30 Minutes to President's Club | No-Nonsense Sales

Nate's Business Case Template Nate Nasralla shares how to craft a one-page business case that your champion can run with. By presenting it early, keeping it simple, and making it feel like an internal doc that earns buy-in from decision-makers.

Nate's Business Case Template One of the largest deals Nate (Co-Founder @ Fluint & Chief Growth Office @ Global Venture Network) ever closed—$30M—was won with a single, unbranded page. No logos. No design. Just black text on white paper. Why? Because it felt internal to the customer—not like a vendor pitch. The structure? Just 5 parts: 1. Priority-Driven Headline – Use the exec's own language 2. Problem Statement – Frame the problem in a way that aligns with what you uniquely solve 3. Recommended Approach – Highlight 3 key things only you can do differently 4. Target Outcomes – Flip the problem into clear, metric-driven results 5. Required Investment – Be honest about time, money, and effort—don't minimize it The key? Anchor the entire narrative in what the executive already cares about. If it sounds like an internal initiative, it gets bought in like one. RESOURCES DISCUSSED ⁠⁠⁠Join our weekly newsletter⁠⁠⁠⁠ ⁠⁠⁠Things you can steal⁠⁠⁠ Save $50 on any 30MPC course⁠⁠⁠ with code “PODCAST” Nate's Business Case

If your first cold email asks for a meeting—you're doing it wrong. In this video, Mark Kosoglow (Co-Founder/CEO @ OperatorChief + Revenue Officer @ Catalyst Software) breaks down a smarter outbound strategy: how to warm up buyers by educating them instead of pitching them. Whether you're an SDR, AE, or founder doing founder-led sales, this framework will help you increase reply rates and book more qualified meetings. RESOURCES DISCUSSED: ⁠Join our weekly newsletter⁠ ⁠Things you can steal⁠ ⁠Save $50 on any 30MPC course⁠ with code “PODCAST”

Mark Kosoglow reveals why most outbound fails before it even starts and how identifying the pain chain can radically improve your team's results.

This is a 30 minute masterclass on the 10 lessons every rep needs to know when it comes to cold calling. Armand and Nick walk you through five lessons each that will leave you feeling ready to put in the work and pick up the phones! ✅ Inside this episode: You learn how to navigate rejection from a single person and find an alternative route through other people in the company to close the deal How to improve your script when you're struggling Handling rude responses and understanding they're going to happen regardless, you're doing nothing wrong! How to get someone's attention (Hint: It's not, “How's your day going?” You get to say silly things on cold calls, as long as you do it with confidence! RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST”

Alex Kremer shares tactical leadership strategies to help sales managers build engaged teams by using breath work for presence, empowering reps, and structuring effective 1:1s that drive results.

Most leaders treat team meetings like a routine checklist, but they're one of the few moments you have everyone's full attention each week. Here's how Alex Kremer (founder & CEO @ Alluviance) keeps his team motivated each time they meet: Start with Presence Get Your Team Involved Connect the Dots to a Bigger Impact The goal isn't just to share numbers but to create a culture where your team feels valued and invested. Make your meetings a place for growth, not just updates. Watch the full episode TOMORROW ALEX'S PATH TO PRESIDENTS CLUB: Founder & CEO @ Alluviance Host @ Rising Leader Podcast Head of Sales @ Catalyst Software RESOURCES DISCUSSED: ⁠Join our weekly newsletter⁠ ⁠Things you can steal⁠ ⁠Save $50 on any 30MPC course⁠ with code “PODCAST”

Learn how Max Licht wins complex 6 and 7-figure enterprise deals by shadowing his prospects' workflows, de-risking every technical blocker, and turning IT stakeholders into deal accelerators.

