Careers at Cayman First

At Cayman First, we’re always looking for people to fit a variety of roles requiring a diverse range of skills and talents, from a variety of backgrounds. We are looking for driven, lively people to enrich our team – people who understand the level of trust that our customers put in us, and the responsibility on our shoulders that comes with that.

Are you compassionate and determined to deliver the best for our customers? If you think you can embody our core values and want to make a meaningful difference to the people and communities that we serve, then a career with Cayman First could be for you. Whether you’re just starting out, or looking for a new company to evolve your experience, Cayman First is waiting for you.

Are you F.I.R.S.T?

Current Opportunities

General Applications

Cayman First is always open to connecting with talented and motivated individuals to join our team. If you don’t see a job opening that fits your interests and qualifications, please feel free to submit your application for future opportunities.

Claims Manager, Property and Casualty

The Claims Manager for Cayman First’s property and department is responsible for leading our Claims team to ensure accurate and efficient processing of claims and maintaining high levels of customer satisfaction. The Claims Manager will also play a key role in developing and implementing strategies to mitigate risks and improve claims management and processes.

Claims Examiner – Health Insurance

The Claims Examiner is responsible for handling, evaluating, and assessing healthcare claims for our customers in accordance with applicable policy and service standards. You will play an important role by supporting work efforts of the Claims team all while prioritizing customer service excellence.

Underwriter – Property and Casualty

As an Underwriter for our Property and Casualty Broker Unit, the successful candidate will liaise with brokers to maintain a positive relationship and help educate them on our products and services. They will be responsible for managing retention targets for renewals, underwriting risks, providing customer service to brokers including creating quotations and accurately adding and processing renewals while performing other administrative duties.

Assistant Underwriter – Property and Casualty

As an Assistant Underwriter you will be supporting the back-office retention team in the Property and Casualty department. This role predominantly focuses on renewals and retentions, but may involve supporting customers that have a query, addressing a complaint and providing detailed information about policies, products, and services.