Influential Women in Captive Insurance: Lesley Thompson
Lesley Thompson, Leader, WTW (Cayman)
Lesley Thompson has more than 25 years of international professional experience in accounting, insurance and structured finance. She started her career in finance within commerce and industry in London, before taking a finance manager position in Angola, West Africa.
Enjoying her international experience, Thompson 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 US Virgin Islands, for some of the top Fortune 100 companies, private companies, as well as for-profit and not-for-profit healthcare institutions.
In 2005, she 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 Willis Towers Watson (WTW). During this time, Thompson has established a record of excellent client service, generating and building relationships, managing projects from concept to completion, creative problem-solving and designing business strategies.
Since 2006, Thompson has been approved by the Cayman Islands Monetary Authority to act as a director for licensed entities.
She 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 and special purpose vehicles in multiple jurisdictions, both on and offshore.
Effective March 2020, she became the leader of the Cayman office of WTW. She is a director and secretary of Willis Towers Watson Management (Cayman).
How did you get started in the captive insurance industry?
After qualifying as an accountant while working in London, I changed jobs and spent a year working as a finance manager for an international shipping and freight forwarding company in Angola, West Africa. At the end of my contract, I moved back to the UK and started researching finance positions overseas.
In a bookstore off Trafalgar Square, I found a book on 101 careers abroad and under “accountant” it listed a recruitment agency in Scotland. Within a month after contacting them, I was shortlisted for a position in Bermuda with Aon and was subsequently offered the role. I moved to Bermuda in January 2000 to start my career in the insurance industry.
Who inspired you or acted as a mentor in your career?
No single person in particular has mentored me in my career, but I have had some really great pieces of advice and support along the way which has been invaluable. The biggest support was my parents, who instilled in me the viewpoint that you can do anything you want if you set your mind to it.
What do you think deters people from entering the world of captives?
I would say the biggest limiting aspect is knowledge of the industry itself. Insurance and captives is not something shared at a school or even university level perspective. I am the head of the Insurance Managers Association of Cayman’s Educational Scholarship Fund, and this is an area the fund will be focusing over the next few years.
How can mentorship and sponsorship programmes be designed to better support the career development of women?
“Programmes focused on the next generation and women leaders are particularly important.”
Since I joined the industry 25 years ago, the number of women in the industry has grown significantly, particularly in senior roles, but there is still more needed. Mentorship in particular has historically not been widespread with women on either side of the mentor/mentee relationship, so it is important that senior women embrace mentorship and sponsorship programmes in order to further open opportunities for the next generation.
Programmes focused on the next generation and women leaders are particularly important, especially when supported by your organisation.
In what ways can companies in the sector create a more inclusive culture that actively promotes gender diversity at all levels?
Companies need to have diversity (not only of gender) as a core value, and this should be apparent in all aspects of the day-to-day workings of the organisation. In 2023 and 2024 I was fortunate to have been nominated for WTW’s SHE Leads and its women-focused Leadership Effectiveness Acceleration Program (LEAP).
Both programmes were intensive and very well managed, and I learned a great deal during this time as well as building up a peer network of senior women throughout the organisation.
What challenges are gender-specific to women in the captives industry?
Gender-specific challenges are decreasing, but the balancing of family commitments (young or old) and work is always a tough one. One good thing to come out of the COVID-19 pandemic was the shift from the 9 to 5, Monday to Friday, working hours perception. In a truly hybrid working environment, you can accomplish your commitments on a more flexible timeframe.
What solutions would you like to see?
Companies need to understand and support their colleagues and create and promote cohesive and equal opportunity environments. This is something that I believe WTW does very well, and I am proud to be a global colleague paying it forward.
What are your ambitions?
I want to continue to grow personally and professionally, while building a great and expanding team. I believe in education, training and mentorship and I share this with my team so that they can continue to develop and assume my responsibilities, thereby allowing me to pursue further opportunities.
Click here to read Captive International’s first Influential Women in Captive Insurance publication, celebrating the women transforming the captive sector through their sustained excellence and leadership.
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