Director, Actuarial Pricing

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September 17

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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 actuarial pricing, reserving, and forecasting engine and manage a small team of senior actuarial analysts • Own pricing & reserving across products: set assumptions, methods, guardrails; run experience studies and trend analyses • Lead forecasting & capital views with Finance/FP&A; translate drivers into executive and board narratives • Manage and develop senior actuarial analysts: work review, coaching, prioritization • Build and scale models/tools (Excel + SQL/Python/R or actuarial platforms) with version control, documentation, and testing • Support regulatory work: rate filings, actuarial memoranda, and audit support; coordinate with external actuaries • Provide decision support: evaluate product changes, pricing actions, benefit design, and cost initiatives with scenario planning and sensitivity testing • Partner with Data/Engineering to improve data quality, automation, and reproducibility • Improve operating cadence: shorter reporting cycles, clear variance attribution, and consolidated dashboards

🎯 Requirements

• 8+ years in actuarial roles (health insurance/healthtech strongly preferred), including people leadership of senior actuarial analysts • Deep experience in pricing, reserving, forecasting, and experience studies • Advanced Excel; working fluency with SQL; familiarity with actuarial tools • ASA (minimum); FSA/MAAA preferred • Crisp communicator who can translate complex math into executive-ready insights and decisions • Bias for action with strong controls mindset: move fast while maintaining methods/audit trails • 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.