In Conversation With: Stephen O'Connor

As one of the founders of TUE (now trading as part of Specialist Risk Europe), Stephen O’Connor has built a career broking complex Liability risks between Dublin and London. An integral part of the leadership team today, he reflects on what has changed, what has stayed the same, and how TUE continues to evolve within Specialist Risk Group (SRG) while keeping the same principles that defined it from the start.

Finding a path into insurance

Stephen’s route into insurance wasn’t planned. After leaving college, he spent time in Australia before moving to London at 20 and trying a few different jobs.

“I tried estate agencies and a money broking house,” he says. “A few older family friends and their sons were in the insurance market, so brought me in on a trip around Lloyd’s. Once I had seen it, I thought my skill set would suit that environment.”

His first boss, Sarah Kelly, taught him how to think ahead and laterally. As one of the first female brokers in Lloyd’s, she needed to trade differently. “Back then there was a tendency to be angry or aggressive by some people if they didn’t get their way, but she taught me to be more tactical. Sarah would wait, plan her presentation, think through the strategy.”

“People think insurance can be a bit boring,” he adds, “but that’s never the case for us. We meet wonderful clients and deal with some great underwriters.”

Building relationships that last

Today, Stephen focuses on maintaining and growing relationships that shape TUE, with brokers, clients, and underwriters alike.

His approach is built on the same trust and communication that defined TUE from the start. “London underwriters had plenty of expertise,” he says, “but they did not always know the background or the local challenges. We built trust by explaining that properly. If you abused that trust, you would not be back next year.”

“We never relied on one or two markets,” he continues. “When the market was hard, we got creative. When it is softer, you keep your discipline and stay relevant.”

Being part of SRG has strengthened that approach. “It gives us more scope, more people and expertise to call on, but we still do what we have always done, find solutions for brokers and get the job done.”

Seeing beyond the numbers

For Stephen, good broking is about understanding what sits behind the figures.

“You could have an Employer’s Liability risk where there have been three or four claims,” he says, “but those employees may have left the business. Just because a risk has had a problem does not mean it is a bad one. It is about risk management and engagement.”

“It is always a team effort,” he adds. “We will bounce ideas off trusted syndicates, benchmark where we think the market is, and come up with a plan. Sometimes the answer is conventional, sometimes it is not. The important thing is you look at it properly and work out the best route.”

What brokers value most

Asked what brokers look for in a wholesale partner, Stephen does not hesitate.

“Service, encompassing communication.” he says. “And early communication. If we cannot help, we will say that straight away. If we can, we will get on it quickly and talk things through. It works both ways, if the local market is half the price, tell us. It saves everyone’s time.”

He adds that reliability matters just as much. “You build credit with people over the years, but you cannot live on that. You have to keep proving yourself. Claims are a big part of that too, get involved early, help the broker, and keep the communication going.”

“Like a lot of growing businesses, we’ve had a few challenges, but these have really been addressed recently and I’m positive going into 2026.”

Rewarding moments

Some of the most satisfying moments in Stephen’s career have come from helping clients who might otherwise have struggled to stay in business.

“There were times when the local market just could not deliver,” he says. “Without a London solution, some of those clients might have had to close. Seeing them grow after that, that is rewarding.”

Looking ahead

Stephen sees the market continuing to change but remaining full of opportunity.

“The landscape has shifted with consolidation and Brexit regulations,” he says. “It is harder for new businesses to start up, governance, compliance, capital requirements, but there is still definitely a place for specialists to add value. The key is to stay relevant with clear, bespoke products.”

He is also focused on what is next. “There is a lot of capacity around at the moment, but it will not stay that way forever. The opportunities will come from areas like environmental risks, Cyber, AI, anything that threatens a balance sheet. If you are innovative and you understand the exposures, there is room to engage.”

TUE has been steady across Liability, Property, PI and Equine for over 20 years. “Our expertise aligns well with the other specialist strengths within the Group, including Miles Smith, a long-standing Lloyd's broker. Being a part of SRG strengthens what we already do, rather than changing it.”

He also sees the wider Group as a positive step for the next phase. “It gives us wider reach, access to more markets and expertise across the Group, but it has not changed how we work with brokers. We are still the same people, just with a stronger network behind us.”

Advice for newcomers

“Be honest,” Stephen says. “If you are showing a risk to an underwriter, give them the full picture. Do not be afraid to ask questions. And pick up the phone, not everything can be done by email. Communication counts.”

Finish the sentence

When a complex risk lands on your desk, think TUE because… “we think outside the box."