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Interview with Isaac Espinoza Managing Director of Root Reinsurance Company, Ltd.

January 2022 Derek Stenson

We’re starting the New Year with a focus on new technology in insurance. For this issue’s Q&A Conyers Coverage sat down with Isaac Espinoza, Managing Director of Root Reinsurance Company, Ltd. the captive reinsurer of Root, Inc., the leading mobile-first insurance carrier and the largest P&C InsurTech firm in the U.S., for a discussion on the state of the industry, why he feels that the term “InsurTech” may become obsolete, and why the Cayman Islands is a great place for established InsurTech companies to set up a captive reinsurer.

Conyers Coverage: We understand that you had a circuitous path to working in the insurance industry. Can you tell us a bit about it and your career to-date?

Isaac Espinoza: My career path has been anything but typical, but I wouldn’t have it any other way. I started out studying to be an engineer and working on a computer science degree focused on data mining, machine learning, and artificial intelligence. In today’s job market that is one of the hottest degrees you can have, but the Dotcom bubble burst while I was going to school in California so there was less demand for engineers than there had been previously. I found myself applying for internships and full-time roles in a market that simply wasn’t hiring.  Given the heavy Maths base of my degree, I started the process of getting credentialed as an actuary.

Fortunately, you don’t need a degree in Actuarial science to be an actuary, you get credentialed by passing exams.  After I passed my first exam, I had several internship offers where I took a position at Farmers Insurance and following graduation, started working at a company called Fireman’s Fund, a subsidiary of Germany-based insurance giant, Allianz. During my time there I became qualified as a Fellow of the Casualty Actuarial Society, and became intrigued by the reinsurance industry.

Conyers Coverage: What about the reinsurance industry appealed to you?

Isaac Espinoza: Reinsurance is much more open-ended than P&C insurance. The agreements you make are more customised and it’s also a heavier relationship business. When people talk about reinsurers they often refer to how technical they are, but it’s also very business-oriented and relationship-based. When I look at a reinsurer compared to an insurer, the main difference is the number of people involved – you still deal with big transactions but it’s really cool to be part of a smaller deal team.


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Interview with Isaac Espinoza Managing Director of Root Reinsurance Company, Ltd.


Derek Stenson

Cayman Islands   +1 345 814 7392


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