Max Licht (Enterprise AE @ MaestroQA) breaks down his shadow-based discovery process. This technique goes beyond typical discovery calls, allowing you to witness firsthand where inefficiencies and bottlenecks are happening. 1. Identify the Painful Process - Research the customer's current workflow and tools (e.g., Excel, Salesforce) to understand the manual, time-consuming steps involved. - This reveals where inefficiencies exist, giving you a clear picture of the pain your solution can alleviate. It also helps you identify the "drag them through the glass" moments where the pain is most acute, which is critical for building urgency. 2. Set Up the Shadowing Session - Frame the shadow as a collaborative step to fully understand their process. Instead of just making claims, say something like, *“Before I make any promises, I want to fully understand your current reporting process to see where we can add the most value.”* - This approach shifts the focus from selling to problem-solving, making you a trusted partner rather than just a vendor. It also sets the stage for a more meaningful business case. 3. Conduct the Shadow - Watch the prospect use their current tools and processes. Take notes, capture screenshots, and pay attention to friction points, inefficiencies, and workarounds they rely on. - Seeing the workflow in action often reveals unspoken pain points and limitations that even the prospect might not articulate in a standard discovery call. This firsthand observation helps you tailor your pitch to the reality of their day-to-day work. 4. Use Shadows to Build a Business Case - Use the insights gathered to frame your solution as a direct response to the pain points you observed. For example, highlight how your tool eliminates specific inefficiencies, reduces manual steps, or streamlines complex reporting. - This concrete evidence makes your pitch more credible and aligns your solution directly with their business goals, increasing the likelihood of internal buy-in. 5. Follow Up Strategically - After the shadow, summarize your findings in a follow-up email or meeting, highlighting specific pain points you observed and how your solution can address them. Use this to drive urgency and move the deal forward. - This reinforces your credibility as a problem-solver and keeps the conversation anchored in real, observed issues, rather than hypothetical value propositions. 6. Use the Shadow as a Catalyst for Future Conversations - Reference specific pain points in later stages of the sales cycle, using them to frame your solution as a clear, tangible fix for their current frustrations. - This approach keeps the focus on solving their problems, reducing friction in the decision-making process and increasing the likelihood of a successful close. RESOURCES DISCUSSED: ⁠Join our weekly newsletter⁠ ⁠Things you can steal⁠ ⁠Save $50 on any 30MPC course with code “PODCAST”

Mark Nietzel returns with the exact systems he used to lead his team to 110% of quota and earn a President's Club trip to Barcelona. This episode is a tactical blueprint for pipeline accountability, deal progression, and how leaders can maximize the impact of onsites.

Get the official 30MPC Aligned Mutual Action Plan: https://30mpc.teamaligned.com/room/67a4ccb055dca14b5ff5be3a?avk=daf0c1b1e0bc Quantifying business impact without triggering sales pressure is hard, but Meredith Chandler shows you exactly how to do it. From confident pricing to bulletproof ROI framing, this episode is a tactical masterclass.

Sales leaders—your CRM and dashboards are probably working against you. John Sherer shares tactical ways to clean the clutter, focus on the right metrics, and finally get reports that drive action (not confusion).

FOUR ACTIONABLE TAKEAWAYS: Use the "Why, What, How" framework to communicate hard changes—always start with the why to reduce the shiver effect and maintain trust. Don't sugarcoat bad news—treat your team like adults, be honest about challenges, and frame positives where appropriate. Create a lever cheat sheet for your sellers so they know what they can give (discounts, services) and what to ask for in return to protect deal value. After major changes like a RIF, give the team a week to process, then reset expectations with managers leading the charge into the "new normal." PATH TO PRESIDENT'S CLUB: Chief Revenue Officer, Postal VP of International Sales, Wrike Senior Director of Sales, Wrike RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST”

Enterprise sellers: this one's a masterclass in leading high-impact discovery. Jen Allen-Knuth shares how to uncover deal-driving problems, guide calls with precision, and win executive trust with better prep and positioning.

Guestie VP of Sales Jonah Mandel is back—and he's bringing a battle-tested blueprint for leading a 60-person sales org. From onboarding frameworks to emotional pulse checks, this episode is a masterclass in scalable, high-intent leadership.

FOUR ACTIONABLE TAKEAWAYS: Position yourself as a partner, not a decision-maker, during negotiations. Frame your CFO or leadership as the final approver to deflect pressure and control the conversation Use a sliding scale for discounts based on timeline. Offer steeper discounts for faster signatures to create urgency without arbitrary end-of-month pressure Steer discovery and demos toward problems that matter. Don't get stuck solving small issues—recommend workflows tied to real business impact and executive priorities Drive deal velocity without discounting by pre-scheduling the implementation call. Lock in post-sale steps early to create natural pressure toward closing PATH TO PRESIDENT'S CLUB: Head of Sales, Unified GTM Strategic Accounts, Lattice Enterprise Account Executive, Lattice Mid-Market Account Executive, Lattice Business Development Representative, Lattice RESOURCES DISCUSSED: ⁠Join our weekly newsletter⁠⁠ ⁠⁠Things you can steal

ACTIONABLE TAKEAWAYS: Get Permission to Reframe: Before turning a perceived weakness into a strength, ask for permission to tell the story. This keeps the approach authentic and avoids sounding overly salesy. Anchor High for Multithreading: When requesting additional stakeholders, ask for more than you need. If they say no to six but yes to two, you've still gained ground. Reframe Intentional Limitations: When faced with an objection or missing feature, consider if it's intentional by design. Reframe it as a benefit aligned with the prospect's goals. Prep for Large Meetings: Divide the room strategically. Prep with your champion, pre-call each stakeholder, then personalize questions in the meeting to tailor the conversation. DAVID'S PATH TO PRESIDENTS CLUB: Senior Account Executive MM @ LinkedIn Account Executive SMB @ LinkedIn Sales Development Representative @ LinkedIn Creator Manager @ LinkedIn RESOURCES DISCUSSED: ⁠Join our weekly newsletter⁠ ⁠Things you can steal⁠

