Tapojoy Chatterjee is Vice President and Head of Product at Swiggy Food and Dineout Experiences. Before Swiggy, he spent nearly a decade at Amazon, where he helped build the Amazon Ads business in India, launched miniTV, and even holds a US patent.

In this rich, candid conversation, Tapojoy shares:

• His 3-step playbook to stay ahead of paradigm shifts like AI

• The 4 habits that quietly compound into career breakthroughs

• Using side projects as powerful tools to bridge skill gaps

• Exactly what it takes to get promoted—whether you're at a lean startup or a layered org

If you want to learn what it takes to build a 10X Career, this episode is for you!

In The Career Clinic, Tapojoy answers your questions about cross-functional collaboration and execution, providing clear frameworks to tackle tricky workplace like:

• How to unblock projects when the other team won’t budge

• How to say no at work without sounding defensive

• How to update leadership the smart way

• How to hold peers accountable without ruining relationships

  
  

  Some key takeaways:

• Raise your hand before you think you’re ready: From his first school computer class to product management at Amazon—Tapojoy didn’t wait for perfect readiness. He jumped in, learned fast, and delivered.

• Compound curiosity into a career advantage: Intentional, curiosity-led learning from side projects and observation is as powerful as formal training.

• Build a bias for execution: Credibility comes from consistent delivery—track records matter.

• Take intentional career bets: Be deliberate about placing smart bets on growing trends. Early risk-taking has limited downside, but exponential upside.

• Master saying no (and yes): Protect your energy by learning to decline clearly, transparently, and kindly—show trade-offs clearly.

• Promotions differ by company size: Understand that promotions in startups rely heavily on your direct impact with founders, while large orgs demand cross-functional visibility and wide stakeholder support.

• Reflection is a career accelerator: Don’t wait for annual reviews. Regular self-reflection (weekly or daily) sharpens judgment and growth.

In this episode we cover:

Referenced:

• The CEO Factory by Sudhir Sitapati https://amzn.in/d/akQtm8F

• The Lean Product Playbook by Dan Olsen https://amzn.in/d/hThFJrP

• Only the Paranoid Survive by Andy Grove https://amzn.in/d/2t6mAlC

• The Power of Moments by Chip Heath & Dan Heath https://amzn.in/d/iYbL9yk

Editing and production: GreyLabs Media https://www.instagram.com/greylabsmedia/

Recording: https://riverside.fm/