That Worked

Paul Monasterio - CEO and Co-Founder of Kalepa: Being Transparent, Finding the Ideal Co-Founder, and First Customers


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Paul Monasterio is the CEO and Co-Founder of Kalepa. Kalepa's AI-powered Copilot workbench empowers underwriters to write more profitable business faster. Kalepa was recognized as one of the most innovative insurtechs in the world as part of FinTech Global’s Insurtech 100 in 2022 and 2023.


Before founding Kalepa, Paul was an executive at Facebook, Mastercard, and Applied Predictive Technologies. Paul also graduated with a PhD in Nuclear Science and Engineering at MIT. 


In this episode, you’ll learn:

  • What to look for in a Co-Founder
  • The importance of finding the right first customer
  • The benefits of having sales experience as a founder
  • The importance of full transparency in every interview 
  • The value of working for a startup before starting a company 


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That WorkedBy Callan Harrington