In Depth

David Cramer is the co-founder of Sentry, the leading open-source error monitoring tool used by over 90,000 companies. A self-taught engineer, he went from 9th grade high school dropout and Burger King manager to building one of the most widely adopted developer tools in the world — by working hard and rejecting conventional wisdom. As of 2022, Sentry is valued at over $3 billion. David now serves as Chief Product Officer, after previously holding roles as CEO and CTO. In this episode, we discuss: How David went from managing a Burger King to landing his first job as a software engineer How an code snippet grew into a ubiquitous monitoring platform Why open source is an underrated distribution hack How a ruthless competitive streak and obsession with excellence fueled Sentry's rise And so much more… Referenced: Aaron Levie Beats by Dre Cursor Dan Levine Datadog Disqus Dropbox Heroku Max Levchin Okta Omar Johnson Oracle Sentry Satya Nadella Stripe Uber VS Code WindSurf Y Combinator Yandex Where to find David: LinkedIn Twitter/X Where to find Brett: LinkedIn Twitter/X Where to find First Round Capital: Website First Round Review Twitter/X YouTube Timestamps: (4:01) Learning to code through gaming (6:31) Dropping out of high school (9:47) Building infrastructure at Disqus (10:20) “Software is not that hard” (12:45) Early interest in open source (15:45) The birth of Sentry (23:37) Two common founder mistakes (27:13) David's unwavering focus (28:17) Sentry's journey to venture backing (36:43) Finding conviction in decisions (41:11) How Sentry found PMF (46:34) More confidence, less ego (48:08) Is sales valuable? (51:31) David's personal philosophy (1:01:17) Money is not the hardest problem (1:06:27) Marketing won't fix a bad product (1:10:34) What makes Sentry's market unique (1:16:24) “You're gonna mess up” (1:22:08) Why brand will always matter (1:30:51) Eliminating all competition

Karri Saarinen is the co-founder and CEO of Linear, the project management tool built for high-performance software teams. Since its founding in 2019, Linear has achieved a valuation of $1.25B as of 10th June 2025 and now counts companies like OpenAI, Ramp and Vercel as customers. Before founding Linear, Karri led design at Airbnb and Coinbase, and previously co-founded Kippt, a bookmarking tool acquired by Coinbase. In today's episode, we discuss Karri's childhood love for computers that shaped his career The lessons he learned from a failed first startup Linear's founding principles The early validation strategies used to shape the product Why Karri believes in small teams And much more… Referenced Airbnb Brian Armstrong Brian Chesky Coinbase Jori Lallo Linear Tuomas Artman Y Combinator Where to find Karri LinkedIn Twitter/X Where to find Brett LinkedIn Twitter/X Where to find First Round Capital Website First Round Review Twitter/X YouTube Timestamps (1:37) Childhood roots in computers and design (6:54) Founding Kippt and lessons from a failed bookmarking startup (13:14) Lessons from a serial entrepreneur (19:32) Why teams shouldn't grow too quickly (25: 03) Linear's early beginnings (36:55) The unexpected power of intuition (42:41) Linear's unusual approach to user growth (47:29) What shaped Linear's early product roadmap (52:02) Startups shouldn't try to boil the ocean (57:30) The power of extreme focus (59:18) Design “something for someone” (1:04:29) Flexibility vs. simplicity (1:17:27) Lead your team with strong principles (1:24:45) Design founders vs. engineering founders

Wes Kao is an executive coach, advisor, and instructor, best known for her newsletter on high-impact communication, and for co-founding course platform Maven and the AltMBA with Seth Godin. Across her career, Wes has helped leaders communicate with clarity and conviction, whether it's rallying a team, pitching investors, or influencing stakeholders. In this episode, Wes and Brett unpack how founders can be more persuasive, why playing to your strengths is critical, and how everyone can raise their own standards. --- In today's episode, we discuss: Wes' “personality-message fit” framework Why charisma is misunderstood How anyone can improve their communication What being told you need to “be more strategic” actually means and much more… --- Referenced: AltMBA: https://altmba.com/ Maven: https://maven.com/ Seth Godin: https://www.sethgodin.com/ Udemy: https://www.udemy.com/ --- Where to find Wes: LinkedIn: https://www.linkedin.com/in/weskao --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: (1:54) Charisma is misunderstood (4:44) What underpins authenticity? (13:53) Clarity in communication (16:02) Start with your ideal outcome (22:05) The role of power dynamics (26:39) Should you work on weaknesses? (29:02) Effective self-reflection (32:13) Role-strength fit (37:39) What do you resent? (39:17) “Be more strategic” (45:20) Stack ranking (51:45) How AltMBA started (60:04) Defining your craft

Rick Song is the co-founder and CEO of Persona, the identity verification platform used by some of the world's largest companies. Before starting Persona, Rick worked on identity fraud and risk products at Square, which laid the groundwork for what would become Persona's highly technical, horizontal platform. Since founding the company, Rick has scaled Persona into a category-defining leader, recently raising a $200M Series D at a $2B valuation. In today's episode, we discuss: How Rick's skepticism shaped Persona's early strategy What it takes to scale a true platform company Successful execution in hypercompetitive markets What Rick's learned from his co-founder, Charles Yeh and much more… Referenced: Accenture: accenture.com Anthropic: anthropic.com Braze: braze.com Bridgewater Associates: bridgewater.com Charles Yeh: linkedin.com/in/charlesyeh/ Christie Kim: linkedin.com/in/christiekimck/ Clay: clay.com Kareem Amin: linkedin.com/in/kareemamin/ MIT: mit.edu Newfront: newfront.com Palantir: palantir.com/ Persona: withpersona.com Rippling: rippling.com Scale AI: scale.com Snowflake: snowflake.com Square: squareup.com Y Combinator: ycombinator.com Zachary Van Zant: linkedin.com/in/zacharyv/ Where to find Rick: LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/ Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps: (0:05) Life before Persona (2:11) The push from Charles (3:09) Early reluctance and low expectations (9:50) Winning the first $50 customer (13:08)“Invalidating” Persona (16:43) How Persona found their edge (19:35) Transitioning from MVP to platform (24:18) Turning down a $5K deal on principle (26:47) Generalizing bespoke solutions (28:28) Finding product-market fit (33:51) Founder-led sales and consultative approach (39:30) Building a culture of reactivity (45:47) Landing the first enterprise customers (51:34) Silicon Valley's obsession with frameworks (58:17) Developing first principles thinking (1:00:24) Stay competitor-informed

Adit Abraham is the co-founder and CEO of Reducto, which helps leading AI teams extract and structure data from complex documents and spreadsheets in their pipeline. Within 6 months of launching, Reducto went from 0→7 figures in ARR. Reducto has grown to process tens of millions of pages monthly for companies ranging from startups to Fortune 10 enterprises. They just announced a $24M Series A. Before Reducto, Adit was a Product Manager at Google, working on Ads and Search, and conducted machine learning research at MIT's Media Lab. --- In today's episode, we discuss: How listening to customers revealed an opportunity to pivot The weekend project that became Reducto's breakthrough Landing a Fortune 10 customer A technical founder's guide to sales Key insights from Reducto's fundraising journey Advice for founders: “You're going to fail” Much more --- Referenced: Anthropic: https://www.anthropic.com/ Chetan Puttagunta: https://www.linkedin.com/in/chetanputtagunta/ Diana Hu: https://www.linkedin.com/in/sdianahu/ Liz Wessel: https://www.linkedin.com/in/elizabethwessel/ Raunak Chowdhuri: https://www.linkedin.com/in/sauhaarda/ Reducto: https://reducto.ai/ Scale AI: https://scale.com/ Stripe: https://stripe.com/ Textract: https://aws.amazon.com/textract/ Y Combinator: https://www.ycombinator.com/ --- Where to find Adit: LinkedIn: https://www.linkedin.com/in/aditabraham/ --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: (00:00) Hackathons, YC, and an unexpected pivot (05:23) The weekend project that became Reducto's breakthrough (09:11) How customer signal led to PDF processing (14:46) Landing a Fortune 10 customer (22:42) Building “transferable features” (25:58) How caring beats sales skills in startup growth (30:28) The strategy behind Reducto's horizontal expansion (36:18) Hire slow, go-to-market fast (41:45) A technical founder's guide to sales (43:45) “You're going to fail” (46:27) Why startups win (48:30) Key insights from Reducto's fundraising journey (51:43) Less structure, more impact (55:00) How frustrations shaped Reducto's culture (57:35) The question you should always ask in meetings

Jeff Shiner is the CEO of 1Password, the access management company used by over 100,000 businesses and millions of individuals worldwide. He joined 1Password as CEO in 2012, when the team was just under 20 people. Under Jeff's leadership, 1Password expanded into B2B, launched a SaaS platform, and scaled from a small family-run operation into a global company. In 2019, Jeff led 1Password through its first-ever funding round – a $200M Series A from Accel – to build out its go-to-market team and accelerate product development. Before joining 1Password, Jeff held senior roles at IBM and led teams through multiple acquisitions and integrations. --- In today's episode, we discuss: Why bootstrapping isn't always what it's cracked up to be The switch from a consumer product to B2B Launching before billing — and why that worked When being “too secure” nearly killed the product Becoming CEO… without telling anyone Much more --- Referenced: 1Password: https://1password.com Accel: https://www.accel.com Arun Mathew: https://www.linkedin.com/in/arun-mathew-b7186412/ David Teare: https://www.linkedin.com/in/daveteare/ Floodgate: https://floodgate.com LastPass: https://www.lastpass.com Mike Maples: https://www.linkedin.com/in/maples/ Natalia Karimov: https://1password.com/company/meet-the-team/natalia-karimov Roustem Karimov: https://www.linkedin.com/in/roustem/?originalSubdomain=ca Sara Teare: https://1password.com/company/meet-the-team/sara-teare Shopify: https://www.shopify.com Tobi Lütke: https://www.linkedin.com/in/tobiaslutke/ --- Where to find Jeff: LinkedIn: https://www.linkedin.com/in/jshiner --- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson --- Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast --- Timestamps: 0:03 – How Jeff got involved with 1Password 2:01 – How 1Password was initially set up 10:41 – The secret CEO 13:44 – What Jeff's first six months encompassed 16:13 – The lightbulb moment that caused a pivot 17:50 – 1Password's unusual company journey 22:08 – Creating an aligned product roadmap 29:19 – Retaining a customer-centric focus at scale 30:40 – Why 1Password's first B2B product failed 39:43 – How Jeff thinks about competitors 46:44 – Building different go-to-market functions 52:45 – Staying bootstrapped for 15 years 57:17 – Jeff's one regret 1:02:00 – 1Password's most pivotal moments

Adam Guild is the co-founder and CEO at Owner, an online food ordering system for independent restaurants. Within a year, Owner went from being about to run out of money to having hundreds of customers. Last year, they raised a $33M Series B. Adam's entrepreneurial journey began as a teenager when he built a successful Minecraft server, which led him to drop out of high school to become a founder. His passion for helping small businesses was sparked by his mom's struggles running a dog grooming shop, which led him to launch the early iteration of Owner. -- In today's episode, we discuss: How working with a small business kickstarted Owner Adam's unusual outbound strategy Why the pandemic accelerated Owner's success How Owner's pivot led to “hyperbolic” product-market fit The two qualities Adam looks for in new hires -- Referenced: Alex Bard: https://www.linkedin.com/in/alexbard/ Dean Bloembergen: https://www.linkedin.com/in/deanbloembergen/ Guisados: https://www.guisados.la/ HubSpot: https://www.hubspot.com/ Jack Altman: https://www.linkedin.com/in/jackealtman/ Kimbal Musk: https://www.linkedin.com/in/kimbalmusk/ Modern Restaurant Management: https://modernrestaurantmanagement.com/ Naval Ravikant: https://www.linkedin.com/in/navalr/ Neil Patel: https://www.linkedin.com/in/neilkpatel/ Peter Thiel: https://www.linkedin.com/in/peterthiel/ P.F. Chang's: https://www.pfchangs.com/ Sean Rad: https://www.linkedin.com/in/seanrad/ Thiel Fellowship: https://thielfellowship.org/ Tim Ferriss: https://www.linkedin.com/in/timferriss/ Y Combinator: https://www.ycombinator.com/ -- Where to find Adam: LinkedIn: https://www.linkedin.com/in/adamharrisonguild/ -- Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast -- Timestamps: (00:00) Intro (01:29) Adam's first business (04:15) The transition from Minecraft to Owner (05:58) The dark side of the gaming industry (14:20 Adam's scrappy strategy to landing his first customers (16:52) The COVID pivot (21:31) The quest to find product-market fit (30:53) What actually worked to get new customers (36:03) Inside Owner's explosive growth (46:41) How Owner secured its crucial first round of funding (53:34) The bet on going multi-product (64:28) What Adam wishes he knew at 17 (76:22) Sales-led vs. product-led growth

Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era. – In today's episode, we discuss: Eeke's wealth of experience as an executive leader The challenges companies face when hiring new executives Common hiring red flags and pitfalls Practical advice for measuring success Why learning your strengths is an underrated piece of the process – Referenced: ASML: https://www.asml.com/en Claire Hughes Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/ Constellate: https://constellate.team/ John Collison: https://www.linkedin.com/in/johnbcollison/ Mike Maples Jr.: https://www.linkedin.com/in/maples/ Patrick Collison: https://www.linkedin.com/in/patrickcollison/ Retool: https://retool.com/ Stripe: https://stripe.com/ Will Gaybrik: https://www.linkedin.com/in/william-gaybrick-5730347/ – Where to find Eeke: LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Should you ‘buy or build' a leader (03:45) Why do executive hires fail so often? (09:35) Why the stakes are so high for leadership hires (12:26) The hardest document Eeke ever wrote (14:06) Two red flags in a new hire (17:27) An example of an outstanding leader (21:40) What creates dysfunctional exec relationships (22:38) The three steps towards hiring successful leaders (30:30) What you should know about outside hires (33:12) Eeke's advice for easing leadership transitions (42:06) How to notice success patterns (47:21) Why high-functioning executive teams are like parents (52:02) The most surprising lesson from Eeke's first stint at Stripe (55:11) The leadership data Eeke wishes we had

Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional 401(k) plans—largely due to confusing fee structures. After launching Guideline to address those problems head-on, the company has seen remarkable growth, hitting $120 million in ARR by June 2024. In this conversation, Kevin shares pivotal moments that shaped Guideline's trajectory, including a strategic partnership with Gusto. He also explains how his “Do the hard thing first” mindset helped the team build an industry-leading platform and disrupt an entrenched market. – Referenced: ADP: https://www.adp.com/ Aydin Senkut: https://www.linkedin.com/in/aydins/ CalSavers: https://www.calsavers.com/ DoorDash: https://www.doordash.com/ Fidelity: https://www.fidelity.com/ Guideline: https://www.guideline.com/ Gusto: https://gusto.com/ Intuit: https://www.intuit.com/ Jeremy Caballero: https://www.linkedin.com/in/jeremycaballero/ John Zimmer: https://www.linkedin.com/in/johnzimmer11/ Josh Reeves: https://www.linkedin.com/in/joshuareeves/ Mike Nelson: https://www.linkedin.com/in/mnelsonio/ Leah Solivan: https://www.linkedin.com/in/leahsolivan/ Paychex: https://www.paychex.com/ Plaid: https://plaid.com/ Taskrabbit: https://www.taskrabbit.com/ Tomer London: https://www.linkedin.com/in/tomerlondon/ – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevinbusque/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser: “I don't believe in stealth mode” (02:51) Inspiration behind Guideline (07:56) Lessons from a year's research before Guideline (10:44) Identifying market pull for Guideline (14:28) What Kevin learnt before shipping their first product (19:10) How Guideline set their fees up (27:51) The surprising range of Guideline's early customers (31:48) Kevin's insights from the Gusto integration (39:48) Guideline's first year (44:44) Working with Plaid as Guideline's first customer (53:28) Guideline's auto-enrollment feature (57:53) Lucky 8: Kevin's unexpected pricing strategy (62:04) Franchise opportunities (64:49) Kevin's reflections on Taskrabbit (71:36) Will Guideline ever go multi-product? (72:37) Kevin's take on product-market fit (73:30) Guideline's compounding advantage (78:51) The challenges faced by introverted leaders

Bill Magnuson is the co-founder and CEO at Braze, along with Kevin Wang, who joined as employee #8 and serves as the CPO. The two MIT graduates have built Braze into a publicly listed customer engagement platform with a $4.4B market cap. In 2023, Braze surpassed $500M in CARR, and serves over 2,200 customers worldwide. Before Braze, Bill spent time at Bridgewater Associates. Kevin's academic background is in brain & cognitive sciences, and prior to joining Braze he worked at Accenture and Brewgene. – In today's episode, we discuss: The Braze founders' early insights into the mobile revolution How a TechCrunch Hackathon sparked Braze's creation The journey from 1,000 beta signups to 2,200+ paying customers Breaking traditional lean startup rules Navigating early fundraising challenges Finding product market fit by “fishing in every pond” Approaching competition strategically like a boxer Much more – Referenced: Accenture: https://www.accenture.com/ Appboy: https://www.braze.com/resources/articles/appboy-social-network-for-mobile-apps Bipul Sinha: https://www.linkedin.com/in/bipulsinha/ Braze: https://www.braze.com/ Bridgewater Associates: https://www.bridgewater.com/ Jon Hyman: https://www.linkedin.com/in/jon-hyman/ Mark Ghermezian: https://x.com/markgher MIT: https://www.mit.edu/ Rubrik: https://www.rubrik.com/ WeWork: https://www.wework.com/ – Where to find Bill: LinkedIn: https://www.linkedin.com/in/billmagnuson/ Twitter/X: https://x.com/billmag – Where to find Kevin: LinkedIn: https://www.linkedin.com/in/kevin-wang-96131916/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser: Finding “terminal value” product market fit (00:24) Introduction (02:34) Bill's insights into the mobile revolution (04:43) Lessons from Bridgewater Associates (09:12) First principles thinking in action at Braze (14:14) Meeting co-founders at an NYC Hackathon (24:35) Braze's scrappy scaling (33:37) Early product development (39:37) From 1,000 beta signups to 2,200+ paying customers (43:51) Braze's fundraising struggles (47:01) Breaking the rules of a lean startup (53:02) Riding the mobile wave to success (60:02) Building a global customer base (64:04) The never-ending quest for PMF (70:29) 3 things every founder needs to know (73:56) Navigating competition like a boxer (79:03) When scale helps or hurts (80:32) 1 thing they've learned from each other

Varun Anand is the co-founder and Head of Operations at Clay, a GTM development environment that combines data and AI to help over 5000 companies power everything from CRM enrichment to highly targeted outreach campaigns. Clay recently announced their Series B expansion, raising $40M at a $1.25B valuation. Before Clay, Varun was the Director of Operations at Newfront and the Head of Expansion at Candid. Varun also spent four years working on Hillary Clinton's presidential campaign. – In today's episode, we discuss: Clay's unconventional GTM machine 3 changes that unlocked Clay's upmarket motion Layering enterprise customers on top of PLG Scrappy sales tactics: WhatsApp groups, Reddit threads, and reverse demos Thinking long-term about brand and content Building an elite team of people who are “technical enough” Clay's contrarian take on compensation Much more – Referenced: Anthropic: https://www.anthropic.com/ Clay: https://www.clay.com/ Clay's Series B expansion: https://www.clay.com/blog/series-b-expansion Eric Nowoslawski: https://www.linkedin.com/in/outboundphd/ Figma: https://www.figma.com/ Jesse Ouellette: https://www.linkedin.com/in/jesseoue/ Kareem Amin: https://www.linkedin.com/in/kareemamin/ Nick Merrill: https://www.linkedin.com/in/nick-merrill-64562310/ Notion: https://www.notion.com/ Oyster: https://www.oysterhr.com/ Pave: https://www.pave.com/ Rippling: https://www.rippling.com/ Snowflake: https://www.snowflake.com/ Verkada: https://www.verkada.com/ Webflow: https://webflow.com/ Yash Tekriwal: https://www.linkedin.com/in/yashtekriwal/ – Where to find Varun: LinkedIn: https://www.linkedin.com/in/vaanand/ Twitter/X: https://x.com/vxanand – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Teaser + Introduction (03:13) Turning traditional GTM on its head (05:37) How Clay hustled for its first customers: Reddit threads & WhatsApp groups (08:53) Unpacking Clay's credit-based pricing (14:29) Building Clay's self-serve engine (16:54) Why Clay rejected the usage-based model (19:04) Clay's big bet on content (23:59) How "reverse demos" win enterprise deals (27:49) 3 changes that unlocked Clay's upmarket motion (36:59) How to build trust with enterprise buyers (38:49) Applying the land and expand model (40:40) Hiring people who are “technical enough” (46:33) Inside Clay's hands-on interviewing process (48:15) Why Clay invested in brand from day-one (50:21) Clay's contrarian take on compensation (58:35) The person who shaped Varun's career

Tristan Handy is the Founder and CEO at dbt Labs, a cloud-based data management platform that has raised over $400M to date, and was last valued at $4.2B in 2022. Dbt Labs has grown from just three companies using its free tool in 2016 to an ecosystem of 30,000+ enterprise users. Before founding dbt Labs, Tristan was the VP of Marketing at RJMetrics and the Director of Operations at Squarespace. – In today's episode, we discuss: Dbt's explosive growth The strategic pivot from consulting to a software company Unexpected strategies for building a tech category from scratch The critical moment: Why and when dbt Labs sought venture funding How to drive commercial adoption after open-sourcing Two things every founder CEO should do Much more – Referenced: Amazon Redshift: https://aws.amazon.com/redshift/ Bob Moore: https://www.linkedin.com/in/robertjmoore/ Crossbeam: https://www.crossbeam.com/ dbt Labs: https://www.getdbt.com/ Drew Banin: https://www.linkedin.com/in/drewbanin/ Jerry Colonna: https://www.reboot.io/team/jerry-colonna/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics SeatGeek: https://seatgeek.com/ Steve Ritter: https://www.linkedin.com/in/steve-ritter-69495210/ Squarespace: https://www.squarespace.com/ – Where to find Tristan: LinkedIn: https://www.linkedin.com/in/tristanhandy/ Twitter/X: https://x.com/jthandy – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:56) The critical oversight in data analysis (05:41) Becoming an “accidental founder” (07:04) Inside the unique decision to start a consultancy (08:17) The game-changing principle behind dbt Labs' rapid growth (11:20) Finding dbt Labs' first customers (15:52) Consulting's hidden scalability (17:25) How dbt Labs created a new category (21:03) The anti-demo strategy (23:59) Community hacking: the Slack group that changed everything (26:00) The open source philosophy (27:39) When growth went exponential (28:49) How consulting engagements shaped the roadmap (30:02) Fundraising only when “things started to break” (32:40) Consultancy superpowers: the hidden advantages (34:04) Pivoting from consulting to software (40:00) Key monetization strategies (48:56) Why “begrudging” CEOs can be successful (51:02) Advice for finding PMF: “It's not a playbook” (51:59) Lowering your standards is a hack (53:30) Navigating emotional overwhelm (54:25) Every CEO needs a coach

Yuhki Yamashita is the Chief Product Officer at Figma, leading the product and design teams. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps. Yuhki was also a product manager at Google (YouTube iOS app) and Microsoft (Hotmail). Additionally, he has taught introductory computer science at Harvard University. In today's episode, we discuss: How Figma approaches new products, prioritization, and storytelling Product culture at Uber, Microsoft, Google The difference between “good” and “extraordinary” PMs Tactical advice for storytelling The “un-learning” required in new jobs and industries – Referenced: Figjam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Figma Dev Mode: https://www.figma.com/dev-mode/ Figma Slides: https://www.figma.com/slides/ – Where to find Yuhki: LinkedIn: https://www.linkedin.com/in/yuhki/ Twitter/X: https://x.com/yuhkiyam – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – (00:00) Introduction (02:50) Figma's early days (09:11) Product culture across companies (13:42) Knowing when to change things (17:40) How business goals impact product expansion (21:00) Advice for going multi-product (24:30) The skills of a “0 to 1” PM (27:36) Identifying entrepreneurial talent (29:06) Why aren't there more designer founders? (35:22) How Figma launches new products (41:19) “0 to 1” versus “1 to 10” talent (46:01) The role of storytelling at Figma (49:22) How Figma prioritizes product (55:11) Advice for product storytelling (59:02) “Good” vs “extraordinary” product managers (61:21) Why product simplicity matters (63:52) The importance of taste in product and design (67:56) The biggest influence on Yuhki's product thinking

