Vice President, Underwriting

Role Overview

Ready to help us transform healthcare? Bring your true colours to blue. Reporting directly to the Chief Financial Officer, the Vice President of Underwriting will lead and oversee the underwriting function, ensuring strategic alignment with business goals and risk management objectives. The successful candidate will be a results‑oriented leader who can effectively lead underwriting teams to strategically support and manage risk effectively, develop and maintain underwriting guidelines, policies and procedures, and establish pricing models and methodologies based on risk assessment and market conditions.

The successful candidate, who will lead a 60‑person team, will have proven experience in recruiting, managing, and mentoring highly effective, innovative and collaborative teams. The successful candidate will work closely and collaboratively with the Chief Financial Officer and key peer stakeholders across actuarial, treasury, finance, sales and legal departments to optimize risk selection and policy pricing strategies, while serving a wide range of internal clients including the Chief Executive Officer and other members of the executive team, business and functional unit leaders.

This role requires a dynamic leader with proven expertise in underwriting strategy, team leadership and collaboration across organizational levels. This full-time role is eligible for our FLEX persona and candidates are expected to be in our Boston or Hingham office location on Tuesday and Wednesday each week at minimum.

• Lead and oversee the underwriting process for individual and group health plans
• Review complex medical applications, analyzing medical history, and assessing risk factors to determine coverage eligibility and premium levels
• Ensure adherence to all state and federal regulation requirements regarding health insurance underwriting
• Conduct and monitor audits to maintain underwriting quality and accuracy
• Monitor industry trends and adapt underwriting practices to evolving regulations
• Identify and address potential compliance issues
• Partner closely with actuarial teams to assess risk and establish competitive pricing
• Collaborate with sales teams to provide underwriting support that address customer needs and support growth initiatives
• Communicate underwriting decisions effectively to brokers and policyholders

• Shaping strategy:
  Ability to develop, manage and implement thoughtful underwriting strategies to achieve business goals, with a proven track record of providing strategic analysis and counsel to executive leaders in complex environments.
• Execution-oriented:
  Demonstrated ability to execute effectively for high-impact and demonstrated outcomes.
• Leading teams:
  Strong track record of leading, managing, and inspiring teams, including recruiting, developing, and retaining top talent.
• Influencing collaboratively:
  Exceptional ability to influence and engage internal and external stakeholders.

This document is not an exhaustive list of all responsibilities, skills, duties, requirements, or working conditions associated with the job. Employees may be required to perform other job‑related duties.

• Strong commitment to the Company’s mission and values
• Strong attention to detail and ability to deliver high-quality results
• “Player‑coach” mindset, with the ability to balance strategic leadership with hands‑on support
• Strong interpersonal skills to build healthy, collaborative, and trusting relationships across the Company.
• Self‑motivated problem‑solver and a curious thinker
• Strong executive presence with excellent communication and interpersonal skills

• Bachelor’s degree required (healthcare, business, mathematics or…