FOUR ACTIONABLE TAKEAWAYS: Schedule Everything: Cold call success starts with structure. Use scheduled power hours, follow-ups, and prospecting blocks to bring order and focus to your SDRs' day. Create Rituals That Boost Energy: Host a weekly kickoff meeting to align the team, recognize wins, and run call reviews. Energy is everything—ritualize it. Hold Reps to Input Standards: 150 dials per day is the expectation. If reps fall short, diagnose whether it's a skill, will, or workflow issue and address it head-on. Use Your Top Reps as the Spark: Find your believers and get them dialing in public. Team momentum starts with a few people on fire—and then it spreads. COLIN'S PATH TO PRESIDENT'S CLUB: SVP of Revenue, Orum VP of Sales, Namely Senior Director of Sales, Namely Sales Manager, Zocdoc Sales Executive, Zocdoc RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Assume your buyer has 60 seconds to pitch your product internally. When sending recaps or justification materials, skip the deck send 2–3 crisp bullets that clearly communicate the top reasons to buy. Reset the agenda mid-call if needed. If a buyer jumps straight into content or things go off the rails, pause and suggest how to best use the remaining time. This keeps the call focused and productive. Use a “vibey demo” to open, then do deeper discovery later. Morgan starts with a product overview to spark curiosity, then uses the second call to dig into what resonated and why—leading to richer discovery. Reverse-engineer problems from product interest. When a buyer reacts positively to a feature, follow up with, “People usually want that because they're struggling with X or Y—what's going on in your world?” PATH TO PRESIDENT'S CLUB Sales Engineer @ Squint Head of Solutions Architecture @ Pave Field CTO @ Sisense Sales Engineering Manager @ Sisense RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Set Multiple Agendas: Before showing a high-level demo, re-establish the agenda. Explain what you'll show, present it, then recap by tying it back to the meeting's outcome. Dangle the Carrot: Identify one problem to address in your demo, then ask for two or three more use cases. Use curiosity to uncover additional discovery points before diving into the demo. Anchor to an Outcome: Start the call by setting a clear decision-oriented goal, such as determining if further evaluation is worth their time. Be Blunt About Goals: In rip-and-replace scenarios, state the stakes directly, like weighing the pain of switching versus the potential benefits. This disarming honesty builds trust. MARK'S PATH TO PRESIDENTS CLUB: Commercial Sales Manager @ Procore Sales Manager, Emerging @ Procore Enterprise Account Executive @ Procore Senior Account Executive, Mid-Market @ Procore RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Michelle Cecil Episode

ACTIONABLE TAKEAWAYS: Time-Box Your Tools: Avoid checking Slack or email first thing in the morning—protect your focus by starting the day with intention. Buyer Actions > Seller Actions: Sales progress should be measured by what the buyer does, not how many activities the seller logs. Build a Momentum Score: Track 7–10 buyer behaviors (like demo views or EB engagement) to score deal health and predict close rates. Deals Must Survive 3 Rings: Every deal faces three negotiation phases—champion, procurement, and final signer, so plan resources accordingly. REX'S PATH TO PRESIDENTS CLUB: Chief Revenue Officer @ Consensus Senior Vice President of Sales @ Consensus Vice President of Sales @ Consensus Director of Sales @ HireVue RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

Here are our 15 favorite tips from all 300 episodes of the 30 Minutes to Presidents Club Podcast Top 3 Cold Calling Tips Use "The Ledge" to buy yourself a second after objections with a preset line like “This one's totally on me.” Chunk up problems by translating tactical pain into executive-level consequences to earn senior interest. Watch the full ep A Tailored Permission Opener earns attention by referencing a relevant trigger and owning that it's a cold call. Top 3 Cold Email Tips Run the triple by stacking a call, email, and LinkedIn touch to show you're a real human and boost response rates. Use relevant personalization by connecting a specific trigger to a problem you can solve. Trigger templates let you templatize personalization at scale while keeping it relevant and problem-focused. Top 3 Discovery Tips PPO (Purpose, Plan, Outcome) sets clear call expectations and avoids meandering discovery. Bucket questions steer conversations toward known problem areas while establishing credibility. Humbling disclaimers help you ask hard or sensitive questions without putting the prospect on the defensive. Top 3 Deal Process Tips The champion sandwich uses a prep call, exec meeting, and debrief to drive alignment and control. Test champions by asking how they'll justify the deal internally to reveal their true influence. Popcorn pricing anchors buyers toward larger packages with outsized perceived value. Top 3 Leadership Tips Document the wiggle (WGLL) by showing reps what great looks like with real examples and proof. Practice forward by role-playing for upcoming meetings instead of only reviewing past ones. Invert the hiring funnel by selling top candidates early, then opting them into deeper interviews and testing.

