New pressures, enduring challenges: insurance and inclusion

There are many pressures and challenges facing the insurance industry – perhaps one of them is a lack of diversity, or maybe that is the solution. Bermuda:Re+ILS explores the views of some of the senior female leaders at the front line of that change.

The re/insurance industry is at a pivotal moment. Mounting global risk, rising regulatory complexity and persistent talent shortages are converging with a deeper – and long overdue – push for inclusion. For Bermuda, one of the world's leading reinsurance hubs, these challenges are not abstract. They’re local, personal and shaping the careers and companies of today’s professionals, especially women who are steadily reshaping the industry’s future.

From climate change to cyber risk, and from shifting market cycles to calls for greater diversity, leaders in Bermuda’s insurance ecosystem are navigating a landscape that is increasingly demanding, but deeply human.

Market/operational pressures: a new norm

The sector is under growing strain. Climate-related catastrophe losses are increasing in frequency and severity, putting pressure on underwriting models and capital buffers. According to Swiss Re’s Sigma 1/2025 research, insured global losses from natural catastrophes totalled $137 billion in 2024, exceeding the ten-year average and reflecting an era of elevated volatility.

Simultaneously, inflation and interest rate fluctuations have introduced significant complexity to asset-liability management. Carriers are facing tighter margins, while clients demand tailored products that address evolving exposures – from supply chain disruption to intangible risks like reputation and ESG compliance.

Digital transformation, long promised but often delayed, has finally become essential. McKinsey & Company’s report ‘The future of AI in the insurance industry’, published July 2025, attributes legacy infrastructure as a hindrance to technological progress, stating: “Insurers will need to modernise this legacy infrastructure to fully harness AI, overcoming rigid IT systems that lack scalability and real-time processing power.”

Behind these macro issues are real people, making difficult decisions daily, often while carrying the invisible weight of being “the only one in the room”. We interviewed many of them for this publication; some of their perspectives are shared here.

Visibility, voice, value

“It has been very normal throughout my entire career to be the only woman or one of the few women present in a room, whether that’s a boardroom meeting, a client meeting or a presentation,” Carrie Kelley, CEO of Price Forbes, told this publication. “It’s given me the opportunity to find my own voice and bring a different perspective to the table, which I have viewed as an opportunity.”

This blend of pressure and opportunity is echoed by other women in Bermuda’s re/insurance community, many of whom have not just faced professional headwinds, but also quietly transformed how leadership is defined in a traditionally male-dominated sector.

“For many years, I was often the only woman – and the youngest voice – in the boardroom,” shares Shanna Lespere, of the Bermuda Monetary Authority (BMA). “The journey was not always easy, but it reinforced the importance of consistently demonstrating deep technical competence… As women, we are not often given a second chance, so I have always made it a priority to be exceptionally well-prepared and professional in every setting.”

For Michelle Bailey, head of professional at Axa XL, the challenge has been multifaceted: “Balancing single motherhood with climbing the corporate ladder was tough. I leaned on a strong network of family and friends and learned to ask for help. Another challenge was navigating rooms where I was the only one who looked like me. I let my work speak for itself and committed to being excellent.”

Inclusion is not just representation

The pressures facing the industry aren’t limited to performance metrics – they intersect deeply with identity, values and culture. Yvette Pierre, of the BMA, offers a powerful reflection: “I have navigated challenges influenced by gender, age, nationality and faith […] Although the experiences were difficult, they taught me the importance of holding firm to my self-worth.”

For Chiara Nannini, of Conyers, being the only woman in a room wasn’t a barrier, but it brought its own awareness: “While these situations haven’t held me back, they can make you acutely aware of gender imbalances. Over time, I’ve learned to assert myself and make my voice heard, but these experiences underline the importance of creating inclusive spaces.”

Inclusion is about more than hiring. It’s about shaping work environments where difference is seen as strength – and where policies, flexibility and opportunity reflect real life.

The toll of work-life balance

The myth of “having it all” remains one of the industry’s most persistent fictions. For Flavia Doyle, of Aspen, years of part-time and flexible work were essential to navigating both a demanding job and raising a family.

“Balancing a demanding career while raising a family has been one of the greatest challenges of my professional life [...] You can’t be a perfect parent while also delivering flawlessly at work, something I had to learn the hard way,” Doyle shares. “The hardest part was letting go of the guilt and accepting that I was doing enough.”

Erica Robinson-McLeod, of Artex Capital Solutions, echoes this: “I would not say there is any one key theme to challenges I’ve faced during my career other than the perennial ‘work/life’ balance challenge that is thematic when raising young children at key stages of one’s career.”

The need for supportive infrastructure – flexibility, understanding leadership and policies that reflect caregiving realities – is not just a women’s issue. It’s a business imperative.

Talent and culture

Across Bermuda and beyond, attracting and retaining talent remains a significant concern. The competition for skilled professionals – particularly in actuarial science, risk modelling and cyber insurance – is fierce. Yet as Sandra DeSilva, founder, president and CEO of Nova and Mythen Re, notes, the answer might lie closer than we think.

“It is challenging to find good people. But the truth is, they are all around us,” she says. “I found that working towards achieving something intellectually challenging brings out the best in one another. I am grateful for the incredible people I have had the honour to work with.”

Fostering talent means not only hiring for potential, but nurturing that potential within inclusive and transparent cultures. It means making room at the table, and then actively listening.

When speaking to workplace culture challenges, Mary DeSilva, of Artex Capital Solutions, puts it succinctly: “To overcome these obstacles, I focused on understanding the underlying structures and building networks with colleagues. By fostering open communication and collaboration, I created a more positive and cohesive environment.”

Resilience through inclusion

Despite its challenges, the insurance and reinsurance industry is full of opportunity. Its mission, mitigating risk and safeguarding stability, is deeply relevant in a world where uncertainty is the only constant. But to rise to the occasion, the industry must expand who it listens to, how it leads and where it invests in change.

As Melinda Mayne, of Appleby, wisely observes: “Knowledge is not something you gain without immersing yourself... It does not happen overnight.”

The insurance sector must now apply this same curiosity and persistence to reshaping its culture, evolving systems so that all professionals, especially women and historically underrepresented groups, can thrive.

It’s not enough to face complexity with competence alone. The leaders who will define the industry’s next chapter will be those who champion equity, demonstrate humility and foster resilience.

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