna from the Exit Five team on for a conversation post Drive 2025 - to talk about lessons learned and behind the scenes from our annual marketing conference in Vermont. Snag your tickets for next year now exitfive.com/driveTimestamps(00:00) - – Intro (02:08) - – Why events are making a comeback in B2B marketing (06:08) - – What Drive is and how it started (11:08) - – Why every event should start with the landing page (14:08) - – Lessons from year one and how feedback shaped Drive 2025 (19:08) - – Treating events like products, not projects (21:08) - – Building connection through “third spaces” and excursions (26:08) - – Why community is the real ROI of in-person events (32:43) - – The biggest Drive mishap (and what it taught us) (37:43) - – Post-event strategy: why the event isn't over when it ends (47:43) - – Favorite moments, lessons, and shoutouts from Drive 2025 Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/ ***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#293 Email Marketing | I'm trying to make my way from Vermont to New York and back with a mini episode talking about email (is email dead?), direct mail, the Dream 100, and a smart lesson from a non-B2B marketer. Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/ ***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#291 In-Person Events | I decided to break the pattern with a solo podcast, just me and my phone, walking around the woods at my home in Vermont on a damp October morning before heading to NYC for the Exit Five meetup. I talk about my goals for the week, our plans, why we're hosting a dinner, the value of meeting in-person, remote vs. in office work, and other ramblings.*If you listened to this: DM me on LinkedIn or email dave@exitifve.com - tell me what you want me to cover on this podcast as it relates to marketing, business, or life. Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/ ***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#290 AI Workflows | In this episode, Dave is joined by Dan Guenet, GTM Engineer at Compound Growth Marketing, and Eoin Clancy, Head of Growth at AirOps. Both guests are at the forefront of building AI workflows that make marketing more efficient and scalable, from content creation to sales enablement.Dave, Dan, and Eoin cover:How to use Clay, Zapier, and AirOps to build repeatable GTM systems that scale without burning bandwidthThe frameworks behind automating webinar production, sales transcript analysis, and content refreshes with AIWhy marketers need to bridge the gap between AI hype and real execution, and where to start with building practical workflowsTogether, they break down the exact tools, prompts, and processes they're using to turn AI from theory into impact across B2B marketing teams.Timestamps(00:00) - – Intro (02:08) - – The gap between AI hype and real execution (06:08) - – Dan's background and how GTM Engineering came to life (09:08) - – Building repeatable webinar systems with Clay (13:08) - – How to scale content and events without burning bandwidth (18:08) - – Eoin's content creation workflow using AirOps (23:08) - – Turning sales transcripts into actionable GTM insights (33:43) - – Using Zapier Agents to automate product marketing tasks (41:43) - – Refreshing SEO content with AI for better performance (49:43) - – Where AI fits in your team and how to start small Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#289 Strategy | Dave is joined by Sydney Sloan, Chief Marketing Officer at G2, where she's leading the charge on integrating AI into marketing, rethinking team structures, and modernizing how B2B brands build trust. Sydney brings decades of experience from companies like Adobe, Alfresco, and Salesloft, and now oversees one of the largest software marketplaces in the world.Dave and Sydney cover:How to design events that truly drive pipeline, using frameworks like “Think, Feel, Do” to plan with purposeA smarter way to measure event ROI with Sydney's “Revenue in the Room” approachHow AI is transforming the buyer journey and reshaping what modern marketing teams look likeAn episode that will leave you rethinking your marketing strategy, from the events you run to the org you build.Timestamps(00:00) - – Intro (03:08) - – The return of in-person events (06:08) - – Building community through smarter event design (08:08) - – Inside G2's “AI in Action” roadshow (11:08) - – The “Think, Feel, Do” event framework (14:08) - – Why details make or break events (17:08) - – Measuring success with “Revenue in the Room” (20:08) - – Post-event follow-up that drives results (27:43) - – How AI is reshaping the buyer journey (43:43) - – Rethinking marketing orgs for the AI era Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#288 AI in Marketing | In this episode, Dave is joined by three B2B marketing leaders: Sara Ajemian, Head of Brand & Communications at SOCi, Jennifer Delevante-Moulen, CMO at Knak, and Tara Robertson, CMO at Bitly. Together they share real-world perspectives on how AI is actually shaping marketing teams today—what's working, what's not, and how leaders are adapting.Dave and the panel cover:The most overhyped AI use cases in B2B marketing (and where human nuance still wins)Real success stories, including building an AI-powered content research engine, scaling global localization, and using AI to make creative teams more data-drivenHow CMOs are personally using AI as a strategic thought partner for board prep, customer insights, and team coachingWhether you're experimenting with new tools or figuring out how to bring AI into your strategy, this conversation gives a grounded look at what B2B marketing leaders are really doing today.Timestamps(00:00) - – Intro (03:08) - – Meet the panel: SOCi, Knak, Bitly (07:08) - – Has AI met or missed expectations? (11:53) - – The most overhyped AI use cases (15:08) - – Why human nuance still matters in personalization (20:08) - – The imposter syndrome of AI adoption (23:08) - – The power of AI with memory (25:48) - – Best AI use cases from the panel (31:43) - – Scaling global localization with AI (34:43) - – Training brand teams to be more data-driven (38:43) - – How CMOs personally use AI in their workflow (42:43) - – Using AI as a strategic thought partner (46:43) - – Coaching teams with AI feedback loops (48:43) - – The frustrations of iteration and tool updates (52:43) - – Is leadership pushing AI adoption? (56:43) - – Budgeting and building a modern AI-enabled tech stack (59:43) - – Final takeaways and closing Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#287 Brand Marketing | In this episode, Matt is joined by Amrita Gurney, a veteran B2B marketing leader who has scaled some of Canada's fastest-growing startups and now works as a fractional CMO. At Float, she led bold offline campaigns, from billboards and buses to TV spots, that helped the company stand out against major banks and build lasting brand recall.Matt and Amrita cover:Why offline ads like billboards and transit campaigns are making a comeback in B2B marketingHow creative choices — bold colors, emotional messaging, and relatable personas — can make or break brand campaignsWhat B2B marketers should know about budget allocation, measuring recall, and balancing brand vs. performance marketingWhether you're running your first brand campaign or rethinking your spend mix, this episode will give you fresh ideas on how to stand out in B2B marketing.Timestamps(00:00) - – Intro (03:08) - – Amrita's background and career journey (04:28) - – Why Float invested in offline ads (06:08) - – Launching their first billboard campaign (08:08) - – Taking bold risks with creative (10:08) - – Human-centered messaging vs. product copy (12:08) - – Expanding into buses, subways, and airports (15:08) - – Testing (or not testing) creative concepts (16:08) - – What brand recall really means in B2B (18:08) - – Measuring lift from offline campaigns (22:43) - – Balancing brand vs. performance spend (24:43) - – Lessons from consumer marketing in B2B (26:43) - – How they chose cities and placements (29:43) - – Budget breakdown and allocation (33:43) - – Tracking TV ad performance (35:43) - – How long to run campaigns for impact (36:43) - – Advice for marketers considering offline ads (38:43) - – Closing thoughts and takeaways Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#286 Growth | In this episode, Dave is joined by Kevin White, Head of Marketing at Common Room, a leading customer intelligence platform for go-to-market teams. Kevin shares insights from his experience helping teams capture and act on digital breadcrumbs to optimize their marketing and sales efforts.Dave and Kevin cover:How to be a good marketer even when you're not the Subject Matter ExpertSignal-based marketing and how it is transforming the buyer's journey by focusing on the right actions instead of just clicksB2B influencer marketing plays that workTimestamps(00:00) - - Intro to Kevin (06:17) - - How to Be Good At Marketing When You're Not a Subject Matter Expert (08:55) - - Why You Should Stay Close to Your Customer (16:14) - - How to Manage a Marketing Team with Limited Resources (18:33) - - Eliminating Ineffective Marketing Efforts to Drive Real Results (25:06) - - Signups and Demos Boost From LinkedIn (26:12) - - How to Attribute ROI in Multi-Platform Marketing (30:22) - - Creating Authentic and Valuable Content (35:01) - - Generating Pipeline with Economic Buyer Signals (36:42) - - Increasing Digital Touchpoints (40:40) - - How To Maximize Actionability, Volume, and Conversion Rate (42:26) - - LinkedIn Measurement Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Knak.Email (in my humble opinion) is the still the greatest marketing channel of all-time.It's the only way you can truly “own” your audience.But when it comes to building the emails - if you've ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. That's why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.Frustrated by clunky email builders? You need Knak.Tired of ‘hoping' the email you sent looks good across all devices? Just test in Knak first.Big team making it hard to collaborate and get approvals? Definitely Knak.And the best part? Everything takes a fraction of the time.See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more

