Senior Product Design Strategist

📍 Job Overview

Job Title: Senior Product Design Strategist

Company: Omada Health

Location: Remote, USA

Job Type: Full-Time

Category: Product & Design Strategy

Date Posted: 2026-09-22

Experience Level: 8+ Years (Senior Level)

Remote Status: Fully Remote

🚀 Role Summary

• Leads high-leverage, ambiguous scopes of work in product and design strategy, translating user needs and business opportunities into validated experiences.

• Operates as a senior individual contributor, setting strategic direction for collections of related experiences rather than single features.

• Leverages AI as a core operational partner for tasks including research synthesis, prototyping, spec drafting, and analysis to accelerate the design-to-validation cycle.

• Drives product innovation in 0 to 1 spaces, defining new products and experiences from undefined problem spaces through to measurable results.

• Owns the end-to-end product lifecycle from problem framing and direction setting to vision casting and cross-functional alignment.

📝 Enhancement Note: This role is positioned as a senior individual contributor (IC) focused on strategic product and design initiatives within Omada Health. The emphasis on AI as a co-intelligent partner and the "0 to 1" problem-solving indicates a need for individuals who can navigate significant ambiguity and drive innovation. The role requires a blend of strategic thinking, design craft, and operational awareness, particularly within the regulated health tech sector.

📈 Primary Responsibilities

• Problem Framing: Translate ambiguous user needs, business opportunities, and member experiences into clearly scoped, evidence-backed understandings of problems worth solving through rigorous user journey mapping, research study design, data analysis (quantitative and qualitative), and competitive/inspiration research.

• Direction Setting: Reconcile diverse inputs (research, data, engineering, business) into a clear, evidence-based point of view on product direction, arbitrating competing requests through prioritization and trade-offs, and designing/analyzing evaluations for go/no-go decisions.

• Vision Casting: Make future product states tangible and compelling through roadmap ownership aligned with corporate OKRs, executive communication and narrative building, product marketing collaboration, and high-quality visual/interaction design and prototyping.

• Alignment: Ensure seamless cross-functional collaboration by managing stakeholder syncs, facilitating clear handoffs to engineering and operations teams, integrating clinical, legal, and regulatory guidance, and owning launch/release readiness decisions in partnership with Product Ops.

• AI Orchestration & Prototyping: Actively direct AI tools for design, spec, and analysis tasks, and create low- to high-fidelity prototypes, including coded experiences, to test viability, desirability, and feasibility.

📝 Enhancement Note: The responsibilities are structured around four key pillars: Problem Framing, Direction Setting, Vision Casting, and Alignment. This structure emphasizes a strategic, end-to-end ownership model for complex product challenges. The explicit mention of AI orchestration and prototyping as core craft skills highlights the modern, tech-forward approach Omada Health expects from its strategists.

🎓 Skills & Qualifications

Education: While not explicitly stated, a Bachelor's or Master's degree in Design, Product Management, Human-Computer Interaction, Business, or a related field is typically expected for senior roles of this nature.

Experience:

• 8+ years of experience solving complex, ambiguous problems across product management, design, and/or research.

• Proven 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.

• 3-5 years of experience owning a multi-quarter roadmap and communicating it persuasively to executive and cross-functional audiences.

• Experience partnering with clinical, legal, regulatory, or other high-stakes compliance functions in health, wellness, fintech, or another regulated domain.

• Experience mentoring or informally leading other ICs. Required Skills:

• Strategic Thinking: Strong, evidence-based point of view with the judgment to reconcile diverse inputs into clear product direction.

• Problem Framing & Synthesis: Ability to turn ambiguous asks into scoped, buildable work, synthesizing quantitative and qualitative data.

• Roadmap Ownership & Narrative: Developing and owning multi-quarter roadmaps aligned with company objectives and communicating them effectively.

• Cross-functional Collaboration: Facilitating workshops, managing stakeholder syncs, and ensuring alignment across diverse teams.

• Prototyping: High craft in building low- to high-fidelity mockups, click-through flows, and potentially coded experiences.

• AI Orchestration & Prompting Fluency: Directing AI tools effectively across design, spec, and analysis tasks.

• Data-Informed Strategy: Interpreting product analytics, clinical outcomes, and other data to inform strategy.

• Executive Communication: Excellent skills in influencing decisions across senior leadership.

• Technical Literacy: Sufficient understanding to reason about feasibility and scope trade-offs with engineering and operations.

