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
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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