
FORTY Under 40: Jessica Powell
Jessica Powell, senior vice president, Aon Insurance Managers (Cayman).
Powell is responsible for the delivery of comprehensive management services to a portfolio of offshore captive clients. These services include assistance with feasibility studies, incorporation procedures and the ongoing management of all aspects of a captive’s operations, including financial planning and reporting, daily operational management activities, continuous liaising with service providers and ensuring that clients are in compliance with the local regulator.
Powell was a recipient of the Insurance Managers Association of Cayman (IMAC) academic scholarship (2005) and interned with various insurance managers in the Cayman Islands while completing her BA. She joined the Aon team upon completion of her master’s degree in 2011, and now shares her 12+ years of captive insurance experience in servicing a diverse client portfolio through which she has developed strong relationships with her clients and industry professionals.
She gained her bachelor of science in business administration in June 2009 from the University of Miami as well as her master’s in international business from Temple University (2011).
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 have really started to recognise myself as a leader. Being in this industry, and with the same company – Aon – for so many years, there’s always been a sight on moving forward, upward, and just bettering my skillset, which relies on access and exposure to mentorship. In receiving this nomination and reviewing some of the feedback from my colleagues, I’m proud to be thought of as a mentor in my own right and in my own way. I have gotten more involved in industry practice groups both within and outside of my day-to-day role, which has allowed me to continue that growth, while affording me access to other professionals with similar mindsets and reinforcing my perceived contexts of the industry and of management styles. Creating a safe place to allow colleagues and peers to continuously learn will always benefit the industry tenfold.
I think the approach to framing career opportunities available is a blind spot for this industry.
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 challenge is always what the right balance is; whether that be work/life balance, personal vs. professional growth, seeking growth and mentorship and providing that mentorship and being available to all out-of-office commitments. And I’ve learned that that balance is so different from person to person. I value empathy and I strive to be empathetic so there is some sort of flexibility to find the right balance(s) for myself and those I work with.
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?
It’s critical to be responsive to change in this industry, one that is specialised and constantly evolving, sensitive to a variety of factors that impact our clients and our business in a variety of ways. My entire career has been in this space and I think the approach to framing career opportunities available is a blind spot for this industry and our focus on the next generation if we are going to expand the awareness of and access to the unique services and capability our industry affords our clients.
We’ve developed a trainee programme at Aon that has been bolstered in recent years and I have had the pleasure of sitting on a variety of Insurance Managers Association of Cayman (“IMAC”) committees and currently chair its educational scholarship fund. I have personal investment in ensuring these initiatives enrich both my local and professional communities.
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?
I see my role evolving through deeper specialisation and broader strategic impact. I am particularly focused on the healthcare practice as my primary focus with Aon, however I want to also continue to build my expertise in the reinsurance space, given the momentum we’re seeing in the Cayman Islands. I also think we will see the impact of AI on our overall business and efficiencies over the next several years and am interested to explore how these tools will improve efficiency and support our clients.
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?
Balancing professional excellence with meaningful community contribution is less a trade-off of the two and more of what I see as a responsibility. I’ve been fortunate to build a career that challenges and stretches me, from a young Caymanian high school graduate to a leadership position at Aon Cayman, these opportunities do not happen in a silo. Giving back to my community is personal for me. Having had been a scholarship recipient myself, I understand first-hand the impact that kind of support can have on young professionals at the start of their career.
I don’t see professional success and community engagement as separate pursuits; I like to think that the discipline, empathy and purpose I get from community involvement makes me a better leader, while my professional role allows me to advocate, mentor and invest back into the Cayman Islands, my community, and the industry. Being recognised on a FORTY Under 40 list is an honour, what matters most to me is how I can use the recognition to continue making a positive and lasting impact.
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