Steve Blank is an Adjunct Professor at Stanford University, where he co-created the "Hacking for Defense" curriculum for the Department of Defense. As a consultant to top defense and intelligence organizations, Steve brings cutting-edge strategies to the national security sector. Before entering academia, Steve built eight different startups. He helped launch the Lean Startup movement with his May 2013 Harvard Business Review cover story. Steve also authored the acclaimed business books "The Four Steps to the Epiphany" and "The Startup Owner's Manual.” This episode's is guest host is Meka Asonye, a Partner at First Round Capital. Before joining First Round as an investor, Meka led go-to-market teams at both Stripe and Mixpanel. – In today's episode we discuss: Commercial versus military market strategies Finding mission solution fit The hidden challenges most startups miss Building relationships in National Security The new generation of “defense founders” Much more – Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder/ Department of Defense: https://www.defense.gov/ Eric Ries: https://www.linkedin.com/in/eries/ Hacking for Defense: https://hackingfordefense-prod.stanford.edu/ How Saboteurs Threaten Innovation: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ How to find your customer in the Dept of Defense: https://steveblank.com/2024/09/17/the-directory-of-dod-program-executive-offices-and-officers-peos/ Mission Model Canvas: https://steveblank.com/2019/09/ Pete Newell: https://www.linkedin.com/in/petenewell/ Special Operations Command: https://www.socom.mil/ The Frozen Middle: https://steveblank.com/2024/07/30/why-large-organizations-struggle-with-disruption-and-what-to-do-about-it/ The Hacking for Defense Manual: https://stanfordh4d.substack.com/p/the-hacking-for-defense-manual-a The Hacking for Defense Course: https://www.h4d.us/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The Secret History of Silicon Valley: https://steveblank.com/secret-history/ – Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ – Where to find Meka: LinkedIn: https://www.linkedin.com/in/mekaasonye/ Twitter/X: https://x.com/bigmekastyle – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:27) Validating ideas for defense products (03:57) Guide to military sales and procurement (07:15) Rethinking GTM strategies (10:13) Building a network in national security (15:07) The dual-use debate (18:35) Behind the rising number of “defense founders” (22:30) “Mission solution fit” (24:35) Breaking new ground in military tech (26:09) Essential resources for any defense founder (28:59) What's missing from Silicon Valley

Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations. In today's episode, we discuss: How LiveRamp went from $30M to $200M ARR in 3 years Anneka's jack-of-all-trades career Why specialist hires can backfire When leaders should get in the weeds One area every PM can improve in Rubrik's approach to building product Much more – Referenced: Acxiom: https://www.acxiom.com/ Acxiom's acquisition of LiveRamp: https://tinyurl.com/2shm83de Amazon: https://www.amazon.com/ Auren Hoffman: https://www.linkedin.com/in/auren/ Dentsu: https://www.dentsu.com/ Dentsu's acquisition of Merkle: https://tinyurl.com/yvxe6fws James Arra: https://www.linkedin.com/in/james-arra-a43a06/ LiveRamp: https://liveramp.com/ Merkle: https://www.merkle.com/ Rubrik: https://www.rubrik.com/ Slack: https://www.slack.com/ Travis May: https://www.linkedin.com/in/stmay/ – Where to find Anneka Gupta: LinkedIn: https://www.linkedin.com/in/annekagupta/ Twitter/X: https://x.com/annekagupta – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:11) Inside LiveRamp's unique growth journey (12:18) Anneka's first PM role (14:20) Leading LiveRamp's marketing function (16:17) Why the best product doesn't win (21:06) Crafting products for different personas (24:53) Transitioning Acxiom's customers to LiveRamp (33:54) Why Acxiom chose to buy not build (36:40) Anneka's leap to GM and product leader (38:22) How 17 diverse roles shaped Anneka's CPO approach (40:54) The hidden career growth hack (43:15) Where domain experience is overrated (50:33) Mastering the art of altitude shifting (53:54) PMs should undergo the same training as sales reps (59:37) Strategies for selling to new personas (62:40) Lessons from Anneka's mistake at LiveRamp (67:56) Who had an outsized impact on Anneka

Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business School. - In today's episode, we discuss: Understanding the key drivers of startup success Applying the Growth Lever framework Several case studies Customer-centric growth tactics Adapting growth levers for different business models - Referenced: Airbnb: https://www.airbnb.com/ Bold Commerce: https://boldcommerce.com/ Calm: https://www.calm.com/ Caribou: https://www.usecaribou.com/ eBay: https://www.ebay.com/ FATMAP: https://fatmap.com/ Growth Levers and How to Find Them: https://www.systm.co/growth-levers-matt-lerner-book PayPal: https://www.paypal.com/ Peter Karpas: https://www.linkedin.com/in/peterkarpas/ Popsa: https://popsa.com/ Shopify: https://www.shopify.com/ Sonic Jobs: https://www.sonicjobs.com/ SYSTM: https://www.systm.co/ - Where to find Matt Lerner: LinkedIn: https://www.linkedin.com/in/matthewlerner/ Twitter/X: https://x.com/matthlerner - Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson - Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast - Timestamps: (00:00) Intro (03:11) The hidden truth about startup success (05:10) Popsa's journey: A case study in growth (07:31) Breaking down the growth lever framework (11:30) Understanding the customer's journey (14:14) The art of customer interviews (18:07) Unlocking growth through customer insights (24:23) The triple threat: Founder failure modes (27:32) The power of founder-led growth strategies (32:42) Unlocking growth bottlenecks (36:40) Timing and implementation of growth strategies (39:43) Founder red flags (41:32) Crafting effective growth experiments (43:14) Why customer mindset is the ultimate growth driver (46:19) The power law of business (48:59) Why startups don't need paid marketing (50:47) Growth levers for sales-driven companies (53:43) Matt's own application of growth principles (55:39) Growth levers in B2B sales (57:05) Finding customer "locksmith moments" (64:08) The mentor who shaped Matt's thinking

Bob Moore is the co-founder and CEO at Crossbeam, a “LinkedIn for data” platform that helps companies find overlapping opportunities with their partners. Crossbeam has raised US$117M to date and recently acquired Reveal in 2024. Bob previously cofounded RJMetrics (now part of Adobe Commerce Cloud) and Stitch Data (acquired by Talend). He is also the author of Ecosystem-Led Growth. In today's episode, we discuss: The unique way he evaluated and validated startup ideas Lessons learned from falling in and out of product-market fit How to recognize and act on market shifts that impact your business Specific tactics for distribution and building with conviction vs. consensus Creating scalable and durable startups Unlocking network effects in software Getting mergers right – Referenced: Adobe's acquisition of Magento: https://techcrunch.com/2018/05/21/adobe-to-acquire-magento-for-1-6-b/ Amazon Redshift: https://aws.amazon.com/redshift/ Chris Merrick: https://www.linkedin.com/in/merrickchristopher/ Crossbeam: https://www.crossbeam.com/ Crossbeam/Reveal merger: https://www.crossbeam.com/crossbeam-and-reveal-merger-announcement/ Ecosystem-Led Growth: https://www.robertjmoore.com/book Jake Stein: https://www.linkedin.com/in/jakestein/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Reveal: https://reveal.co/ Rick Nucci: https://www.linkedin.com/in/ricknucci/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics Simon Bouchez: https://www.linkedin.com/in/simonbouchez/ Stitch Data: https://www.stitchdata.com/ Talend's acquisition of Stitch Data: https://www.businessinsider.com/talend-acquires-stitch-2018-11 The 4 Levels of PMF: https://pmf.firstround.com/levels – Where to find Bob Moore: LinkedIn: https://www.linkedin.com/in/robertjmoore/ Twitter/X: https://x.com/robertjmoore – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Intro (02:44) Tactics for finding founder-market fit (06:17) Speaking to founders about startup ideas (11:16) Why founders loved Crossbeam (19:34) How RJMetrics found market fit then lost it (29:46) Lessons from RJMetrics' exit (38:06) The importance of intellectual honesty (39:33) Building with conviction versus consensus (42:41) Lessons from a three-time founder (50:26) Building and distributing Crossbeam (57:58) The “joint jam” sales tactic (60:35) Unlocking network effects in a software business (63:27) Why Crossbeam merged with its competitor (72:51) Who had an outsized impact on Bob

Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he's since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as a founder, and his perspectives on the critical junctures in company building. – In today's episode, we also discuss: Eoghan's reflections since leaving Intercom The value of intuition and first-principles thinking The changes Eoghan made upon returning to Intercom How Eoghan increased Intercom's productivity by 41% Tactical advice on hiring top talent Why you can't make small improvements in big categories Crafting a culture of ruthless honesty and transparency Why software branding is in crisis – Referenced: 37signals: https://37signals.com Basecamp: https://basecamp.com Brian Halligan (HubSpot): https://www.linkedin.com/in/brianhalligan David Heinemeier Hansson (37signals, Basecamp): https://www.linkedin.com/in/david-heinemeier-hansson-374b18221 Intercom: https://www.intercom.com Jason Fried (37signals, Basecamp): https://www.linkedin.com/in/jason-fried Salesforce: https://www.salesforce.com Marc Benioff (Salesforce): https://www.linkedin.com/in/marcbenioff Zendesk: https://www.zendesk.com – Where to find Eoghan: LinkedIn: https://www.linkedin.com/in/eoghanmccabe/ Twitter/X: https://x.com/eoghan – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps 0:00:00 - Founder intuition vs. standard practice 0:25:00 - Silicon Valley knowledge loops 0:28:13 - Building an executive team 0:36:38 - Eoghan's return to Intercom 0:42:02 - Transparent and honest leadership 0:46:42 - Changing Intercom's strategy 0:54:22 - AI and category disruption 1:03:17 - How Intercom thinks about brand 1:10:40 - Eoghan's inspirations

Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox. – In today's episode, we discuss: Marketing lessons from OpenAI, Stripe, and Retool The 3 pillars of Stripe's approach to brand How to manage resource allocation as a marketer Adapting marketing strategy to different business models Advice for early marketing hires – Referenced: Coca-Cola AI-generated wish card campaign: https://theprint.in/ani-press-releases/coca-cola-ignites-diwali-celebrations-with-unique-personalized-ai-generated-wish-cards/1840093/ Cristina Cordova: https://www.linkedin.com/in/cristinajcordova/ Gong: https://www.gong.io/ Greg Brockman: https://www.linkedin.com/in/thegdb/ Kenzo Fong: https://www.linkedin.com/in/kenzofong/ Retool: https://retool.com/ Stripe's “Capture the Flag” campaign: https://techcrunch.com/2012/08/22/stripes-capture-the-flag-2-0-a-hands-on-contest-for-app-developers-to-test-their-security-know-how/ Stripe Press: https://press.stripe.com/ Stripe Sigma: https://stripe.com/us/sigma Tanya Khakbaz: https://www.linkedin.com/in/tanya-khakbaz-a725732/ – Where to find Krithika Muthukumar: LinkedIn: https://www.linkedin.com/in/krithix/ Twitter/X: https://x.com/krithix – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Timestamps: (00:00) Intro (02:43) Getting involved in Stripe (05:37) Evaluating success in product marketing (06:35) The 3 pillars of Stripe's approach to brand (12:10) Managing resource allocation as Stripe grew (17:22) How Stripe scaled taste (21:30) Were Stripe reviews micromanaging? (24:16) Marketing under founders with strong marketing skills (26:44) Advice for early marketing hires (31:52) Marketing at Retool vs Stripe (33:59) Marketing to mid-market vs SMB vs enterprise (37:02) Marketing programs that had an outsized impact (39:59) Marketing horizontal vs vertical products (43:20) Lessons from OpenAI (52:22) Inside OpenAI's recent website relaunch (55:57) How OpenAI's marketers use OpenAI tooling (59:53) When to start hiring marketers (61:34) How to screen early marketing hires (66:39) The biggest influences on Krithika's career (67:52) Outro

Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs. – In today's episode, we discuss: Sam's advice for future engineers What's next for AI How to develop technical taste The importance of asking “what if” questions Lessons on market timing Scaling a software company in 2024 – Referenced: Amazon: https://amazon.com Box: https://www.box.com/ Elon Musk: https://twitter.com/elonmusk Google Docs: https://docs.google.com Itzhak Perlman: https://itzhakperlman.com/ Microsoft: https://www.microsoft.com Netflix: https://www.netflix.com Tesla: https://www.tesla.com/ The Innovator's Dilemma: https://www.amazon.com.au/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 TurboTax: https://turbotax.intuit.com/ Uber: https://www.uber.com/ Walmart: https://www.walmart.com/ Workday: https://www.workday.com/ Writely: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/ – Where to find Sam Schillace: LinkedIn: https://www.linkedin.com/in/schillace/ Newsletter: https://sundaylettersfromsam.substack.com/ Twitter/X: https://twitter.com/sschillace – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:54) Lessons on market timing (07:30) Developing technical taste (09:51) Asking “what if” questions (14:03) Building Google Docs (19:32) The decline of Google apps (20:57) The Innovator's Dilemma facing Microsoft (22:53) The differences between Google and Microsoft (24:42) How to build a winning product (27:46) Becoming an optimist (29:12) Why engineering teams aren't smaller (32:00) Sam's prediction about AI (34:11) Capturing the value of AI (37:43) How you should think about AI (45:33) Advice for future engineers (48:18) What makes a great engineer (49:45) One thing the best engineers do (51:37) Microsoft's new leverage (56:01) Scaling software in 2024 (59:50) The future of AI across several sectors (64:28) What Sam and a violinist have in common

