Sidecar Health

Health insurance that's finally fair.

Director of Underwriting

UnderwriterUnderwriterFull TimeRemoteLeadTeam 201-500Since 2018H1B SponsorCompany SiteLinkedIn

Location

United States

Posted

97 days ago

Salary

Not specified

Seniority

Lead

Bachelor Degree8 yrs expEnglish

Job Description

• 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

Job 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.

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