Underwriting Coordinator
Ryan Specialty
Director of Underwriting
Sidecar Health
full-time
Posted on:
Location: 🇺🇸 United States
Visit company websiteJob Level
Lead
About the role
- Lead Sidecar Health’s group underwriting function as a player-coach, personally underwriting large and complex group cases while managing the underwriting team
- Manage, mentor, and develop a team of group underwriters and oversee day-to-day operations
- Establish and maintain underwriting guidelines, policies, and processes balancing competitiveness, risk, and profitability
- Partner with Sales and Client Success to support new business opportunities, renewals, and finalist presentations
- Provide creative underwriting solutions to win new accounts while protecting financial performance
- Collaborate with Actuarial, Product, Finance, and Client Success to inform pricing strategies, renewals, and long-term client value
- Review and approve escalated underwriting decisions to ensure alignment with strategy
- Monitor underwriting performance and portfolio results, identifying trends and implementing corrective actions
- Build and maintain relationships with brokers, consultants, and reinsurers to support growth and reinsurance strategies
- Promote a culture of accountability, collaboration, and continuous improvement
- Report to the VP of Actuarial & Underwriting
Requirements
- 8+ years of experience in group underwriting within health insurance or healthcare-related financial services, with progressive responsibility in leadership and decision-making
- Proven ability as a “player-coach” — comfortable leading a team while directly underwriting complex, high-profile cases
- Demonstrated success partnering with Sales to win new business and support strategic client relationships
- Deep knowledge of group underwriting methodologies, funding arrangements (fully insured, self-funded/ASO), stop-loss, and healthcare cost drivers
- Strong analytical and problem-solving skills with the ability to balance growth opportunities against risk considerations
- Executive presence with excellent communication, negotiation, and relationship-building skills
- Familiarity with reinsurance markets and strategies preferred
- Comfort operating in a fast-paced, high-growth environment where adaptability is key
- Bachelor’s degree
