Posted Sep 15, 2026

Principal Underwriter

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Wellfleet, a Berkshire Hathaway company, delivers customer-centric accident and health insurance, with quality service and uncompromising ethics. Wellfleet works to protect people against risk throughout every stage of life - from grade school to college to the workplace. Founded in 1993 as Consolidated Health Plans (CHP), Wellfleet, headquartered in Springfield, Mass., is one of the nation's leading providers of health and accident insurance products to the higher education market. Wellfleet Workplace Benefits, a Berkshire Hathaway Company, seeks an experienced Principal Underwriter to join our growing team! This position is responsible for taking a lead role in underwriting Wellfleet's larger and/or complex prospects and renewals within established guidelines and for developing solutions to opportunities that maintain appropriate risk controls. The Principal Underwriter must be able to analyze data such as past claim experience to determine eligibility, rates, and underwriting offers. Knowledge of assigned insurance products and plan designs is also crucial for this role. They will provide guidance and work direction to junior group underwriters and may directly manage assigned underwriting team members. In addition to a strong technical acumen, this role must develop and maintain relationships with internal and external partners by answering questions and obtaining information on which to base decisions. The Principal Underwriter must explain and justify underwriting courses of action through clear and concise written and verbal communication to appropriate parties. In this role, you will... • Evaluate risk and develop timely and successful prospect and renewal quotes for current and potential clients, focusing on the most complex and large group insurance opportunities based on experience data. • Contribute to division profitability by analyzing/assessing client profitability through experience and expense analysis and attention to product line performance. • Document and communicate decisions to necessary areas in the division. Review cases exceeding underwriter's review level. • Manage and retain Underwriting files including rating tools and group correspondence for future needs. • Responsible for managing, leading and developing direct reports as assigned. • Collaborate with the Sales team on presentations for brokers/schools. • Conduct 1:1 weekly (or bi-weekly) "check-ins" with direct report(s) to identify staff priorities and provide assistance/guidance as necessary. • Responsible for identifying performance goals and development needs for direct report(s), if assigned, and monitoring progress. • Support the development of junior underwriters in understanding underwriting concepts. • Work effectively with our Account Management team to determine deadlines and priorities. • Maintain positive relationships and effective communication with internal and external stakeholders, providing timely updates and addressing concerns. • Assist with responses to RFPs (Request for Proposals). • Research the market to help determine the best target prospects. • Assist with Wellfleet and underwriting projects, including process improvement, as necessary. • Perform other duties as assigned. We are looking for candidates with... • Bachelor's degree with 8+ years of underwriting experience in accident and health insurance, or equivalent combination of education and experience. • Experience underwriting market specific risks (Special Risk, Group Health Insurance, or Workplace), a plus. • Excellent communication skills both verbal and written with demonstrated ability to present complex topics in a clear manner. • Self-starter with an ability to solve problems and handle a fast-paced environment. • Demonstrates the ability to work well in teams and form partnerships to complete projects. • Possess a strong attention to detail. • Responsive with the ability to adhere to strict deadlines. • Proficient with MS Office Suite including Microsoft Word, Excel, PowerPoint, and Outlook • Demonstrated ability to effectively develop team members and monitor performance. Why Wellfleet? Here at Wellfleet, we foster a culture of growth that enables engaged and high-performing professionals to be empowered to deliver our mission and vision. Our employees are a team devoted to providing customer service that exceeds expectations of our members and clients. Successful team members continually look for ways to improve product delivery and value. Wellfleet offers a competitive compensation package and comprehensive benefits package including life, health and dental, vision, 401K retirement plan, short- and long-term disability coverage, flexible/dependent care spending account, tuition reimbursement, and business casual dress. Are you interested in exploring a career at Wellfleet? Explore our open positions. General: Wellfleet is part of the MedPro Group family. As such, all Wellfleet team members are employees of MedPro Group Inc. We are an Equal Opportunity Employer. The annual gross base salary range is $89,000 to $145,000. This range anticipates the low and high end of the salary for this position. Actual salaries will vary and are based on factors such as a candidate's qualifications, skills and competencies. Salary is one component of Wellfleet's total compensation and benefits package, which includes medical, vision and dental insurance options, life and accident insurance, 401(k), and short-term and long-term disability insurance. For a more detailed overview, visit our careers website at: wellfleetinsurance.com/about/careers. #LI-KS1 #LI-Remote