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

20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

04 Apr 2025

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Ishan Mukherjee is the Co-Founder/CEO of Rox, a Sequoia-backed AI-powered sales productivity platform. Before Rox, he was the Chief Growth Officer at New Relic where he scaled the self-serve business from $0-$100M in ARR. Prior to New Relic, Ishan founded Pixie Labs (acq by New Relic). Before that he led product at Siri Knowledge Graph at Apple, Lattice Data (acquired by Apple), Premise Data, and Amazon Robotics. Ishan was also an early engineer in Kiva (acquired by Amazon) where he joined after graduating from MIT. In Today’s Episode We Discuss: 04:50 Biggest Lessons Scaling New Relic’s PLG to $100M in ARR 05:59 How to Do PLG and Enterprise at the Same Time 07:00 How to do Content in a PLG World 08:50 Performance Marketing or Organic Content: What Works for PLG 10:27 Why You Should Stop Marketing at Events 11:47 Why SEM is a Cartel 14:15 Why Unpaid Design Partners are BS 17:17 How AI Changes the World of Enterprise Sales: Commit-Based vs. Usage-Based  20:49 How to do Sales Compensation Plans 24:44 How to Ramp New Sales Reps 25:03 The Impact of AI on Sales Research 29:18 How to do Deep Customer Research in an AI World 35:56 Changing Spending Patterns in SaaS 41:41 Retention and Churn in Enterprise AI 43:31 The Future of Sales Teams with AI 44:45 Hiring and Scaling Sales Teams 54:28 Quickfire    

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