ACTIONABLE TAKEAWAYS: SPFs for Short-Term Change: Use SPFs to drive short-term behavior changes. Long-term shifts should align with consistent metrics in your "iron square" framework. Strict Holdover Rules: Allow one quarter for closing open opportunities after a territory change if they're past stage two. No exceptions ensure fairness and consistency. The Iron Square: Track rep productivity with win rate, AE-sourced pipeline, total pipeline generation, and forecast accuracy, with quota attainment as the central North Star. Customer-First Processes: Avoid letting internal rules disrupt customer experience. Build buffer zones in ROEs and territories to minimize deal handoffs. ELEANOR'S PATH TO PRESIDENTS CLUB: Head of Sales @ Retool Global Head of Commercial Retention & Regional Director of Commercial Sales @ Segment Global Head of Commercial Renewals and Retention @ Segment Head of Customer Success and Solutions engineering @ Clever Inc RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

Want more? Join the 30MPC Discovery Course TODAY and get first dibs: https://clubpass.30mpc.com/discovery-course YouTube video version: https://www.youtube.com/watch?v=y0H6G7toc9s ACTIONABLE TAKEAWAYS: Structure Your Call in 3 Parts: Great discovery calls have three distinct chapters—(1) the first five minutes to establish credibility and set your PPO agenda (Purpose, Plan, Outcome), (2) the next 20 minutes to uncover meaningful problems while building trust, and (3) the last five minutes to run your Five Minute Drill and determine if it's worth setting a next step. Use Discovery Trees to Guide Questions: Map out your prospect's problems in four layers—situation, operational pain, executive problem, and business impact. Use simple transitions like “so what?” to climb down the tree, and reverse it when execs start with big priorities. Don't just ask questions—build a roadmap first. Balance Give and Take: If you only ask questions, you're interrogating. Use playbacks, pile-ons, praise, and parallel stories to add value throughout the call and build trust. Use vertical questions to go deeper on one topic instead of jumping all over the place. Run a Tight Five Minute Drill: In the last five minutes, validate if they want to solve the problem, when they want to solve it, and how they buy. Suggest the timeline and buying process based on what you've seen work—not what they think they should do. If they're serious, schedule the next step while you're still on the call.

Join the 30MPC Discovery Course waitlist TODAY and get first dibs: https://clubpass.30mpc.com/discovery-course. FOUR ACTIONABLE TAKEAWAYS Run firmographic sprints with customer interviews. Ask about headwinds/tailwinds, KPIs, where they learn, and which sales emails stand out to better understand their world. Prep customers before training sessions. Make it clear their job is to teach the buyer's world—not give a product testimonial—so reps get true industry insight. Structure sprints for learning and sharing. Start with external education, then shift to reps sharing industry insights weekly to build confidence and fluency. Use recognition over cash to motivate. A visible $100 spiff with scarcity and public praise was more effective than a quiet commission boost. Recognition > raw dollars. PATH TO PRESIDENT'S CLUB Founder, Speaker, & Workshop Leader @ Sales Melon Author (The Transparency Sale & The Transparent Sales Leader) Managing Director @ VentureScale Chief Revenue Officer @ PowerReviews RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

Join the 30MPC Discovery Course waitlist TODAY and get first dibs + $25 off your first TWO months of Club Pass: https://clubpass.30mpc.com/discovery-course. FOUR ACTIONABLE TAKEAWAYS Assume your buyer has 60 seconds to pitch your product internally. When sending recaps or justification materials, skip the deck—send 2–3 crisp bullets that clearly communicate the top reasons to buy. Reset the agenda mid-call if needed. If a buyer jumps straight into content or things go off the rails, pause and suggest how to best use the remaining time. This keeps the call focused and productive. Use a “vibey demo” to open, then do deeper discovery later. Morgan starts with a product overview to spark curiosity, then uses the second call to dig into what resonated and why—leading to richer discovery. Reverse-engineer problems from product interest. When a buyer reacts positively to a feature, follow up with, “People usually want that because they're struggling with X or Y—what's going on in your world?” PATH TO PRESIDENT'S CLUB Strategic Account Director @ Pave Enterprise Account Executive @ Pave Healthcare & Life Science Account Executive @ Carta Client Strategist @ PwC RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

