Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible 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 seeking a Senior Actuarial Analyst to own actuarial and financial analytics that drive our business forward. You'll lead and shape key workstreams across pricing, and strategic planning while mentoring junior team members and partnering with leaders across the organization. This role is ideal for someone who combines deep technical expertise with business judgment and wants to make a meaningful impact at a fast-paced, growth-stage health tech company.
What You'll Do
- Own and drive actuarial workstreams related to pricing, forecasting, product development, and experience studies
- Develop and enhance complex financial models and tools to drive decision-making across finance, product, and operations
- Perform deep-dive analyses to understand cost drivers, trends, and risks; present findings and recommendations to senior leadership
- Mentor and review the work of junior actuarial analysts
- Explore and implement AI-driven approaches to improve the efficiency, accuracy, and scalability of actuarial processes
- Ensure models, assumptions, and methodologies are well-documented, tested, and continuously improved
What You'll Bring
- 4+ years of experience in actuarial roles, ideally in health insurance or a related field
- Bachelor’s degree in Mathematics, Actuarial Science, Statistics, Economics, or related discipline
- Strong proficiency in Excel, with exposure to SQL, R, Python, or actuarial modeling tools (e.g., Prophet, SAS) a plus
- Curiosity about emerging technologies, including AI/ML, and how they can be applied to actuarial work
- Progress towards actuarial credentials (e.g., ASA or near-ASA designation)
- Strong communication and storytelling skills to translate data into action
- Ability to balance accuracy with speed in a fast-moving environment
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.
In taking a market-based approach to compensation, base pay may vary depending on location. Additionally, base pay may vary considerably depending on job-related skills and experience. The current expected salary range for this position is: $110,000 - $130,000.
Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.
Sidecar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sidecar Health and has not been reviewed or approved by Sidecar Health.
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Fair & Transparent Compensation — Compensation in tech and product roles is described as market‑aligned and competitive. Feedback suggests many in these functions feel total pay stacks up well against peers.
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Healthcare Strength — Employer‑paid major‑medical coverage for employees and family is highlighted, positioning health benefits as a strong component of total rewards. Feedback suggests low denial rates, added navigation tools, and center‑of‑excellence partnerships reinforce the plan’s practical value.
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Equity Value & Accessibility — Total rewards are presented to include stock options and bonuses in addition to salary. Feedback suggests these elements can meaningfully enhance perceived upside beyond base pay.
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What We Do
Sidecar Health is changing the health industry with modern, common-sense health insurance that finally gives consumers control over costs and choices. We are a passionate group of people-people on a mission to make quality healthcare affordable and accessible for everyone.
Why Work With Us
Being a growth-stage distributed startup, transparent and asynchronous communication is critical. We'll provide you with the resources and tools you need, and regularly seek your feedback through quarterly engagement pulses on what is or isn't working well.
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