Pushing the door open on talent
Lancashire Bermuda CEO Jennifer Wilson’s path from finance to the top job reflects the breadth of expertise underpinning Bermuda’s reinsurance market. As the island looks to its next generation, she says showing young people the full range of opportunities will be critical.
When she took on the role in March 2026, she brought a different perspective to the job. Her career had been built largely in finance, including years looking across the business through financial planning and analysis.
For an industry where underwriting talent often commands the spotlight, her ascent offers a reminder of just how many disciplines sit behind Bermuda’s position as a global reinsurance centre, and how many different routes there are into its leadership.
“The accountant in me initially jumps to cost vs benefit for many of my decisions. But it isn’t that simple, and my work on three to ten-year forecasts across the insurance cycle combined with ongoing capital management analysis serves me well to look at the long-term needs of the business combined with short-term considerations,” Wilson told Bermuda:Re+ILS.
That longer view is particularly relevant as she settles into a role that takes her well beyond the numbers. Wilson remains group financial planning and analysis (FP&A) director alongside being CEO, but the latter requires a far wider view of what the Bermuda operation will need to deliver in future. “This is a new challenge and an opportunity to become more involved in the workings of other departments,” she said.
There was already considerable crossover in her previous role. The annual budgeting process requires input from across the organisation, giving FP&A a window into different departments and their priorities. The CEO role takes that further.
“In this role I need to understand the wider staffing and resource needs now and in the future, to ensure our Bermuda office can continue to deliver our part of the group strategy efficiently and effectively.”
It is a challenge that goes to the heart of a wider question for Bermuda. The island has spent decades building an extraordinary concentration of re/insurance expertise. Keeping that advantage means attracting established specialists, developing the people who will occupy those roles in the future and making clear to younger professionals just how wide the industry’s doors actually are.
More than underwriters
Lancashire’s own history provides useful context. The company began life in Bermuda and, more than two decades later, the island remains the beating heart. “Bermuda is where we started in 2005, and our island operations continue to be integral to the wider Lancashire group. Our head office is here, group board meetings are held here and this is where strategic decisions are debated and decided,” Wilson said.
That continued presence says something about what Bermuda has built around its re/insurance market. For Wilson, one of the island’s greatest advantages is the expertise concentrated within a remarkably small geographical area. “The talent pool concentrated on this island is incredible. This includes underwriters, actuaries, accountants, lawyers and more,” she said.
It is the “and more” that increasingly matters. The underwriting expertise for which Bermuda is known sits within a far broader network of skills. Actuaries model the risks, finance teams consider capital and performance, claims professionals respond when those risks materialise, operations teams keep increasingly complex businesses functioning, while lawyers, accountants and regulators form part of the infrastructure surrounding them.
Lancashire’s recent internship programme brought that breadth into focus for Wilson. It offered an opportunity not simply to introduce young people to reinsurance, but to show them what actually happens inside a reinsurance company.
“The programme really served to highlight the variety of jobs available within a re/insurance company. Underwriting, actuarial and finance options are well known and frequently discussed. But we got the chance to highlight the importance of our operations and claims departments as well.”
Visibility matters for the future of Bermuda’s talent pool. A young person who does not see themselves as an underwriter or actuary might assume the industry has little to offer them; Wilson’s message defies that misconception. “Each department has a role to play, and the skill sets and backgrounds required in each are extremely varied, which gives a wide range of younger professionals a chance to enter the extremely interesting re/insurance industry in Bermuda.”
Her own career makes the case neatly. Finance provided one route into the industry, but it also became a route across it. FP&A required an understanding of how different departments contribute to the wider business, while forecasting across the insurance cycle meant looking beyond immediate results to what Lancashire might need several years ahead.
Now that perspective is being applied to the Bermuda operation as a whole.
An ecosystem built over time
The depth of that talent pool is one reason Lancashire remains firmly rooted on the island 20 years after it was established there.
There are others. Wilson describes regulation by the Bermuda Monetary Authority as “world class”, while the island’s location provides a practical bridge between two of the global insurance industry’s most important markets. “Our work hours straddle both UK and US hours which is very helpful to our clients,” she said.
Taken together, those advantages help explain why Bermuda remains much more than a place where reinsurance companies are incorporated. In Lancashire’s case, it is where the head office sits, its board meets and group strategy is debated. The concentration of people around those activities is difficult to separate from Bermuda’s appeal.
That does not make the talent question static. An ecosystem built over decades still needs replenishing. For Wilson, the opportunity begins with making the industry accessible to people with a wider variety of interests and skills. The internship programme is one route. The careers of people already within the market are another.
Her own move into the CEO role is evidence that leadership does not need to emerge from a single discipline.
Keeping good people
Attracting people into the industry is only part of the equation. Bermuda’s footprint also means talented employees have considerable visibility of the companies around them. This is why Wilson believes in the importance of cultivating the right culture.
“Bermuda is a very small island with a close-knit business community, so culture can be the deciding factor in whether talented people stay at or join a company,” she said. For Lancashire, that creates another challenge: how to preserve the characteristics of the organisation as the organisation itself changes.
Wilson has spent most of her career at Lancashire and has watched many of its current leaders grow into their positions. Its nine-member group executive team comprises long-serving staff – five women and four men – and she believes shared history has created room for genuine disagreement. “There is a level of comfort among the members which means there is the ability to challenge and debate topics that is refreshing,” she said.
She points to group CEO Alex Maloney as setting the tone: “Alex is very open and honest in town hall meetings with staff. He takes questions and is comfortable answering without a prepared script.”
That openness has been influential in retaining the culture as the company has expanded, which often makes maintaining some of the characteristics of a smaller organisation harder. “While one of our taglines is ‘underwriting comes first’, all departments have an important role to play in the ongoing success of the business,” Wilson said.
Alex Maloney’s focus, she added, has been on “working to retain the positive and vibrant culture we had when we were 100 people as we grow towards 500 staff”, something she is also striving to ensure the Bermuda office prioritises.
Wilson’s own approach is deliberately collaborative. “Micromanaging is not my style,” she said. Her Bermuda executive team draws on multiple departments, giving her access to different perspectives before decisions are made. The aim is straightforward: to have everyone “pulling in the same direction”.
Building the next generation
The question for Bermuda is how to turn the depth it already has into something that can sustain the market for another generation. That is partly about attracting young people, but it is also about what happens once they arrive. Careers rarely follow a straight line, and the value of a market with so many disciplines concentrated in one place is the opportunity to move between them, build a broader understanding of the business and, over time, take on different responsibilities.
Wilson’s own progression is one example of what that can look like, without suggesting it is the only route. The next generation of Bermuda leaders will inevitably come from different backgrounds and bring different skills to the businesses they eventually lead.
For a market that has spent decades developing specialist expertise, that diversity of experience should be an asset. The task now is to keep creating the conditions in which people can enter the industry, find where their strengths lie and see a future for themselves within it.
Some will begin behind underwriting desks. Others will arrive through actuarial, finance, claims or operations. What matters is that they can see the doors in the first place.
Read the full Bermuda:Re+ILS Annual 2026 here.
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