Medical Underwriter II

Senior Medical Underwriter

Branford or Farmington, CT/ Hybrid

Company Summary

Founded in 2000 and acquired as an operating company of Amwins in 2016, True Benefit (An Amwins Company)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: sales, pricing, technology, data analytics and project management.

Amwins Group, Inc. (our parent company) is the largest Property & Casualty and group benefits Wholesale Insurance Broker in the US. Amwins is a privately held company that is a leader in the insurance industry, and a company with a long-term vision for success and a culture that truly values associates, their contributions, and their families.

Our environment and culture question the status quo in the health care industry and leverages our relationships and resources to improve the health and well-being of our clients and their employees. True Benefit is looking to add a Medical Underwriter II to their growing team in Branford, CT (near New Haven) or Farmington (near Hartford). This position will be a hybrid work arrangement.

Job Description

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 include but are not limited to:

• 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.

We are looking for the following background and attributes:

• 5+ years of group healthcare rating/Underwriting
• Experience MUST be from medical 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

We strive to be an employer of choice and offer a unique blend of benefits and perks.

• Competitive and comprehensive compensation
• Benefits program that includes:
  • Medical, Dental, Vision, Prescription, Disability and Group Life insurance
  • 401k matching
  • Competitive Paid Time Off (Vacation, Sick, Paid Holidays)
  • Eligible for incentive bonus once requirements are met
  • Charitable donation matching
  • Supportive Environment
  • Business Casual attire

Equal Opportunity Policy: The acceptance of the requested information for consideration and referral of candidates will be without regard to a candidate’s race, creed, color, age, gender, marital status, veteran status, national origin, sexual orientation/identification/expression, disability status, or weight and will be based solely on the candidate’s qualifications for the position. We are an equal opportunity employer.

Pursuant to Connecticut regulation, the compensation range for this position is as stated and includes eligibility for performance-based bonuses.

Connecticut Pay Range

$75,000—$95,000 USD