Join the 30MPC Discovery Course waitlist TODAY and get first dibs + $25 off your first TWO months of Club Pass: https://clubpass.30mpc.com/discovery-course. FOUR ACTIONABLE TAKEAWAYS KPIC + Make Them Hold It: In demos, tie each feature to the prospect's problem, impact, and desired change—then ask them to visualize how they'd use it in their world. Assume, Don't Assert: Instead of saying “we can solve this,” say “assuming we can solve this, what would change?” It builds trust and invites them into the solution. Confirm Before Next Steps: Before talking price or next calls, ask if they believe it solves their problem. If they say yes, follow up with “what stood out to you?” Tie Next Steps to Their Goals: Frame multithreading as being in their best interest. “To solve this, we'll need [person] on board. How can we make that happen?” COURTANY'S PATH TO PRESIDENT'S CLUB Director, Growth Sales @ Unbounce Director of Growth Sales @ Insightly Sales Manager, Growth @ Insightly Senior Account Executive @ Insightly Corporate Account Executive @ UserTesting RESOURCES DISCUSSED Read: Join our weekly newsletter Steal: Templates, drips, scripts

Join the 30MPC Discovery Course waitlist TODAY and get first dibs + $25 off your first TWO months of Club Pass: https://clubpass.30mpc.com/discovery-course. FOUR ACTIONABLE TAKEAWAYS Demo with KPIC + Make Them Hold It: Tie each feature to a known problem and impact, then ask how they'd use it to make the solution tangible and relevant. Use “Assuming We Can…”: Frame your solution as a possibility to lower defenses. This pulls the prospect in and gets them imagining success without feeling sold to. Reference Problem Children: Personalize the demo by naming specific team members or pain points, making it easier for the buyer to visualize solving their real-world problems. Multithread with Purpose: Frame next steps as critical to their success, not yours—“To get you what you want, we'll need Jane's input too. How can we involve her?” KD'S PATH TO PRESIDENT'S CLUB CRO @ Finally SVP of Sales and Partnerships @ Bench Accounting Practice Lead, Revenue Leadership @ Winning by Design VP of Inside Sales @ PatientPop Inc. Head of Sales Enablement & Development @ ServiceTitan VP of Sales @ SnackNation RESOURCES DISCUSSED Read: Join our weekly newsletter Steal: Templates, drips, scripts

Join the 30MPC Discovery Course waitlist TODAY and get first dibs + $25 off your first TWO months of Club Pass: https://clubpass.30mpc.com/discovery-course. FOUR ACTIONABLE TAKEAWAYS Establish a Clear Reference Policy: Without a structured reference policy, reference calls become chaotic, frustrating customers and reps alike. Set clear guidelines to manage them effectively. Optimize the Time Between Meetings: Sales doesn't just happen in meetings. Define clear steps for reps to take between meetings to maintain momentum and advance deals. Leverage Your Network for Referrals: Take a list of active discovery calls, cross-reference with Sales Navigator, and identify referral opportunities from leadership, investors, and past customers. Strategically Introduce Connections: If a referral is strong, facilitate an immediate intro. If weaker, have the AE use it as a warm door opener to build rapport before making the ask. KELVIN'S PATH TO PRESIDENT'S CLUB Sr Sales Manager @ Vitally.io Sales Manager @ Vitally.io Sales Manager @ Drift Manager, Renewals & Account Management @ Drift RESOURCES DISCUSSED Read: Join our weekly newsletter Steal: Templates, drips, scripts

Join the 30MPC Discovery Course waitlist TODAY and get first dibs + $25 off your first TWO months of Club Pass: https://clubpass.30mpc.com/discovery-course. FOUR ACTIONABLE TAKEAWAYS Match Tonality to Questions: Tone discongruence kills trust. If your tone doesn't match your question, prospects get skeptical. Adjust your delivery to align with the intent of your ask. Don't Push Economic Impact Too Soon: Mid-level managers may not care about bottom-line impact. Save deep financial discussions for decision-makers who influence the balance sheet. Three Levels of Problem Questions: First, identify the problem. Second, uncover its effects. Third, quantify the impact in time or money to drive urgency. Use Questions with Leads: Instead of open-ended asks, provide multiple-choice-style prompts. This makes answering easier and positions you as an informed advisor. KD'S PATH TO PRESIDENT'S CLUB CRO @ Finally SVP of Sales and Partnerships @ Bench Accounting Practice Lead, Revenue Leadership @ Winning by Design VP of Inside Sales @ PatientPop Inc. Head of Sales Enablement & Development @ ServiceTitan VP of Sales @ SnackNation RESOURCES DISCUSSED Read: Join our weekly newsletter Steal: Templates, drips, scripts

ACTIONABLE TAKEAWAYS: Limit Pricing Options to Three: Offering more than three options overwhelms prospects. Present only the most relevant three to simplify decision-making. Leverage Value-Add Incentives: Highlight low-cost-to-you, high-value items (like waived fees or extra features) to steer prospects toward larger packages. Present Pricing with a Range: Start with a floor price and give a range based on factors, allowing flexibility while avoiding sticker shock. Use Strategic Comparisons: Position your premium option near a slightly lower-tier offer to make it an attractive choice, while avoiding comparisons to much cheaper options. BELAL'S PATH TO PRESIDENT'S CLUB Founder @ LearnToSell.io Head of Sales @ GTM Buddy Enterprise Account Executive @ ClearBit Head of Business Development @ BioIQ RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

