Director of Underwriting

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 commonthe 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! 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 partnerdirectly 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.

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

What You'll Get

Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.