Underwriter Development Program Jobs in Middletown, CT

Senior Medical Underwriter

Branford or Farmington, Connecticut | Hybrid

True Benefit, an Amwins Group company, is adding a Senior Medical Underwriter in Branford or Farmington, Connecticut. This incremental hire supports continued business growth.

True Benefit is an employee benefits consulting and healthcare underwriting program manager supporting a leading Professional Employer Organization (PEO) platform. Please visit us at www.amwins.com/opco/true-benefit. We manage more than $2.3 billion in annual healthcare premium for over 150,000 insured employees nationwide. True Benefit has been part of Amwins Group, the world's largest wholesale insurance distributor, since 2016. Please visit us at www.amwins.com.

Why This Opportunity

This opportunity is designed for an experienced group medical underwriter who wants to remain close to the technical work while gaining broader influence across pricing, sales partnership, talent development and underwriting strategy.

• Work on complex level-funded, self-funded, minimum-premium and other alternative-funded cases.
• Remain a hands-on senior individual contributor while mentoring colleagues and helping shape underwriting standards.
• Partner directly with sales teams and carrier partners on competitive case strategy and pricing decisions.
• Contribute to training, process improvement and the continued scalability of the underwriting operation.
• Benefit from hybrid flexibility and the resources, stability, and long-term perspective of True Benefit and Amwins.

Position Overview

As Senior Medical Underwriter, you will evaluate and price group medical opportunities, develop benefit and risk recommendations, and partner with sales and carrier teams to produce competitive solutions while protecting the financial integrity of the business. You will apply your expertise across level-funded, self-funded, minimum-premium and other alternative funding arrangements.

This is a visible role and you will be trusted to exercise sound underwriting judgment, explain complex decisions clearly, mentor junior underwriters and help strengthen underwriting quality and consistency.

Hybrid Work Arrangement

• Hybrid work arrangement requiring two days per week in either True Benefit's Branford or Farmington, Connecticut office.
• The remaining workdays may be worked remotely, subject to business and team needs

Responsibilities

Group Medical Pricing and Risk Assessment

• Develop rate quotes, benefit recommendations and risk arrangements for group medical opportunities.
• Evaluate fully insured, level-funded, self-funded, minimum-premium and other alternative funding arrangements.
• Assess complex cases quickly and apply underwriting protocols consistently.
• Balance sound risk assessment with growth objectives to protect the book of business while supporting membership growth.

Sales and Carrier Partnership

• Collaborate with sales teams and carrier partners to develop competitive, market-aligned solutions that meet prospect needs and maintain financial integrity.
• Clearly communicate underwriting decisions, pricing considerations and case strategy to internal stakeholders and external partners.
• Serve as a subject matter expert on group medical underwriting, alternative funding strategies and evolving market trends.

Underwriting Leadership and Development

• Educate internal teams and sales partners on underwriting principles, methods and funding arrangements.
• Actively support and collaborate with other underwriters to promote consistent standards across cases.
• Mentor and coach junior underwriters through peer review, real-time feedback and technical guidance.
• Assist in developing underwriting training tools, resources and educational materials.

Process Improvement and Innovation

• Recommend and support process improvements that strengthen underwriting efficiency, accuracy and scalability.

Qualifications

Required

• Bachelor's degree.
• 5 or more years of group healthcare rating and underwriting experience.
• Group medical underwriting experience gained through a health insurance carrier, employee benefits brokerage, benefits administrator or comparable organization.
• Direct experience with self-funded and level-funded group health arrangements, including group medical pricing and risk assessment.
• Ability to work effectively in a fast-paced, high-production environment.
• Strong strategic thinking, judgment, and decision-making skills.
• Excellent analytical, organizational, interpersonal and communication skills, including the ability to explain complex underwriting concepts clearly to technical and nontechnical audiences.
• Ability to work collaboratively in a team-based environment.
• Advanced Microsoft Excel and PowerPoint skills.

Preferred

• Experience pricing large-group health plans within the PEO market.
• Experience with minimum-premium arrangements.
• Experience mentoring or reviewing the work of less-experienced underwriters and contributing to training resources.
• Working knowledge of Power BI or Tableau.
• Professional certification such as CEBS or CSFS.

What We Offer

True Benefit and Amwins offer the entrepreneurial environment of a growing specialty business, backed by the scale and stability of the nation's largest wholesale insurance distributor.

• Competitive and comprehensive compensation.
• Eligibility for an incentive bonus once applicable requirements are met.
• Medical, dental, vision, prescription, disability and group life insurance with no waiting period.
• 401(k) matching and competitive paid time off, including paid holidays.
• Charitable donation matching.
• A collaborative, supportive environment that values technical expertise and professional growth.