Cayman First Expands Management Team with Three Senior Appointments

Cayman First Insurance Company (“Cayman First”) is pleased to announce three strategic senior appointments, effective immediately, as the company strengthens its management team following a year of significant milestones.

Drew Osborne, previously Claims Manager of Group Insurance Services, has been appointed Provider Relations Manager. Glenda Broadnax-McCoy joins Cayman First as Claims Manager of Group Insurance Services, and Jehan Fernandez steps into the role of Claims Manager for Property & Casualty.

These appointments reflect Cayman First’s ongoing commitment to delivering exceptional service and innovation, as the company builds on 40 years of service to the Cayman Islands community, celebrated in 2024.

Osborne started in the Customer Care Department at Cayman First in 2013, advancing to Assistant Customer Care Manager and later Claims Manager of General Insurance Services in 2022. Over the last 12 years, his leadership and expertise have been instrumental in improving Cayman First’s claims operations and enhancing client satisfaction. In his new role, Osborne will focus on strengthening relationships with healthcare providers and partners.

“We are thrilled to see Drew step into the role of Provider Relations Manager,” said Chris Hind, Chief Executive Officer of Cayman First. “His extensive experience in client service and operations, combined with his proven leadership, makes him the ideal candidate to foster these vital partnerships.”

Broadnax-McCoy brings a wealth of experience in healthcare and insurance operations, specialising in claims processing, eligibility maintenance, team leadership, and cross-functional team leadership. Her previous roles include leadership positions at Envolve Dental/Centene Corp and Delta Dental in the US.

She will report to Polly Pickels, Vice President of Group Insurance Services, and help lead efforts to enhance claims management processes while supporting technological advancements to improve the customer experience.

“Glenda’s deep expertise in healthcare and insurance operations will be invaluable as we focus on improving the customer journey and integrating innovative technology,” said Pickels.

Fernandez brings over 12 years of experience in claims management across auto, property, liability, and subrogation lines of business. His expertise spans handling claims for residential and commercial properties, including those involving catastrophic events.

Reporting to Natasha Pettier, Vice President of Property & Casualty, Fernandez will help oversee the division’s claims operations, ensuring high-quality service and efficient processes.

“Jehan’s industry knowledge and impressive track record make him an outstanding addition to our management team,” said Pettier. “His skills will ensure we continue to deliver exceptional client experiences.”

Cayman First remains committed to delivering innovative insurance solutions and exceptional service as it continues to be a market leader in the Cayman Islands.

“Each of these individuals brings unique expertise and leadership qualities that will enhance our group life and health, and property and casualty businesses,” Hind said. “Their combined experience will deepen our relationships with brokers, consultants, and clients while driving growth and operational excellence.”