Preferred Skills:

• Deep craft in at least 2 specialist areas (Design, Product Management, Strategy, Research, or Operations) with working fluency across others.

• Experience designing or leading strategy for clinical, care delivery, or chronic condition management experiences.

• Experience building production-adjacent or fully coded prototypes.

• Experience in a startup setting, demonstrating a builder mindset: self-driven, action-oriented, and energized by end-to-end ownership.

• Experience running vendor and partner evaluations, including build-vs-buy business cases.

📝 Enhancement Note: The requirements emphasize a "T-shaped" professional, meaning deep expertise in at least two areas (e.g., Design, PM, Research) coupled with broad working fluency across others. The explicit requirement for AI tool proficiency and experience in regulated domains like health tech are critical differentiators.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrations of successful problem framing for ambiguous, undefined challenges.

• Case studies showcasing the ability to carry work from 0 to 1, from initial concept through to a shipped and measured outcome.

• Examples of roadmap development and strategic narrative creation for executive audiences.

• Evidence of driving alignment and managing stakeholders across multiple functions (e.g., Engineering, Clinical, Ops).

• Prototypes (low- to high-fidelity, potentially coded) that illustrate complex ideas and user flows.

• Work samples that highlight AI-assisted design and prototyping processes. Process Documentation:

• Documentation of research synthesis and data analysis methodologies used to inform product decisions.

• Examples of how research findings and data were translated into clear product direction and requirements.

• Artifacts demonstrating cross-functional handoffs and collaboration with engineering, operations, and compliance teams.

• Evidence of defining success metrics and evaluating product performance post-launch.

📝 Enhancement Note: Applicants should prepare a portfolio that clearly articulates their strategic process, not just final deliverables. Emphasis should be placed on showcasing how they navigate ambiguity, leverage data and AI, and drive cross-functional alignment to achieve measurable product outcomes, particularly in complex or regulated environments.

💵 Compensation & Benefits

Salary Range: Based on Omada Health's provided salary zones for the US:

• Zone 1: $192,280 - $240,350 USD per year

• Zone 2: $183,920 - $229,900 USD per year

• Zone 3: $167,200 - $209,000 USD per year Benefits:

• Competitive salary with a generous annual cash bonus.

• Equity grants and an Employee Stock Purchasing Plan (ESPP).

• Remote-first work-from-home culture.

• Flexible Time Off (FTO) policy.

• Generous parental leave.

• Comprehensive health, dental, and vision insurance with above-market employer contributions.

• 401k retirement savings plan.

• Lifestyle Spending Account (LSA).

• Mental Health Support Solutions.

• Other benefits as outlined by the company.

Working Hours: While not explicitly stated, a standard full-time role typically implies approximately 40 hours per week. The remote-first and flexible time off policies suggest a degree of autonomy and flexibility in managing work hours to meet objectives.

📝 Enhancement Note: The salary ranges are tiered by geographic zones within the USA. Applicants should identify which zone their primary residence falls into to understand the applicable salary band. The compensation package is robust, including base salary, bonus, equity, and comprehensive benefits, reflecting a senior-level offering. The salary estimation is based on the provided ranges and is considered a primary data source.

🎯 Team & Company Context

🏢 Company Culture

Industry: Healthcare Technology (Health Tech), Digital Health, Chronic Disease Management. Omada Health operates at the intersection of healthcare delivery and technology, aiming to improve chronic condition management through virtual-first solutions.

Company Size: Omada Health is a publicly traded company (Nasdaq: OMDA) with a significant employee base, indicating a mature organization with established processes while retaining a startup-like drive.

Founded: Founded in 2011, with origins from IDEO, emphasizing a deep-rooted commitment to human-centered design and innovation in healthcare.

Team Structure:

• The Product + Design Strategist operates as a senior individual contributor, likely within a broader Product or Design organization.

• This role requires close collaboration with Product Managers, UX Designers, Researchers, Data Analysts, Engineering teams, and Product Operations.

• Leadership is primarily through influence, craft, and mentorship, rather than direct people management, though informal leadership of other ICs is expected. Methodology:

• Human-Centered Design: A foundational principle, stemming from its IDEO origins, focusing on deep user understanding and empathy.

• Data-Informed Decision Making: Utilizing quantitative and qualitative data, including product analytics and clinical outcomes, to guide strategy and product development.

• AI Integration: Actively incorporating AI as a co-intelligent partner in design, research, and analysis processes.

• Agile & Iterative Development: Implied by the need for rapid prototyping, validation, and iterative improvement in a fast-paced tech environment.