#285 Creative Strategy | In this episode, Dave is joined by Pranav Piyush, Founder & CEO of Paramark, a measurement platform helping B2B and B2C companies run smarter marketing experiments. Pranav is known for turning strategy documents into repeatable creative processes that generate campaigns, ads, and content tied directly to a company's story.Dave and Pranav cover:How to translate your company narrative into concrete marketing campaigns and creative hooks across channelsWhy creative output (not measurement) is the biggest bottleneck for most B2B marketing teams todayThe frameworks like category entry points, jobs-to-be-done, and behavioral psychology that help marketers spark fresh, testable campaign ideas month after monthYou can expect a practical, example-filled conversation on turning strategy into execution and building a creative engine that never runs dry.Timestamps(00:00) - – Intro and audience roll call (05:09) - – Why narratives often get stuck in a Google Doc (08:09) - – Foundational docs you need before creating campaigns (13:09) - – Category entry points and jobs-to-be-done explained (17:09) - – How to feed company inputs into AI tools (23:09) - – Generating ad campaign ideas with real examples (25:09) - – Using analogies (like basketball) to explain complex concepts (29:54) - – Where AI falls short (and why human judgment matters) (32:54) - – Mining sales call transcripts for campaign hooks (36:54) - – Turning customer objections into marketing messages (40:54) - – Repurposing podcasts, presentations, and blog posts into new formats (44:54) - – Systemizing idea generation for repeatable output (48:54) - – Closing thoughts and audience Q&A Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