Casey Winters is a legendary advisor on scaling, product and growth. He's worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub. – In today's episode, we discuss: What every marketplace founder should think about Why marketplaces are different Finding product market fit Key ingredients to scaling a marketplace Strategies for acquiring demand and supply – Referenced: Airbnb: https://airbnb.com/ Bill Gurley: https://www.linkedin.com/in/billgurley/ Blue Apron: https://www.blueapron.com/ Booking.com: https://www.booking.com/ DoorDash: https://www.doordash.com/ eBay: https://ebay.com/ Eventbrite: https://www.eventbrite.com/ Expedia: https://www.expedia.com/ Faire: https://www.faire.com/ Fermat Commerce: https://www.fermatcommerce.com/ Grubhub: https://www.grubhub.com/ Lyft: https://www.lyft.com/ Pinterest: https://www.pinterest.com/ Postmates: https://postmates.com/ Shopify: https://www.shopify.com/ Simon Rothman: https://www.linkedin.com/in/simonrothman/ Square: https://squareup.com/ Tony Xu: https://www.linkedin.com/in/xutony/ Turo: https://turo.com/ Uber: https://www.uber.com/ Zillow: https://www.zillow.com/ – Where to find Casey Winters LinkedIn: https://www.linkedin.com/in/caseywinters/ Twitter/X: https://twitter.com/onecaseman Website: https://caseyaccidental.com/ – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:30) Ingredients for a successful marketplace (05:34) Creating scalable growth loops (08:42) Emerging marketplaces in 2024 (10:56) 2 ways to acquire supply and demand (15:39) What's unique about building a marketplace (18:27) When to focus on the demand side (23:10) Who to hire (26:22) Finding sticky customers (26:27) What Grubhub should've done (30:19) Uber versus Lyft (34:23) One thing all marketplace founders should know (34:45) Finding product market fit (40:45) Single versus multi-category marketplaces (43:02) When to expand (44:22) The best low-frequency marketplace (46:00) The product is supply, not software (50:48) No value in car-sharing (56:11) Improving supply and demand over time (61:04) The “setup, aha, and habit” framework (66:27) Avoid these marketplace mistakes (71:16) 2 people who influenced Casey's thinking

Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas. — In today's episode, we discuss: The key ingredients of Sentry's success Sentry's developer-centric approach Lessons on pricing, packaging, and product from VMware Being an external CEO at a startup Forging successful relationships with founders — Referenced: Building for the Fortune 500,000: https://blog.sentry.io/building-for-the-fortune-500-000/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Chris Jennings: https://www.linkedin.com/in/chriskjennings/ David Cramer: https://www.linkedin.com/in/dmcramer/ FRC's product market fit framework: https://pmf.firstround.com/ Martin Casado: https://www.linkedin.com/in/martincasado/ Pat Gelsinger: https://www.linkedin.com/in/patgelsinger/ Raghu Raghuram: https://www.linkedin.com/in/raghuraghuram/ Riverbed: https://www.riverbed.com/ Sentry: https://sentry.io/ Todd Bazakas: https://www.linkedin.com/in/todd-bazakas-b5a2533/ Veritas: https://www.veritas.com/ VMware: https://www.vmware.com/ — Where to find Milin Desai: LinkedIn: https://www.linkedin.com/in/milin-desai-464757/ Twitter/X: https://twitter.com/virtualmilin — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) Joining Sentry as an external CEO (06:27) The CEO/founder relationship (09:37) Lessons from VMware (13:04) What PMs did differently at VMware (18:04) Becoming the need, not the want (20:53) Scaling Sentry (23:07) Building for the “Fortune 500,000” (27:02) Open versus closed source product (30:43) The key ingredients to Sentry's success (36:21) How Milin updated his playbook at Sentry (38:49) Focus on packaging, not pricing (40:29) “Build for the many, not the few” (41:53) Sentry's B2D model (45:10) The second product mindset (51:03) Contrarian take on building for enterprise (52:50) Several people who influenced Milin

Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple. — In today's episode, we discuss: Lessons on culture, org-design, and product from Rippling Characteristics of great CEOs How to a better executive leader Leading with kindness and impatience How to fight entropy — Referenced: Andy Roddick: https://www.atptour.com/en/players/andy-roddick/r485/overview Apple: https://www.apple.com Bain & Company: https://www.bain.com/ Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive) Conscious Business: https://www.amazon.com.au/Conscious-Business-Build-Value-Through/dp/1622032020 Google: https://www.google.com Inkling: https://www.inkling.com/ McCaw Cellular: https://en.wikipedia.org/wiki/McCaw_Cellular_Communications McKinsey: https://www.mckinsey.com/ Microsoft: https://www.microsoft.com Oracle: https://www.oracle.com Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Peter Currie: https://en.wikipedia.org/wiki/Peter_Currie_(businessman) Rippling: https://www.rippling.com The Effective Executive: https://www.amazon.com.au/Effective-Executive-Peter-Ferdinand-Drucker/dp/0060833459 — Where to find Matt MacInnis: LinkedIn: https://www.linkedin.com/in/macinnis/ Twitter/X: https://twitter.com/stanine — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14) Great CEOs don't worry about their weaknesses (06:31) The third-time founder mindset (08:09) Why every great CEO is impatient (11:54) How executives fight entropy (19:11) Experience ≠ wisdom (21:26) Managing workplace politics (24:02) Why all businesses should dogfood (26:20) Overseeing employee expenses (27:43) The best CEOs don't need coaching (29:55) The hidden cost of advice (40:40) Why execs are “tortured but happy” (44:16) Clear versus first principles thinking (51:09) Finding first principles thinkers (53:13) Why people overcomplicate culture (55:53) Don't make this mistake when interviewing (59:26) The importance of anti-patterns (61:27) Important business values (63:28) How Matt thinks about output (66:33) Rippling's key leadership principle (71:02) Why kindness matters (72:03) Freeing yourself from self-doubt

Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent. —  In today's episode, we discuss: Lessons from Amazon, Microsoft, and Square “Minimum Remarkable Products” versus Minimum Viable Products Navigating different work cultures in big tech Insider reactions to the disruptive launch of AWS “Pioneer” versus “fast-follower” companies —  Referenced: Amazon: https://www.amazon.com Amazon Web Services: https://aws.amazon.com Bill Gates: https://www.linkedin.com/in/williamhgates Block, Inc: https://block.xyz Cash App: https://cash.app Fast Company - Back To Square One: https://www.fastcompany.com/3033412/back-to-square-one Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1 Jack Dorsey: https://twitter.com/Jack James Hamilton: https://www.linkedin.com/in/jameshamilton4 Jeff Bezos: https://twitter.com/jeffbezos Microsoft: https://www.microsoft.com Oracle Corporation: https://www.oracle.com Sarah Friar: https://www.linkedin.com/in/sarah-friar Square: https://squareup.com Tom Szkutak: https://www.linkedin.com/in/tom-szkutak-4b59817 WSJ - Mobile-Payments Startup Square Discusses Possible Sale: https://www.wsj.com/articles/SB10001424052702303825604579513882989476424 —  Where to find Alyssa Henry: LinkedIn: https://linkedin.com/in/alyssa-henry-0905692 Twitter/X: https://twitter.com/alyssahhenry —  Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:20) Lessons from Microsoft and Amazon (08:29) Noticeable consistencies in the human condition (10:50) Differences in culture at Amazon, Microsoft and Square (13:27) Why “customers come first,” even above employees and community (14:01) Why fast-followers can be less customer-focused (15:50) The challenge of commercializing research projects (18:58) Joining Square and “building a picture” of the org (24:55) Knowing what to replicate from past companies (27:45) Questioning norms in new companies (28:41) The importance of effective communication systems (31:31) How to operationalize company values (33:38) Why shared beliefs are crucial for good company culture (37:05) Building Minimal Remarkable Products at Square (38:13) How to scale an aesthetic (42:46) Org design lessons from Square (50:06) How to align different teams behind business priorities (52:57) Lessons learned from fierce competition (57:39) The “fast follower” vs “pioneer” playbook (61:05) The original thinking behind AWS (66:08) The unlikely origin of Amazon CloudFront and other products (73:47) How Jeff Bezos influenced Alyssa

Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company's assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple. — In today's episode, we discuss: Why founders should build platforms, not apps The importance of “delighting” customers How Daffy is disrupting donor-advised-funds Lessons on strategy from LinkedIn How to think about leadership transitions — Referenced: Andy Rachleff: https://www.linkedin.com/in/rachleff/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Daffy: https://www.daffy.org/ Daffy's 2023 Year in Review: https://www.daffy.org/resources/year-in-review-2023 eBay: https://www.ebay.com/ Jeff Weiner: https://www.linkedin.com/in/jeffweiner08/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Robinhood: https://robinhood.com/ Ryan Roslansky: https://www.linkedin.com/in/ryanroslansky/ The Innovator's Dilemma: https://www.amazon.com/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 Tim Cook: https://www.apple.com/leadership/tim-cook/ Wealthfront: https://www.wealthfront.com/ — Where to find Adam Nash: LinkedIn: https://www.linkedin.com/in/adamnash/ Twitter/X: https://twitter.com/adamnash — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:08) Why the last 10 years have been less disruptive (06:15) Why we think about luck wrong (08:39) How eBay survived the dot com bubble (14:37) The value of building platforms, not apps (22:18) What made LinkedIn successful (27:31) Good company strategy = good product strategy (30:58) Setting LinkedIn's strategy in 2009 (36:41) Why KaChing didn't work (40:56) Pivoting to Wealthfront (43:23) Universal lesson on customer acquisition (45:11) Treating growth like a product problem (49:01) Advice on successful leadership transitions (54:20) How to delegate moral authority (60:24) The problem with metrics and customer requests (66:41) Apple's approach to “delighting” customers (69:16) The 70/20/10 rule you've never heard about (70:29) How Daffy ships “delight features”

Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage. — In today's episode, we discuss: Why Eilon was so bullish on recording sales calls How Gong knew they had product market fit The importance of design partners Expanding into multi-product offerings Lessons from riding the AI wave since 2015 The future of AI in B2B sales efficiency — Referenced: Act-On Software: https://act-on.com/ Amit Bendov: https://www.linkedin.com/in/amitbendov/ BlueJeans: https://www.bluejeans.com/ Crossing the Chasm: https://www.amazon.com/Crossing-Chasm-3rd-Geoffrey-Moore/dp/0062292986 Gong: https://www.gong.io/ Mistral: https://mistral.ai/ OpenAI: https://openai.com/ Salesforce: https://salesforce.com/ Webcollage: https://www.crunchbase.com/organization/webcollage Webex: https://www.webex.com/ Zoom: https://zoom.us/ — Where to find Eilon Reshef: LinkedIn: https://www.linkedin.com/in/eilonreshef/ — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:32) Eilon's unwavering conviction in Gong (09:34) Initial reactions to Gong's demo (13:48) Keeping the beta lean (15:33) Gong's monetization strategy (16:38) Early signs of product market fit (18:14) The importance of design partners to Gong's growth (21:52) Why VCs were afraid to invest (23:43) Reaching 100 customers (26:10) Eilon's unique product roadmap framework (28:22) Going from $2M to $9M ARR in one year (29:02) The journey to multi-product (30:52) How Gong measures success (34:07) Lessons from building AI products for sales (37:45) Predicting the future of B2B sales (38:48) The concept of “raving fans” (39:31) Why it's “easier” for second-time founders (42:00) Eilon's favorite books (42:45) Gong in 2024

Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis' first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft. — In today's episode, we discuss: Lessons on culture and product from Amazon, Apple, and Microsoft Building and scaling DevTools Finding product market fit and monetizing it Why AI is complicating product market fit How Dennis prioritizes mental health as a founder The common mistake people make when hiring — Referenced: Apple's acquisition of Buddybuild: https://www.cnbc.com/2018/01/02/apple-agrees-to-buy-buddybuild.html AWS: https://aws.amazon.com Bitbucket: https://bitbucket.org Confluence: https://www.atlassian.com/software/confluence GitHub: https://github.com GitLab: https://gitlab.com Looker: https://looker.com Microsoft Azure: https://azure.microsoft.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Stripe: https://stripe.com Twilio: https://twilio.com Unblocked: https://getunblocked.com/ — Where to find Dennis Pilarinos: LinkedIn: https://www.linkedin.com/in/dennispi Twitter/X: https://twitter.com/dennispilarinos — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:18) Why building for developers is different (07:28) Buddybuild's origin story (10:40) Early signs of product market fit (12:22) Managing mental health as a second-time founder (21:09) Building and scaling Unblocked (29:52) Dennis' cautious take on AI (34:20) Being customer-obsessed (35:25) Unblocked's decision-making process (38:31) Don't over-index on competency when hiring (43:36) Why great product is everything (45:41) Monetizing product market fit (48:21) The power of positioning (51:48) Why Dennis doesn't do demos (54:45) How to deal with customer feedback (57:29) Stewart Butterfield's impact on Dennis

