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InsTech - insurance & innovation with Matthew Grant & Robin Merttens

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

InsTech - insurance & innovation with Matthew Grant & Robin Merttens

InsTech

Entrepreneurship, Investing, Business

4.850 Ratings

🗓️ 14 September 2025

⏱️ 31 minutes

🧾️ Download transcript

Summary

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. 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! Sign up to the InsTech newsletter for a fresh view on the world every Wednesday morning. 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 [email protected] 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.

Transcript

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0:00.0

Hello, welcome or welcome back to the Instac podcast, Soya here.

0:14.7

And this week, Robin is joined by Jonathan Spry on a rather interesting conversation involving cyber.

0:21.9

Jonathan is the CEO and co-founder of Inveloid Risk, one of the earliest voices pushing portfolio

0:27.4

level data-driven underwriting in cyber.

0:30.2

In this episode, Robin digs into the nine-year journey from MGA to hybrid underwriter

0:35.3

across Lloyds and Bermuda, why casual inference matters more than buzzwords,

0:40.4

and how portfolio optimization changes the game for tail risk. We also explore AI liability,

0:47.1

where it lives, who should carry it, and whether it's becoming a new class or a silent exposure,

0:52.6

and what algorithmic underwriting really means in a softer market.

0:56.9

Lean in, pour yourself a coffee and enjoy the conversation.

1:00.1

There's one surprising take on the future of cyber you won't want to miss.

1:08.1

Well, it's Intertech podcast time again and my guest today is Jonathan Spry. He's the CEO and co-founder

1:15.6

of Envelop Risk. Welcome, Jonathan. It's great to be here, Robin. Hi.

1:20.6

Well, you're a longstanding supporter of Instects. I see from my records that you've been

1:24.7

a member since 2019, and then you've never done a podcast.

1:28.5

That's either because we're mean or because you're shy. Which one is it?

1:33.5

I suspect it's probably more than I'm a little bit shy. So Inveloc's nine years old.

1:39.0

We've got a sort of backstory to tell, a little bit of history to catch up on.

1:43.1

For those who don't know, tell us what

1:44.8

Invelop Risk does. Well, Invelder Risk was really set up as a technology company. We're founded on the

1:50.4

principles of machine learning and analytics, but we made a decision to focus on cyber early on in

1:56.8

our being and have chosen equally to earn our living from underwriting. So we set up, firstly, an

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