AmWINS Group
Healthcare Underwriting - Regional Underwriting Lead
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 Healthcare Underwriting - Regional Underwriting Lead to their growing team in Branford, CT (near New Haven) or Farmington, CT (near Hartford). This position will be a hybrid work arrangement.
Job Description
The Healthcare Underwriting - Regional Underwriting Lead 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.
Key Responsibilities
Underwriting Strategy & Execution:
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.
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 Healthcare Underwriting - Regional Underwriting Lead to their growing team in Branford, CT (near New Haven) or Farmington, CT (near Hartford). This position will be a hybrid work arrangement.
Job Description
The Healthcare Underwriting - Regional Underwriting Lead 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.
Key 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, level-funded & 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 liaise with development and support teams to address issues and help prioritize potential work.
- 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.
- 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.
- 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 regarding pricing updates or market specific dynamics and/or challenges.
- 8+ years of group healthcare rating/underwriting.
- Bachelor's degree in Business, Economics or other applicable major.
- Experience MUST be from medical group benefits insurance industry (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 with 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 interpersonal skills.
- Well-developed verbal and written communication skills.
- Ability to work well in 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.
- 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 an 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.