May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer's own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant. —  In today's episode, we discuss: Advice for AI founders in 2024 Why it's difficult to scale AI products for enterprise The secret to finding champions Signs of a healthy co-founder relationship The future of agentic AI —  Referenced: Accenture: https://www.accenture.com ChatGPT: https://chat.openai.com/ Dropbox: https://www.dropbox.com Goldman Sachs: https://www.goldmansachs.com/ Grammarly: https://www.grammarly.com Jill Kramer: https://www.linkedin.com/in/jill-kramer-64230840/ L'Oreal: https://www.loreal.com/ Northwestern Mutual: https://www.northwesternmutual.com/ Palmyra: https://writer.com/blog/palmyra/ Retrieved Augmented Generation: https://blogs.nvidia.com/blog/what-is-retrieval-augmented-generation/ United Healthcare: https://www.uhc.com/ Vanguard: https://global.vanguard.com/ Waseem Alshikh: https://www.linkedin.com/in/waseemalshikh/ Writer: https://writer.com/ —  Where to find May Habib: LinkedIn: https://www.linkedin.com/in/may-habib/ Twitter/X: https://twitter.com/may_habib —  Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:34) Writer's origin story (06:30) Building a full-stack generative AI platform for enterprise (11:56) The #1 challenge building Writer (15:41) Writer's approach to finding champion customers (20:29) How Writer is winning the enterprise space (27:11) Signs Writer found product-market-fit (29:26) Scaling LLMs for specific use cases (31:53) Writer's goals for 2024 (33:57) Advice for 0 to 1 founders (35:53) Creating a culture of “connect, challenge, and own”

Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy. — In today's episode, we discuss: How AI is reshaping the software landscape Bridging the gap between ideas and software Why YC almost rejected Replit four times Replit's fundraising difficulties, and how Paul Graham helped The secret lever Replit pulled to scale ahead of its competition Replit's impressive distribution engine — Referenced: 7 Powers: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319/ Codecademy: https://www.codecademy.com/ Hacker News: https://news.ycombinator.com/ I Am a Strange Loop: https://www.amazon.com/Am-Strange-Loop-Douglas-Hofstadter/dp/0465030793 Mythical Man-Month: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959 On the Naturalness of Software: https://people.inf.ethz.ch/suz/publications/natural.pdf OpenAI: https://openai.com/ Paul Graham: https://twitter.com/paulg Python: https://www.python.org/ Read Write Own: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593731387/ Replit: https://replit.com/ Roy Bahat: https://www.linkedin.com/in/roybahat/ Sam Altman: https://twitter.com/sama The Innovator's Dilemma: https://www.amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780/ The Little Schemer: https://www.amazon.com/Little-Schemer-Daniel-P-Friedman/dp/0262560992/ Y Combinator: https://www.ycombinator.com/ — Where to find Amjad Masad: LinkedIn: https://www.linkedin.com/in/amjadmasad Twitter/X: https://twitter.com/amasad — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:31) Replit's origin story (08:24) Starting Facebook's JavaScript infrastructure team (10:36) Amjad's unique path to entrepreneurship (16:04) How Replit got its early users (17:00) Replit's fundraising difficulties (17:54) Why YC almost rejected Replit four times (20:23) Building Replit's distribution engine (22:08) Drivers of Replit's growth (27:41) What Silicon Valley gets wrong (30:09) Replit's monetization strategy (32:29) Integrating AI into the platform (36:18) The impact of AI on software engineering (39:40) Defining the new “software creator” role (41:43) How to keep up with developments in AI (46:24) Replit's goals for 2024 (48:11) Advice for founders: defy conventional wisdom (51:12) Amjad's 4 favorite books

Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor. — In today's episode, we discuss: Key product strategies used by Square and Gusto The pros and cons of building for SMBs How to build horizontal after creating a wedge The catch with building vertical SaaS How product teams can move faster Developing product sense and intuition — Referenced: Alyssa Henry: https://www.linkedin.com/in/alyssa-henry-0905692/ Copilot: https://copilot.microsoft.com/ Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/ Gusto: https://gusto.com/ High Output Management: https://amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 Marty Cagan: https://www.linkedin.com/in/cagan/ Opendoor: https://www.opendoor.com/ Silicon Valley Product Group: https://www.svpg.com/ Square: https://squareup.com/ The Three Horizons Model: https://www.mckinsey.com/enduring-ideas-the-three-horizons-of-growth Toast: https://pos.toasttab.com/ — Where to find Michael Cieri: LinkedIn: https://www.linkedin.com/in/michaelcieri/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:41) Why SMBs require unique software solutions (05:58) The level of specificity required when building for SMBs (08:47) Finding Square's form-fitting solution (11:48) Building vertical versus horizontal SaaS (14:34) Inside Square and Gusto's decision making framework (16:15) How to build horizontally from a wedge product (23:00) Using the Three Horizons Model (25:29) How to craft a compelling vision for products (28:51) How to assess Horizon 3 bets (32:08) How to give employees the freedom to try things (34:24) Creating a risk-taking culture (37:27) Essential advice for new PMs (40:27) Common thread with bad product pitches (42:29) Applying the Horizon framework at Gusto (44:46) Developing good product sense (47:43) 5 signs of great product sense (49:03) Why product sense is like athletic ability (51:43) How to ship faster without increasing headcount (56:10) People who had an outsized impact on Michael

Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages. — In this episode, we discuss: Common customer success mistakes Creating a world-class customer success org Tactics for hiring exceptional talent How to structure compensation packages Where customer success fits into the wider org Key early-stage customer success metrics and rituals Successful strategies from Box, Medallia, and LinkedIn — Referenced: Aaron Levie: https://www.linkedin.com/in/boxaaron/ Box: https://www.box.com/ David Love: https://www.linkedin.com/in/david-s-love/ Gainsight: https://www.gainsight.com/ Jon Herstein: https://www.linkedin.com/in/jonherstein/ Jonathan Lister: https://www.linkedin.com/in/jonathanlister/ Ken Fine: https://www.linkedin.com/in/kmfine/ Medallia: https://www.medallia.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Opower: https://www.oracle.com/utilities/opower-energy-efficiency/ — Where to find Stephanie Berner: LinkedIn: https://www.linkedin.com/in/stephanieberner/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:21) Formalizing customer success at a startup (05:01) Hiring ICs before CSMs (06:22) Tactics for hiring standout talent (11:39) 3 questions to ask candidates (15:38) Fail-case patterns among customer success hires (17:49) Considering candidates with non-traditional backgrounds (21:21) Indexing toward a bias for action (24:17) What v1 of customer success looks like (26:03) Key early-stage customer success metrics (28:21) Whether customer success or sales should own renewals (30:40) Where customer success fits into the org (32:14) Why customer success doesn't report to an executive (33:48) Distinguishing a product problem from a customer success one (35:18) Simple way to deal with customer churn (39:21) Tactics to get customers to give honest feedback (40:58) What happens when customer success and product teams collaborate (44:14) Rituals for zero-to-one customer success (48:23) How to structure an early customer success team (52:01) Structuring compensation packages (54:35) Aligning customer success with the business model (60:14) The role of customer success in B2B software (62:17) Common customer success mistakes (67:44) People who had an outsized impact on Stephanie

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he's more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose'. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership. — In today's episode, we discuss: Lopp's “utopia” — where engineers have time to create and invent What makes an excellent engineering leader The flexibility required for managerial roles in different contexts Navigating internal dynamics between design, engineering, and product How to build and grow effective engineering orgs The importance of understanding individual motivations Key lessons from over 30 years in the industry — Referenced: AOL: https://aol.com Apple: https://www.apple.com Borland: https://en.wikipedia.org/wiki/Borland Netscape: https://en.wikipedia.org/wiki/Netscape Palantir: https://www.palantir.com/ Phillipe Kahn: https://www.linkedin.com/in/philippekahn/ Pinterest: https://www.pinterest.com/ Slack: https://slack.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Tom Paquin: https://www.linkedin.com/in/tom-paquin-240b4b2/ — Where to find Michael Lopp: Blog: https://randsinrepose.com/ LinkedIn: https://www.linkedin.com/in/michaellopp/ Twitter/X: https://twitter.com/rands — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Beginning career at Borland (05:41) The difficulty with shipping software at scale (07:52) Why it's harder to ship today than ever before (09:42) What makes a startup operationally sound (11:23) Why engineers should have concrete time to invent (19:42) How PMs can improve engineering culture (21:35) An engineer's perspective on good product management (23:36) The role of product compared to design and engineering (26:38) How micromanagement kills creativity (29:35) Fostering a debate culture in an org (31:26) Declarative versus prescriptive leadership (36:09) 3 ideas on leadership from Lopp's upcoming book (38:29) Understanding employee motivation (42:28) Advice on discovering what motivates people (46:06) Why teams should reorg every 6 months (48:32) One thing all successful leaders do (52:22) Why sound judgment is crucial for decision-making (53:45) Crystallized lessons from working at software giants (56:19) Why Lopp is afraid of becoming irrelevant (57:58) The number one leadership lesson from Lopp's career (59:32) What Lopp has changed his mind on over time (61:12) People who had an outsized impact on Lopp

Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012. — In today's episode, we discuss: Creating a community of power users How to stay ruthlessly focused and make decisions faster Clay's principles for finding product-market-fit Why a company is the reflection of its founder's personality Aligning your own psychology with the business The mindset change from a first to second-time founder — Referenced: Airtable: https://www.airtable.com/ Clay: https://www.clay.com/ Figma: https://www.figma.com/ Internal Family Systems: https://ifs-institute.com/ NetSuite: https://www.netsuite.com/ Notion: https://www.notion.com Sailthru: https://www.sailthru.com/ — Where to find Kareem Amin: LinkedIn: https://www.linkedin.com/in/kareemamin/ Twitter/X: https://twitter.com/kareemamin — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:36) Clay's origin story (05:54) Building for a specific customer (10:42) Knowing when to build for a broader customer-base (12:46) The life spiral framework (15:52) How founders can make better decisions (18:57) Kareem's principles for product-market-fit (25:36) Clay's customer journey (30:04) Interesting tactic to find power users (34:00) How to know you have product-market-fit (37:11) The impact of founder psychology on the business (39:41) Mastering commitment to sprints (40:47) How Kareem's own personality affected his company (43:31) Actionable advice to understand founder psychology (46:25) Why focus is misunderstood (47:09) The mindset shift from a first to second-time founder (50:28) What's next for Clay (52:14) The best piece of advice Kareem has actioned

Kyle Parrish, Figma's first sales hire, built the company's zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York. — In today's episode, we discuss: The right time to build a sales function Hiring and scaling a successful sales org Building a unique sales culture Career advice for ambitious salespeople Figma's early sales motion How to integrate your first sales hire Navigating the founder/Head of Sales relationship — Referenced: Amanda Kleha: https://www.linkedin.com/in/amanda-kleha-015599/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Claire Butler: https://www.linkedin.com/in/clairetbutler/ Dropbox: https://www.dropbox.com/ Dylan Field: https://www.linkedin.com/in/dylanfield/ FigJam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Kevin Egan: https://www.linkedin.com/in/kevin-egan-59719/ Oliver Jay: https://www.linkedin.com/in/oliverjayleadership/ Praveer Melwani: https://www.linkedin.com/in/praveer-melwani/ Salesforce: https://www.salesforce.com/ Slack: https://www.slack.com/ — Where to find Kyle Parrish: LinkedIn: https://www.linkedin.com/in/kparrish8/ Twitter/X: https://twitter.com/KyleHParrish — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:10) What founders need to figure out before hiring salespeople (03:48) Who to hire as your first salesperson (05:34) Transitioning away from founder-led sales (07:07) Tactics for hiring great salespeople (12:50) The ideal experience sales candidates should have (13:49) Common traits of successful salespeople (18:45) What it was like being Figma's first sales hire (19:59) Interesting tactic to integrate the first sales hire (21:16) How Figma executed its early sales motion (32:27) Why Figma changed its customer narrative (34:03) Building outbound sales strategy at Figma (36:17) Segmented pricing and no discounts (41:55) Kyle's transition from Dropbox to Figma (47:25) Creating a world-class sales culture (51:46) How Figma does sales differently (54:02) Building the initial sales team around a passion for the product (57:12) Figma's unique hiring process for salespeople (60:40) Advice for founders hiring their first salesperson (63:18) The secret to Dylan Field's success (64:33) How to scale yourself as an early hire (66:25) Oliver Jay's impact on Kyle

Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company's global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana's total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company's expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses. — In today's episode, we discuss: Common mistakes PLG companies make The “PLG trap” and how to avoid it The playbook for transitioning into enterprise How and when to build an enterprise sales team How PLG companies can break $10 billion market cap Why it's difficult to emulate Atlassian, Slack or Salesforce — Referenced: Airtable: https://www.airtable.com/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Bitbucket: https://bitbucket.org/product/ Confluent: https://www.confluent.io/ Daniel Shapero: https://www.linkedin.com/in/dshapero/ Datadog: https://www.datadoghq.com/ Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ Dropbox: https://www.dropbox.com/ Dustin Moskovitz: https://www.linkedin.com/in/dmoskov/ Jay Simons: https://www.linkedin.com/in/jaysimons/ Jira: https://www.atlassian.com/software/jira Justin Rosenstein: https://www.linkedin.com/in/justinrosenstein/ Kim Scott: https://www.linkedin.com/in/kimm4/ Salesforce: https://www.salesforce.com/ Slack: https://slack.com/ The PLG Trap: https://www.linkedin.com/pulse/plg-trap-oliver-jay/ The seed, land, and expand framework: https://www.endgame.io/blog/seed-land-expand-framework Zendesk: https://www.zendesk.com/ — Where to find Oliver Jay: LinkedIn: https://www.linkedin.com/in/oliverjayleadership/ Website: https://www.oliverjayleadership.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:23) Differences between PLG and enterprise companies (05:56) Avoiding the “PLG trap” (07:39) Transitioning to enterprise feels like building two companies (10:57) Thinking about user value versus company value (13:58) The relationship between OKRs and executive champions (14:59) Dropbox had almost no company value (15:33) The strategy PLG companies should avoid (18:30) Why Dropbox is worth $10b, not $50b (19:41) The story of Asana's expansion (21:16) Asana's unique customer success team (23:27) How product strategy relates to finding champions (25:03) How Asana structured its GTM org (27:11) What Oliver would have done differently with Asana's GTM (29:45) Getting executive-level buy-in (31:49) Asana's concept of “selling clarity” (33:18) An inside look at Asana's transition into enterprise (37:59) The champion tree framework (40:43) Structuring Asana's early enterprise sales team (44:27) The impact of company size on GTM (47:20) Common sales mistake (48:29) The seed, land, and expand framework (51:43) Oliver's advice to founders (54:13) Why building horizontally may be a mistake (55:32) Common challenges faced by PLG companies (58:30) How PLG companies can break the $10b market cap (60:17) Why emulating Atlassian's playbook is difficult (63:21) People who had an outsized impact on Oliver

Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve's career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner's Manual. — In today's episode, we discuss: Why there aren't more successful startups How to improve entrepreneurship in the USA Misunderstood aspects of the Lean Startup methodology Common traits shared by outlier founders Why successful entrepreneurs are irrational (and need to be) How founders can transition to CEOs Why some second-time founders fail Building in existing versus new markets The Four Steps to the Epiphany in 2023 — Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder Allen Michels: https://en.wikipedia.org/wiki/Allen_Michels Ben Wegbreit, Co-founder of E.piphany: https://www.linkedin.com/in/ben-wegbreit-22192/ Convergent Technologies: https://en.wikipedia.org/wiki/Convergent_Technologies Eric Ries: https://www.linkedin.com/in/eries/ Gordon Bell: https://www.linkedin.com/in/gordon-bell-3035b43/ JB Straubel: https://www.linkedin.com/in/jb-straubel-b694981/ Kathy Eisenhardt: https://www.linkedin.com/in/kathleen-eisenhardt-5642247/ Roger Siboni, former CEO of E.piphany: https://theorg.com/org/coupa-software/org-chart/roger-siboni Satya Nadella: https://www.linkedin.com/in/satyanadella/ Steve Ballmer: https://www.linkedin.com/in/steve-ballmer-7087a8157/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The semiconductor industry - explained: https://steveblank.com/2022/01/25/the-semiconductor-ecosystem/ The three pillars of world class corporate innovation: https://steveblank.com/2022/11/11/the-three-pillars-of-world-class-corporate-innovation/ Tina Seelig: https://www.linkedin.com/in/tinaseelig/ Tom Mueller, Ex-SpaceX Propulsion CTO: https://www.linkedin.com/in/thomas-mueller-2094513b/ Why corporate entrepreneurs are extraordinary: https://steveblank.com/2015/08/25/why-corporate-entrepreneurs-are-extraordinary-the-rebel-alliance/ Why entrepreneurs start companies rather than join them: https://steveblank.com/2018/04/11/why-entrepreneurs-start-companies-rather-than-join-them/ — Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Why there aren't more successful startups (06:07) Outlier founders have similar childhoods (10:34) How to be a successful founder CEO (12:00) Why entrepreneurship should be taught in schools (16:39) The importance of curiosity (19:57) The role of instincts in entrepreneurship (22:31) Having profound beliefs in a vision (24:17) Building in existing versus new markets (29:09) What second-time founders can get wrong (33:49) Why founders need to be irrational (39:28) Common traits shared by outlier founders (45:05) Evaluating what makes a startup successful (49:44) Steve's assessment of Satya Nadella at Microsoft (52:26) What it takes to build an incredible company (60:45) The Four Steps to the Epiphany in 2023 (64:36) The origins of The Four Steps to the Epiphany

Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes' list of “America's Richest Self-Made Women 2023” with an estimated net worth of $520m. — In today's episode we discuss: The origins of Confluent, Kafka, and Oscilar How to become a successful second-time founder Advice for monetizing open source product Neha's unique GTM strategies How Confluent ran two businesses within one company Neha's path to founder market fit — Referenced: Apache Kafka: https://kafka.apache.org/ Confluent: https://www.confluent.io/ Confluent Cloud: https://www.confluent.io/confluent-cloud/ Jay Kreps, co-founder at Confluent: https://www.linkedin.com/in/jaykreps/ Jun Rao, co-founder at Confluent: https://www.linkedin.com/in/junrao/ MongoDB: https://www.mongodb.com/ Oscilar: https://oscilar.com/ — Where to find Neha: LinkedIn: https://www.linkedin.com/in/nehanarkhede/ Twitter/X: https://twitter.com/nehanarkhede Website: https://www.nehanarkhede.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14)The origin story of Kafka (05:24) Co-creating Kafka at LinkedIn (07:31) Why open sourcing Kafka was a masterstroke (11:04) The unique nature of Confluent's Zero to One phase (16:35) Building for a specific customer early on (18:42) Inside Confluent's successful launch (20:12) Establishing Confluent as an enterprise company (22:00) The role of developer evangelism in Confluent's success (23:49) Using developer evangelism in category creation (26:41) Navigating early co-founder dynamics (30:06) Leveraging complementary founder skills (31:56) Advice for future founders (32:45) Building Confluent with monetization in mind (34:38) Monetizing open source products (36:05) GTM for subscription Saas versus consumption SaaS (39:48) The importance of founder-led GTM sales (40:58) Neha's order of operations for GTM sales (42:33) When to build out outbound sales (44:34) Adding SaaS to a software business (48:54) Choosing what to license and what to open source (52:38) How Confluent's co-founders decided on SaaS offering (56:04) Neha's journey as a second-time founder (58:54) Building Oscilar differently to Confluent (63:21) Going from speculation to product realization (69:06) Solving problems people are willing to pay for (71:13) Neha's “proactive research sprint” tactic (72:54) How Neha has applied this tactic

Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google's collaborative, conversational, and experimental AI tool that's bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to inquire about and summarize YouTube videos. — In today's episode, we discuss: Key lessons from Bard's development process Ethics in AI How Bard shipped fast What separates Bard from competitors The future of LLM, Generative AI, and AGI Advice for aspiring AI developers — Referenced: Bard: https://bard.google.com/ ChatGPT: https://chat.openai.com/ Duet AI: https://cloud.google.com/duet-ai Free courses on machine learning by Andrew Ng: https://www.andrewng.org/courses/ Google Assistant: https://assistant.google.com/ Introducing Google Assistant to Bard: https://blog.google/products/assistant/google-assistant-bard-generative-ai/ Large Language Model (LLM): https://en.wikipedia.org/wiki/Large_language_model Meena: https://blog.research.google/2020/01/towards-conversational-agent-that-can.html Sissie Hsiao (GM at Bard): https://www.linkedin.com/in/sissie-hsiao-b24243/ Steve Stoute: https://www.linkedin.com/in/stevestoute/ UnitedMasters: https://unitedmasters.com/ — Where to find Jack Krawczyk: Twitter/X: https://twitter.com/JackK LinkedIn: https://www.linkedin.com/in/jack--k — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:17) Bard's origin story (03:54) Deciding on the application of Bard (05:59) The ethical considerations around building Bard (10:19) Why Bard launched to the public so early (13:30) Risk-taking at big companies versus smaller ones (16:20) Bard's early user research (21:21) Bard versus ChatGPT (25:01) The cultural and product principles behind Bard (30:56) Insight into Bard's impressive development speed (35:17) Deciding when to ship Bard (41:41) Why Bard is different from other products Jack has built (46:30) Evaluating Bard's original spec (48:02) Insight into Bard's product roadmap (56:00) The toughest challenges Bard has faced (57:50) What's special about team-building at Bard (62:54) Addressing Bard's negative press (67:49) Advice for aspiring LLM companies (69:15) Advice for non-LLM companies (71:05) The biggest barriers to advancing AI (75:45) How product people can use or build with AI (77:24) How AI is changing product leadership (79:20) People who had an outsized impact on Jack

Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber's Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle. — In today's episode we discuss: How to form an engineering strategy Common engineering management mistakes, and how to avoid them Advice for explaining, measuring, and optimizing engineering velocity Will's nuanced approach to organizational policies Why it's sometimes counterproductive to tell someone not to micromanage — Referenced: Accelerate (book): https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 Calm: https://www.calm.com/ Carta: https://www.carta.com/ DORA: https://dora.dev/ Good Strategy, Bad Strategy (book): https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 JavaScript: https://www.javascript.com/ KAFKA: https://kafka.apache.org/ Minto Pyramid (framework): https://untools.co/minto-pyramid Ruby on Rails: https://rubyonrails.org/ SPACE (framework): https://queue.acm.org/detail.cfm Stripe: https://www.stripe.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Will Larson: Twitter/X: https://twitter.com/lethain LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ Personal website/blog: https://lethain.com/ An Elegant Puzzle (book): https://www.amazon.com/Elegant-Puzzle-Systems-Engineering-Management/dp/1732265186 Staff Engineer (book): https://staffeng.com/book — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) The nuances of taking lessons from old companies (14:28) The value of writing down engineering principles (17:03) How to structure a strategy document (18:48) The 2 parts of any engineering strategy (21:08) Advice for turning strategy into action (23:44) Carta's unique "navigator" model (24:50) The Hidden Variable Problem (29:59) Explaining, measuring, and optimizing velocity (35:28) Useful metrics for engineering orgs (39:08) The balance between micromanagement and understanding details (43:03) Management anti-patterns (45:49) How to execute policies whilst managing their exceptions (47:56) What an excellent engineering executive looks like (53:53) How Will has evolved as an engineering executive (56:56) How to communicate with executives (63:18) Things that derail meetings (66:10) How to approach presentation feedback (67:30) A bad sign when working with direct reports (69:13) Advice for growing as an early-career engineer (71:11) Will's model for developing engineering teams (74:33) Sources of inspiration for Will's views on engineering management

Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine's “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online. — In today's episode we discuss: The origins of Runway The limitations of being “customer-driven” when building in AI How Runway balances research development with product development How goal-setting and planning is different for AI products Advice for early-stage AI founders — Referenced: Containerization: https://aws.amazon.com/what-is/containerization/ Docker: https://www.docker.com/ Green screen tool by Runway: https://runwayml.com/green-screen/ Hugging Face: https://huggingface.co/ Hugging Face Spaces: https://huggingface.co/spaces Hugging Face Model Hub: https://huggingface.co/docs/hub/models-the-hub Replicate: https://replicate.com/ Runway Gen-1: https://research.runwayml.com/gen1 Runway Gen-2: https://research.runwayml.com/gen2 Runway's 30 AI Magic Tools: https://runwayml.com/ai-magic-tools/ — Where to find Anastasis Germanidis: Twitter/X: https://twitter.com/agermanidis LinkedIn: https://www.linkedin.com/in/agermanidis Personal website: https://agermanidis.com/ Personal blog: https://blog.agermanidis.com/ — Where to find Todd Jackson: Twitter/X: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:23) The unique story of how Runway's co-founders met (08:27) The origins of Runway (09:28) Forming the initial product (13:55) Turning Runway into a company (14:41)Approach to initial market segments (18:53) Early-adopters (21:20) The limitations of being “customer-driven” (25:54) Forming a vocal community (27:08) Fostering community (29:05) The progression of Runway's tech and use-cases (33:08) How they picked users for early release (34:00) Expanding past the first 100 users of Gen-2 (35:33) Runway's approach to safety and content moderation (36:44) Balancing product development and research development (43:51) Runway's org structure (45:08) Goal-setting amidst constant change in AI (46:50) Why Runway doesn't plan very far ahead (50:26) Advice to early-stage AI founders (53:11) Will AI replace video editors? (55:04) When Runway had the most momentum (56:49) Anastasis' #1 piece of advice

