Key People

The Castletown Group team comprises experienced professionals specialising in insurance, risk management, accounting, treasury, corporate and compliance services.

Key members of the team include the following:

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Ross Dennett

Director, Castletown Insurance Services Limited, Thomas Miller Isle of Man Limited

Ross Dennett has 24 years broking and captive management experience.  Prime point of contact for, predominantly, listed companies ensuring that the management services provided are delivered to the highest standard. Control and coordination of the client insurance arrangements including underwriting, reinsurance arrangements and claims handling in liaison with insurers, brokers and the client captive management team. Completed Full Time Executive MBA at Henleyin 2005.

Ross is currently Chairman of the Isle of Man Captive Association Executive Committee.


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Stephen Morris

Director, Castletown Insurance Services Limited

12 years experience in the financial services sector, initially with a London based consultancy specialising in wholesale and retail banking and then focussing on the offshore insurance sector. A Chartered Accountant also holds a Masters Degree and Doctorate in mechanical engineering. Responsible for the day to day management of half of the Company’s client portfolio which varies from brand name multinationals with extensive reinsurance programmes through to privately owned captives and mutuals. 


Keith Allen

Director, Castletown Insurance Services Limited

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Angela O’Connor

Director, Castletown Insurance Services, Castletown Insurance Company, Castletown Risk Solutions
ACII Chartered Insurer, ACCA (Affiliate)

Angela joined the Castletown Group upon its formation in 1998, initially as an insurance executive, before becoming Director for a number of group entities.  

An experienced professional with a broad range of skills both in the area of insurance and accounting, Angela is head of accounting and oversees the compliance function. Apart from this work, she undertakes statistical analysis for clients with more complex claims profiles.

Angela began her insurance career with The Scottish Widows Fund and Life Assurance Society, at the firm’s head office in Edinburgh, where she spent five years in the life assurance industry. Angela started working with captives in 1996.

Angela is an Associate of The Chartered Insurance Institute (ACII), Chartered Insurer and a affiliate of the Association of Chartered Certified Accountants. 


Richard Drinkwater

Director, Castletown Insurance Services Limited
BA(Hons), BSc(Hons), ACIB

Richard founded Castletown Insurance Group with a team of colleagues in 1998. A trusted and well respected insurance professional with over 25 years’ experience, Richard works as the Client and New Business Director, encompassing a wide range of experience and an excellent record of achieving cost effective insurance strategies to develop and meet the needs of a global client base. 


After graduating, he joined KPMG in their specialist insurance department and in 1990 joined AIG (Europe) as a political risk and trade credit underwriter. Richard came to the Isle of Man in 1995 when he entered the captive insurance sector.

Richard holds a BA (Hons) degree in Law & Psychology from Oxford Brookes University and a BSc (Hons) degree in Financial Services from UMIST (University of Manchester Institute of Science & Technology). Richard is an Associate of the Chartered Institute of Bankers (AICB) and was formerly the Chairman of the Isle of Man Captive Association.

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Angela Christian

Associate Director, Castletown Insurance Services Limited,
Castletown Insurance Company Limited: Underwriting
ACII, Chartered Insurer 

Angela joined Castletown Insurance Services in 2001, bringing with her more than 20 years’ extensive knowledge of the insurance industry. As well as acting as associate director, Angela is responsible for a broad portfolio of key clients for the Castletown Group. 

Angela began her career in insurance in 1979 when she joined Commercial Union, now Aviva. Over the course of ten years, Angela worked in the sales and administration function of both general and life divisions, before pursuing a career in captive management in 1989.

Angela is an Associate of The Chartered Insurance Institute (ACII), having qualified in 1992 and was granted Chartered status in 1995. 

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John Hankinson

Associate Director, Castletown Insurance Services Limited: Accounting

John joined Castletown Insurance Services Limited in 2004 as an accountant. Included in John’s international client portfolio are heavy industrial conglomerates within the energy, shipping and manufacturing sectors.   

Trained as an accountant at Wolsey Hall College, Oxford, John started his career in 1985 with a family run practice. In 1994, John joined Michal Simm and Co, where he gained his wealth of accounting knowledge and the Isle of Man finance sector, specialising in auditing, taxation and company administration for property development firms and investment trusts. 

As well as his accounting responsibilities, John draws upon a comprehensive knowledge of the financial markets to play an active role in banking liaison.  

Elaine MacMurchie

Following seven years in the IT department of a UK Plc, Elaine moved to the insurance sector in 1991, where she worked for Scottish Widows. Elaine moved to the Isle of Man in 1996, and continued to work in insurance, but also worked in corporate administration.  

Elaine joined The Castletown Group in 2001 following 10 years in the insurance industry. As well as acting as account handler for large corporate clients, Elaine draws upon multiple talents to fulfil an extremely varied role heading up the day to day operational side of the business which encompasses credit control, bookkeeping, treasury, company secretarial, human resources and IT.