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 looking for a strong Staff Product Designer (Contractor) to help overhaul our member experience. This role is pivotal in shaping a high-consumer-grade app that empowers people to navigate healthcare confidently. You’ll report to and work closely with the VP of Member Experience, supporting key initiatives that improve how members engage with our product. You should be equally comfortable with big-picture thinking and hands-on design execution.
What You'll Do
- Own and lead end-to-end product design initiatives for members, including the onboarding experience for new users
- Shape strategy to educate and guide members toward more informed healthcare decisions across the entire journey
- Present and communicate design concepts to cross-functional stakeholders and senior leadership, adjusting your approach based on fidelity and audience
- Collaborate with Product, Engineering, and Marketing to ensure a cohesive and engaging user experience
- Validate and iterate on designs through user research and usability testing
- Maintain a high level of detail during implementation by working closely with Engineering and QA teams
- Advocate for user-centered design principles and design best practices across the organization
What You'll Bring
- 7+ years of design experience designing consumer-facing mobile and web applications, with a portfolio that highlights impact on end users
- A collaborative partner who’s worked closely with Product Managers, Engineers, and Researchers to ship high-quality product solutions
- Comfortable presenting design rationale to cross-functional teams and executive stakeholders
- Experienced at incorporating both qualitative and quantitative insights into your design process
- Strategic and able to translate business goals into thoughtful, innovative design solutions
- Proficient in tools like Figma, Sketch, or similar
- Detail-oriented with excellent visual design skills
- Self-motivated and able to manage multiple projects independently
Why Join Us:
- Be part of a mission-driven company that is transforming the health insurance industry.
- Work in a dynamic and collaborative environment with a passionate team.
- Opportunity to make a significant impact on the member experience and help shape the future of healthcare.
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.
Sidecar Health Insights
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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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