The AI Playbook for Sales: How to Book More Meetings & Close More Deals With AI | Jake Dunlap | Ep. 286 (Sell)

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

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

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

4 Feb 41min

ACTIONABLE TAKEAWAYS Know Competitors' Fiscal Periods: Be aware of when your competitors’ fiscal periods end to anticipate price drops and position yourself better. Phased Approach: When price matters, propose only the essentials for day one to make your quote smaller and easier to accept. Timeline Stack: Identify key timeline drivers, like contract end dates or business seasonality, to create urgency. Turn Want into Why: During discovery, dig deeper to find the real business problem behind a customer’s desire for change. JOHNNY'S PATH TO PRESIDENTS CLUB Commercial Account Executive @ Talkdesk Enterprise Sales Development Manager @Talkdesk Team Lead, Enterprise Sales Development @ Mimeo Enterprise SDR @ Mimeo RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

3 Feb 41min

Nick, Armand, and Mark Kosoglow talk through how and when you should make different sales hires as your sales team grows. ACTIONABLE TAKEAWAYS: Hire Builders First: Early sales hires should create processes, while later hires follow them. CEO Sales Involvement: Founders should sell until they define the product and process, then transition to AEs. Scaling Key Roles: Maintain a 1:1 AE to SDR ratio early, shifting to 2:1 later. Hire RevOps early; SE and enablement depend on need. Manager & Director Timing: Keep managers at 8 reps max, stretching to 10-12 if needed. Delay director hires until managing at least three managers. RESOURCES DISCUSSED: Stages of Sales Leader Episode Join our weekly newsletter Things you can steal

30 Jan 55min

ACTIONABLE TAKEAWAYS: Align Messaging to Roles: End users want simplicity, managers focus on team metrics, and execs care about goals and risk. Match your message accordingly. Use Credible Content: Share third-party sources like Gartner or HBR instead of only company case studies to build trust. Amplify the Problem Early: Send data or insights highlighting the problem’s urgency in the early stages of the sales cycle. Simplify Implementation Late: Provide resources like change management guides to ease rollout and reduce risk. KRYSTEN'S PATH TO PRESIDENTS CLUB: Founder @ KrystenConner.com Enterprise Account Executive @ UserGems Enterprise+ Account Executive @ Outreach Enterprise Accounts, Financial Services @ Tableau Software Strategic Accounts @ PowerSchool RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal

28 Jan 40min