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

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The Twenty Minute VC

Finance, Venturecapital, Tech News, News, Siliconvalley, Technology, Investing, Startups, Business

4.4 • 637 Ratings

🗓️ 27 June 2025

⏱️ 77 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	This is 20 Sales with me, Harry Stebbing. Now, 20 Sales is the monthly show where we sit down with the best sales leaders in the world to discuss how they start and scale sales teams successfully.
0:10.0	Today we have one of the best joining us. Kim Graves. Kim leads sales, pre-sales, customer success and renewals at Notion, where she recently spearheaded record-breaking 2024 growth and led the expansion
0:22.5	of Notion's AI-powered go-to-market strategy across North America. She's also held incredible
0:27.2	roles at Slack, where she spent an incredible seven years and Salesforce, and she also co-founded
0:32.8	20 sales, where she's invested in some of the best go-to-market technologies. But before we dive into the show today, is your finance team a cost center tied up in
0:42.3	enforcing policies, bogged down by cumbersome processes, and drowning in operational busy
0:47.7	work? Well, what if you could unlock seamless, strategic finance that actually fuels your
0:52.8	business growth? This is why leading global growth
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1:00.8	with conversational AI to deliver best user experience for everybody dealing with company spending.
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2:08.5	And speaking of incredible companies, let's talk about Brex, the ultimate financial stack for startups.
	...

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