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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

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.

01:09:26

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Episode guests

Ishan Mukherjee

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Episode notes

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Quick takeaways

Sales team sizes may decrease by 10-20%, focusing on a smaller number of highly effective salespeople who build lasting relationships.

The rise of product-led growth necessitates a balance between accessible product strategies and the demands of enterprise sales.

AI's integration into sales operations will require companies to rethink customer engagement and adapt training practices for evolving skills.

Deep dives

Future of Sales Teams

Sales teams are expected to shrink significantly, potentially by 10 to 20% in size compared to current levels. This shift is attributed to the realization that the top 10% of salespeople generate a staggering 90% of revenue. As the sales landscape becomes increasingly challenging, it's believed that many in the current generation may not be prepared for the heightened competition ahead. This underscores the need for a paradigm shift where fewer, more effective sales professionals focus on building long-term, non-transactional relationships with clients.

Intro

5min

Navigating Product-Led Growth Challenges

10min

The Evolving Sales Landscape

14min

Understanding Buyer Psychology and Evolving Software Expectations

2min

Revolutionizing Sales with Data and AI

16min

Navigating the Sales Landscape in AI Software

12min

The Importance of Team Building and Pragmatic Hiring in Startups

2min

Elevating Sales Through Gamification

6min

Transformative Sales Strategies and Innovative Solutions

4min

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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