Building a future in the diverse world of re/insurance
AI might be grabbing the headlines, but, in re/insurance, it is still people and their relationships that drive the business. That is one of the many reasons why many of the senior leaders would recommend this industry to a new generation.
In Bermuda, where the turquoise ocean meets a thriving global financial hub, re/insurance is more than just a pillar of the economy – it’s a vibrant, challenging and deeply rewarding industry that continues to evolve in step with the world’s most pressing risks.
From traditional underwriting to cutting-edge roles in AI and climate analytics, the re/insurance sector is full of possibilities, especially for those with curiosity and a drive to make a real impact.
At first glance, re/insurance might seem like a niche field. But look a little closer and it becomes clear it’s one of the most dynamic and globalised industries out there. And in Bermuda – a jurisdiction known for punching well above its weight – the opportunities are even more unique.
People-driven, tech-enabled
In an era dominated by technology, one of the industry’s most enduring strengths is its human core. While AI, automation and analytics are transforming how work gets done, the heart of re/insurance remains relationships.
“What originally attracted me to the industry is that it is a relationship-driven business,” said Carrie Kelley, CEO of Price Forbes, speaking to this publication. “We often talk about technology and AI and how we can become more effective as brokers and underwriters and conduct business more efficiently, but no matter how many advancements we make in that space, deals will always be done on the back of relationships and reputation, and that's never going to go away.”
Kelley was one of many to offer similar sentiments. Michelle Bailey, head of professional, Bermuda, at Axa XL, echoed this sentiment while highlighting the industry’s complexity and constant evolution: “This industry offers opportunities to engage with Fortune 1000 leaders and tackle intellectually stimulating challenges. It’s financially rewarding and ever-evolving, especially with roles in AI and cybersecurity opening up.
“Our industry touches nearly every sector of the economy, and so no two days are alike. It’s very stimulating and incredibly diverse; beyond underwriting and claims, there are roles in communications, finance, marketing and more.”
This duality – high-tech and high-touch – is part of what keeps the work so interesting. It’s also what draws people from an array of professional backgrounds, educational paths and even countries into re/insurance.
Bermuda’s global gateway
For many, the re/insurance sector opens doors to the world.
“Insurance is a global industry, allowing professionals to work in different regions and explore international career opportunities,” said Melinda Mayne, a senior associate at Appleby.
In Bermuda, the international nature of the industry is especially pronounced. It’s one of the only places in the world where you can work on billion-dollar transactions in the morning and be at the beach by late afternoon. The island’s access to global markets, favourable regulatory climate and strong reputation as a risk capital make it a uniquely influential player in the global risk landscape.
“This is a complex and remarkable industry,” said Mary Desilva, SVP, head of risk and compliance at Artex Capital Solutions. “Bermuda specifically serves as a leading global insurance hub internationally, with a favourable regulatory climate and the ability to connect directly with regulators. The exposure to specialised areas of the market is endless, offering vast opportunities.”
That reach is also personal. “For Bermudians like me, insurance is integral to the local economy, making it an inevitable area of interest,” said Chiara Nannini, director of Conyers. “The industry’s prominence on the island sparks curiosity about what drives its success. Additionally, the dynamic nature of the sector, coupled with its global reach and local significance, makes it a compelling and rewarding field to work in.”
Equity, representation and culture
In recent years, the re/insurance industry has taken meaningful steps toward improving diversity, equity, and inclusion – particularly around gender representation and leadership visibility. While progress continues, many leaders are candid about both the opportunities and the work still ahead.
“There are many women in the industry, particularly in legal roles, but we still need more female representation at the C-suite level,” said Nannini. “Factors such as motherhood and cost-of-living challenges contribute to women leaving the workforce at higher rates, so addressing these underlying issues is crucial. I’d love to see more women not only entering the sector but thriving in leadership roles.”
That ambition is gaining traction. “There are significant opportunities for women in this sector to achieve career growth,” said Mary Desilva. “By adding our unique strengths and perspectives to the mix, women can drive meaningful change and innovation.”
For Sandra DeSilva, founder, president and chief executive officer of Nova and Mythen Re, that change is already under way. “It is a very challenging industry, and the era of change is at an inflexion point with different types of products and platforms entering the market,” she said. “Women bring unique perspectives that are invaluable in shaping the future of our field. By stepping into these roles, they not only empower themselves but also inspire future generations to break barriers.”
Flavia Doyle, who has spent two decades with Aspen, sees the tides turning. “There’s never been a better time to be a woman in this industry,” she said. “The landscape is evolving with more visible leaders, stronger support networks and a growing commitment to equity and inclusion across the board.”
So many ways in… and up
One of the most compelling aspects of the industry is its sheer variety. While many assume a narrow path – actuarial, underwriting, broking – the reality is far broader and more creative.
“The insurance industry is a great place to build a career,” said Doyle. “It offers diverse paths spanning quantitative, strategic and client-facing roles. It’s dynamic, more agile than banking and more forward-looking than it’s often given credit for. Innovation is driving real change, with technology, product development and risk modelling evolving rapidly.”
Erica Robinson-McLeod, EVP, chief legal counsel at Artex Capital Solutions, reinforced this sense of possibility. “It is not restricted only to those who want to underwrite risk, and the areas of expertise continue to develop and expand, providing all kinds of opportunities,” she said. “Although cyclical in nature, the industry is tried and tested and is here to stay. If anything, there’s only room for growth and expansion, particularly in terms of closing the protection gap.”
Robinson-McLeod also emphasised the importance of personal initiative: “Initiative and hard work can take you as far as you want in this industry. The sector does so much to support and engage those who are keen to pursue a career within reinsurance.”
It’s a point of view shared by many across the industry. “In my experience, a career in insurance brings new challenges and opportunities at every stage – if you’re willing to look for them,” said Doyle. “If you stay curious and proactive, there’s always something new to tackle, learn from and grow into.”
Inclusion: a door that opens wide
Re/insurance isn’t just for a specific type of background or education. In fact, some of the most compelling stories come from those who stumbled into the field and never looked back.
“The re/insurance industry welcomes people from all walks of life,” said Grace Sousa, VP, head of operations at Ariel Re. “Coming from a background where opportunities were limited, I found in this field a space to grow beyond expectations. I only wish I’d discovered it sooner – it’s brought me pride, joy and the chance to learn from truly remarkable people.”
That inclusivity and potential is part of what makes the industry not just resilient, but human.
The re/insurance industry plays a crucial role in the global economy, but beyond that, it offers a diverse range of opportunities for people from various backgrounds. In Bermuda and beyond, the industry presents significant challenges and prospects. Whether you are interested in building relationships, driving innovation or tackling complex global issues, the re/insurance sector provides a solid career path with real potential.
And as more people discover what’s possible, its future will only grow stronger.
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