Basic Information
| Attribute | Detail |
|---|---|
| Full Name | Leslie Robinson |
| Birth – Death | c. 1967 – October 29, 2024 (age 57) |
| Primary Sector | Captive Insurance & Financial Services Regulation |
| Key Roles | SVP, Head of Underwriting & Claims, Willis Towers Watson (2018–2024); Chair, Bermuda Captive Conference (2020–2022); Founding Strategic Director, Bermuda Captive Network (2021–2024); Senate Member, Bermuda Upper House (2022–2024) |
| Years of Service | 33+ years |
| Posthumous Honor | Fred Reiss Lifetime Achievement Award, Bermuda Captive Conference (June 2025) |
Early Life and Rise in Bermuda’s Financial Services
Leslie Robinson began her career in Bermuda’s financial services sector in the early 1990s, quickly gravitating toward the captive insurance niche—a specialized area where companies create their own insurance subsidiaries to underwrite unique risks. Over the next decade, she honed her expertise in captive management and broking, working with some of the island’s most innovative captives. Her deep understanding of regulatory frameworks and risk transfer mechanisms laid the foundation for her later leadership roles.
Willis Towers Watson Tenure (2018–2024)
In 2018, Robinson joined Willis Towers Watson’s Bermuda office as Senior Vice President and Head of Underwriting & Claims. In this capacity, she oversaw underwriting strategy for one of Bermuda’s largest captive insurers, managing portfolios exceeding $5 billion in gross written premium. Under her leadership, the team streamlined claims processes—reducing average settlement times by 20%—and introduced data-driven underwriting tools that improved loss ratios across multiple industries.
Industry Leadership and Conference Stewardship
Robinson’s commitment to industry collaboration led to her election as Chair of the Bermuda Captive Conference (BCC) from 2020 to 2022. Facing the unprecedented challenges of the COVID-19 pandemic, she pioneered virtual and hybrid conference formats that drew record attendance—over 1,200 delegates in 2021—and expanded international participation. Her deft navigation of health guidelines and digital platforms ensured that Bermuda remained the global hub for captive insurance dialogue.
Mentorship, Inclusion, and the Bermuda Captive Network
In 2021, recognizing the need for greater diversity and professional development in the captive sector, Robinson co-founded the Bermuda Captive Network (BCN) as its Strategic Director. She spearheaded mentorship programs pairing seasoned executives with emerging talent, launched an annual scholarship for underrepresented groups in finance, and hosted quarterly roundtables on innovation in risk transfer. Through BCN’s initiatives, dozens of protégés have since ascended to leadership roles across the industry.
Public Service: Senate Appointment and Regulatory Reform
In 2022, Robinson was appointed a Member of the Senate in Bermuda’s Upper House, where she championed financial inclusion and systemic reform. She co-authored legislation to modernize captive insurance regulations, reducing administrative burdens while enhancing corporate governance standards. Her efforts fostered a more competitive environment for small and medium-sized captives, earning praise from both regulators and industry stakeholders.
Posthumous Recognition and Legacy
Although Leslie Robinson passed away on October 29, 2024, her impact was celebrated with the Fred Reiss Lifetime Achievement Award at the Bermuda Captive Conference in June 2025. The award citation highlighted her “transformative leadership and unwavering commitment to mentorship, innovation, and regulatory excellence” in Bermuda’s captive community. Peers have noted that her vision and advocacy reshaped the island’s financial services landscape, leaving a legacy of collaboration and inclusivity.
| Year | Role/Activity | Impact |
|---|---|---|
| 1991 | Entry into Bermuda Financial Services | Developed captive broking expertise |
| 2018 | SVP, Underwriting & Claims, WTW | Optimized claims processes; $5 B+ portfolio management |
| 2020–2022 | Chair, Bermuda Captive Conference | Virtual/hybrid events with 1,200+ delegates |
| 2021–2024 | Founding Strategic Director, Bermuda Captive Network | Mentorship & diversity initiatives |
| 2022–2024 | Senate Member, Bermuda Upper House | Regulatory reform & financial inclusion |
| June 2025 | Fred Reiss Lifetime Achievement Award | Posthumous industry honor |
FAQ
What was Leslie Robinson’s primary sector expertise?
She specialized in captive insurance underwriting, claims management, and regulatory affairs within Bermuda’s financial services sector.
Which major award was bestowed posthumously on Leslie Robinson?
She received the Fred Reiss Lifetime Achievement Award at the Bermuda Captive Conference in June 2025 for her transformative contributions.
What was her role at Willis Towers Watson?
From 2018 to 2024, she served as Senior Vice President, Head of Underwriting & Claims, overseeing a portfolio exceeding $5 billion in premiums.
How did she innovate the Bermuda Captive Conference?
As Chair (2020–2022), she transitioned the event to successful virtual and hybrid formats, attracting record international participation.
What initiatives did she lead through the Bermuda Captive Network?
She launched mentorship programs, diversity scholarships, and innovation roundtables to cultivate the next generation of captive insurance leaders.
Where can I learn more about her contrasted legacy alongside other industry figures?
For an example of a different industry legacy, see Fraser C Robinson Iii, whose family story influenced Michelle Obama’s values.