Guillermo Rauch is the CEO of Vercel, a frontend-as-a-service product that was valued at $2.5b in 2021. Vercel serves customers like Uber, Notion and Zapier, and their React framework - Next.js - is used by over 500,000 developers and designers worldwide. Guillermo started his first company at age 11 in Buenos Aires and moved to San Francisco at age 18. In 2013, he sold his company Cloudup to Automattic (the company behind WordPress), and in 2015 he founded Vercel. — In today's episode we discuss: Guillermo's fascinating path into tech Learnings from building Cloudup and selling the company to Automattic (the company behind WordPress) Vercel's origin story and path to product market fit How to make an open source business successful Vercel's unique philosophy on developer experience Insights and predictions on the future of AI — Referenced: Algolia: https://www.algolia.com/ Apache Zookeeper: https://zookeeper.apache.org/ Apache Kafka: https://kafka.apache.org/ AWS: https://www.aws.training/ C++: https://www.techtarget.com/searchdatamanagement/definition/C Clerk: https://clerk-tech.com/ Cloudup: https://cloudup.com/ Commerce Cloud: https://www.salesforce.com/products/commerce/ Contentful: https://www.contentful.com/ Debian: https://www.debian.org/ Fintool: https://www.fintool.com/ Figma: https://www.figma.com/ GitLab: https://about.gitlab.com/ IRC: https://en.wikipedia.org/wiki/Internet_Relay_Chat KDE: https://kde.org/ Linux: https://en.wikipedia.org/wiki/Linux Mozilla: https://www.mozilla.org MooTools (UI library): https://mootools.net/ Next.js: https://nextjs.org/ React Native: https://reactnative.dev/ Red Hat: https://www.redhat.com/ Redpanda: https://redpanda.com/ Resend: https://resend.com/ Rust: https://www.rust-lang.org/ Salesforce: https://www.salesforce.com Servo: https://servo.org/ Shopify: https://www.shopify.com/ Socket.io: https://socket.io/ Symphony: https://symphony.com/ Trilio: https://trilio.io/ Twilio: https://www.twilio.com Vercel: https://vercel.com/ V0.dev: https://v0.dev/ — Where to find Guillermo: Twitter/x: https://twitter.com/rauchg LinkedIn: https://www.linkedin.com/in/rauchg/ Personal website: https://rauchg.com/ — Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (02:35) Becoming an “internet celebrity” at age 11 (08:30) Guillermo's first company: Cloudup (11:09) Biggest learnings from Cloudup and WordPress (15:06) The insights behind starting Vercel (17:11) Sources of validation for Vercel (20:29) How Vercel formed its V1 product (23:25) Navigating the early reactions from competitors and users (25:58) The paradox of developers and how it impacted Next.js (31:20) Advice on finding product market fit (34:48) The forces behind a trend towards "Front-end Cloud” (38:35) Why people now pay so much attention to the front-end (40:06) How to make an open source business successful (44:54) Insights on product positioning and category creation (48:52) Vercel's journey through becoming multi-product (51:44) Guillermo's take on the future of AI (53:43) Heuristics for building better product experiences (55:49) AI insights from Vercel's customers (57:37) How AI might change engineering in the next 10-20 years (62:43) Guillermo's favorite advice (65:45) Guillermo's advice to himself of 10 years ago

Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b. — In today's episode we discuss: How GitLab layered a commercial model on top of open source roots GitLab's main marketing metrics Examples, benefits, and downsides of a transparent company culture How GitLab serves enterprise customers, and a passionate developer community Unique marketing lessons from working in an open core company An example of a recent marketing campaign — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Ashley Kramer: Twitter/x: https://twitter.com/ashleyekramer LinkedIn: https://www.linkedin.com/in/ashleyekramer/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Referenced: CISO: https://www.cisco.com/c/en/us/products/security/what-is-ciso.html DevSecOps: https://about.gitlab.com/topics/devsecops/ E-Group: https://about.gitlab.com/company/team/e-group/ GitLab: https://gitlab.com GitLab legal team's SAFE framework: https://about.gitlab.com/handbook/legal/safe-framework/ GitLab's open core business model: https://handbook.gitlab.com/handbook/company/stewardship/ GitLab's open source employee handbook: https://handbook.gitlab.com/handbook/people-group/ GitLab's open source marketing handbook: https://about.gitlab.com/handbook/marketing/ GitLab's open source remote handbook: https://handbook.gitlab.com/handbook/company/culture/all-remote/guide/ Sid Sijbrandij, CEO of GitLab: https://www.linkedin.com/in/sijbrandij/ Tableau: https://www.tableau.com/ — Timestamps: (00:00) Intro (02:34) Marketing in closed vs open source companies (07:40) The role of marketing at GitLab (09:23) The tensions of being a commercial, open source company (12:36) Advice for nurturing community and dealing with disagreements (15:02) GitLab's main marketing metrics (20:26) The thinking behind GitLab's org structure, in and around marketing (28:19) Selling to enterprise as an open core company (29:53) The difference between open core and open source (30:39) Serving many different customer segments (35:10) GitLab's planning process (39:22) An example of GitLab's marketing in practice (42:12) How marketing collaborates with product (45:55) Marketing lessons from working in an open core company (49:46) Examples of GitLab's focus on transparency (52:22) Why GitLab is transparent about their marketing (54:59) 2 examples of GitLab's uniquely transparent culture (58:35) The downsides of being a transparent company (60:13) GitLab's meeting structure and cadence (62:04) Benefits of having an engineering and product background as CMO (71:09) People who made an outsized impact on Ashley's career

Colin Zima is the co-founder and CEO of Omni, a business intelligence tool that has raised over $26.9m. Prior to starting Omni, Colin was Chief Analytics Officer and VP of Product at Looker, which was acquired by Google for $2.6b. Colin was an early employee at Looker, and stood up its high-touch customer support arm, which turned into a cornerstone competitive advantage for the company. — In today's episode we discuss: Lessons from Looker When, why and how to invest in white-glove customer support Tactics for scaling high-touch customer support Colin's intuition-based approach to product How Looker hit their goals for 24 quarters in a row The founding story of Omni Colin's hot takes on picking startups, hiring PMs, and more — Referenced: Amazon Redshift: https://aws.amazon.com/redshift/ BigQuery: https://cloud.google.com/bigquery Hotel Tonight: https://www.hoteltonight.com/ Omni: https://omni.co/ Ramp: https://ramp.com/ Rillet: https://rillet.com/ Snowflake: https://www.snowflake.com/en/ Tableau: https://www.tableau.com/ TechCrunch article on Looker's acquisition by Google: https://techcrunch.com/2020/02/13/google-closes-2-6b-looker-acquisition/ Vanta's founder on the In Depth podcast: https://review.firstround.com/podcast/episode-86 — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Colin Zima: Twitter: https://twitter.com/drinkzima?lang=en LinkedIn: https://www.linkedin.com/in/colinzima/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:30) Colin's unique entry into Looker (04:35) How Colin talks to users (08:20) How Colin's scope at Looker expanded (10:53) Why and how to provide white-glove customer support (20:25) Which companies should invest heavily in customer support? (22:49) Hiring for and hiring from customer support (27:40) The #1 thing for making customer support effective at scale (29:32) The culture of customer support at Omni (32:57) Insights on product strategy (41:33) The role of intuition vs data in product decisions (44:25) The merits and downsides of an intuition-driven approach to product (48:36) Insights from hitting every goal for 24 quarters straight (55:07) The founding story of Omni (58:10) How Colin maintains intellectual honesty as a founder (60:02) How Colin thinks about what to copy vs not copy from Looker (63:25) How to pick which startup to join (66:07) The most underrated trait in early stage startup employees (68:11) Colin's take on founder-market-fit (69:42] Unpopular opinion on how to hire good PMs (72:28) The people who made an outsized impact on Colin's career

Wade Foster is the Co-founder & CEO at Zapier, a platform for building workflow automations without a developer. Zapier was started during 2011 in Columbia, Missouri, and by 2021, it was valued at $5b, having only raised $1.3m. Prior to founding Zapier, Wade had just two professional jobs, and had never managed or hired anyone. He worked as a PM on a web app used by 20k students, and as an Email Marketing Manager at Veterans United - a role that had a significant influence on Zapier's eventual success. In today's episode, we discuss: The stories and thinking behind Zapier's most unorthodox decisions How Wade thinks about product market fit How Zapier built their powerful distribution engine The fascinating story of Veterans United, and its impact on Zapier How Wade thinks about fundraising Why Wade lives by “don't hire ‘til it hurts” Key lessons on people management Referenced: Basecamp: https://basecamp.com/ Bingo Card Creator: https://www.bingocardcreator.com Bryan Helmig, Co-founder of Zapier: https://www.linkedin.com/in/bryanhelmig John Wooden quote: https://www.thewoodeneffect.com/be-quick-but-dont-hurry/ Mailchimp: https://mailchimp.com/ Mike Knoop, Co-founder of Zapier: https://www.linkedin.com/in/mikeknoop Patrick Mckenzie, creator of Bingo Card Creator: https://www.linkedin.com/in/patrickmckenzie/ PayPal: https://www.paypal.com/ Salesforce: https://www.salesforce.com/ SMBs: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business Stripe: https://stripe.com/ Thinking in Bets by Annie Duke: https://www.amazon.com.au/Thinking-Bets-Annie-Duke/dp/0735216355 Tony Xu, CEO of DoorDash: https://www.linkedin.com/in/xutony/ Twilio: https://www.twilio.com/ Veterans United Home Loans: https://www.veteransunited.com/ Zapier: https://zapier.com/ Where to find Brett Berson Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find Wade Foster Twitter: https://twitter.com/wadefoster LinkedIn: https://www.linkedin.com/in/wadefoster Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (05:46) The fascinating story of Veterans United (06:55) Lessons from Veterans United (08:35) The most important things Zapier got right (10:13) How Zapier built their powerful distribution engine (16:56) Why Zapier didn't move to focusing on enterprise (19:06) How Wade thinks about product market fit (24:26) The role of skill vs luck in Zapier's success (26:23) What was hard about building Zapier (30:03) Key lessons on people management (32:35) Rule of thumb: "don't hire ‘til it hurts” (36:42) Zapier's #1 hiring mistake (42:50) How to test for scrappiness in the hiring process (44:31) Do hiring playbooks transfer between companies? (50:01) The 12 year evolution of Zapier's product (53:20) How Zapier makes product decisions (55:40) How Zapier thought about competition (60:11) How to foster intellectual honesty in yourself and your org (65:35) The people who most impacted Wade's worldviews

Laura Behrens Wu is the Founder & CEO at Shippo, a company that has raised $100m+ and was last valued at $1b in 2021. Shippo provides an API and dashboard that makes shipping easy for e-commerce businesses, marketplaces, and platforms. Prior to starting Shippo, Laura graduated from Harvard University, and was heavily influenced by a short internship at LendUp, which exposed her to Silicon Valley and startup culture.  In today's episode we discuss: Shippo's pivot-stricken origin story Finding product-market-fit, again and again and again Laura's unique take on founder-market-fit Advice on talking to users The 3 Horizons Framework for prioritizing resources across a core business and longer-term bets The email Laura sends every Sunday because of Frank Slootman's advice Referenced: Amp It Up by Frank Slootman: https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115 Expedia: https://www.expedia.com/ FedEx: https://www.fedex.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ Jerry Colonna: https://www.linkedin.com/in/jerry-colonna-reboot/ Josh Koppelman: https://www.linkedin.com/in/jkoppelman/ Khalid Halim: https://review.firstround.com/the-science-of-speaking-is-the-art-of-being-heard LendUp: https://www.lendup.com/ Shippo: https://goshippo.com/ Shopify: https://www.shopify.com/ SMBs: https://www.fool.com/the-ascent/small-business/articles/smb-business/ Stripe: https://stripe.com/ UPS: https://www.ups.com/us/en/global.page 70/20/10 rule from Google: https://www.itonics-innovation.com/blog/702010-rule-of-innovation Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 Where to find Laura Behrens Wu: Twitter: https://twitter.com/LauraBehrensWu LinkedIn https://www.linkedin.com/in/laurabehrenswu Personal website: https://laurabehrenswu.com/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:36) The Shippo origin story (06:57) Why they pivoted into Shippo (11:01) How they got their first customers (13:27) The role of timing in Shippo's early success (14:40) The value of being an outsider (17:49) When founder-market-fit is and isn't necessary (19:07) The path to product-market-fit (22:06) What kept the Shippo team persisting (24:41) Advice on talking to users (29:28) Shippo's fundraising journey (34:26) Finding product-market-fit again and again (37:54) The 3 Horizons Framework (45:04) Shippo's culture and early team (49:17) Hiring people you can learn from (50:40) Laura's most impactful hires (52:12) Frank Slootman's "Sunday Email” (55:43) Laura's #1 piece of advice for founders (57:34) The most memorable influences on Laura's career

Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you've seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama's first presidential campaign. In today's episode, we discuss: Rewind's journey to Product Market Fit Lessons from Optimizely and being a second time founder Dan's one-of-a-kind Twitter fundraising strategy Dan's hot takes on the future of AI Where to build in AI, and what makes a “wrapper” thin versus thick Referenced: Apple's Silicon: https://www.macrumors.com/guide/apple-silicon/ ChatGPT: https://chat.openai.com/ Dan publicly sharing his own 360 performance reviews: https://twitter.com/dsiroker/status/1689763756459675650 Dan's public Twitter fundraise: https://twitter.com/dsiroker/status/1646895452317700097 Dan's Rewind demo tweet: https://twitter.com/dsiroker/status/1638799931891920897 Google Glass: https://en.wikipedia.org/wiki/Google_Glass Google Wave: https://en.wikipedia.org/wiki/Google_Wave Maslow's Hierarchy of Needs: https://www.simplypsychology.org/maslow.html Optimizely: https://www.optimizely.com/ Paul Graham: https://twitter.com/paulg Rahul Vohra's framework for measuring and optimizing Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit Rewind AI: https://www.rewind.ai/ Scribe (which morphed into Rewind): https://www.scribe.ai/about The Mom Test book: https://www.momtestbook.com/ Where to find Dan Siroker: Twitter: https://twitter.com/dsiroker LinkedIn: https://www.linkedin.com/in/dsiroker Personal website: https://siroker.com/ Blog: https://medium.com/@dsiroker Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:25) Rewind's origin story (04:04) How Rewind works (07:24) Managing scope when building Rewind (13:47) How Dan thought about early user feedback (17:08) Rewind's cultural mantra for shipping and validating fast (18:35) Product positioning as a category creator (20:39) Lessons from being a 2nd time founder (26:11) Cultural values at Optimizely and Rewind (28:22) How Dan defines and operationalizes Product Market Fit (32:06) Audience segmentation (34:32) Measuring Product Market Fit (36:23) Dan's take on the current AI hype (38:11) What makes a "wrapper" thin vs thick? (39:50) Where founders should and shouldn't build within the AI ecosystem (43:22) Trends in consumer expectations around data privacy (46:59) What AI might look like 10 years from now (51:09) Dan's one-of-a-kind public Twitter fundraise (59:40) What's next for Rewind? (61:26) The influence of Paul Graham (62:47) Dan's #1 piece of advice (64:23) Dan's #1 book recommendation

Sprig is an AI-powered user insights platform that has raised over $88m. Today's discussion features two key individuals in Sprig's journey so far: Ryan Glasgow, Sprig's CEO and founder; and Kevin Mandich, Sprig's Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego. In today's episode, we discuss: Key lessons from the Sprig founding story Product development in the pre vs. post-LLM world How to overcome AI skepticism How to evaluate new models and how to know when to switch Why you need an ML engineer Sprig's “AI Squad” team structure How Sprig upskills all team members on AI Referenced: Auto-GPT: https://github.com/Significant-Gravitas/Auto-GPT Chat GPT: https://chat.openai.com Google's BERT model: https://en.wikipedia.org/wiki/BERT_(language_model) Jira: https://www.atlassian.com/software/jira Jobs to Be Done Framework: https://hbr.org/2016/09/know-your-customers-jobs-to-be-done Langchain: https://www.langchain.com/ Sprig: https://sprig.com/ Where to find Ryan Glasgow: Twitter: https://twitter.com/ryanglasgow LinkedIn: https://www.linkedin.com/in/ryanglasgow/ Where to find Kevin Mandich: Twitter: https://twitter.com/kevinmandich LinkedIn: https://www.linkedin.com/in/kevinmandich/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:50) Intro (04:57) What attracted Kevin to Sprig (05:53) Kevin's background before Sprig (07:56) How Ryan gained conviction about Kevin (09:55) Key technical challenges and how they solved them (18:46) How to overcome AI skepticism (21:47) The early difficulties of building an ML-enabled product (25:06) Evaluating new models and knowing when to switch (35:09) Using Chat GPT (37:23) Product development in the pre vs. post-LLM world (39:53) The impact of AI hype on Sprig's product development (45:36) Balancing AI automation with user-psychology (48:47) Do recent LLMs reduce Sprig's competitive advantage? (51:00) The importance of "selling the vision" to customers (54:40) How Sprig structures teams (57:25) How Sprig upskills all team members on AI (60:25) 3 key tips for companies trying to navigate AI (66:05) Major limitations with LLMs right now (70:27) The future of AI and the future of Sprig

Saumil Mehta is the GM of Square's flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert. In today's episode we discuss: The principles of effective org design Signs your company needs a re-org Square's GM-led org design, and the reasoning behind it Lessons on incentive-design, pricing, planning, and decision-making at scale The step-by-step process behind a recent re-org at Square 5 lessons from Alyssa Henry, CEO at Square Referenced: Alyssa Henry, CEO at Square: https://www.linkedin.com/in/alyssa-henry-0905692 Saumil's 6 key principles for effective re-orgs: https://medium.com/@saumil/avoid-the-reorg-from-hell-with-six-key-principles-f8c9cbdfb0bd Saumil's blog post about “Building Better Products with Escalation”: https://medium.com/swlh/well-that-escalated-quickly-building-better-products-with-escalation-feb259d733c9 Square: https://squareup.com/gb/en Where to find Saumil Mehta: Twitter: https://twitter.com/saumil Linkedin: https://www.linkedin.com/in/saumilmehta1/ Blog: https://medium.com/@saumil Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps [00:02:22] Intro [00:04:20] The principles of effective org design [00:04:32] #1 Align on goals [00:06:14] #2 Separate design considerations from human considerations [00:08:03] #3 Define clear reasons each team exists [00:09:21] #4 Design for durability [00:09:49] #5 Be very intentional with comms [00:10:14] Some stories behind the principles [00:13:55] How to know when you need a re-org [00:16:14] Managing inevitable tradeoffs in org design [00:20:45] Square's "GM-led" structure [00:23:05] Why Square centralized GTM [00:25:39] Managing pricing and packaging across a complex org [00:29:28] Examples of Square's written principles [00:31:19] How Square determines what each GM owns [00:38:35] Collaboration across GMs and products [00:40:32] Key lessons on planning and decision-making at scale [00:43:15] Designing incentives across a massive org [00:49:03] Two reasons GM structures go wrong [00:52:03] 6 Step re-org walkthrough [00:52:37] Step 1: Triggering the re-org [00:53:59] Step 2: Sketching a proposed org design [00:56:17] Step 3: Checking against key criteria [00:59:22] Step 4: Finalizing approach with leadership [01:00:04] Step 5: Planning comms [01:01:58] Step 6: Executing comms [01:04:20] Signals a re-org worked vs failed [01:07:13] 5 lessons from Alyssa Henry, CEO at Square

Kellan Elliott-McCrea is a Head of Engineering at Adobe, overseeing Frame.io, a newly acquired video review and collaboration platform. He is known for his experience and expertise as an engineering leader. He was previously a VPE at Dropbox, and CTO at Etsy where he built and led a team of 300 people, from tech and platform reboot through to IPO. Kellan also built and scaled teams at Flickr, and has a coaching and advising practice for companies looking to supercharge their engineering teams.  In today's episode, we discuss: How software engineering has changed in the last 10-15 years The future of software engineering, and the impact of AI The importance of alignment and tactics for achieving it How to think about and enable engineering productivity Lessons on culture from Adobe, Dropbox, and Flickr Concrete tips for being a better manager Rituals for building business literacy throughout an org Referenced: Adobe: https://www.adobe.com Dropbox: https://www.dropbox.com/ Flickr: https://www.flickr.com/ Frame: https://www.frame.io/ How Complex Systems Fail, by Richard I. Cook, MD: https://how.complexsystems.fail/ How Etsy Grew their Number of Female Engineers by Almost 500% in One Year https://review.firstround.com/How-Etsy-Grew-their-Number-of-Female-Engineers-by-500-in-One-Year Where to find Kellan Elliott-McCrea: Twitter: https://www.twitter.com/kellan LinkedIn: https://www.linkedin.com/in/kellanem Website: https://kellanem.com/ Personal blog: https://laughingmeme.org/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:02:58] Engineering orgs now vs 15 years ago [00:05:57] Why engineering teams are bigger despite better tools [00:10:45] How to think about engineering productivity [00:15:50] Questioning common compensation models [00:19:39] Slow teams are misaligned teams [00:23:56] How to achieve alignment in engineering teams [00:29:12] How to co-ordinate better across teams [00:35:23] Why so few companies successfully go multi-product [00:38:02] Which elements of successful orgs replicate? [00:41:53] How to approach a new org system at a new company [00:45:48] The value of information sharing and coaching [00:48:55] Best practices for communicating with and across teams [00:51:05] How to approach disagreements [00:54:27] What high-quality engineering management looks like [00:58:37] How to increase organizational capacity [00:63:20] Tactics and rituals for enabling effective teams [00:66:05] How to build business literacy [00:68:30] Kellan's biggest inspirations

Alex Kracov is the CEO and Co-Founder at Dock, and the former VP of Marketing at Lattice. Alex joined Lattice as the first marketer and third employee, and he helped to grow the business from seed to 1850+ customers. Prior to Lattice, Alex was a consultant at Blue State Digital — the team that elected President Obama and orchestrated projects at Google. Since leaving Lattice in 2021, Alex co-founded Dock, a B2B platform that has streamlined the customer buying experience for clients like Loom, Origin, and Instabug.  In today's episode, we discuss: The 2023 SaaS marketing playbook How to start your early-stage B2B marketing How to prioritize resources across multiple marketing bets How to think about attribution Lattice's unorthodox million-dollar marketing campaign How to hire for early marketing roles What makes a standout marketer Advice for building your first website Referenced: Dock: https://www.dock.us/ Lattice: https://lattice.com/ Jack Altman: https://www.linkedin.com/in/jackealtman J Zac Stein: https://www.linkedin.com/in/jzacstein Where to find Alex Kracov: Twitter: https://twitter.com/kracov/ LinkedIn: https://www.linkedin.com/in/alexkracov Website: https://www.kracov.co/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:00:00] Intro [00:02:45] The challenges and opportunities in early-stage B2B marketing [00:05:13] How to think about short-term versus long-term marketing goals [00:07:31] Allocating resources across marketing bets [00:09:13] Signs your marketing is working [00:11:20] The most underutilized marketing strategy [00:13:03] Creating your company's first website [00:14:22] How Lattice formed its brand messaging and positioning [00:18:22] Dock's innovative approach to marketing software [00:20:14] The first thing people should see on your website [00:23:10] Lattice's most successful early-stage marketing tactics [00:28:05] Determining which marketing strategies are still relevant [00:30:25] Lattice's unorthodox million-dollar marketing campaign [00:33:26] Why Alex had an outsized impact at Lattice [00:37:05] Lessons from his first marketing hires [00:39:41] When to scale your marketing team [00:40:55] Building an effective early-stage marketing team [00:42:30] A tough conversation with the CEO & Co-founder of Lattice [00:44:46] Achieving early-stage marketing alignment [00:46:20] Transitioning from employee to entrepreneur [00:49:19] Getting the most out of conferences [00:50:47] Selecting marketing channels in the early stages [00:52:44] Hiring marketers for experience versus potential [00:56:34] The 2023 SaaS marketing stack [00:58:19] Advice for Zero to One marketing [00:60:46] What successful B2B marketing looks like

Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber. In today's episode, we discuss: Best-practice product management How to achieve alignment at scale The importance of cross-functional performance Anique's unique approach to finding top organizational talent How to hire for roles outside your area of expertise Common fail cases with internal and external recruitment Tactics for effective interviews Referenced: Loom: https://www.loom.com/ Navan (formerly TripActions): https://navan.com/ Teach for America: https://www.teachforamerica.org/ Uber: https://www.uber.com/ Where to find Anique Drumright: Twitter: https://twitter.com/aniqued LinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1a Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:03:00] The similarities and differences between PM and executive leadership roles [00:06:53] How Loom uses storytelling when launching a product [00:10:01] Managing cross-functional scope and performance [00:13:41] Goal-setting with functional leads [00:16:59] The importance and difficulty of organizational alignment [00:20:40] How Uber achieved alignment at scale [00:24:06] Rituals for staying aligned [00:25:23] Loom's winning one-on-one format [00:27:49] When and how to help functional leads [00:29:13] Hiring for roles outside your area of expertise [00:32:55] Go-to interview questions for prospective leaders [00:33:55] Changing the hiring process for roles outside your area of expertise [00:36:09] Common patterns of failed external hires [00:37:40] Common patterns of failed internal hires [00:39:05] Avoiding over-promotion in your organization [00:40:51] What inspires people in a company [00:45:40] Tactics for getting honest answers in interviews [00:47:12] Asking the right questions during reference checks [00:51:29] A month in the life of a COO [00:52:52] The importance of employee energy levels [00:54:53] Loom's leadership dynamics and why it works [00:57:30] People who had an outsized impact on Anique's career