Company Website: https://www.omadahealth.com/

📝 Enhancement Note: Omada Health's culture is deeply influenced by its founding principles in human-centered design and its mission to transform chronic disease care. The integration of AI and the remote-first approach are key aspects of its current operational strategy. Understanding the company's mission and its design-centric ethos is crucial for prospective candidates.

📈 Career & Growth Analysis

Operations Career Level: Senior Individual Contributor (IC). This level signifies a high degree of autonomy, strategic impact, and the expectation to lead complex initiatives without direct reports. The role requires a blend of deep craft expertise and broad strategic influence.

Reporting Structure: The role reports into a Product + Design Director or similar leadership position. Collaboration is highly cross-functional, involving peers in Engineering, Product Management, UX Design, Data Analytics, and Product Operations.

Operations Impact: This role has a direct and significant impact on the company's ability to innovate and deliver on its mission. By defining and shaping new product experiences, the strategist influences member outcomes, customer acquisition, and the company's competitive positioning in the digital health market. Their work directly contributes to revenue growth and operational efficiency through better product design and strategy.

Growth Opportunities:

• Deepening Specialization: Opportunity to become a recognized expert in specific areas of product strategy, design, or operations within the health tech domain.

• Strategic Leadership: Progression to a Product + Design Director or similar leadership role, potentially managing a team and overseeing larger strategic portfolios.

• Cross-Functional Expertise: Expanding influence and understanding across different business functions, contributing to broader strategic initiatives.

• Industry Influence: Contributing to the advancement of human-centered design and AI integration within the digital health industry.

• Mentorship: Formal or informal opportunities to mentor junior designers, product managers, or researchers.

📝 Enhancement Note: This role offers substantial growth potential for individuals looking to make a significant strategic impact within a mission-driven health tech company. The path likely involves deepening expertise, expanding strategic influence, and potentially moving into leadership positions.

🌐 Work Environment

Office Type: Remote-first. This indicates a distributed workforce where the primary mode of interaction and work is conducted digitally.

Office Location(s): While the role is remote across the USA, Omada Health has a physical presence, which may influence team cohesion and occasional in-person gatherings (though not explicitly stated for this role). The provided salary zones are based on geographic location within the USA.

Workspace Context:

• Digital Collaboration: Emphasis on digital tools for communication, collaboration, and project management (e.g., Slack, Zoom, Figma, project management software).

• Autonomy & Flexibility: Remote-first work allows for significant autonomy in managing one's workspace and schedule, balanced with team collaboration needs.

• Focus on Outcomes: The culture prioritizes delivering results and impact, which is conducive to a remote environment where performance is measured by output.

• Access to Tools: Expectation of access to necessary software, hardware, and potentially stipends for home office setup.

Work Schedule: Standard full-time hours (approximately 40 hours/week) are expected, but the remote-first nature and Flexible Time Off policy suggest a degree of flexibility in managing daily schedules to achieve objectives and maintain work-life balance.

📝 Enhancement Note: The remote-first environment at Omada Health necessitates strong self-discipline, proactive communication, and proficiency with digital collaboration tools. Candidates should be comfortable working independently and asynchronously while also actively engaging with distributed teams.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a recruiter screen to assess basic qualifications, cultural fit, and interest.

• Hiring Manager Interview: Discussion focused on experience, strategic thinking, problem-solving approach, and alignment with the role's core responsibilities.

• Portfolio Review & Presentation: A critical stage where candidates present their work, demonstrating their process, strategic thinking, and impact through case studies. This often involves a presentation to a panel of peers and leaders.

• Cross-functional Interviews: Meetings with potential collaborators from Engineering, Design, Product Management, and potentially Clinical/Operations to assess working style and collaboration skills.

• Executive Interview: A final discussion with senior leadership to assess strategic alignment, executive communication skills, and overall fit for the company's direction.

Portfolio Review Tips:

• Tell a Story: Structure your portfolio around compelling narratives that highlight the problem, your process, the insights gained (especially from data and AI), the solutions you developed, and the measurable impact.

• Show Your Process: Clearly articulate your strategic thinking, research methodologies, how you framed problems, and how you made trade-offs. Emphasize your 0-to-1 experience.

• Highlight AI Integration: Showcase specific examples of how you've used AI tools (e.g., Claude Code, Figma Make, Cursor) to accelerate your work, improve rigor, or achieve better outcomes.