#284 Brand | Dave sits down with Ari Yablok, Head of Brand at Island, to share his approach to creating a brand in the cybersecurity space. Ari shares his journey from agency life to leading the brand narrative at Island, where he helped build the concept of the "enterprise browser."Dave and Ari Cover:The key differences between category creation and strategic positioning, and why it matters for B2B marketersThe steps to building a brand story that resonates with both your internal team and your target audienceHow focusing on the last 20% of branding efforts can elevate your company above the competitionTimestamps(00:00) - - Intro to Ari (04:33) - - Rapidly Growing Enterprise Browser Company Secures $375M in Series D Funding (08:42) - - SEO Strategy vs Branding (14:09) - - How Brand is an Art and a Science (19:24) - - Challenges in Cybersecurity Branding (21:08) - - Early Stage Marketing (29:48) - - Cognitive Behavioral Branding (34:57) - - How Ari Manages Projects with the Brand Team (37:07) - - Comfortable vs. Uncomfortable Approaches to Brand Strategy (41:25) - - What Founders Really Want to Do (46:31) - - Balancing the Day-to-Day with Visionary Goals Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

#285 Marketing Leadership | In this episode, Dave is joined by Sylvia Lepoidevin, CMO of Kandji, a leading platform for managing and securing Apple devices in the workplace. Sylvia shares her journey from employee #4 to CMO at Kandji, driving the company's growth to a $850M valuation. She talks about her experience building efficient marketing teams, leveraging AI, and creating impactful brand experiences.Dave and Sylvia cover:How AI is reshaping marketing roles and enabling smaller, more efficient teamsStrategies for internal marketing that align and energize cross-functional teamsProduct launches and creative campaigns for brand-driven growthTimestamps(00:00) - - Intro to Sylvia (04:57) - - From Marketing Hire to CMO (09:42) - - Understanding Equity and Financial Outcomes (12:24) - - Wealth and Career Growth (15:04) - - Why It's Important to Have a Clear Career Narrative (19:56) - - Mastering Storytelling in Team Meetings (23:14) - - How to Engage Your Team (23:50) - - Leveraging Feedback Loops to Build a Successful Team (31:06) - - AI Is Enabling Smaller, More Efficient Teams (34:49) - - AI's Impact on Marketing (37:49) - - How Kandji Is Expanding Their Team (40:40) - - Achieving 10x Growth Through Product-Led Strategies (44:20) - - Leveraging Competitor and Apple-Specific Keywords (47:44) - - Minimizing Hiring Risk: Test Roles First Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

