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Director, Stop Loss Underwriting

Remote, USA Full-time Posted 2026-06-12

Imagine360 is currently seeking a Director, Stop Loss Underwriting to join our team. The Director, Stop Loss Underwriting is responsible for executing the underwriting and risk strategies for the organization. The Director will help establish underwriting strategy and direct underwriting staff to generate quotes compliant with that strategy. The director supervises the Manager of Stop Loss Administration to ensure our clients experience a well-coordinated, streamlined stop loss quote and binding process. As stop loss subject matter expert, this person will serve as a resource for sales and other departments. The role will analyze stop loss quotes to understand how Imagine360's cost containment solutions, including, but not limited to metric-based pricing and contracting strategies, influence rates. Position Location: 100% Remote Responsibilities include but are not limited to: Create meaningful relationships with Broker partners, that support company and client growth and cost containment objectives. Develop and maintain processes and guidelines for underwriting. Recommend plan and insurance changes to improve our clients' self funding experience. Manage staff of underwriters. Underwrite risks and issue proposals directly as needed. Support the sales process by contributing subject matter expertise and related education to team members in Sales and Marketing. Support the development of new solutions that include stop loss with industry experience and subject matter expertise. Develop team members to ensure the successful execution of their role responsibilities and professional development. Required Experience / Education: Minimum of 8 years of experience in medical stop loss underwriting for an insurance carrier. Experience managing staff strongly preferred Highly developed knowledge and understanding of healthcare payers, health plan administration and medical service providers In-depth knowledge of medical stop loss products Bachelor's Degree from an accredited institution Master's or other advanced degree preferred Life & Health Insurance License required, or obtain within 1 year of employment Skills Motivating leader with comfort directing staff Ability to develop strong relationships with team members and influence work product and outcomes without direct management responsibility Strong analytical and business case analysis skills Ability to multitask and prioritize amongst multiple priorities Exemplary communication skills, including written, verbal and presentation Proficiency in Microsoft Office Suite; Demonstrated competency in learning computer-based tools Ability to explain complex proposals to both technical and non-technical audiences Entrepreneurial, with creative thinking skills What can Imagine360 offer you? Multiple Health Plan Options, including a 100% Employer Paid Benefit Options 100% Company paid employee premiums for Dental, Vision, STA, & LTD, plus Life Insurance Parental Leave Policy 20 days PTO to start / 10 Paid Holidays Tuition reimbursement 401k Company contribution Professional development initiatives / continuous learning opportunities Opportunities to participate in and support the company's diversity and inclusion initiatives Want to see our latest job opportunities? Follow us on LinkedIn Imagine360 is a health plan solution company that combines 50+ years of self-funding healthcare expertise. Over the years, we've helped thousands of employers save billions on healthcare. Our breakthrough total health plan solution is fixing today's one-size-fits-none PPO insurance problems with powerful, customized, member-focused solutions. Imagine360 is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status. RECRUITMENT AGENCIES PLEASE NOTE: Imagine360 will only accept applications from agencies/business partners that have been invited to work on a specific role. Candidate Resumes/CV's submitted without permission or directly to Hiring Managers will be considered unsolicited, and no fee will be payable. Thank you for your cooperation Apply To This Job

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