• Demonstrate Impact: Quantify results whenever possible. Use metrics related to user engagement, adoption, clinical outcomes, business goals, or efficiency gains.

• Tailor to Omada: Research Omada Health's mission, products, and values. Frame your examples to show how your skills and experience align with their specific challenges and goals in digital health.

• Prepare for Questions: Anticipate questions about your decision-making process, how you handle ambiguity, stakeholder management, and your approach to regulated environments.

Challenge Preparation:

• Strategic Case Study: Be prepared for a take-home assignment or a live case study that requires you to frame a problem, propose a strategic direction, and outline a plan for validation and execution, potentially involving AI tools.

• Problem-Solving Scenarios: Practice articulating how you would approach ambiguous problems, synthesize conflicting information, and make difficult trade-offs.

• Presentation Skills: Rehearse your presentation style to be clear, concise, engaging, and confident, especially when discussing complex strategies and data.

📝 Enhancement Note: The portfolio review is paramount for this role. Candidates must be prepared to deeply articulate their strategic process, demonstrate hands-on application of AI tools, and showcase tangible impact, particularly in complex, regulated domains.

🛠 Tools & Technology Stack

Primary Tools:

• Prototyping & Design: Figma (highly likely, given industry standard), potentially with plugins or integrations for AI (e.g., Figma Make). Other AI-assisted prototyping tools like Claude Code, Cursor, Lovable are explicitly mentioned as required craft skills.

• Collaboration: Slack, Zoom, Google Workspace (Docs, Sheets, Slides).

• Project Management: Tools like Jira, Asana, or Trello may be used for backlog grooming and sprint planning, though Product Ops often manages the day-to-day checklist.

• Documentation: Confluence or similar knowledge base tools for maintaining decision logs and research repositories.

Analytics & Reporting:

• Product Analytics: Tools like Amplitude, Mixpanel, or Google Analytics for tracking product performance, user behavior, and conversion metrics.

• Data Analysis: SQL for direct data querying, and potentially Python/R for more advanced analysis. Proficiency with self-serve analytics tools is expected.

• Data Visualization: Tableau, Looker, or similar for creating dashboards and communicating insights.

CRM & Automation: While not a primary focus for this role, familiarity with CRM systems (e.g., Salesforce) and marketing automation platforms may be beneficial for understanding customer journeys and business context.

AI & Research Tools:

• AI Design/Spec Tools: Claude Code, Claude Design, Cursor, Lovable, or similar.

• Research Platforms: UserTesting.com, Dovetail, or similar for qualitative research synthesis.

📝 Enhancement Note: Proficiency with modern design and prototyping tools, especially those integrating AI, is essential. Candidates should also be comfortable with data analysis tools and methodologies to inform strategy and measure outcomes.

👥 Team Culture & Values

Operations Values:

• Cultivate Trust: Emphasizes active listening, kindness, and providing respectful, candid feedback. Operations professionals should foster an environment of psychological safety.

• Seek Context: Encourages thorough research and understanding before acting, leading to faster progress and better decision-making. This applies to understanding business needs, user problems, and system dependencies.

• Act Boldly: Promotes innovation, problem-solving, and seizing opportunities to improve processes and member experiences. Operations professionals are expected to be proactive and drive change.

• Deliver Results: Prioritizes impact and measured outcomes over mere activity. A results-oriented mindset is key for operations roles focused on efficiency and effectiveness.

• Succeed Together: Stresses prioritizing company progress above individual or team goals, fostering a collaborative and unified approach. Operations often acts as a central connector.

• Remember Why We’re Here: Connects daily work to the larger mission of transforming healthcare, motivating resilience and commitment through challenges.

Collaboration Style:

• Cross-functional Integration: Operations is inherently cross-functional, requiring seamless integration with Product, Engineering, Design, Sales, Marketing, and Clinical teams.

• Data-Driven Dialogue: Collaboration is often facilitated through shared data insights and metrics, ensuring discussions are grounded in evidence.

• Proactive Communication: In a remote-first environment, proactive and clear communication is vital for maintaining alignment and momentum.

• Feedback Loops: An open culture of feedback is encouraged, enabling continuous improvement of processes and products.

📝 Enhancement Note: The company values are deeply integrated into its operations. Candidates should demonstrate how their work ethic and approach align with these values, particularly in fostering trust, seeking context, acting boldly, delivering results, and succeeding together, all within a mission-driven context.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Ambiguity: The role inherently involves tackling undefined problems and shaping new product areas, requiring comfort with uncertainty and the ability to create clarity.