#281 CRO | Matt is joined by Haley Carpenter, founder of Chirpy, a conversion rate optimization agency. Haley has nearly a decade of CRO experience across agency, SaaS, and eCommerce, and she's known for helping brands use research and testing to make smarter marketing decisions.Matt and Haley cover:Why CRO isn't just A/B testing, and how research should guide every optimization effortHow to approach CRO when you don't have massive website traffic, including scrappy testing methods and toolsThe role of messaging, value props, and social proof in driving higher conversions (and where B2B often lags behind DTC)By the end, you'll have a clearer picture of how to approach CRO as a system, not just a set of tests.Timestamps(00:00) - – Intro (02:09) - – Who is Haley Carpenter (03:09) - – What CRO really means (06:09) - – Research vs. testing explained (10:09) - – Where to start CRO on a website (13:09) - – Testing with limited traffic (17:09) - – Using data for smarter decisions (20:09) - – Building a culture of testing (24:09) - – How to report CRO results (29:09) - – Scrappy tools: Clarity & Hotjar (34:54) - – What B2B can learn from DTC (38:54) - – Why messaging matters more than features (42:54) - – The power of social proof (48:54) - – Common blockers to CRO success (50:54) - – A surprising test result (+7% sales) (52:54) - – Vanity metrics vs. real business outcomes (56:54) - – Closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

#281 Growth | In this episode, Dave is joined by Chris Walker, CEO of Passetto, and a prominent voice on LinkedIn, where he has been pushing the boundaries of B2B marketing for years. Chris shares actionable insights and tactics on social media strategy, what has changed in marketing over the last five years, and how to build effective feedback loops and flywheels.Dave and Chris also cover:The future of GTM and the evolving role of the CMOWhy sustainable growth is the only path forwardThe transformative role AI will play in B2B marketingTimestamps(00:53) - - Intro to Chris Walker (03:49) - - Managing different perspectives on social media (08:21) - - The ROI of podcasts and social media engagement (13:44) - - Why real-time feedback loops are valuable (19:19) - - Shifting from "growth at all costs" to sustainable growth (25:09) - - Rethinking marketing measurement and ROI (33:04) - - Splitting marketing teams: strategy vs. pipeline creation (40:09) - - How AI is reshaping B2B marketing teams (48:14) - - Chris's approach to creativity and focus (52:59) - - Predictions for the future of B2B marketing (54:37) - - Outro Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

#280 Strategy | In this episode, Dave is joined by Gurdeep Dhillon, CMO of Contentstack. Gurdeep has built an impressive career leading marketing at some of the biggest names in enterprise software, from SAP to Adobe, Marketo to Zoura. Now at Content Stack, he's challenging conventional B2B marketing wisdom in rethinking how enterprise companies should approach demand generation and brand building. In this conversation, Dave and Gurdeep dive deep into why marketing is ultimately a game of memory and reputation, not just lead generation.Dave and Gurdeep cover:The role of Demand Gen in 2025 (and what's changed)Why Brand and Reputation should be prioritized over Lead GenerationProven strategies to create urgency and close sales deals in enterprise marketsA glimpse into ContentStack's team structure and how they plan for growthTimestamps(00:00) - - Intro to Gurdeep (06:51) - - Brand and Audience Marketing (08:03) - - How the Role of Demand Gen is Changing (12:13) - - Brand and Reputation > Lead Generation (17:03) - - How Contentstack is Doing Demand Gen (19:41) - - How to Create Urgency to Win Sales Deals (21:22) - - Making a Good Offer in B2B Marketing (22:38) - - Why Being Bold and Taking Risks is Important in Marketing (28:57) - - Selling Your Vision to Leadership (31:38) - - How Contentstack Has Over 10,000 Global ICP Accounts (36:21) - - Team Structure at Contentstack (41:19) - - Running Marketing and Operating a High-Performing Team (43:35) - - Setting Effective Annual Plans (45:50) - - AI's Role in Marketing (49:24) - - Closing Thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

