Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

We’re hiring a Director of Actuarial Pricing to lead Sidecar Health’s actuarial pricing, reserving, and forecasting engine - and to manage a small team of senior actuarial analysts. You’ll turn data into clear decisions for leadership, own core actuarial work products (pricing, reserves, filings), and raise the bar on modeling quality, speed, and control. This is a hands-on leadership role in a fast-paced, growth-stage health tech company.

What You'll Do

• Own pricing & reserving across products; set assumptions, methods, and guardrails; run experience studies and trend analyses
• Lead forecasting & capital views in partnership with Finance/FP&A; translate drivers into clear narratives for executives and the board
• Manage & develop a small team of senior actuarial analysts (work review, coaching, prioritization)
• Build & scale models/tools (Excel + SQL/Python/R or actuarial platforms) with version control, documentation, and testing
• Regulatory excellence: contribute to rate filings, actuarial memoranda, and audit support; coordinate with external actuaries as needed
• Decision support: evaluate product changes, pricing actions, benefit design, and cost initiatives with scenario planning and sensitivity testing
• Data partnership: work with Data/Engineering to improve data quality, speed, and accessibility; enhance automation and reproducibility
• Raise operating cadence: shorter reporting cycles, clear variance attribution, and “one source of truth” dashboards

What You'll Bring

• 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: you move fast and keep methods/audit trails clean
• Bachelor's Degree

What You'll Get

• 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.