Senior Underwriter, Group Healthcare Insurance - True Benefit : Job Details

Senior Underwriter — Group Healthcare

Branford or Farmington, CT (hybrid)

True Benefit, an Amwins Group company, is conducting a candidate search for a Senior Underwriter with experience in group healthcare insurance. This a hybrid role with offices in either Branford or Farmington, CT.

Founded in 2000, True Benefit and acquired as an operating company of Amwins Group in 2016, True Benefit assists businesses in developing comprehensive strategies for their employee benefit programs. True Benefit acts as a program manager for health care underwriting and has $2.3+B of health care premium under plan management for over 150,000 insured employees across the country. Our rapidly growing company is looking for top talent to join our team. True Benefit is a thriving company and there are enormous opportunities for additional growth in our business in multiple areas: underwriting, sales, pricing, technology, data analytics and project management. We are licensed life & health producers in 22 states, focused on the East Coast.

Emphasis is paid on innovative approaches to engage both the employer and employee in benefit programs that drive value for the consumer and mitigate the rising cost of health care. We provide end-to-end assistance in the benefit marketplace. With a resolute team of seasoned insurance professionals, we help our clients through:

• Driving Fortune 500 solutions to small and mid-sized employer groups.
• Strategic sales support.
• Account management.
• Wellness and consumer driven health plans.
• Business risk evaluations through strong in-house underwriting.
• Education and training distribution channels on effective health care and benefit strategies.

True Benefit's parent is Amwins Group. Amwins is the largest wholesale brokerage and group insurance administrator in the US with annual placed premiums more than $44.5B. We are privately held with the employees owning the majority stake. We have over 65+ operating companies across 5 divisions, over 175+ locations around the world, and 7.5k employees. Amwins has expertise across a diversified mix of property, casualty, and group benefits products, and offers value-added services to support these products, including product development, underwriting, premium and claims administration, and actuarial services. Please visit our website at www.amwins.com

Position Overview

We're looking for a sharp, strategic healthcare underwriter with strong expertise in alternate funding arrangements including level-funded, self-funded and minimum premium benefit arrangements. If you excel at quickly assessing complex situations, applying underwriting protocols, and driving consensus across teams, we want you on our team. This consultative role requires both analytical precision and clear, confident communication. As a key contributor, you'll help shape pricing strategies and deliver best-in-class underwriting support in a fast-paced, collaborative environment.

Responsibilities

• Lead the development of rate quotes, benefit recommendations, and risk arrangements—with a strong understanding of level-funded and alternative funding strategies.
• Balance sound risk assessment with growth objectives to protect the book of business while expanding membership.
• Collaborate closely with the sales team and carrier partners to deliver market-aligned, competitive solutions that meet prospects' needs and maintain financial integrity.
• Serve as a subject matter expert in underwriting, continuously educating internal teams and sales partners on underwriting principles, funding arrangements, and evolving market trends.
• Actively contribute to a team-based underwriting culture, supporting peers and promoting consistent standards across cases.
• Mentor and coach junior underwriters, conducting peer reviews and fostering development through real-time feedback and training support.
• Assist in building training tools and materials, helping formalize underwriting education across levels.
• Support innovation and process improvement efforts, offering insights that enhance underwriting efficiency, accuracy, and scalability.

Qualifications

• Not less than 5 years of group healthcare rating/underwriting.
• Experience MUST be from healthcare group benefits insurance industry (either brokerage or insurance carrier).
• Able to work in a fast-paced, high production environment.
• Strategic thinking and decision-making skills.
• Excellent analytical, organizational, and interpersonal skills.
• Self-funded and level-funded experience.
• Well-developed verbal and written communication skills.
• Ability to work well in a team-based environment.
• Advanced Microsoft Excel and PowerPoint Skills; Basic Power BI or Tableau a plus.
• PEO large group health pricing experience a plus.
• Bachelor's degree required.