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Management Team

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Management Team

Ian Kilpatrick - President and CEO

Ian Kilpatrick, a British citizen with permanent residence status in the Cayman Islands, has 30 years of experience in the international insurance and finance business. In 1993 Mr. Kilpatrick founded the Crusader International Group in the Cayman Islands and the Lionheart Insurance Group in the United States, specializing in risk management services, alternative risk transfer, life insurance and annuities and retail insurance. As Chairman of the Board and business development creator, he spends a lot of his time traveling around the world marketing and promoting the products and services offered by Crusader and Lionheart.

He is currently a Director of the Captive Insurance Companies Association and the founding chairman of the Cayman Insurance Managers Association. Mr. Kilpatrick contributes articles to the Cayman Financial Services Review and other industry publications.

Before founding the Crusader International Group, Mr. Kilpatrick owned and managed Telecheck Cayman Ltd. and brought to market a second company to fund the company’s credit cards, which was one of Grand Cayman's first public offerings by a local company. Prior to this Mr. Kilpatrick was a major shareholder of Insurance Management Consultants (Cayman) Ltd., building it into the largest independent captive management company in the Cayman Islands. He is also Chair of Advantage Life and Annuity SPC of Grand Cayman.

Simon Kilpatrick - Executive Vice President, Captive Insurance Management & Consulting

Simon Kilpatrick has over 16 years of experience in the financial services and insurance industry, specializing in private banking, investment management and captive insurance.  Prior to Joining Lionheart Insurance Group, Simon worked for the Bank of Bermuda in both Bermuda and the Cayman Islands as a portfolio manager and financial controller, and Coutts (Cayman) Limited as the Manager, Investments.

A graduate of the College of William and Mary in Virginia, Simon is a member of the CFA institute and a CFA Charter holder since 2002.  He also holds an Associate in Captive Insurance (ACI) designation from the International Center for Captive Insurance Education.  Simon is an active member of the South Carolina Insurance Association and of the Friendly Society Restored, a South Carolina captive industry advocacy group.

Simon is responsible for both the Captive Insurance and Structured Finance units.  His responsibilities include new business development, client service, product development, and the business operations of the US offices.  In addition to overseeing Lionheart Insurance Management, LLC, Simon is responsible for the operations of Lionheart Insurance Agency, LLC and sits on the underwriting committee of the Group’s agency captive, Chesapeake Bay Insurance Company.  Simon acts in an advisory capacity to the investment committees of numerous captive insurance companies and assists with the creation of their investment policy statements and the ongoing investment decision process.

Fiona J. Moseley - Executive Vice President, Wealth Management & Asset Protection

Fiona Moseley brings substantial experience and expertise to Lionheart Insurance Group in the integration of offshore life and annuity structures, captive insurance programs and wealth and estate planning. She joined Crusader International Management at its inception in 1993, serving most recently as its Managing Director. She also serves as the Director of two insurance-related Segregated Portfolio Companies and as Secretary on several other SPCs that are established as financing or mutual fund vehicles. Prior to joining our Group, she worked with the founder of Crusader and KilpatrickMead on a number of captive insurance projects.

Fiona is the Secretary of the Insurance Managers Association Cayman Ltd., and a Director of the Rotary Club of Grand Cayman Central.

As Lionheart's Executive Vice President, Wealth Management & Asset Protection, Fiona is primarily responsible for managing the Company's wealth management operations, with particular focus on developing new products and clients, ensuring client satisfaction, and providing guidance and counsel across the company on all wealth management topics.

Stuart Jessop - Executive Vice President, Finance & Administration

Stuart Jessop is a qualified chartered accountant (ICAEW). He joined Lionheart Insurance Group in 2005 as Senior Vice President, Finance and Administration for Crusader International Management and as the Group Financial Controller. He began his career with Ernst & Young in London, where he specialized in both audit and non-audit assignments for financial services clients.

Stuart then worked for National Westminster Bank Plc (now part of the Royal Bank of Scotland Plc) in London as an Internal Audit Manager with the Corporate Banking Division. He subsequently transferred to the group's Coutts Offshore Private Bank division in the Bahamas, Cayman Islands and the Isle of Man, where he worked in a number of roles, including internal audit, finance and accounting, and banking and securities operations, with an emphasis on offshore financial services and products.

He is responsible for planning, developing, implementing, and reviewing financial policies and procedures for Lionheart and ensuring that effective accounting and administrative functions are in place to support the business development and client service functions across the Company's Wealth Management, Structured Risk Finance, and Captive Insurance products.