2025 Fred Reiss Awarded To Leslie Robinson
The late Leslie Robinson will be posthumously awarded the 2025 Fred Reiss Lifetime Achievement Award for her outstanding leadership, mentorship, and transformative impact on Bermuda’s captive insurance industry.
A spokesperson said, “The Bermuda Captive Conference is proud to announce that the late Leslie Robinson will be posthumously awarded the 2025 Fred Reiss Lifetime Achievement Award, in recognition of her outstanding service and enduring impact on Bermuda’s captive insurance industry.
“Leslie Robinson was more than a respected industry professional—she was a tireless advocate, mentor, and leader whose contributions helped shape the jurisdiction’s reputation on the global stage. A former Chair of the Bermuda Captive Conference and an integral member of the Bermuda Captive Network, Leslie was a passionate ambassador for the island’s risk sector and a champion for inclusion, education, and industry advancement.
“Her leadership through pivotal moments in the industry cannot be overstated. As Chair of the Bermuda Captive Conference from 2020 to 2022, Leslie guided the organisation through one of its most challenging periods during the pandemic. Under her stewardship, the conference successfully transitioned into a virtual, then hybrid model, helping maintain Bermuda’s visibility and momentum in the international marketplace while fostering meaningful dialogue and connection among industry participants.
“Leslie was also one of the founding Strategic Directors of the Bermuda Captive Network when it launched in 2021, playing a key role in shaping the structure, vision, and values of the organisation. Her focus on broadening the Network’s reach, fostering mentorship opportunities, and elevating Bermuda’s captive voice both locally and abroad made her an indispensable part of its early success.
“Throughout her career, Leslie was deeply committed to promoting Bermuda as a leading domicile for captive insurance. She represented the jurisdiction at global industry events and international business forums, where her knowledge, professionalism, and personal warmth left a lasting impression. Whether speaking on panels, mentoring young professionals, or engaging with international stakeholders, Leslie consistently advanced the narrative of Bermuda’s strength, stability, and innovation as a captive insurance hub.”
“Leslie’s loss continues to be felt deeply by all who knew her,” said Séadna Kirwan, Bermuda Captive Conference Chair. “She was a unifying force in our community and a leader in every sense of the word. Her contributions to the captive industry – and to Bermuda’s professional and civic life were extraordinary. We are honoured to celebrate her legacy through this award.”
“Senator Robinson was larger than life and a true champion of the captive insurance industry. Her contributions are legendary, and it is deeply appreciated that Senator Robinson’s illustrious legacy is being remembered in this way,” said Jason Hayward, Minister of Economy and Labour.
The spokesperson said, “The award, named after Fred Reiss, the visionary who pioneered the captive insurance concept in 1962, recognises individuals whose work has left a lasting mark on Bermuda’s insurance landscape. Since its inception, the honour has been bestowed on figures who have shaped the evolution of the jurisdiction, including Bala Nadarajah, Eduardo Fox, Cyril Whitter, Cathy Duffy, Jeremy Cox, Brian R. Hall, Michael Burns and Jill Husbands.
“Leslie Robinson now joins this distinguished group of honorees, celebrated not only for her leadership but for the way she led – with conviction, kindness, and an unwavering commitment to Bermuda’s success.
“A veteran of the insurance and financial services industry, Leslie brought a unique combination of deep technical knowledge and unrelenting passion to every role she held. She served as Director at WTW Bermuda, where her influence extended across global networks, and her leadership within the Bermuda Captive Network played a pivotal role in elevating the organisation’s visibility and strategic focus.
“Beyond her professional achievements, Leslie served as a Senator in Bermuda’s Upper House, appointed by Premier David Burt in 2022. She used her platform to advocate for equity, opportunity, and systemic change—causes that mirrored her values in the business world.
“A dedicated coach and mentor, Leslie was also among the first women to train with WeSpeak Bermuda, helping other women find and project their voices through public speaking. She gave freely of her time to coach young professionals, participate in teen boot camps, and lend her support to countless initiatives, always with a sense of purpose and humility.
“The award will be presented during the Opening Session of the 2025 Bermuda Captive Conference, taking place Tuesday June 10 at 9:00am in the Harbourview Ballroom at the Hamilton Princess Hotel & Beach Club. Accepting the award on Leslie’s behalf will be Kelechi Jones, her spiritual daughter, alongside younger cousins Che’ Clarke and Scott Clarke – two young professionals whom Leslie mentored and inspired to join the insurance industry.
“This posthumous honour serves not only as a recognition of Leslie’s professional achievements, but as a tribute to the life she lived: one defined by generosity, courage, and a profound commitment to lifting others up.”
