Assistant Underwriter - Health Insurance

ABOUT US

‘First’ is more than our name, it’s our nature. Cayman First is an industry-leading Property & Casualty and Health insurer, delivering best-in-class products and services to respond to the changing needs of individuals, households and businesses. Through our carefully selected network of agents and brokers, we provide protection for our customers today and prepare them for a brighter tomorrow. Cayman First maintains an A- (Excellent) financial strength rating from global credit rating agency AM Best.

PURPOSE OF JOB

As an Assistant Underwriter for our health insurance department, you will be responsible for supporting underwriting operations by managing submission information for new business and renewals, assessing risk data, and coordinating with brokers, clients, and internal teams. The position involves underwriting non-standard and high-risk cases, preparing quotes and documentation, maintaining accurate underwriting records, and responding to coverage inquiries. The successful candidate will apply strong judgment and critical thinking to resolve complex issues, meet performance targets, and contribute to departmental KPIs while ensuring timely, accurate, and compliant processing of health insurance applications and renewals.

JOB RESPONSIBILITIES

• Maintain submission information for new business and renewals. Gather and screen data required for analysis.
• Request additional information from broker/direct client and follow up on outstanding information.
• Utilize critical thinking and solid judgment to solve problems, make decisions, and resolve complex issues inherent in ensuring the departmental goals are achieved.
• Underwrite non-standard cases and submit SHIC high risk applications to HIC for approval of suggested loadings.
• Process necessary documentation to broker.
• Answer phone calls and respond to emails regarding policy coverage or benefits and provide/request information as needed.
• Prepare correspondence (letters, email, etc.) to customers, brokers and third parties as needed.
• Coordinate renewal process (gather risk documentation and issue renewal letters, follow up on outstanding specs).
• Maintain up-to-date information in underwriting systems and risk files.
• Identify cases that require further medical evidence and submit requests for the same.
• Approve and provide health insurance quotes for individual applications and groups up to approved levels.
• Liaise with other departments to solve queries as necessary.
• Gather and share portability information with other insurers upon request.
• Meet or exceed employee monthly performance objectives.
• Contribute to achieving all departmental KPI’s.
• Perform other duties and responsibilities that may be assigned from time to time.

Requirements

• Associate degree in a related field or equivalent work experience preferred.
• Entry-level underwriting experience in group life and health insurance or a related area is desirable.
• Pursuit of a professional certification in life or health insurance (e.g., LOMA or HIA) is an asset.
• Strong analytical, organizational, and multitasking skills.
• Excellent written, verbal, and telephone communication skills.
• Working knowledge of underwriting principles and processes.
• Ability to access, utilize, and analyze relevant reference materials.
• Familiarity with existing underwriting systems.
• Knowledge of policy forms and related documentation.
• Proficiency in Microsoft Word, Excel, and Access.

Benefits

Cayman First offers a competitive compensation package with eligibility for a discretionary bonus, subsidized health insurance for employees and dependents, preferred home and motor insurance, a great company culture and work life balance. Compensation will be commensurate with experience and qualifications.