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 Head of Sales, Americas at Notion, where she recently spearheaded record-breaking 2024 growth and led the expansion of Notion’s AI‑powered go‑to‑market strategy across North America. She previously held senior roles at Slack and Salesforce, and co‑founded 20sales.vc—a venture fund accelerating SaaS sales leaders.

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