Sidecar Health

Director of Underwriting

Sidecar Health

full-time

Posted on:

Origin:  • 🇺🇸 United States

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Job 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