#279 Content Strategy | In this episode, Dave joins Holly Xiao from HeyGen for an unfiltered conversation about where AI and video marketing are headed. Holly leads B2B marketing at HeyGen, an AI-powered video platform, and she sat down with Dave to dig into what's working (and what's not) when it comes to creating content that actually connects.Dave and Holly cover:Why video hits differently in B2B and how to make yours stand out without blowing your budgetHow AI is reshaping the content production cycle and freeing up marketers to focus on storytellingWhy early adoption matters, and how small teams can use AI to punch above their weightYou can expect a candid, practical conversation about how to scale content, stay relevant, and make the most of AI.Timestamps(00:00) - – Intro (01:27) - – Why this conversation matters (02:44) - – AI is making marketing exciting again (03:53) - – Dave's early bet on video (05:53) - – How LinkedIn video exploded (07:10) - – ROI vs. brand building (08:25) - – From connection to conversion (10:10) - – Why video feels more human (12:16) - – “Maybe your videos suck” (14:22) - – The problem with corporate videos (16:10) - – The value of repetition and reps (18:34) - – How AI speeds up content cycles (20:51) - – Real AI tools Dave is using (22:28) - – Decks, data, and automation (24:53) - – Why creativity still wins (27:15) - – The return of the creative CMO (31:14) - – Personalized content at scale (33:13) - – AI vs. in-person experiences (35:55) - – Do audiences care if it's AI? (38:41) - – What makes an AI video work (41:18) - – Using AI to test and scale video (43:59) - – What small teams should do first (47:37) - – Final advice: be an early adopter Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

#278 Content | In this episode, Dave brings together five B2B marketers who aren't just talking about AI, they're actually using it to change how their teams work. Each finalist from the Exit Five x Walnut AI Sessions takes the (virtual) stage to demo their workflow, share results, and answer questions from the judges.Here's what you'll hear:Jillian Hoefer's “content concierge” GPT trained on proprietary research to surface stats, quotes, and data for blogs, sales decks, and thought leadershipJake Heap's workflow using Meshy + VEO 3 to turn a simple mascot into animated 3D brand characters in minutesJessica Lytle's no-code ROI calculator built in Lovable that sales reps now run live on calls to build business casesUgi Djuric's high-volume content engine that scrapes industry news and sales call transcripts, then uses AI to summarize, generate content ideas, and even score leadsAnton Ruis' AI-powered buyer brief builder that pulls real-time economic data and tailors sales messaging to specific personasIt's part workshop, part competition, and packed with creative, tactical ways to put AI to work in B2B marketing today.Timestamps(00:00) - – Dave kicks off in a tux (02:44) - – Record-breaking registrations (03:22) - – Meet the judges: Benny & Jess (08:10) - – Jillian's “victim of repurposing” intro (08:50) - – Building a “content concierge” GPT from research data (10:14) - – Injecting stats + quotes into blogs and decks (14:10) - – How one report fueled 9+ months of content (19:10) - – Jake on bringing AI into marketing ops (20:33) - – Turning a mascot into a 3D character with Meshy (21:18) - – Animating it in VEO 3 (no designer needed) (24:33) - – Cutting animation time from weeks to minutes (30:32) - – Jessica builds a no-code ROI calculator in Lovable (33:41) - – AEs use it live on sales calls (34:25) - – Adding benchmarks + transparency to ROI math (41:43) - – Ugi's AI engine scrapes + summarizes industry news (44:00) - – Training custom GPTs on expert insights (50:40) - – Anton's real-time buyer briefs from economic data (53:15) - – Tailoring briefs for CROs, enablement, PMMs (56:59) - – Judges crown the winning use case + Dave's wrap-up Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***This episode of the Exit Five podcast is brought to you by Qualified.AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.That's where Qualifed comes in with Piper, their AI SDR agent.Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.The Agentic Marketing era has arrived. And if you're a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.You can learn more at qualified.com/exit5

#277 Growth | Dave is joined by Emma Robinson, Head of B2B Marketing at Canva, and Kristine Segrist, VP of Consumer Marketing at Canva. Together, Emma and Kristine lead the teams driving Canva's growth across both enterprise and consumer audiences, helping the company scale into a platform now used by over 95% of the Fortune 500.Dave, Emma, and Kristine cover:How Canva balances brand-building with pipeline accountability, and why they view brand investment as long-term growth.The playbook Canva uses to turn bottom-up adoption into enterprise deals, including how product signals guide upsell and expansion.How their team structure, data science investments, and creative bets (like the Love Your Work campaign) work together to scale B2B marketing without losing Canva's approachable brand identity.This episode offers a practical look at how one of the world's most recognizable platforms approaches B2B growth.Timestamps(00:00) - – Intro (03:48) - – Canva's marketing org structure (06:48) - – Blurring B2B and B2C (11:48) - – How Canva measures marketing impact (16:48) - – Turning free users into enterprise deals (21:48) - – Data science's role in marketing (24:48) - – Balancing brand bets with ROI (31:23) - – Inside the “Love Your Work” campaign (38:23) - – How Canva executes large campaigns (42:23) - – Building enterprise credibility and trust (45:23) - – FedEx case study on brand governance (49:23) - – Lessons from Google and Meta (53:23) - – Why creativity is a marketing superpower (55:23) - – Closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Walnut.Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?Come on, today's buyers don't want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.That's where Walnut comes in.Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond. That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.And the best part? You get real intent data—see which features prospects love, where they drop off, and what's actually driving pipeline. Demo Qualified Leads are the new MQL.Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA? Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!

