"We were adding customers, losing customers, adding customers, losing customers. We were stalling."

Gaurav Bhattacharya had $2.5M ARR and 50 customers. On paper, things looked fine. But momentum wasn't there. Instead of pushing harder, he split his company in two – and nine months later, Jeeva AI had 10,000 users and 300 enterprise customers.

In today's episode, I'm joined by Gaurav Bhattacharya, Founder and CEO of Jeeva AI. After successfully exiting his first healthcare AI startup, Gaurav spent five years building a data intelligence platform to $2.5M ARR before recognising it would never become the great business he wanted. His solution? Split the team in two – one to keep the lights on, one to prove product-market fit for a completely new idea. The result was Jeeva AI, a sales intelligence tool that exploded to 10,000 users in nine months.

Together we unpack:

• How to decide when a "good" business will never become great
• The two-team strategy: keeping lights on whilst proving new product-market fit
• Why pattern recognition is the most underrated founder skill
• How to pivot without killing team morale or burning investor relationships
• The shift from enterprise sales to PLG (and why it required completely different muscles)

👆 If your business is functioning but not truly moving, or you're wondering whether it's time to pivot, this conversation will give you a framework for thinking through your next step.

About Gaurav Bhattacharya

Gaurav Bhattacharya is the Founder and CEO of Jeeva AI. After successfully exiting his first healthcare AI startup, Gaurav spent five years building a data intelligence platform to $2.5M ARR before pivoting to Jeeva AI – a sales intelligence tool that grew to 10,000 users and 300 enterprise customers in nine months. His journey proves that knowing when to walk away is as important as knowing when to persist.

Connect with Gaurav Bhattacharya on LinkedIn: https://www.linkedin.com/in/gaurav-agentic/

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