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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

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Apr 4, 2025
Ishan Mukherjee, Co-founder and CEO of Rox, brings deep insights from his leadership at New Relic, Apple, and Amazon. He discusses how AI is revolutionizing enterprise sales, leading to more efficient teams and faster ramp-ups for sales reps. Ishan critiques the role of unpaid design partners and explains why content strategy is vital in a product-led growth world. He also emphasizes the importance of understanding buyer psychology and advocates for a shift towards usage-based revenue models to meet modern demands.
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ADVICE

Focus and Invest

  • Focus on a specific target audience and tailor your go-to-market strategy accordingly.
  • Invest in the product so it sells itself and then layer in humans to handle commercial aspects.
ADVICE

PLG Investments

  • Prioritize performance marketing and organic content for PLG.
  • Treat free tier users as in the consideration phase, not as converted customers.
ADVICE

Design Partners and Betas

  • Prioritize paid design partners with pilot clauses.
  • Open betas, even if imperfect, reduce sales friction and demonstrate shipping capability.
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