#276 Career Growth | Dave is joined by Kady Srinivasan, CMO at You.com, an AI-first company building infrastructure for enterprise agents. Kady has led marketing at some of the world's most recognizable companies, including Dropbox, Klaviyo, and Lightspeed, where she scaled teams, drove massive revenue growth, and navigated ICP pivots. Now, she's bringing that experience into the fast-changing world of AI.Dave and Kady cover:How to evolve as a CMO across industries, personas, and business modelsThe three core systems CMOs need to scale teams and drive alignmentHow AI is reshaping marketing roles, workflows, and the skills future CMOs will needYou'll walk away with lessons you can apply to your own career, no matter what market or role you're in.Timestamps(00:00) - – Intro (03:03) - – From engineer to reluctant marketer (05:37) - – Gaming years and “coolest mom” cred (07:52) - – The story behind You.com's domain (09:31) - – Why she jumped into AI (12:00) - – Reinventing yourself as a CMO (14:00) - – Fundamentals that never change in marketing (16:13) - – Aligning marketing with company strategy (19:24) - – Pivoting the ICP at Lightspeed (22:26) - – Lessons on cross-functional alignment (25:08) - – Letting go to grow as a leader (27:53) - – Systems every CMO should set up (34:43) - – Why no single playbook works (36:24) - – How AI is reshaping marketing roles (51:04) - – Building an AI-first marketing org and closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Walnut.Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?Come on, today's buyers don't want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.That's where Walnut comes in.Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond. That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.And the best part? You get real intent data—see which features prospects love, where they drop off, and what's actually driving pipeline. Demo Qualified Leads are the new MQL.Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA? Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!

#275 LinkedIn Strategy | In this episode, Dave is joined by Brad Zomick, a B2B marketing consultant and host who has helped founders and executives build their presence on LinkedIn. Together they break down why a strong LinkedIn strategy is no longer optional for founders, it's one of the most effective growth levers in B2B today.Dave and Brad cover:Why LinkedIn is still the best channel for founders to build authority, attract talent, and connect with customersHow to turn everyday founder communications into high-impact LinkedIn contentThe unexpected ROI of founder-led content, from recruiting and partnerships to real-time message testingIf you've been wondering how to turn LinkedIn into a real growth engine for your brand, this episode is your blueprint.Timestamps(00:00) - – Intro (03:48) - – Early days of LinkedIn (09:18) - – Building Drift with founder brand (15:18) - – Why every founder needs LinkedIn (19:18) - – The hidden ROI of posting (27:53) - – Dave's personal posting system (31:23) - – How to never run out of content (35:23) - – Unexpected benefits of being visible (39:53) - – Is it too late to start? (42:53) - – Who inspires Dave today (45:08) - – What's next for Exit Five (46:53) - – Closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Walnut.Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?Come on, today's buyers don't want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.That's where Walnut comes in.Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond. That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.And the best part? You get real intent data—see which features prospects love, where they drop off, and what's actually driving pipeline. Demo Qualified Leads are the new MQL.Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA? Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!