Join the 30MPC Discovery Course waitlist TODAY and get first dibs + $25 off your first TWO months of Club Pass: https://clubpass.30mpc.com/discovery-course. ACTIONABLE TAKEAWAYS: Give Immediate Feedback: Don't wait until later—debrief with reps right after a call while the details are fresh. Sales has lost this habit with back-to-back Zoom meetings, but it's critical for development. Create a Coaching Cadence: If you don't set a structured coaching schedule, it likely won't happen consistently. Define clear coaching sessions, including frequency and focus, to ensure real progress. Structure Call Reviews: Block two hours weekly to review calls. Assign themes (e.g., discovery, negotiation), require reps to provide timestamps, and have them self-diagnose before your feedback. Expand Practice Beyond Role Plays: Role plays aren't the only way to improve. Have reps document key impact questions, map org charts for multithreading, or identify missing stakeholders in deals. CHARLES' PATH TO PRESIDENTS CLUB Founder @ Carroll Sales Consulting VP of Enterprise Sales @ FullStory Head of Enterprise & Strategic Sales @ Recurly Sales Director @ NewsCred RESOURCES DISCUSSED Discovery Course Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Use Humbling Disclaimers: Preface tough questions with softening statements like, “I'm not quite sure how to ask this,” or “This might feel direct.” It lowers defensiveness and makes hard questions land better. Dig Into Prospect Rumblings: Prospects often hint at problems rather than state them outright. Listen for vague concerns and use a humbling disclaimer to drill deeper into the real issue. Refine Bucket Questions: Instead of stating, “Every CRO faces these three problems,” add nuance: “Many CROs I speak with mention challenges like…” This avoids defensiveness and keeps the conversation open. Follow a Clear Flow: Get permission to ask questions, surface problems without assumptions, prompt for real examples, then use humbling disclaimers to quantify impact without making prospects uncomfortable. CHARLES' PATH TO PRESIDENTS CLUB Founder @ DiscoveryCoach.io Sales Enablement Manager @ AlphaSense Lead Revenue Enablement Manager @ CB Insights Senior Sales Training Manager @ CB Insights RESOURCES DISCUSSED Discovery Course Join our weekly newsletter Things you can steal

There is an extreme over-rotation in sales on setting next steps. Setting next steps is NOT always a good thing.

ACTIONABLE TAKEAWAYS: No Last-Minute Coaching: Avoid changing a rep's game plan in the 30 minutes before a call. It signals distrust and forces them to scramble, leading to a worse outcome. Stick to One Coaching Theme: Don't introduce a new area of improvement after every call. Focus feedback on a consistent theme to drive real progress. Align on Call Emotion: Before a discovery call, ask your rep how they want the prospect to feel. This sets the right tone and helps shape their delivery. Know Your Role in Calls: As a manager, decide if you're leading, coaching, or just reading the room. Adapt based on the rep's experience level and the call type. ALEX'S PATH TO PRESIDENT'S CLUB: Founder & CEO @ Alluviance Director of Sales Commercial @ Outreach Director of Sales Corporate @ Outreach Territory Account Executive @ Microsoft RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Deflect Product Questions Early: When a prospect asks about your product upfront, redirect by asking what's happening in their business that made them look in the first place. Avoid the trap of leading with features. Reduce Technical Objections: If a prospect fixates on a small technical blocker, refocus on the bigger business problem. Aligning on major pain points can make minor technical concerns less of a deal-breaker. Dig Beyond Surface Problems: Low win rates aren't the real problem. The true impact is missing revenue targets, losing reps, or struggling to hit quota. Always tie issues to business consequences. Identify the Root Cause Before Solving: Before proposing solutions, confirm the real problem, its impact, and the root cause. Then present your solution in a way that connects all three. KEENAN'S PATH TO PRESIDENTS CLUB: CEO @ A Sales Growth Company Author of Gap Selling VP of Sales @ 2Wire VP of Sales @ Avaya RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Provide Hypotheses, Not Generic Questions: Instead of broad questions, offer informed hypotheses to invite deeper discussion. Ask Questions to Guide Next Steps: Use questions to guide the process without being pushy, keeping the prospect engaged. Teach Process Over Just Problems: Beyond identifying issues, recommend processes (like a custom demo over a POC) to build trust. Uncover Intent Behind Extra Steps: When extra steps are requested, ask what they aim to learn to suggest simpler options. DAN'S PATH TO PRESIDENTS CLUB: Senior Vice President of Global Sales @ Challenger VP of Sales, Account Management @ Challenger VP of Sales, Major Accounts @ Challenger Managing Vice President, Sales & Community @ Evanta RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

