Product + Design Strategist

A Product + Design Strategist can carry a problem from an ambiguous user and business opportunity to a validated experience. As a Product + Design Strategist, you will operate at a senior IC level: leading the highest-leverage, most ambiguous scopes of work at Omada and setting direction for a collection of related experiences rather than a single feature. You translate engineering’s increased pace into more of the right experiences launched for our customers and members, not just more output.

AI is a core part of how this role works day to day as a co-intelligent partner you direct across research synthesis, prototyping, spec drafting, and analysis, extending your judgment so you can move from open question to validated direction faster, with more rigor.

You thrive in ambiguity, especially in 0 to 1 spaces where the problem is not yet defined and the path forward is yours to shape. You bring a strong, evidence-backed point of view, initiative and ability to find answers, and you’re as comfortable in an executive strategy conversation as you are prototyping with users.

Core Responsibilities

A Product + Design Strategist owns four things — problem framing, direction setting, vision casting, and alignment. Everything else is craft in service of these.

Problem framing — turning ambiguous asks, business opportunities, and lived member experience into a scoped, evidence-backed understanding of what’s actually wrong and worth solving.

• Problem framing & requirements — turning a vague ask into a scoped, buildable piece of work.
• User journey mapping — diagnosing end-to-end friction and drop-off with empathy.
• Research study design & execution — running interviews, surveys, and experiments to test assumptions.
• Data analysis (quant + qual) — pulling product performance data and synthesizing qualitative signal into a clear read of the problem.
• Competitive, inspiration, & analogous research — auditing adjacent products for pattern or gap insight.
• Metrics instrumentation — in partnership with data analytics, defining upfront what “solved” will actually look like.

Direction setting — reconciling research, data, engineering, and business input into a clear point of view on what to pursue, and revisiting that call against real evidence once it’s live.

• Synthesis & direction-setting — recommending which directions to pursue and which to drop.
• Prioritization & trade-offs — arbitrating competing product and stakeholder requests with transparent rationale.
• Quantitative and qualitative evaluation design & analysis — defining core questions and hypotheses, then translating results into insights and go/no-go decisions.
• Stop/start/continue investment decisions — revisiting prior bets against evidence of what’s actually working.
• Vendor & partner evaluations — build vs. buy justifications.

Vision casting — making the future state tangible and compelling enough that cross-functional partners, leadership, and members can see it and support it.

• Roadmap ownership & narrative — owning a multi-quarter roadmap that maps to corporate OKRs, key strategic initiatives, operational cadences, and commercial cycles.
• Executive communications & narratives — building the strategic story for budget and prioritization conversations.
• Product marketing & commercial partnerships — carrying the vision into go-to-market and partner contexts.
• Visual & interaction design — makes the vision tangible enough to inform viability, desirability, and feasibility decisions, and to support build and operational planning. Brings strong product taste, and can articulate what makes a health experience good in both strategic and tangible terms.
• Prototyping — building click-through and interactive prototypes to test and communicate ideas.

Alignment — keeping every function that touches the work — engineering, clinical, ops, leadership — moving on the same understanding of what’s being built and why.

• Stakeholder syncs & demos — running team meetings, reviews, and critiques that keep work visible.
• Cross-functional handoff — prepping documents and prototypes that give build and operations teams clarity.
• Clinical, legal, and regulatory partnerships — integrating guidance on safety, quality, and compliance throughout.
• Launch & release readiness — owning the go/no-go call and sequencing logic for a release, in partnership with Product Ops, who runs the operational checklist and cross-team chase.
• Stakeholder alignment on product priorities and vision — resolving cross-functional disagreement directly.