#274 Growth | In this episode, Dave is joined by Sean Lane, Founding Partner at BeaconGTM and RevOps expert, to talk about scaling RevOps in B2B. With over a decade of experience at Drift and other B2B SaaS companies, Sean shares actionable tips for marketers looking to align operations with business goals.Dave and Sean cover:How to build alignment between sales, marketing, and opsWhy early-stage companies must align operational complexity with their growth maturityHow continuous planning helps marketing and ops teams stay agile as business challenges come upTimestamps(00:00) - - Intro to Sean (07:11) - - Going From Founder Led Sales to Having A Professional GTM (09:52) - - How Ops Bridges Business Goals (13:42) - - How To Align Sales, Marketing, and Operations (17:51) - - Why You Need A Clear Marketing Strategy (20:17) - - How To Build A Partnership Between Marketing and Operations (26:41) - - Guidelines for long term vs short term budgeting and planning (32:19) - - Marketing's Role At The Bottom Of The Funnel (37:14) - - How To Get “Hand-raisers” For Your Product In The Customer Journey (41:06) - - Do Engaged Accounts Measure The Success Of Marketing? (42:56) - - Sean's Podcast ROI (45:12) - - AI Use Cases In Ops (50:14) - - How To Hire A Good Ops Person (53:42) - - Closing Remarks Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Walnut.Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?Come on, today's buyers don't want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.That's where Walnut comes in.Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond. That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.And the best part? You get real intent data—see which features prospects love, where they drop off, and what's actually driving pipeline. Demo Qualified Leads are the new MQL.Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA? Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!

#273 Leadership | Matt is joined by Rachel Weeks, a veteran B2B marketing leader with over 20 years of experience guiding companies through acquisitions, layoffs, and tech disruption. Rachel has led both corporate and field marketing teams and is passionate about recognition-driven team cultures that retain and empower top talent.Matt and Rachel cover:How to build a recognition strategy that actually improves retention (without needing a big budget or fancy platform)Why employee motivation dips during times of stress, layoffs, or AI disruption and what great leaders do differentlyThe role of marketing in internal culture: from branding the program to building peer-driven engagementWhether you're managing a small team or leading an entire department, this episode is packed with practical insights to help you build a culture where marketers feel valued, motivated, and ready to stay.Timestamps(00:00) - – Intro (03:48) - – Rachel's background and leadership lens (06:18) - – What actually makes a recognition program work (08:48) - – How marketing supports internal culture building (11:48) - – Recognition during org changes, stress, and funding rounds (14:48) - – The impact of AI on morale and motivation (18:18) - – What happens when recognition disappears (20:18) - – The “10 minutes by Friday” habit (22:48) - – Easy, no-budget ways to recognize team members (25:48) - – Performance-driven vs. values-driven recognition (30:53) - – Monetary vs. non-monetary rewards (and what people really want) (34:23) - – Recognition vs. pay raises: what the data says (38:23) - – Why people leave even when they're paid well (42:23) - – How to ask for (and give) better feedback (47:23) - – Using AI to create space for strategic work (54:23) - – Final thoughts on leadership, retention, and culture Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Walnut.Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?Come on, today's buyers don't want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.That's where Walnut comes in.Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond. That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.And the best part? You get real intent data—see which features prospects love, where they drop off, and what's actually driving pipeline. Demo Qualified Leads are the new MQL.Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA? Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!

#272 Presentation Skills | Matt is joined by Vincent Pierri, a speaking coach who helps executives and marketers craft compelling, high-stakes talks. With a background as a pastor and public communicator, Vincent has developed a repeatable framework that helps B2B marketers improve how they show up in front of a room, whether it's a conference keynote, a boardroom pitch, or a weekly team update.Matt and Vincent cover:The 4-part framework behind talks that stick: Tension, Trust, Teaching, TakeawayHow to pick the right topic for your talk (and avoid cramming in too much)Why authenticity and simplicity matter more than slide design, and how to keep your delivery grounded and effectiveWhether you're prepping for Inbound, Exit Five's Drive, or just your next big internal presentation, this episode will help you nail the structure and mindset behind a talk that resonates.Timestamps(00:00) - - Intro (02:58) - - Vincent's unusual path to speaking coach (06:48) - - Why marketers need this framework (not just keynote speakers) (09:28) - - The first step: pick one real person you want to help (12:38) - - How to narrow your talk down from too many ideas (15:48) - - The 4-part structure: Tension, Trust, Teaching, Takeaway (18:38) - - Why your talk should start with a problem (not your points) (20:13) - - How to build trust by showing vulnerability (23:18) - - The 3 Cs: Catchy one-liner, Creative analogy, Concrete example (30:23) - - How to make your points memorable (and not Googleable) (33:28) - - Why authenticity beats sounding “smart” (35:38) - - What a strong closing takeaway looks like (38:53) - - When (and how) to start practicing your delivery (40:08) - - Why you should build your talk before your deck (42:33) - - How many slides is too many? (46:23) - - Connecting without slides: lessons from the pulpit (48:38) - - Final advice for marketers prepping talks this fall Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Walnut.Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?Come on, today's buyers don't want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.That's where Walnut comes in.Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond. That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.And the best part? You get real intent data—see which features prospects love, where they drop off, and what's actually driving pipeline. Demo Qualified Leads are the new MQL.Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA? Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!

