How Jeeves Scaled Fintech to 25 Countries | CEO Dileep Thazhmon Interview Artwork

Interviews with Leaders in Fintech & Web3

Hear from industry leaders about what is fintech and web3, how to get into it and how to make a mark in the fastest growing sector in the world. Work in Fintech Founder Matt Cheung teams up with Founder Members to interview fintech and web3 founders, CEOs and CTOs about what you can do to gain an edge in fintech and web3. Essential listening for any student, young professional or curious person looking to secure a role in fintech, web3, banking or finance. #fintech #web3

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Interviews with Leaders in Fintech & Web3

How Jeeves Scaled Fintech to 25 Countries | CEO Dileep Thazhmon Interview

April 25, 2026 • Work in Fintech • Season 2 • Episode 24

0:00 | 40:01

Today's guest is Dileep Thazhmon, Founder & CEO of Jeeves, one of the fastest-scaling fintechs to come out of Y Combinator (YC S20)

Before Jeeves, Dileep built PowerInbox (later Jeeng) to $40M in revenue and a ~$100M exit. While running PowerInbox, Dileep ran headfirst into the chaos of cross-border payments, multiple cards, multiple bank accounts, different payment rails in every country, making his CFO's life a daily reconciliation nightmare.

After his exit, he set out to solve that exact problem and founded Jeeves. Today it's valued at over $2B, operates in 25 countries, and powers global spend for thousands of companies.

In the full episode, we cover:

- His early years and the unlikely path that led him into fintech
- How the idea for Jeeves came directly out of his own pain as a founder
- Why B2B fintech is a completely different game from B2C
- His experience going through Y Combinator
- What it's like having Ben Horowitz and a16z as investor
- The fintech opportunities he's most excited about right now
- His hiring philosophy
- The one piece of advice he'd give young graduates

If you're in fintech, building a company, or curious how global fintech actually gets built, this one's worth your time.

Connect with Dileep Thazhmon:

X: https://x.com/thazhmon
LinkedIn: https://www.linkedin.com/in/thazhmon/

Matthew Cheung (Host & Founder Work in Fintech):
https://www.linkedin.com/in/matthewcheung50/

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