• Balancing Stakeholder Needs: Reconciling diverse inputs and priorities from various departments (e.g., Engineering, Clinical, Legal, Business) while maintaining a cohesive product vision.

• Driving Adoption of New Technologies: Effectively integrating and advocating for the use of AI and other advanced tools within established workflows.

• Operating in a Regulated Domain: Ensuring product strategies and designs comply with health industry regulations (e.g., HIPAA, FDA guidelines), requiring close collaboration with legal and clinical teams.

• Measuring Impact in Digital Health: Defining and tracking meaningful outcomes for chronic condition management, which can be complex and long-term.

Learning & Development Opportunities:

• Advanced AI Application: Deepening expertise in leveraging AI for design, research, and strategic decision-making.

• Health Tech Innovation: Gaining specialized knowledge in the unique challenges and opportunities within the digital health and chronic disease management space.

• Strategic Product Leadership: Developing skills in executive communication, roadmap strategy, and influencing organizational direction.

• Cross-functional Mastery: Expanding understanding and influence across diverse business functions.

• Mentorship Programs: Opportunities to learn from and be mentored by senior leaders within Omada Health.

📝 Enhancement Note: This role presents a unique opportunity to tackle complex problems at the forefront of digital health innovation, with significant scope for professional growth in strategic leadership and AI application.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you took a highly ambiguous problem space and defined a clear product opportunity. What was your process, and what was the outcome?" (Focus on problem framing, research, data synthesis, and 0-to-1 experience.)

• "How do you balance competing priorities from different stakeholders (e.g., Engineering, Clinical, Sales) when setting product direction?" (Assess prioritization, trade-off decision-making, and stakeholder management.)

• "Walk me through a product strategy you developed that didn't achieve its intended results. What did you learn, and how did you adapt?" (Evaluate learning agility, humility, and iterative approach.)

• "How have you leveraged AI tools in your design or product strategy process? Provide a specific example of how it improved efficiency or rigor." (Assess practical AI application and understanding of its role as a partner.) Company & Culture Questions:

• "Why Omada Health, and what specifically about our mission resonates with you?" (Gauge alignment with company's purpose and values.)

• "How do you embody our company values (e.g., Cultivate Trust, Seek Context, Act Boldly) in your day-to-day work?" (Assess cultural fit and understanding of values.)

• "Describe your experience working in regulated industries like health tech. What are the key considerations for product strategy and design?" (Evaluate domain-specific knowledge and compliance awareness.) Portfolio Presentation Strategy:

• Structure: Begin with a high-level overview of your career and key achievements, then dive into 2-3 in-depth case studies that showcase your strategic process, 0-to-1 work, AI integration, and impact.

• Process Focus: For each case study, clearly articulate the problem, your role, the methodology used (research, data, AI), key decisions and trade-offs, challenges encountered, the solution, and the measurable outcomes.

• AI Demonstration: Be prepared to show (or describe in detail) how you used AI tools to accelerate research synthesis, ideation, prototyping, or spec drafting.

• Quantify Impact: Use data and metrics to demonstrate the success of your initiatives. If direct metrics are unavailable, articulate proxies or lessons learned.

• Engage the Audience: Be prepared for questions throughout your presentation and tailor your responses to the audience's expertise.

📝 Enhancement Note: Candidates should prepare to articulate their strategic process with depth, showcase practical application of AI, demonstrate impact with data, and align their experience with Omada Health's mission and values. Be ready for scenario-based questions and detailed portfolio walkthroughs.

📌 Application Steps

To apply for this Senior Product Design Strategist position:

• Submit your application through the provided application link on the Omada Health careers page.

• Tailor Your Resume & Cover Letter: Highlight your experience in product strategy, design, 0-to-1 development, AI tool usage, and work in regulated industries. Use keywords from the job description to optimize for Applicant Tracking Systems (ATS).

• Curate Your Portfolio: Select 2-3 of your most impactful projects that best demonstrate your strategic thinking, problem-framing abilities, 0-to-1 experience, AI integration, and measurable outcomes. Ensure it's easily accessible (e.g., PDF, personal website).

• Prepare Your Presentation: Practice presenting your portfolio case studies, focusing on clear storytelling, process articulation, and demonstrating impact. Be ready to discuss your approach to ambiguity and AI.

• Research Omada Health: Understand their mission, product offerings (especially in chronic disease management), company values, and recent news to effectively articulate your interest and fit during interviews.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.