Marsh leaders on captives: innovation, talent and the road ahead
In a changing risk environment, Marsh experts explore how collaboration, technology and new perspectives are transforming captives into strategic assets.
The captive insurance industry stands at a compelling crossroads, shaped by decades of evolution and a new generation of professionals poised to redefine its future. In a recent panel discussion sponsored by Marsh for Captive Review’s 2026 FORTY Under 40 edition, voices from across experience levels reflected on how the sector is changing – and what it demands from those entering it today.
At the heart of the discussion was the experience of entering the captive insurance space in the modern era. For Taylor O’Brien, an account executive, deputy team lead, Captive Solutions for Marsh Risk and one of the 2026 FORTY Under 40 finalists, the journey has been defined by both challenge and opportunity. She described her role as “both challenging and exciting”, noting that “no two days ever look the same, and that’s what I love”. This sense of variety reflects the increasingly complex nature of captive insurance, where professionals must navigate a constantly shifting landscape of risks, regulations and client needs.
O’Brien emphasised that the industry is fundamentally people-driven. “It’s really all about people for me,” she explained, highlighting the importance of collaboration with “clients… colleagues, regulators, auditors, actuaries, just so many talented people”. This interconnectedness is a defining characteristic of the sector, and one that continues to attract new talent. The opportunity to learn continuously, even after more than a decade in the field, underscores the dynamic nature of the profession.
For those starting out, adaptability stands out as a critical skill. O’Brien advised that “being able to pivot [and] change direction is very important”, alongside “critical thinking, problem solving and truly a willingness to just roll up your sleeves and dive in”. Her emphasis on progress over perfection – “you don’t have to be perfect… it’s truly about the progress”–captures a broader shift in workplace culture where experimentation and learning are increasingly valued.
Watch teh full panel discussion below.
Talented assets in an evolving world
From a leadership perspective, the arrival of professionals such as O’Brien signals a significant opportunity. Michelle Sivanayson, managing director, Captive Solutions for Marsh Risk region leader – Islands, described the influx of younger talent as “very exciting”. She pointed to their “fresh perspective” and “strong… comfort [with] technology” as key assets in an industry undergoing transformation. As she noted: “The industry is evolving almost on a daily basis,” making these qualities not just beneficial but essential.
Sivanayson also highlighted the importance of innovation and collaboration. She argued that the next generation must “embrace innovation and new thinking” while maintaining a “collaborative mindset”. In practice, this means working across disciplines and drawing on diverse expertise. “If you want to bring the very best to our clients,” she explained, “it’s equally important that we actually have the right people around the table.”
This emphasis on collaboration reflects the increasingly integrated nature of risk management. Captives are no longer isolated financial tools but part of a broader ecosystem involving consulting, alternative risk transfer and emerging solutions such as parametric insurance. For young professionals, the ability to navigate these interconnected areas – and engage confidently with subject matter experts – will be crucial.
Captives are no longer isolated financial tools but part of a broader ecosystem involving consulting, alternative risk transfer and emerging solutions such as parametric insurance.
Leadership itself is evolving in response to a multi-generational workforce. Sivanayson described her approach as rooted in “open communication” and transparency, which she believes “builds trust” and enables colleagues to “bring the very best of themselves to the table”. She also stressed the importance of empathy, noting that “each of our lifestyles have changed… and we as leaders need to recognise it”. This reflects a broader shift towards more inclusive and flexible leadership styles, designed to support diverse teams.
Graham Rickard, managing director at Marsh, who brings decades of experience in risk management, reinforced the idea that development is a shared responsibility. “It’s really a two-way street,” he said, emphasising that both leaders and newcomers must be adaptable.
While younger professionals are encouraged to take risks – “don’t be afraid to make mistakes” – leaders must also remain open to new ideas. Without this mutual flexibility, he warned, the industry risks stagnation: “We’re just going to continue to maintain the status quo and competitively, that’s not acceptable.”
Rickard’s reflections on the evolution of the captive sector provide important context for these changes. Looking back nearly 30 years, he recalled a time when captives were “very, very siloed”, primarily focused on specific lines such as workers’ compensation or product liability. Today, the landscape is far broader and more integrated, with captives addressing “countless different coverages” and reflecting the complexity of modern risk.
This transformation has elevated the role of captives within organisations. As Sivanayson observed, they have moved “from… a cost saving tool… to… something very sophisticated”, and are now “almost a strategic asset”. This shift is driven by the need for greater control and flexibility in managing risks, particularly in an environment characterised by geopolitical uncertainty and climate change. “Who would have thought,” she remarked, “that captives… could play a really big part… to manage that risk?”
Technology drives change
Technology is another key driver of change. Both Sivanayson and O’Brien highlighted its growing influence on the skills required in the industry. Younger professionals, having “grown up with it”, bring a natural familiarity with digital tools and artificial intelligence. However, this advantage comes with new responsibilities. As Sivanayson noted, they must be “very well versed with analysing this data” and aware of “the risks involved… be it cyber security or… ethical implications.”
O’Brien sees technology as a source of opportunity, enabling professionals to “build their knowledge base… at a fast pace” and focus on “value add activities”. At the same time, she acknowledged the uncertainty of the current environment, describing it as a period where “challenge can also present… great opportunity for innovation”. From cyber threats to pandemic exposures, the range of risks continues to expand and captives are increasingly central to developing creative solutions.
Networking plays a vital role in navigating this complexity. Sivanayson described it as “a true platform for learning, for professional development”, while Rickard likened it to “a practice from a… sport team”, where professionals can observe and learn from one another. Importantly, networking is not a one-way exchange; it allows both experienced and emerging professionals to share insights and challenge assumptions.
Rickard also emphasised the value of exposure to unfamiliar situations. “If it feels uncomfortable… that means it’s working,” he said, encouraging individuals to step outside their comfort zones. This willingness to engage with new ideas and perspectives is essential for both personal growth and industry innovation.
Cross-generational collaboration further amplifies these benefits. Rickard advocated for an “apprenticeship type of model”, where experienced professionals and newcomers work closely together. Such collaboration ensures that institutional knowledge is preserved while also incorporating fresh perspectives. “That sharing yields tremendous dividends,” he noted, particularly when supported by modern tools such as shared digital workspaces.
Questions, mentorship and evolution
As the discussion drew to a close, the panellists offered advice for those entering the industry. O’Brien’s guidance was succinct: “Stay curious… get outside your comfort zone and don’t be afraid to make mistakes.” Sivanayson echoed these themes, adding the importance of asking questions in what she described as “a very unique industry”. For her, curiosity and openness are key to building both confidence and competence.
Rickard added a final dimension: mentorship. He encouraged newcomers to “seek out mentors, both formal… and informal”, noting that experienced professionals are often eager to share their knowledge. This exchange not only accelerates learning but also strengthens the industry as a whole.
Taken together, these insights paint a picture of a sector in transition. The captive insurance industry is becoming more complex, more strategic and more interconnected. At the same time, it remains grounded in relationships, collaboration and continuous learning. As new talent enters the field, supported by experienced leaders and enabled by technology, the future of captives appears both dynamic and resilient.
In the words of O’Brien, it is an industry that is “always evolving” – and it is precisely this evolution that makes it so compelling for the next generation shaping its path forward.
Did you get value from this story? Sign up to our free daily newsletters and get stories like this sent straight to your inbox.
