Director of Engineering, Omada Health

• Have strong product taste, and exceptional technical judgment, and know when simplicity beats novelty
• Have led multiple engineering teams building consumer-facing products at scale, ideally in high-engagement or DTC environments
• Care deeply about end-to-end user experience, including edge cases, failure modes, and support flows
• Excel at influence and tight partnership with Product, Design, and Applied AI, shaping strategy, sequencing, and tradeoffs. Align teams to a single narrative from discovery through delivery
• Have a track record of predictable delivery: turning ambiguity into clear plans, managing dependencies, and hitting commitments without sacrificing quality
• Believe that great engineering reduces operational load, pager fatigue, and member frustration simultaneously
• Are comfortable operating in highly regulated environments and understand that privacy, security, and trust are product features from day 0
• Can turn ambiguous, high-level goals into clear priorities and execution plans for teams
• Believe in Agile principles and be the agent of change when and where required
• 12+ years of experience in engineering leadership, including 5+ years managing managers
• Experience leading multiple product teams delivering best-in-class web and mobile experiences at scale, with a high bar for craft, performance, and reliability
• Strong product instincts paired with a pragmatic, data-driven approach to decision-making
• Proven ability to define success metrics and hold teams accountable to outcomes, not just output, in an Agile environment
• Proven ability to lead quarterly planning/OKRs across multiple teams, including capacity planning, organizational design, dependency management, and data-driven course correction
• Experience hiring, developing, and retaining high-performing engineering leaders
• Deep understanding of mobile (iOS/Android) and web development tradeoffs
• Accountable for a healthy 24/7 on-call and reliability culture: reducing toil, improving incident response, and strengthening learning loops

Desirable

• We’re looking for an experienced Director of Engineering to lead the teams responsible for Omada’s Core User Experience: the front door and day-to-day surfaces that define trust, momentum, and long-term engagement
• This group owns onboarding and experience foundations, home/navigation and discovery, and the support + connection experiences that make the product feel human, resilient, and easy to use
• This is a senior leadership role for someone who cares deeply about how products feel and how they’re built
• You’ll own the technical strategy and execution for the moments that most directly drive trust, engagement, and retention
• You’ll do this through deep partnership with Product and Design, using clear OKRs, strong instrumentation, and disciplined planning to deliver consistently against commitments
• You’ll lead multiple product engineering teams embedded in cross-functional Product and Design squads, owning the end-to-end member experience and the operating system (OKRs, planning, metrics) that keeps delivery predictable:
• Onboarding and experience foundations: first-run flows, setup, and the baseline UX patterns that everything else builds on
• Core engagement surfaces: home, navigation, discovery, and progression, helping members know what to do next and why it matters
• Support and connection: member-facing support flows, messaging, and the care-team tools that enable timely, human intervention
• AI-assisted experiences and workflows: partner with Product, Design, and Applied AI, to apply AI thoughtfully to improve speed, quality, and support effectiveness, while keeping care human-led and trust-first
• Journey reliability: resilient, observable experiences; cross-cutting investments in performance, reliability, and development productivity, in partnership with Platform Engineering
• Your mandate is simple and hard: build experiences members want to come back to, while holding a high bar for quality and operational excellence
• Own the technical and execution strategy for Omada’s core member experience, from first interaction to long-term engagement
• Partner closely with Product, Design and our Applied AI team, to translate behavioral science and product vision into scalable, maintainable systems
• Define Core UX OKRs and success metrics, and lead teams to deliver against quarterly commitments with transparency and predictable execution
• Set a high bar for craft, performance, and reliability in mobile and web experiences, especially in moments that matter (onboarding, navigation, messaging, support)
• Balance new product development with long-term system health, resilience, developer productivity, and product development velocity
• Build systems and experiences that proactively reduce member confusion and operational burden. Support should never be an afterthought
• Grow and mentor Engineering Managers, Staff+ engineers, and future leaders, creating clear paths for impact and progression
• Establish and review metrics for engagement/retention, support burden, crash-free/performance, and delivery predictability, using data to steer priorities and prove OKR movement
• Work with our Platform organization on infrastructure and shared services, while owning reliability outcomes and operational excellence for the member experience domain