FORTY Under 40: Sarah Robey

Sarah Robey, tax partner, KPMG in Bermuda.

Robey specialises in the US and Bermuda taxation of captive insurance companies and the wider insurance and reinsurance sector. With more than 15 years of experience across US federal, state and international tax, she is recognised for technical strength in property and casualty taxation, cross-border structuring, 953(d) elections and captive-specific tax issues.

Robey supports Bermuda’s captive market as it adapts to an evolving regulatory and tax landscape. She advises captive owners, managers and boards on structuring, compliance, financial reporting and regulatory change, including the interaction between US tax rules and Bermuda’s developing framework. Known for translating complex requirements into practical guidance, she helps organisations make sound decisions during periods of uncertainty.

Beyond client work, Robey contributes to the captive insurance community through conference presentations, education forums, training for captive managers and board-level briefings. She is also committed to developing future talent, serving as chair of her firm’s diversity, equity, and inclusion committee and as a member of the KPMG Islands Group’s women’s diversity working group, with a focus on mentorship and inclusive leadership.

Robey holds a bachelor of business administration from Bryant University, an MSc in taxation and is a certified public accountant licensed in Rhode Island.

Looking back at your journey over the past year, what accomplishment are you most proud of, and how has becoming a FORTY Under 40 finalist influenced your perspective on that achievement?

I’m most proud of the role I’ve played in helping Bermuda’s captive insurance industry prepare for and adapt to the introduction of the corporate income tax. This has been a period of significant uncertainty for captive owners and managers, and being able to provide clear, practical guidance through board briefings, industry presentations, training sessions and webcasts has been especially meaningful. My focus has been on translating complex and evolving tax rules into actionable steps so organisations can make informed decisions with confidence.

“The key challenge this year was advising in an environment of real uncertainty as Bermuda implemented a corporate income tax system for the first time.”

Being named a FORTY Under 40 finalist has given me a new perspective on that work. It reinforced that the impact wasn’t just technical, but broader, supporting the resilience and readiness of the jurisdiction as a whole. The recognition has reminded me that leadership often shows up in moments of change, and it motivates me to continue contributing at both a client and industry level as the landscape evolves.

What key challenge did you face in your work this year,? How did you overcome it and what did it teach you about leadership at this stage of your career?

The key challenge this year was advising in an environment of real uncertainty as Bermuda implemented a corporate income tax system for the first time. The framework was new, guidance continued to evolve, and captive owners and managers were trying to understand not only technical compliance requirements, but the broader implications for their structures and long-term strategies.

I overcame this by focusing on judgment and clarity rather than waiting for perfect answers. That meant staying closely engaged with developments, working through scenarios with clients and captive managers, and being transparent about areas of uncertainty while still helping stakeholders move forward with informed, practical decisions.

The experience reinforced that leadership at this stage of my career is about more than technical knowledge. It’s about providing calm, credible guidance in periods of change and helping others navigate complexity with confidence, even when the landscape is still taking shape.

In what ways have you tried to push innovation or rethink traditional approaches within your sector, and what impact has that had on your team or organisation?

I’ve focused on rethinking how highly technical captive tax advice is delivered, shifting from a reactive, compliance-driven approach to a more proactive and strategic one. Rather than treating tax as an isolated technical exercise, I’ve emphasised education, early engagement and practical frameworks that help clients and teams understand implications and make informed decisions sooner.

This approach has strengthened technical confidence within my team and encouraged more collaborative problem-solving, while also enabling captive managers and boards to engage more meaningfully in structuring and governance discussions. The result has been clearer decision-making, earlier risk identification and a more strategic role for tax within the captive insurance lifecycle.

How do you see your role evolving over the next three to five years, and what initiatives are you most excited to pursue as you continue to grow professionally?

Over the next three to five years, I see my role continuing to evolve toward broader industry leadership, combining deep technical expertise with practical, strategic guidance. As tax and regulatory expectations for captives continue to develop, my focus will remain on helping boards, captive managers and organisations navigate complexity with clarity and sound judgment.

I’m most excited about continuing to refine how I support clients and teams through structured analysis and clear communication, particularly in areas where regulatory expectations are still taking shape. Building consistency, strengthening technical understanding and helping organisations make well-informed decisions in a changing environment are the areas where I see the greatest value in my work.

Many of the FORTY Under 40 winners are recognised for both business success and broader impact – how do you balance professional excellence with contributions to your community or industry landscape?

For me, professional excellence and broader industry contribution are closely connected rather than competing priorities. Doing my job well means not only delivering high-quality technical advice to clients, but also helping strengthen understanding and consistency across the captive insurance community more broadly.

I try to balance this by building industry contribution into my day-to-day work through training captive managers, speaking at industry forums, participating in education initiatives and mentoring junior professionals. That also includes my involvement in diversity and inclusion efforts within my firm and the wider region, where the focus is on developing talent, broadening perspectives and creating more inclusive pathways for future leaders. Sharing knowledge and helping others navigate complexity ultimately improves outcomes for clients, teams, and the jurisdiction as a whole. This approach allows me to contribute in a way that’s practical, sustainable, and aligned with the work I do every day.

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