The traditional underwriting career path is becoming less linear, with new roles emerging alongside the specialist route that has long defined the Lloyd's market.
Henry Watts (pictured left), underwriter – portfolio solutions, and Calum Williams (pictured right), deputy head of digital trading, both at AEGIS London, followed very different routes into underwriting before moving into roles that barely existed a decade ago. Neither sees their career as unusual. Instead, both believe it reflects broader changes taking place across the Lloyd's market.
Neither Watts nor Williams arrived in underwriting by design. Both began their careers in the broking world. Watts specialised in fine art and specie broking before moving into underwriting, where he spent more than a decade across fine art and specie and portfolio-focused roles before joining Portfolio Solutions when AEGIS London restructured its underwriting divisions in 2025. Williams started in reinsurance broking, joined the terrorism team, became involved with the OPAL quote-and-bind platform during its early development and gradually transitioned into digital trading, where he now oversees its day-to-day operation across underwriting, product development and distribution.
"I think it's quite hard when you go into insurance – you don't know every single role that is available," Williams said. "You get your foot in the door, and then as time goes on and you get more involved in the business, you understand what roles are available."
The entry point, they suggest, rarely determines where a career ultimately ends up. For both, curiosity, adaptability and a willingness to move across disciplines are becoming just as important as technical expertise. For Watts, the decision was also personal.
"I just didn't see myself underwriting in one single class for the next 30 years as a deep specialist," he said. "I wanted a role that gave me more visibility across multiple classes, structures and routes to market within one portfolio. Not every plan involves leading in every class. For us, following is not a compromise – it's a strategy."
The roles Watts and Williams now occupy demand a broader skillset than those that traditionally defined underwriting careers. Both argue that the fundamentals remain essential, but are no longer enough on their own.
Underwriting a portfolio rather than simply pricing an individual risk is becoming increasingly important. So too is understanding the full distribution chain, from retail broker to wholesaler and into the London market, alongside the technology reshaping how business is traded.
"More and more underwriters need to have that ability to not just stick in their lane for their whole career," Williams said. "Particularly in my role – whilst I don't know how to code and I can't connect two platforms together via API, I can understand how to use it and the potential of technology like that."
Artificial intelligence sits at the centre of that shift, although Williams is sceptical of suggestions that it will replace underwriters.
"There's so much talk about AI replacing people and just going to do the underwriting for you – but I don't believe that," he said. "It will allow you to do more. But you need to have the underwriting context and market experience to ask the right questions and see whether the analysis it gives you back is correct."
He sees that challenge play out regularly when working alongside data scientists.
"The first answer they give you will not be correct. It may be what the data says, but it won't have any context behind it. Only with underwriting experience will you be able to recognise that and push back."
Watts agrees that the core discipline of underwriting remains unchanged.
"That core skill – understanding the full value chain, knowing whether a risk is well-priced or not – hasn't gone away," he said. "If you're not able to utilise the tools available to you, you're going to be left behind by people who will."
For younger underwriters planning their careers, both believe there are long-held assumptions worth questioning.
The idea that success means becoming the recognised authority in a single class remains valuable, and Lloyd's will always depend on deep specialists. But, they argue, it is no longer the only way to build a successful underwriting career.
"That's still incredibly valuable. Lloyd's is built on those kinds of specialists," Watts said. "But that's no longer the only path or the only mark of a successful underwriting career."
Williams also believes the assumption that insurance recruits only from insurance is changing. Data scientists, software engineers, product developers and specialists from banking, retail insurance and other sectors are increasingly becoming part of the London market workforce.
"We used to be what, 60 or 70 underwriters and 30 support staff," Williams said. "Now the percentages are probably the other way – underwriters, and then the rest are all ops, engineers, IT."
Ten years ago, multi-class underwriting roles that still kept people close to trading were relatively uncommon outside senior leadership. Today, portfolio solutions, digital trading and technology-enabled underwriting are creating opportunities that allow people to build broader careers while remaining active underwriters.
"You're no longer confined to a single class career path," Watts said. "Today you can move into multi-class, more portfolio-based roles while still being a trading underwriter, still talking to brokers, still putting lines down. I don't think 10 years ago there was as much of that."
Neither believes these newer career paths will replace traditional underwriting. Instead, they see them as expanding the range of opportunities available to people entering the market, while leaving the need for deep technical specialists unchanged.
"You find out more and realise there's different roles – and you want to get involved," Williams said. "The changing nature of the insurance industry has created new roles that have opened up opportunities to pivot from the traditional class underwriter role into something slightly different. That's what Henry and I have both done."
