Q&A: Gareth Haagman on winning the Young Achiever in Technology and Innovation Award 2025

1. Congratulations on winning Insurance Times’ Young Achiever in Technology and Innovation Award 2025! Can you give our readers some background on what your career has looked like to this point?

I started my career at Goldman Sachs, where I was working as a software engineer in asset and wealth management – that was a very exciting time for me and I got to do a firm-sponsored master’s degree at the same time.

That was around 2023 and, at the same time, the artificial intelligence (AI) boom happened. I got to work on some of the early AI projects in asset management that Goldman was rolling out.

Then I moved to Testudo. Testudo is trying to underwrite generative AI liability risk, which is a really cool and interesting problem. I met [Testudo co-founder] Mark Titmarsh at Goldman, which is how that got kicked off.

2. You won the award for the work you were doing at Testudo. What exactly were you working on?

I think one of the really interesting innovations that I worked on at Testudo was how to solve the lack of data availability for generative AI risk.

There are a lot of people right now who are using things like benchmarks on AI models, or performance evaluations of some kind [to assess risk] and our thesis is that that’s not actually a very good predictor of liability risk.

You can have the best performing model in the world, but that doesn’t mean you aren’t going to get sued for your model doing something it shouldn’t do.

What we were working on at Testudo was a way to mine data from existing lawsuits. Our thesis was essentially ‘via negativa’, or avoidance of the bad.

Our underwriting approach was to find out all the stuff that’s already gone wrong and avoid that.

That information, although it sounds basic, isn’t available. People don’t know where AI has gone wrong, there is no centralised or complete view on that.

The technology that I was building was a way to mine federal and state lawsuits in the US, to keep an up-to-date, daily record of all the new lawsuits and to extract features from those lawsuits that were useful to underwriting that risk.

3. After you won the award, what feedback and congratulations did you get?

I had a lot of positive feedback and not just from within [Testudo]. Mark was super happy about it – I learned everything about insurance from him, so I think it was great for him to see that someone he had been teaching about the market had gone out and won an award.

I was recently in Lloyd’s Lab, and they were all super happy for me. All the guys I’d worked with, they were coming up to me and saying congratulations – that was a really positive thing for me. I had a lot of people from the various syndicates and brokerages that I’d been speaking to reach out.

4. What are your plans for your future career?

I am joining [agentic AI subscription and pricing firm] Paid in the coming weeks. That’s still in the AI space, but it’s not insurance.

My five to 10 year plan is to go and found my own company, in the AI space most likely, assuming all things continue to go well.

Where I’m at right now is I’m still very much enjoying meeting tons of different people and speaking to different markets and industries. The approach that I’m taking is always that I want to be learning from everyone that I can possibly learn from.

I think insurance was a fantastic move for me. I’ve been in a few different industries and I’d say that insurance was the warmest welcome that I got.

Did your award win help you at all during the application for your new job?

It did come up. I think they said, ‘it’s nice to see that you’ve come into an industry very quickly and won an award’. I tried to showcase it as part of my ability to learn.

It was a very positive thing. I love the [insurance] market and I’ll be back at some point as well – this isn’t goodbye for Gareth in insurance, this is just the next chapter.