Jonathan Spry, CEO and co-founder of Envelop Risk, joins Robin Merttens for a deep dive into how data science, AI and portfolio-level modelling are transforming cyber reinsurance. As one of the earliest voices in the industry championing machine learning and systemic risk analysis, Jonathan shares what he's learned over nine years of building Envelop into a leading hybrid underwriter operating across London and Bermuda.

In his own words, this episode is about building smarter ways to understand, underwrite and capitalise on emerging risk — with cyber as just the starting point.

What you'll learn:

Why Jonathan and his team focused on cyber risk and portfolio-level underwriting from day one
The rationale behind favouring systemic insights over individual vulnerabilities
How causal inference provides a leap forward in predicting tail events
Why AI liability is already creating new market opportunities
The need for creative, multi-source data strategies beyond traditional claims
Why Envelop steers clear of SaaS and keeps underwriters embedded in the modelling process
How algorithmic underwriting fits into the next chapter of insurance innovation
Candid thoughts on the AI hype cycle — and what matters more than the buzz

Jonathan also talks through Envelop's shift from MGA to reinsurer, how to think long-term in a volatile market and what kind of partnerships are needed to unlock new forms of risk.

Book recommendation from Jonathan: The Book of Why by Judea Pearl and Dana Mackenzie.

If you like what you’re hearing, please leave us a review on whichever platform you use or contact Robin Merttens on LinkedIn. You can also contact Jonathan Spry on LinkedIn to start a conversation!

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Continuing Professional Development

This InsTech Podcast Episode is accredited by the Chartered Insurance Institute (CII). By listening, you can claim up to 0.5 hours towards your CPD scheme.

By the end of this podcast, you should be able to meet the following Learning Objectives:

Identify the structural and economic drivers pushing insurers toward algorithmic and portfolio underwriting.
Produce a strategy for aligning capital, analytics and data science in cyber reinsurance underwriting.
Summarise how Envelop Risk evolved from an MGA to a hybrid reinsurer and the rationale behind its capital partnerships.

If your organisation is a member of InsTech and you would like to receive a quarterly summary of the CPD hours you have earned, visit the Episode 372 page of the InsTech website or email cpd@instech.co to let us know you have listened to this podcast.

To help us measure the impact of the learning, we would be grateful if you would take a minute to complete a quick feedback survey.

Jonathan Spry, Co-founder & CEO: Envelop Risk: How portfolio thinking and data science are rewiring cyber reinsurance (372)

InsTech - insurance & innovation

Jonathan Spry, Co-founder & CEO: Envelop Risk: How portfolio thinking and data science are rewiring cyber reinsurance (372)