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

Supervisor, Underwriting (Health)

Reporting to the Underwriting Manager, the successful applicant will be responsible for:

> Daily supervision of the Underwriting Unit and assisting in the evaluation and pricing of group life and health prospects within assigned authority limits.

> Obtaining and analyzing account-specific information and preparing information for pricing.

> Reviewing submission information and issuing quote letters.

> Coordinating the renewal and new business process.

> Understanding and utilizing Pricing and Business Intelligence (BI) models in collaboration with management and the Group Actuarial team.


> Bachelor’s degree in Mathematics or related field.
> 3-5 years mid-high level underwriting experience in group life and health or related area.
> Professional certification in life or health insurance, through LOMA or HIA desirable.
> Strong analytical, communication, multi-tasking and organizational skills.
> Strong written, verbal and telephone communication skills
> Knowledge of underwriting principles and process
> Understands how to access, utilize and analyze necessary reference materials
> Knowledge of existing systems
> Knowledge of policy forms and documentation
> Proficiency in Word, Excel & Access


Cayman First offers an attractive salary and benefits package, as well as the opportunity to become a part of a dedicated team of professionals. Salary range for this position is CI$55,000 – $70,000 per annum, commensurate with qualifications and experience.

Cayman First is a leader in insurance in the Cayman Islands, and is part of the Bahamas First Group. The Company has been serving the Cayman Islands for over 35 years, and offers a full range of General and Health insurance products directly to the public and through broker intermediaries. Both the Company and the Group carry “A-” Excellent ratings from A.M Best.

Please submit written applications to:
Human Resources
Cayman First Insurance Company Limited
P.O. Box 2171 Application Deadline:
Grand Cayman KY1-1105 December 6th, 2020

or email to:

Are you interested in joining Cayman First?
Send us your resume today!