PLAYBOOK TAKEAWAYS: Aim for 70% attainment and 70% participation to create a winning culture. Avoid feast-or-famine environments where only a few reps succeed. Use historical data to set quotas based on pipeline, win rates, and deal size. Every quota increase must be backed by an investment in pipeline, win rates, or deal size. Revisit quotas once per year, unless there's a massive skew in attainment. Communicate quota changes with transparency and clear justification. Avoid high attainment with low participation, which creates resentment and turnover. Quota planning should be a business decision, not just a sales decision. Keep top reps busy before adding more headcount to avoid diluting pipeline. Simple, fair comp plans drive engagement and motivation. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Create a Not-To-Do List: Identify low-value tasks to eliminate instead of just adding more effort. Free up time for strategic activities like prospecting and closing. Prioritize RGAs: Focus only on activities that create new pipeline or advance existing deals. Everything else is a distraction. Enterprise Deal Timeline: Q1 is for building a POV and landing initial meetings. Q2 is for discovery and securing an executive sponsor. Q3 is for proposal, negotiation, and procurement. Q4 is for closing. Rule of 100 for Enterprise Outreach: Target the top 20% of accounts with high potential. Reach out to 10 executives with at least 10 touches each—totaling 100 strategic touchpoints per account. PATH TO PRESIDENT'S CLUB Founder of Ian Koniak sales training/consulting Strategic Account Director @ Salesforce.com Director of Sales @ Ricoh RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Segmented Team Structure: Down-market teams focus on landing new logos, passing them to expand teams, while up-market AEs handle both acquisition and expansion with retention-based comp. Enterprise Sales Strategies: Use top-down (sell wall-to-wall) or land-and-expand approaches, with the latter yielding higher LTV by scaling through business units first. Deal Inspection Triggers: Monitor $50K deals at stage 3 for POCs and access to power, and stage 5 for mutual action plans and the paper process. Consistent Review Rhythm: Reps update pipelines Monday, managers review Tuesday, deal reviews happen Wednesday, and Eleanor finalizes calls Thursday. ELEANOR'S PATH TO PRESIDENTS CLUB: Head of Sales @ Retool Global Head of Commercial Retention & Regional Director of Commercial Sales @ Segment Global Head of Commercial Renewals and Retention @ Segment Head of Customer Success and Solutions engineering @ Clever Inc RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal 

ACTIONABLE TAKEAWAYS: Understand Rep Motivation: Identify what drives each rep—money, career growth, or exploration—then get their permission to push them toward that goal, laying the foundation for future coaching. Call Out the Situation First: Before changing a rep's behavior, acknowledge the dynamic at play so both parties are aligned. This prevents resistance and confusion. Leverage Top Performers: Coach high performers by challenging them to reach the next level and putting them in the spotlight to lead trainings, reinforcing best practices for the team. Coach in Buckets: Break down calls into sections and ensure reps get the fundamentals right before refining their style, making feedback more structured and actionable. ALEX'S PATH TO PRESIDENT'S CLUB: Founder & CEO @ Alluviance Director of Sales Commercial @ Outreach Director of Sales Corporate @ Outreach Territory Account Executive @ Microsoft RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Understand the VEX Scale: Classify prospects as Vetted (using a competitor), Educated (familiar but undecided), Cold (new to the space), or Self-Service. Tailor your approach accordingly. Ask About Their Journey: Send an email upfront asking where they are in their learning process. This helps you position the conversation at the right level. Skip Basic Discovery for Vetted Prospects: If they already use a competitor, focus on their current solution's gaps and ideal outcomes instead of re-explaining the category. Avoid Restarting Discovery: When new stakeholders join later calls, recap prior findings first, then ask how those problems impact their specific role. JAKE'S PATH TO PRESIDENT'S CLUB CEO @ Skaled Consulting VP Sales @ Nowait, Inc. (acquired by Yelp) Head of Sales & Customer Success @ Chartbeat Vice President of Sales, Success, and Sales Operations @ Glassdoor RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Identify Strategic Initiatives: Focus on big company bets that are close to revenue, such as IPOs, international expansions, or mergers and acquisitions. Double Personalize Outreach: Combine company-specific observations with industry trends to create messaging that feels hyper-relevant. Build a Strategic Research Framework: Create a table to map key initiatives (e.g., IPO readiness) on one side and sources of information (e.g., 10-K reports, CEO interviews, press releases) on the other. Leverage AI for Efficiency: Use tools like ChatGPT or Copy AI to analyze information from sources like job postings, financial documents, or industry trends. KYLE'S PATH TO PRESIDENT'S CLUB: CMO @ Copy.ai CMO @ Clari VP, Revenue Growth & Enablement @ Clari Director Sales Development & Enablement @ Clari Sr. Director Sales Development & Optimization @ Looker RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Interview Kits for Prep: Send candidates an interview kit outlining expectations, key questions, and details on interviewers. Poor answers indicate lack of prep or poor fit. Evidence-Based Questions Only: Avoid hypotheticals. Ask for proof of past performance (P.O.P.) to assess real experience and capabilities. Screening Videos Save Time: Require a three-minute video on a key trait (e.g., perseverance). Evaluate clarity, instructions-following, and presentation skills before a live interview. Live Deal Review Test: Have candidates walk through a real deal they closed. Assess how they sourced, ran discovery, demoed, and closed, treating it like an actual deal review. KD'S PATH TO PRESIDENT'S CLUB CRO @ Finally SVP of Sales and Partnerships @ Bench Accounting Practice Lead, Revenue Leadership @ Winning by Design VP of Inside Sales @ PatientPop Inc. Head of Sales Enablement & Development @ ServiceTitan VP of Sales @ SnackNation RESOURCES DISCUSSED Read: Join our weekly newsletter Steal: Templates, drips, scripts

