Director of Underwriting

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role
The Director of Underwriting will lead Sidecar Health’s group underwriting function while also serving as a hands-on contributor. Reporting to the VP of Actuarial & Underwriting, this role is both a player-coach and a growth partner — directly underwriting complex, high-value cases while managing, mentoring, and developing a team of underwriters. They will partner closely with Sales and Client Success to support new business opportunities, renewals, and finalist presentations, playing a critical role in driving profitable growth and strengthening Sidecar Health’s presence in the market.

*Must reside in California, Connecticut, Florida, Georgia, New York, Ohio, Texas, Utah, or Washington for consideration*

What You'll Do

• Serve as both a leader and contributor, personally underwriting large and complex group cases while managing the day-to-day operations of the underwriting team
• Lead, mentor, and develop a team of group underwriters, fostering consistency, accuracy, and professional growth
• Establish and maintain underwriting guidelines, policies, and processes that balance competitiveness, risk, and profitability
• Partner with Sales to support new business growth, participating in finalist meetings and broker/consultant discussions as needed
• Provide creative underwriting solutions that help win new accounts while protecting financial performance
• Collaborate cross-functionally with Actuarial, Product, Finance, and Client Success to inform pricing strategies, renewals, and long-term client value
• Review and approve escalated underwriting decisions, applying expert judgment to ensure alignment with strategy
• Monitor underwriting performance and portfolio results, identifying trends and implementing corrective actions when necessary
• Build and maintain strong relationships with brokers, consultants, and reinsurers to enhance growth opportunities and support reinsurance strategies
• Promote a culture of accountability, collaboration, and continuous improvement within the underwriting function

What You'll Bring

• 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

What You'll Get

• Competitive salary, bonus opportunity, and equity package  
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.