Senior Product Design Strategist

Accountabilities:: Problem framing: Turn ambiguous business opportunities, user needs, and member experiences into clearly scoped, evidence-backed problems worth solving. Map end-to-end user journeys, identify friction and drop-off, and use interviews, surveys, experiments, quantitative data, and qualitative research to validate assumptions. Conduct competitive, analogous, and inspiration research while partnering with analytics to define measurable indicators of success. Direction setting: Reconcile research, data, engineering constraints, and business priorities into a clear strategic point of view, including transparent prioritization and trade-off decisions. Define evaluation frameworks, hypotheses, and go/no-go criteria, and revisit previous investments based on real-world evidence. Lead vendor and partner evaluations, including build-versus-buy assessments and business cases. Vision casting: Own multi-quarter product roadmaps aligned with strategic initiatives, OKRs, operating cadences, and commercial priorities. Develop executive narratives and communications that support prioritization, budgeting, and strategic decision-making. Translate product vision into go-to-market and partner contexts while using visual and interaction design to make future experiences tangible. Create low- to high-fidelity, click-through, interactive, and potentially coded prototypes to test concepts and communicate direction. Alignment: Keep engineering, clinical, operations, legal, regulatory, leadership, and other stakeholders aligned around what is being built and why. Lead reviews, critiques, demos, workshops, and stakeholder discussions while resolving disagreements and maintaining momentum. Prepare documentation, prototypes, and specifications that provide clarity for engineering and operational teams. Incorporate clinical, legal, regulatory, safety, and quality guidance throughout product development. Own release go/no-go decisions and sequencing in partnership with Product Operations, while supporting launch and release readiness. Lead through influence, craft, and mentorship rather than formal people management, with day-to-day project coordination and administrative backlog upkeep handled by designated teams and tools. Requirements 8+ years of experience solving complex, ambiguous problems across product management, design, research, or related disciplines, with demonstrated ownership of outcomes across multiple teams. 3–5 years of experience successfully taking work from 0 to 1, defining new products or experiences from an undefined problem through launch and measurable results. Strong evidence-based judgment and the ability to reconcile research, data, engineering, and business considerations into a clear direction while remaining open to changing course when evidence warrants it. 3–5 years of experience owning multi-quarter roadmaps and communicating strategic priorities effectively to executive and cross-functional audiences, including budget and prioritization discussions. Deep expertise in at least two areas such as design, product management, strategy, research, or operations, with working fluency across the others. Exceptional prototyping skills and hands-on experience with modern AI-assisted prototyping and development tools such as Claude Code, Claude Design, Figma Make, Cursor, Lovable, or similar platforms. Strong product, visual, and interaction design capabilities, including experience with design systems, typography, interaction patterns, microcopy, and in-product messaging. Experience writing PRDs and functional specifications, defining success metrics, grooming backlogs, planning sprints, and collaborating with engineering on scope and feasibility. Fluency in product/design/research documentation, decision logs, accessibility review, QA, and knowledge repositories. Strong AI orchestration and prompting skills across research, design, specification, and analysis workflows, with comfort using self-service analytics tools and interpreting quantitative and qualitative data. Experience partnering with clinical, legal, regulatory, compliance, or other high-stakes functions in healthcare, wellness, fintech, or another regulated environment. Excellent executive communication, facilitation, stakeholder management, negotiation, and influence skills, with a demonstrated ability to affect senior-level decisions. Experience mentoring or informally leading other individual contributors without requiring formal people-management responsibility. Sufficient technical literacy to understand engineering feasibility, architecture, scope, and trade-offs. Experience with clinical, care delivery, chronic condition management, or digital health strategy is a plus. Production-adjacent or fully coded prototype experience is a plus. Startup or scale-up experience, with a builder mindset and strong ownership from discovery through launch, is a plus. Experience evaluating vendors and partners, including build-versus-buy decisions, is a plus. Must currently reside in the United States; candidates residing outside the U.S. cannot be employed for this role due to restrictions surrounding access to personal health information. A portfolio is highly recommended and should demonstrate personally produced work at a high level. Benefits Competitive base salary by geographic zone: Zone 1: $192,280–$240,350 USD Zone 2: $183,920–$229,900 USD Zone 3: $167,200–$209,000 USD Generous annual cash bonus opportunity. Equity grants and employee stock purchasing plan (ESPP). Remote-first, work-from-home culture. Flexible Time Off. Generous parental leave. Health, dental, and vision insurance with above-market employer contributions. 401(k) retirement savings plan. Lifestyle Spending Account (LSA). Mental health support solutions. Opportunity to influence product strategy and design across high-impact healthcare experiences. Senior-level exposure to product, engineering, clinical, regulatory, operations, and executive stakeholders. Hands-on work with AI-assisted product development, research, prototyping, and analysis. Collaborative, design-led environment centered on human needs, thoughtful experiences, and measurable outcomes. Commitment to inclusive collaboration, professional growth, and meaningful work in digital healthcare.