Director of Underwriting

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September 5

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Sidecar Health

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Healthcare Insurance

Sidecar Health is a health insurance company that provides comprehensive major medical insurance with upfront pricing and no network restrictions or referral requirements. Their goal is to put employees in control of their healthcare by giving them a clear budget for care and allowing them to choose any doctor without surprise costs. They emphasize access to prescriptions without limitations and protection for unplanned care. Sidecar Health also offers transparent pricing and the option for members to save money if they find providers who charge less than their plan pays. Their offerings include individualized access plans and employer plans, ensuring members always have a choice of qualified doctors.

201 - 500 employees

Founded 2018

⚕️ Healthcare Insurance

📋 Description

• 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

🏖️ Benefits

• 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.