Lead Product Designer

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 at an inflection point as we define a transformed Member Experience and build toward it. As Lead Product Designer, Member & Provider Experience, you’ll help set the experience vision and direction across mobile and web—partnering closely with Product and Engineering leadership to turn complexity into simple, trusted experiences. You’ll lead cross-functional problem solving, raise the bar on quality and craft, and help scale design through strong decision-making, reusable patterns, and a healthy design system that powers speed and quality of delivery.

What You'll Own

• End-to-end member + provider experiences across key journeys, surfaces, and teams

• Experience vision + strategy: a compelling north star, multi-quarter plan, and sequencing that makes it real

• Quality, consistency, and scalability through patterns, standards, and design system stewardship

• Cross-functional facilitation: driving alignment, clarity, and decisions through structured problem-solving

What You'll Do

• Define and communicate a clear experience vision, principles, and strategic roadmap with Product + Engineering

• Facilitate cross-functional discovery and decision-making (workshops, critiques, working sessions) to align teams and resolve tradeoffs

• Influence problem framing, success metrics, and scope using both qualitative insights and quantitative signals

• Design hands-on: flows, IA, interaction models, UI, prototypes—making complex concepts feel obvious

• Translate real constraints (policy, operations, compliance, edge cases, data limits) into consumer-grade experiences that build trust

• Plan or guide research (interviews, usability tests, concept validation), synthesize findings into clear narratives, and drive shipped decisions

• Evolve and govern the design system: scalable patterns, accessibility, documentation, and adoption

• Mentor designers through critique, pairing, and calibration to level up craft and consistency

• Lead an AI-forward design practice: use AI tools to accelerate exploration, synthesis, prototyping, and production; share repeatable workflows that improve team velocity and outcomes

What You'll Bring

• 7+ years designing digital products (or equivalent) at a product/tech company—comfortable moving fast in scrappy, startup-style environments across consumer mobile and/or web

• A portfolio that shows you can simplify complex information through strong IA, hierarchy, and content craft

• Strong interaction + visual craft (layout, typography, systems thinking) and fluency building with design systems at scale

• Demonstrated thoughtful use of AI in day-to-day design practice—paired with a track record of teaching others and helping teams adopt new workflows.

• Proven ability to lead multi-team, cross-functional initiatives and influence senior partners across Product, Engineering, Ops, Support, Compliance, and executive leadership

• Strong facilitation: you can run working sessions that drive clarity, alignment, and decisions

• Experience combining qualitative research with quantitative signals (funnels, analytics, experiments) to prioritize, iterate, and measure impact

• Ability to balance long-term vision and scalability with rapid, iterative delivery

• A strong commitment to accessibility and inclusive design

• Clear, concise communicator who can explain tradeoffs, document decisions, and drive crisp decision-making

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: $160,000 - $180,000.

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.