086: Underwrite Your Career: From London to Bermuda with Hannah Greenwood
This episode is sponsored by Fidelis Insurance Group
Summary
In this episode, Sandra speaks with Hannah Greenwood, Group Chief of Staff and Chief Underwriting Officer (Bermuda) at Fidelis Insurance Group, about how curiosity, courage and consistency shape a global career.
Hannah shares how a Lloyd’s of London internship led her into insurance, how broking taught her the value of team culture and ego-free leadership, and how curiosity opened doors to strategy and M&A. She reflects on staying long enough in one firm to build goodwill, taking on stretch roles that expanded her perspective, and moving from London to Bermuda to help drive underwriting strategy and partnerships.
They discuss how sponsorship grows through consistent delivery, the benefits of taking calculated risks, why you should “underwrite” your own career by gathering information, testing fit, and adjusting as you learn. Hannah also talks candidly about balancing leadership and motherhood, the myth of the perfect time for big life decisions, and the advantages of Bermuda’s concentrated, senior market.
Takeaways
Deliver excellence first. Strong performance in your current role builds credibility and sponsorship naturally
Consistency earns trust. Sponsors appear when people see you deliver results repeatedly
Curiosity opens doors. Asking questions and exploring projects beyond your remit expands your perspective
Longevity creates advocacy. Staying with one organisation long enough builds goodwill and career champions
Take calculated risks. Growth often comes from stepping into roles before you feel fully prepared
Listen widely, decide independently. Advice helps, but only you know what’s right for you
Build layered networks. Supportive relationships sustain you, and transactional ones advance you
Leadership without ego scales influence. The best leaders invest in others and create room for growth
Mobility accelerates learning. Working abroad, especially in smaller markets, can deepen exposure to strategy and leadership
Balance is ongoing. There’s never a perfect time for big life choices, but structure and support make it possible.
Career progression often follows a narrow path; seek diverse experiences
Great leadership invests in people and keeps ego out of the room
About the Sponsor
About the sponsor Fidelis Insurance Group
Fidelis Insurance Group is a global specialty insurance and reinsurance company focused on creating value through strategic capital allocation, expert risk selection and a network of long-term underwriting partnerships.
We have built a strong foundation for scale and profitable growth, underpinned by our disciplined approach to risk selection and our financial strength, which is reflected in our insurer financial strength ratings of A from AM Best, A- from S&P and A3 from Moody’s. Our network of underwriting partners and highly diversified portfolio enable us to proactively navigate market cycles, offer innovative and tailored solutions, capitalize on favorable risk-reward opportunities and produce superior returns for shareholders. Our network of underwriting partners and highly diversified portfolio enable us to execute our strategy of proactively navigating market cycles, offering innovative and tailored solutions, capitalizing on favorable risk-reward opportunities and producing superior returns for shareholders.
For additional information about Fidelis Insurance Group, our people and our products, please visit our website at www.FidelisInsurance.com
About the guest
Connect with Hannah Greenwood on LinkedIn.
Hannah currently serves as Group Chief of Staff, Bermuda Chief Underwriting Officer and is a member of the Executive Leadership Team. Prior to joining the company in 2023, Hannah served as Business manager for Ardonagh where she worked with the CEO of their Capital Solutions arm. Hannah started her career at Lloyd’s before becoming an energy broker at independent NMB, latterly renamed Ed. In 2020, she took on a more strategic role supporting the CEO of the business, with a focus across Specialty lines. Hannah holds a BA in Politics, Philosophy and Economics from the University of Durham, an MBA from Warwick Business School and is ACII qualified.
About the host
Connect with Sandra Lewin on LinkedIn.
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