Cayman First Insurance Company names new leaders in Health and P&C

September 1, 2022







George Town, 1 September 2022 – Cayman First Insurance Company is pleased to announce that Annikki Hill has been appointed to the role of Vice President of Group Insurance Services. Her appointment positions Cayman First to reimagine its health insurance and employee benefits offerings to the Cayman market as the company continues its focus on digital innovation. The company has also named Erwin Freeland as Manager of Property & Casualty Claims following Mr. Freeland’s two-year term as the department’s Assistant Manager.

Ms. Hill brings over 15 years of progressive leadership experience in health insurance. She joins Cayman First most recently from her position as Country Manager and In-house Legal Counsel at Generali Worldwide’s general agent in the Cayman Islands. In her new role, Ms. Hill is responsible for all aspects of Cayman First’s group life and health insurance portfolio, including strategic management, marketing, administration and compliance, underwriting, customer service, claims, and profitability.

“Annikki has a unique skillset and operational background that will allow her to become a dynamic leader within our complex and evolving market,” said Managing Director Roger Balkissoon. “Her extensive leadership experience in group insurance, business development and compliance will enable her to enhance the growth of Cayman First’s health business and deepen relationships with our brokers, consultants and clients. This passion for engaging and collaborating with teams and partners will be a significant asset to Cayman First. I am also delighted to see Erwin step into this broader leadership role in the Claims department. He has extensive experience across the claims function and will continue to provide the exceptional advice and service that our clients and partners expect and deserve.”

Commenting on her appointment, Ms. Hill said, “I am grateful for the opportunity to join the Cayman First team. I have always been aware of the company in the insurance space and even envious of the name ‘Cayman First’. Now, I get to wear it, be a part of its mission, and embody it for our customers and out in the world. ‘First’ in Cayman is the goal and putting Cayman First is the purpose. We have a lot of good work to do.”

Mr. Freeland joined Cayman First’s Claims Department in 2020. Building on 25 years of claims experience in Florida & Cayman, in this new role he will be responsible for the department’s daily operations, litigation, disaster recovery, staff development and vision. With a track record of maintaining high levels of performance in the Property & Casualty space, Mr. Freeland brings his coaching, mentoring and technical skills to an already dynamic and passionate team.

“There is nothing more important to our clients than having their claim handled fairly and efficiently,” said Mr. Freeland. “Restoring our clients after a life-changing event is the fundamental promise of our business and I am excited to lead our team in fulfilling this promise with a strong focus on technology and enhancing the customer experience.”

About Cayman First Insurance Company

Cayman First is an industry-leading Property & Casualty and Health insurer delivering best-in-class products and services that meet the needs of individuals, households and businesses in the Cayman Islands. An integral player in the Personal and Commercial segments of the Cayman Islands insurance market since 1984, the company is regulated by the Cayman Islands Monetary Authority and by the Health Insurance Commission within the Cayman Islands Department of Health Regulatory Services. Cayman First has an AM Best financial strength rating of A- (Excellent) with a stable outlook. It has been part of the Bahamas First Group since 2010 and contributed US$67 million in premiums to the Group in 2021.