The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

27 Jun 2025

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Kim Graves is GM, Americas at Notion, where she oversees all Sales and Customer Success efforts across the region. She brings extensive experience in building and scaling high-performing sales organizations, most notably at Slack where she helped grow revenue from $6M to over $1.5B. In addition to her operational role, Kim serves as a founding partner at 20SALES, a GTM-focused VC firm, where she advises early-stage companies on scaling revenue and optimizing sales processes. Agenda: 07:00 – The Secret to Winning a Discount Conversation 09:30 – Notion's Wild New Sales Method: Mindsets Over Stages 12:00 – Why Great Sellers Never Talk Product Too Soon 14:00 – How Slack Avoided the Biggest PLG Trap of All 17:00 – The Fatal Mistake Founders Make Layering Sales on PLG 20:00 – The "Renaissance Reps" That Build Billion-Dollar Motions 23:00 – How to Spot True Grit in a Sales Hire (Without Asking Directly) 26:00 – The Case Study Test That Filters Out Bullshitters 30:00 – The Real Reason Most Reps Fail Onboarding 33:00 – Should Reps Own Their Own Pipeline? Kim's Take Is Clear 36:00 – Why Cold Calling Works in 2025 (And Nobody Does It) 39:00 – The Sales Team Audit: The REKS Framework That Changes Everything 43:00 – How to Avoid Hiring the Wrong Rep Under Pressure 45:00 – When Sales Feels Second Class: PLG vs Enterprise Tension 47:00 – The One Thing Reps Still Do That AI Will Obliterate 50:00 – AI Sales Tools: Why Every Startup Is Failing to Get It Right 53:00 – Will We Have More or Fewer Reps in 5 Years? 56:00 – Enterprises Are Scared of AI – Here's How You Break In Anyway 59:00 – Kim's Secret for Getting Past Gatekeepers and Fake Champions 1:09:00 – Kim's Hardest Phase at Slack and How She Survived It

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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

This episode hasn't been transcribed yet

Other episodes from The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

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