#73 - Becoming the CEO of your territory in your path to President’s Club (Anthony Cessario, VP of Industries & GTM Solutions @ Clari)

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. 🎙 ACTIONABLE TAKEAWAYS: Use ChatGPT to explain your prospect’s business “like I’m 10” for clarity and messaging insight. Beat your prospect to the punch with a hypothesis to steer discovery toward winnable problems. Mirror high-level goals and “before state” language to make case studies resonate more deeply. Size the “status quo” problem by auditing lost pipeline, then use it to build urgency and buy-in. JEN’S PATH TO PRESIDENT’S CLUB: Founder @ Demand Gen Head of Growth @ Lavender Chief Evangelist @ Challenger Enterprise Sales Director @ Challenger RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST”

6 Touko 202535min

🎙 ACTIONABLE TAKEAWAYS: Coach reps on storytelling—it’s a foundational skill that improves every sales conversation. Evaluate rep interview performance based on the questions they ask, not just their answers. Run mock pitches with target persona info—test prep, not product knowledge. Benchmark rep candidates one level below your best AEs to fairly assess potential. ANDREW’S PATH TO PRESIDENT’S CLUB: Head of Sales @ Superhuman Sr Director of Sales @ Scale AI Head of Global Email Sales & GTM @ TwilioManager Enterprise Sales @ Twilio RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST”

5 Touko 202536min

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. 🎙 ACTIONABLE TAKEAWAYS: Win the first 30 days or lose the next 300—structure onboarding to build lasting habits. Idiot-proof dashboards so any leader can read them like a story, not a spreadsheet. Track rep engagement by reverse-sorting Slack conversations and checking in every 6 weeks. Use low-stakes "training leads" before letting reps handle high-revenue inbound. JONAH MANDEL’S PATH TO PRESIDENT’S CLUB: VP of Global Sales @ Guesty VP of Sales & Customer Success @ Capchase VP of Sales & Partnerships @ Alibaba Sales Manager @ ShopKeep RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST”

1 Touko 202536min

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

29 Huhti 202533min

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

28 Huhti 202536min

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

24 Huhti 202534min

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 30MPC Big Team Demo Deck

22 Huhti 202532min

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

21 Huhti 202536min