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

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

Episoder(1428)

20VC: Figma's 250% Pop - The Greatest IPO Mispricing Ever | Meta and Microsoft Blowout Quarters: Broken Down | Cognition Raises at $15BN and Ramp at $22BN | CRV Downsizing and What It Means for LPs and GPs

20VC: Figma's 250% Pop - The Greatest IPO Mispricing Ever | Meta and Microsoft Blowout Quarters: Broken Down | Cognition Raises at $15BN and Ramp at $22BN | CRV Downsizing and What It Means for LPs and GPs

Agenda: 00:00 – The Worst IPO Mis-Pricing Ever: What Really Happened at Figma 02:30 – Fidelity vs Founders: How Important is Fidelity When Going Public 07:00 – Why Founders Secretly Want a Pop, Even I...

7 Aug 20251h 20min

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20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Ron Gabrisko is the Chief Revenue Officer at Databricks, where he joined in 2016. Under his leadership, Databricks has scaled from $0 to $3.7BN annualized revenue. He has grown the sales team from 0 t...

4 Aug 20251h 15min

20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

20VC: Inside Carnegie Mellon's $4BN Endowment | Why 90% of LPs Shouldn't Invest in VC | The $140BN Problem with Multi-Stage Funds | The Hidden Math Behind DPI, TVPI, and Illiquidity with Miles Dieffenbach

Miles Dieffenbach is Managing Director of Investments at Carnegie Mellon University, where he helps oversee a $4 billion endowment with a focus on venture capital, private equity, and alternative inve...

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20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

20VC: Benchmark Loses Another Partner | Elad Gil Raises a Monster $1.5BN Solo GP Fund | Why Apple Need a Management Overhaul | Why Google is the Best Performing Hyperscaler | Will Cursor Hit $4BN ARR & Lovable $400M ARR by EOY 2026?

Agenda: 00:00 - Why Benchmark Is Bleeding Partners (and Why That's the New Normal) 04:57 - "I Wouldn't Leave Benchmark… Unless I Had THIS" — Jason on Brand vs Autonomy 09:01 - The Rise of the Solo GP ...

31 Jul 20251h 21min

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

20VC: a16z's Martin Casado on Anthropic vs OpenAI: Where Value Accrues | Cursor vs Replit vs Lovable: Who Wins and Who Loses | The One Sin in AI Investing | Why Open Source is a National Security Risk with China

Martin Casado is a General Partner @ a16z where he leads the firms $1.25BN infrastructure fund. At a16z, Martin has led investments in companies like Cursor, dbt Labs, and Fivetran to name a few. Befo...

28 Jul 20251h 10min

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

Fernando Fanton is one of the most respected product leaders in Europe, having held Chief Product Officer roles at Monzo and Just Eat. He previously led product and tech at Rappi, one of Latin America...

27 Jul 20251h 7min

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

20VC: Lovable Raises at $2BN & Hits $100M ARR | Is Cursor Worth $28BN at $1BN in ARR | How Do All Providers Deal with Anthropic Dependency Risk | Are Seed Funds F******: Have Mega Funds Won | Figma IPO Breakdown: Where Does it Price?

Agenda: 00:00 – Did Jason Just Kill Replit? 03:45 – Why Claude Lies To You and Cannot Be Trusted 06:50 – You Cannot Trust Agents. Period. 10:20 – Why Windsurf Was Dead Without Claude 12:30 – Cursor v...

24 Jul 20251h 21min

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

20VC: Scaling to $1BN+ in Revenue with No Funding: Surge AI | The Most Insane Scaling Story in Tech |

Edwin Chen is the Founder and CEO of Surge. Founded in 2020, Surge has scaled to $1BN+ in revenue with zero external funding. At the same time, their competitor, Scale.ai raised over $1.3BN to reach $...

21 Jul 20251h 6min

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