Core Skills

Product + Design Strategists are T-shaped: every Strategist can operate across all of this at a working level, and leans deeper into a Design, PM, research, and/or operational specialty depending on the scope they’re leading. The craft toolkit a Product + Design Strategist draws on includes:

• Prototyping — low- to high-fidelity mockups and click-through flows to test and communicate ideas, including coded experiences that give users and stakeholders a more immersive way to test.
• Visual & interaction design — applying design system components, typography, and interaction patterns to real screens and other touchpoints; drafting microcopy and in-product messaging.
• Writing PRDs/specs — documenting functional requirements and success metrics for engineering handoff.
• Backlog grooming & sprint planning — writing and prioritizing tickets, estimating scope with engineering.
• Product/design/research documentation — maintaining decision logs and research repositories so knowledge supports entire teams.
• Accessibility & QA review — checking designs and built product against accessibility standards.
• AI orchestration & prompting fluency — directing AI tools effectively across design, spec, and analysis work.
• Data-informed strategy — interpreting quantitative and qualitative data, such as product analytics and clinical outcomes, to inform product strategy and build.
• Facilitation — running workshops, critiques, and cross-functional working sessions in service of decision-making and alignment.
• Engineering/technical literacy — enough fluency to reason about feasibility and scope trade-offs in partnership with Eng and Ops.

We’d love to talk more if you have...

• 8+ years of experience solving complex, ambiguous problems across product management, design, and/or research, including a track record of owning outcomes at a multi-team level.
• 3-5 years of demonstrated success carrying work from 0 to 1 — defining new products or experiences from an undefined problem space through to a shipped, measurable result.
• A strong, evidence-based point of view, with the judgment to reconcile research, data, engineering, and business input into a clear direction — and the conviction to defend it and the humility to revise it.
• 3-5 years of experience owning a multi-quarter roadmap and communicating it persuasively to executive and cross-functional audiences, including budget and prioritization conversations.
• High craft in at least 2 specialist areas (design, product management, strategy, research, or operations), with genuine working fluency across the others.
• Excellence in prototyping, and fluency with modern AI-assisted prototyping and building tools (e.g., Claude Code, Claude Design, Figma Make, Cursor, Lovable, or similar) — this is a required, hands-on craft skill for this role, not a nice-to-have.
• Experience partnering with clinical, legal, regulatory, or other high-stakes compliance functions in health, wellness, fintech, or another regulated domain.
• Excellent executive communication and stakeholder management skills, with a 3-5 year track record of influencing decisions across senior leadership.
• Experience mentoring or informally leading other ICs, even without formal people-management responsibility.
• Fluency with AI orchestration and prompting across design, spec, and analysis work, and comfort pulling data directly from self-serve analytics tools.

Bonus points if you have...

• Experience designing or leading strategy for clinical, care delivery, or chronic condition management experiences.
• Experience building production-adjacent or fully coded prototypes.
• A background as a specialist in 2 areas (Design, PM, or Research) who has deliberately broadened into other health or technology disciplines rather than staying siloed.
• Experience in a startup setting, operating like a builder — self-driven, biased toward action, and energized by owning problems from discovery through launch.
• Experience running vendor and partner evaluations, including build-vs-buy business cases.

What this role is not:

To protect focus, Product + Design Strategists are not expected to own all day-to-day project coordination and status reporting (Product Ops and automated tooling own the checklist and cross-team chase once you’ve made the go/no-go call), detailed design of every screen and flow (owned by UX Design and Engineering, enabled by design-system-aware prototyping and coding tools), high-volume or specialized content production (owned by the content platform team), or administrative backlog upkeep (AI-assisted or Eng-owned). Formal people management of other Strategists sits with Product + Design Directors; Strategists at this level lead through influence, craft, and mentorship rather than direct reports.

Our Design Roots

Omada was founded in 2011 out of IDEO, where our founders explored how human-centered design could be applied to chronic health challenges. What began as an internal project grounded in deep user research evolved into a new approach to digital care.

That origin continues to shape how we work today. We place a strong emphasis on understanding real human needs, designing from first principles, and creating experiences that are not only effective, but engaging and thoughtfully crafted.

Design is not a layer at Omada. It is foundational to how we build products, make decisions, and deliver care.