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Sidecar Health

Remote

Lead Product Designer

full-time • Remote • Remote • $160,000 - $180,000
new

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.