Underwriting Director, Mid-Market

About the role The Underwriting Director, Mid-Market, is responsible for profitably underwriting stop-loss insurance for new and renewing groups across the 50-300 life space. This is a fully remote, senior individual contributor role with management potential. What you’ll do

• Underwrite new business and renewals for experience-rated groups in the 50-300 life space across level-funded and traditional stop loss products.
• Build and maintain strong working relationships with sales, actuarial, and clinical teams.
• Set clear expectations with sales on turnaround times and consistently deliver on them.
• Develop deep familiarity with Optimyl’s products and platform, and contribute feedback that shapes future iterations.
• Mentor existing claims-based underwriters.

Ideal profile

• 10+ years underwriting medical stop loss, with a focus on the 50-300 group size.
• At least 5 years at an MGU or pure-play stop loss carrier; majority of career at a respected MGU preferred.
• Comfort working in a lean, fast-moving environment without heavy oversight.
• Familiarity with stop loss manuals and current underwriting tools, including AI-assisted platforms.

Why Work at Optimyl? At Optimyl Benefits, we’re focused on simplifying healthcare for small employers and building a workplace where people can do meaningful work and continue to grow. Benefits include: Competitive compensation Comprehensive health coverage (medical, dental, vision) Employer-paid life insurance and disability coverage 401(k) retirement plan with employer match Generous paid time off and company holidays We support growth through hands-on learning, exposure to new challenges, and opportunities to expand responsibilities as the company evolves.