FOUR ACTIONABLE LEADERSHIP TAKEAWAYS ChatGPT Research Triangle: Before outreach, prompt ChatGPT with the industry (including sub-industry), job title, and your product's value. This ensures messaging aligns with trends relevant to the prospect. Use Industry Jargon: Ask ChatGPT for insider terminology that VPs in specific industries use. This makes your messaging sound more credible and tailored to their world. Refine Email Sequences: Provide ChatGPT with your email templates and ask it to integrate industry-specific revenue drivers. This keeps messaging structured while adding personalization. Smarter Discovery Questions: Use ChatGPT insights to refine questions that demonstrate expertise. Instead of generic asks, tailor them to industry trends and job-specific challenges. PATH TO PRESIDENT'S CLUB CEO @ Skaled Consulting VP Sales @ Nowait, Inc. (acquired by Yelp) Head of Sales & Customer Success @ Chartbeat Vice President of Sales, Success, and Sales Operations @ Glassdoor RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

ACTIONABLE TAKEAWAYS: Signal Prioritization: Categorize signals (e.g., high-intent, time-based) with different response SLAs to ensure timely outreach. Call Blitz Culture: Multiple weekly call blitzes with a virtual sales floor create a high-energy, team-building cold calling environment. Effective Personalization: Don't rely on signals alone; combine them with company insights to craft personalized, compelling outreach. 80/20 Email Framework: Provide reps with an 80% completed template (signal, company insight, ideal state, light CTA), letting them personalize the final 20%. FLORIN'S PATH TO PRESIDENTS CLUB: Head of Sales Development @ Common Room Director of Sales @ Barley Senior Manager, Sales Development @ Loopio Manager, Sales Development @ Loopio RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

FOUR ACTIONABLE TAKEAWAYS Focus on High-Impact Problems: Prioritize fixing widespread issues over the loudest complaints. High-volume problems drive more meaningful change than squeaky-wheel issues. Leverage 2x Multipliers: Target improvements that can double key metrics rather than marginal gains. Align leadership early so they understand why other issues aren't top priority. Weekly Wiggle Wednesdays: Hold a one-hour leadership meeting to refine sales tactics. Use the four D's: define, document, demonstrate, and deliberately practice new strategies. Transparent 1:1 Tracking: Link manager-rep 1:1 docs to the director's 1:1 doc. Track each rep's key metric, issue diagnosis, and growth plan for better coaching visibility. KD'S PATH TO PRESIDENT'S CLUB CRO @ Finally SVP of Sales and Partnerships @ Bench Accounting Practice Lead, Revenue Leadership @ Winning by Design VP of Inside Sales @ PatientPop Inc. Head of Sales Enablement & Development @ ServiceTitan VP of Sales @ SnackNation RESOURCES DISCUSSED Read: Join our weekly newsletter Steal: Templates, drips, scripts

ACTIONABLE TAKEAWAYS: Permission-Based Introduction: Identify an executive, then request an intro to their top lieutenant by tying outreach to an executive-level metric they care about. Funding Intent Matters: Don't just track funding announcements—dig into how the company plans to use the money and align outreach to support that goal. AE & SDR Account Strategy: AEs select accounts, build a POV, and own outreach to execs, while SDRs focus on below-the-line contacts with AE guidance. Account Tiering System: Rank accounts as green (30-50), yellow (130), or red (30-50) based on deal size and buying likelihood to prioritize outreach effectively. MADDY'S PATH TO PRESIDENTS CLUB: Account Executive @ Webflow Account Executive @ SafeGraph Account Executive @ Procore Technologies Account Executive @ Procore Technologies Senior Business Development Rep @ Procore RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal