Product Roadmap: Q3 2024 (Book launch, care package, 5 weeks of phones, host change)

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 

24 Feb 39min

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

20 Feb 41min

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

18 Feb 39min

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

17 Feb 40min

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

13 Feb 40min

FOUR ACTIONABLE 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

11 Feb 42min

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

10 Feb 35min

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

6 Feb 41min