FORTY Under 40: Taylor O’Brien
Taylor O’Brien, account executive, deputy team lead, Marsh Captive Solutions.
O’Brien earned a BSc in accounting and finance from the University of Vermont in 2014 and began her career at Marsh as a client service accountant. In this role, she was introduced to the captive insurance industry and managed the day-to-day operations of a diverse portfolio of captive insurance companies across multiple domiciles and industries. Over time, O’Brien advanced into more senior positions, broadening her expertise and responsibilities within the captive insurance sector.
Committed to continuous professional development, O’Brien earned a master’s degree with a certificate in business management in 2019, obtained her CPA licence in 2020 and achieved the associate in risk management designation in 2024. In her current role, she focuses on team development, delivering strategic insights and executing captive insurance strategies for her clients. O’Brien is a strong advocate for growth, connectivity and continuous learning, working closely with colleagues to ensure a high standard of service and client satisfaction.
Balancing personal growth, colleague development, delivering exemplary client service and positioning for the future requires careful management.
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 am most proud of my role as a dependable leader guiding my team through a complex and transition. Despite the inherent challenges, our team remained focused and united, delivering exceptional results through resilience and collaboration. This experience reinforced my conviction in the power of strong leadership and collective effort to successfully navigate uncertainty.
Being named a FORTY Under 40 finalist has provided meaningful recognition of these achievements and broadened my perspective on leadership and impact. This honour motivates me to continue fostering growth, both by mentoring others and seeking mentorship myself and inspires me to lead with renewed purpose and dedication in the years ahead.
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?
Fierce competition for talent and rapid expansion of the captive insurance industry continues to present a significant challenge. Successfully balancing personal growth, colleague development, delivering exemplary client service and positioning for the future requires careful management.
This experience reinforced that successful leadership requires adaptability, empowering team members to take initiative and leading by example to build confidence and foster a collaborative environment.
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 have actively driven innovation by co-leading a project, which successfully achieved 100% data completion across the US. This accomplishment enabled us to transform existing data into actionable insights, thereby enhancing the quality and intelligence of our decision-making processes. The data also serves as the basis for Marsh’s Benchmarking report presented at RIMs. Concurrently, I have prioritised cultivating a culture where feedback is not only welcomed but expected, fostering stronger collaboration and cohesion within the team. This approach has significantly improved our collective performance and engagement. Moving forward, I am committed to exploring additional ways to leverage our data resources creatively and maintain an open dialogue that encourages continuous improvement and innovation.
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?
More connectivity across the industry with continued enhanced leadership opportunities. I’m passionate about colleagues and continuous knowledge sharing. I see myself continuing to pursue professional challenges as well as educational expansion. I was proud to join the VCIA conference committee and advocacy committee this past year. I look forward to continued involvement and sharing of information and experiences with others.
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?
By giving myself grace. It’s really about making sure you focus on the things that recharge and energise you. For me, that means getting involved in the community, volunteering and meeting new people. These are the things that give me purpose and keep me motivated to do my best. Even though time is tight, carving out space for what truly matters is essential. Being intentional about how I spend my time has helped me stay balanced and fulfilled both at work and in my personal life.
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