Derek Stenson > Conyers > Grand Cayman, Cayman Islands > Lawyer Profile

PO BOX 2681
Cayman Islands

Work Department





Derek Stenson is a Partner in the Cayman Islands office of Conyers Dill & Pearman. Derek joined Conyers in 2018. He specialises in insurance, reinsurance and structured products, as well as a broad range of corporate and finance matters.

Derek has extensive experience advising a wide range of international financial and insurance institutions on all aspects of insurance and reinsurance law and regulation. Derek also has particular expertise advising on repackagings and collateralized loan obligations, corporate finance and M&A transactions, portfolio transfers, restructurings, stock exchange listings, mergers, migrations, contractual negotiations and regulatory and compliance matters.

Derek has been consistently ranked as a recommended Lawyer in Legal 500 since 2014. Clients highlight him having “outstanding knowledge, responsiveness and collaboration with other advisors”. They also note that he is “intelligent, diligent, responsive and hardworking”.




  • Insurance Sub-Committee of Cayman Finance
  • Reinsurance Sub-Committee of Cayman Finance
  • Marketing Committee of Insurance Managers Association of the Cayman Islands
  • Editorial Board of Captive Insight

Lawyer Rankings

Cayman Islands > Insurance/reinsurance

(Leading individuals)

Derek StensonConyers

The dedicated team of insurance specialists at Conyers possess an extensive track record across the full spectrum of insurance work, which it handles for a broad client base comprising insurers, reinsurers, captive owners, insurance managers and insurance consultants. Most notably, the department, which is led by Derek Stenson , frequently handles major reinsurer establishments, mergers and migrations, as well as insurance-related M&A, regulatory advisory issues, insurance litigation and insurance-linked securities work. Other noteworthy advisers include counsel Rob Humphries and associate Philippa Gilkes , both of whom are well-versed in regulatory, commercial and transactional matters arising from the insurance and reinsurance sphere.

Cayman Islands > Regulatory and compliance

The cross-departmental regulatory and compliance group at Conyers fields practice area specialists who demonstrate expertise in the AML, FATCA/CRS and economic substance regimes, among others. Robert Lindley specialises in regulatory issues affecting pensions, private trust companies, foundation companies and other trust structures. Insurance specialist Derek Stenson  advises insurance-related entities on privacy and data protection requirements, and also prepares regulatory applications for new insurance companies.