Regional Underwriting Lead, Group Healthcare Insurance - True Benefit : Job Details

Regional Underwriting Lead — Group Healthcare

Branford or Farmington, CT (hybrid)

True Benefit, an Amwins Group company, is conducting a candidate search for a Regional Underwriting Lead — Group Healthcare. 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

The Regional Underwriting Lead — Group Healthcare is both a strategic and hands-on leadership role responsible for overseeing underwriting operations across a designated territory. This position specializes in alternate funding arrangements – including level-funded, self-funded and minimum premium benefit models – as well as PEO-based risk structures. Key responsibilities include guiding case-level underwriting decisions, leading training initiatives, and building strong partnerships with internal teams and external stakeholders. The role blends tactical oversight with broader accountability for underwriting quality, education, and innovation—ensuring profitability while driving market growth.

Responsibilities

Underwriting Strategy & Execution:

• Prepare and guide rate quotations, benefit recommendations, and risk structures with a focus on accurate risk assessment and pricing that supports both profitability and membership growth.
• Lead underwriting of PEO group health plans, applying a deep understanding of medical underwriting, self-funded, level-funded and stop-loss arrangements, and composite/tiered rating methodologies.
• Work across multiple markets supported by the organization, with a specialization in regional nuances for new business practices.
• Review complex or escalated cases, and when necessary, facilitate further review by senior leadership.
• Maintain understanding of our core technologies (pricing tool, reporting tools, etc.) and consult with development and support teams to address issues and help prioritize potential work.

Team Leadership & Development:

• Lead, mentor, and coach underwriters at all levels—from junior underwriters to market specialists—supporting both their technical and professional growth.
• Provide peer review, case support, and real-time guidance to ensure consistent application of underwriting guidelines.
• Actively support and collaborate with peers and team members to drive a culture of shared learning and accountability.
• Participate in interviewing and onboarding of new underwriting hires and contribute to talent development efforts.

Training & Knowledge Sharing:

• Develop and deliver comprehensive training programs for both the underwriting team and internal/external sales staff, with a focus on underwriting principles, market changes, and carrier-specific practices.
• Support Market Specialists with the creation and upkeep of underwriting reference materials, market-specific business rules, and internal best practice documentation.
• Serve as an internal expert and go-to resource for underwriting-related inquiries, escalations, and process guidance.

Stakeholder Engagement:

• Foster strong relationships with the sales teams and leaders as well as broker and carrier partners to support deal structuring, client retention, and consultative selling.
• Collaborate closely with leadership, digital, actuarial, and operations teams to align on risk philosophy and process improvement initiatives.
• Collaborate with carrier partners to maintain strong, cohesive relationships.
• Participate in carrier update discussions on pricing updates or market specific dynamics and/or challenges.

Qualifications

• Not less than 8 years of group healthcare rating/underwriting.
• Not less than 2 years of professional team leadership.
• Bachelor's degree in risk insurance, business, economics, or other applicable major.
• Must be experienced in medical group medical underwriting (either brokerage or insurance carrier).
• Deep understanding of underwriting within self-funded and level-funded products.
• Experience with PEO underwriting, including composite rating and master policy risk is preferred.
• Strong grasp of state-specific regulatory frameworks including ACA, ERISA, and HIPAA.
• Proven ability to mentor, coach, and educate underwriting and sales professionals.
• Strategic thinking and decision-making skills.
• Excellent analytical, organizational, and people skills.
• 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.
• Professional certifications such as CEBS, or CSFS are desirable.