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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

69 min • 4 april 2025

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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