Sidecar Health · 1 month ago
Director of Underwriting
United States
Full-time
Remote
Senior Level, Lead/Staff
8+ years expSidecar Health is redefining health insurance with a mission to make healthcare affordable and attainable for everyone. The Director of Underwriting will lead the underwriting function, managing a team while directly underwriting complex cases and collaborating with Sales and Client Success to drive profitable growth.
FinTechHealth CareHealth InsuranceInsuranceInsurTech
Responsibilities
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
Qualification
Required
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
Bachelor's degree
Preferred
Familiarity with reinsurance markets and strategies preferred
Comfort operating in a fast-paced, high-growth environment where adaptability is key
Benefits
Comprehensive Medical, Dental, and Vision benefits
A 401k retirement plan
Paid vacation and company holidays
Company
Sidecar Health
Sidecar Health's employer plans empower members with transparency, control, and financial incentives to make smart healthcare decisions.
201-500 employees
Funding
Current Stage
Late StageTotal Funding
$328MKey Investors
Koch Disruptive TechnologiesDrive CapitalCathay Innovation
2024-06-26Series D· $165M
2021-01-26Series C· $125M
2020-07-23Series B· $20M
Leadership Team
Patrick Quigley
Chief Executive Officer
Veronica Osetinsky
Chief Operating Officer
Recent News
2025-11-14
2025-09-24
Company data provided by crunchbase