Lesley Thompson

Lesley is the leader of the Cayman Islands office of WTW since March 2020. She has over 25 years’ international professional experience in accounting, insurance and structured finance. She started her career in finance within commerce and industry in London, UK, before taking a Finance Manager position with a Shipping and Freight Forwarding company in Angola, West Africa.

Enjoying her international experience, Lesley started her insurance career with Aon in Bermuda in 2000. During her time with Aon, she managed a large portfolio of complex captives domiciled in Bermuda and the U.S.V.I., for some of the top Fortune 100 companies, private companies, as well as “for profit” and “not for profit” healthcare institutions. In 2005, Lesley moved to the Cayman Islands where she has worked with multi-jurisdictional independent captive managers and led the insurance management services of the Maples Group for four years prior to joining WTW.

During this time, Lesley has established a proven record of excellent client service, generating and building relationships, managing projects from concept to completion, creative problem solving and designing business strategies. Lesley is experienced in all stages of the life cycle of companies, from incorporation to liquidation. Her experience includes Single Parent, Association, Group, Agency, Not-for Profit, Private Placement Life & Annuity, Rent-a-Captive, Segregated Portfolio Companies, Insurance Linked Securities (“ILS”) and Special Purpose Vehicles (“SPV’s”) in multiple jurisdictions, both on and off-shore.

Education and Credentials
Lesley holds a Bachelor of Arts Degree in Accounting and Finance from Manchester Metropolitan University, is a Chartered Management Accountant, a Fellow of Captive Insurance, a Chartered Global Management Accountant and an Accredited Director. She is a member of the Cayman Islands Institute of Professional Accountants and is a Notary Public of the Cayman Islands.

Lesley is also a past Board President of the International Center for Captive Insurance Education (ICCIE), and the Chair of the Executive Committee of the Insurance Managers Association of Cayman (Cayman International Insurance (“IMAC”)).