#271 GTM Engineering | In this episode, Dave is joined by John Short, CEO of Compound Growth Marketing, along with Cammy Keiler, Justin Johnson, and Dan Guenet. Together, they break down the rise of GTM engineering, what it is, how it differs from RevOps, and why B2B teams are investing in it.Dave and the crew cover:The core difference between RevOps and GTM engineering (and why the latter is more focused on building than just integrating)Real GTM engineering use cases, from AI-powered sales tools to mid-funnel campaigns that go way beyond ebooksHow GTM engineers are driving higher revenue per employee and why this role should be one of your first five marketing hiresWhether you're hiring or just GTM-curious, you'll leave this episode with a clear definition of the role, real-world examples, and tactical ways GTM engineers drive impact.Timestamps(00:00) - – Intro (03:33) - – Why this topic resonated with 1,200+ registrants (05:48) - – What even is **GTM engineering? (08:03) - – GTM engineering vs. RevOps vs. Marketing Ops (11:18) - – How AI is driving this role forward (14:28) - – Real examples: ABM campaigns, mid-funnel tools, sales call analysis (19:38) - – Tools GTM engineers are using today (Clay, Unify, GPTs) (23:03) - – Role of GTM engineering in revenue per employee (27:18) - – How GTM engineers enable sales + reduce headcount (31:33) - – What Dan actually does all day as a GTM engineer (36:23) - – Custom GPTs for sales and marketing teams (39:38) - – What MCP servers are (and why they matter) (44:08) - – Claude, Gamma, and AI-powered content systems (46:53) - – Why this isn't just PLG (or ABM, or RevOps) (50:43) - – When to hire a GTM engineer (53:23) - – Big feelings about the role (and why they exist) (55:33) - – Closing thoughts + what to take away Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Walnut.Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?Come on, today's buyers don't want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.That's where Walnut comes in.Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond. That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.And the best part? You get real intent data—see which features prospects love, where they drop off, and what's actually driving pipeline. Demo Qualified Leads are the new MQL.Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA? Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!

#270 Strategy | Dave is joined by Holly Xiao, Head of B2B Marketing at HeyGen, an AI video generation platform that helps teams produce personalized, high-quality content, fast. Holly has led marketing at high-growth startups and now runs the enterprise GTM motion at HeyGen, where she blends strategy, creative execution, and AI-powered workflows to reach modern B2B buyers.Dave and Holly cover:The 4 channels her lean team is betting on to drive enterprise pipeline (and what's not working anymore)How B2B marketers are using AI video for event marketing, sales enablement, onboarding, and beyondWhy SEO is falling short and how HeyGen is shifting focus to webinars, events, and YouTube insteadIf you're figuring out how to use AI in your marketing or just trying to do more with less, this one's full of practical ideas to help you think differently about team structure, channels, and strategy.Timestamps(00:00) - – Intro (03:48) - – Holly's nonlinear path to marketing (06:48) - – Getting started in marketing ops (08:48) - – Why she joined an AI startup (10:48) - – How HeyGen's marketing org works (13:48) - – PLG vs SLG: Key differences (15:48) - – The 4 channels driving pipeline (17:48) - – What's working: Events + webinars (19:48) - – Booth strategy that stands out (24:23) - – Brand vs demand events (26:23) - – Building community and user events (27:53) - – SEO is declining. Now what? (30:23) - – Running marketing in 2-month sprints (33:23) - – Aligning product and marketing cadence (35:23) - – Her daily AI tools (36:53) - – ChatGPT vs Gemini workflows (38:23) - – Real AI video use cases (40:23) - – Personalized event promos with avatars (41:23) - – Support, training, and onboarding videos (42:23) - – Fortune telling and music videos?! (43:23) - – Why AI won't replace marketers Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership***Today's episode is brought to you by Walnut.Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?Come on, today's buyers don't want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.That's where Walnut comes in.Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond. That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.And the best part? You get real intent data—see which features prospects love, where they drop off, and what's actually driving pipeline. Demo Qualified Leads are the new MQL.Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA? Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!