Executive Director, Digital Engineering

We're building a world of health around every individual - shaping a more connected, convenient and compassionate health experience. At CVS Health®, you'll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger - helping to simplify health care one person, one family and one community at a time.

Health
100 is an AI‑native health technology platform that unifies pharmacies, providers, insurers, PBMs, and digital health solutions into a single, consumer‑focused ecosystem. Health
100 is reimagining how members engage with their health - combining AI-powered assistance, personalized care navigation, and seamless digital experiences to improve outcomes  Executive Director of Digital Engineering, you will lead the strategic vision, development and execution of our digital health roadmap. You will drive innovation, manage cross‑functional teams, and ensure the delivery of high quality products that exceed consumer expectations.

As a key strategic leader, you will partner deeply with stakeholders across Health
100 to understand consumers, current product landscape, operational needs, and business goals - developing long‑term visions, technical strategies, and roadmaps that deliver value. Design thinking is at the center of all you do, ensuring consumer centricity is the core of everything we build so that we deliver the right value to the right person at the right time.

• Own sprint planning, delivery tracking, and release readiness across Health
  100 engineering squads.
• Drive day‑to‑day delivery velocity - identifying blockers, resolving dependencies, and keeping the team moving.
• Maintain and enforce engineering quality standards: code reviews, testing coverage, CI/CD hygiene, and deployment readiness.
• Lead iterative delivery cycles - from feature scoping to pilot release to scale - in close partnership with product management.
• Own the engineering definition of done for each feature, ensuring compliance, security, and performance requirements are met before release.

• Directly manage a hybrid team of internal software engineers and external vendor contributors across the full‑stack.
• Hold vendor partners accountable to delivery commitments, quality standards, and Health
  100's engineering practices - not just headcount.
• Identify and reinforce resourcing gaps proactively - through hiring, vendor engagement, or reallocation.
• Actively develop engineers on the team - providing technical mentorship, feedback, and growth opportunities.

• Provide hands‑on technical guidance across frontend (web and mobile), backend services, APIs, and integrations.
• Participate meaningfully in system design and architecture reviews - raising implementation risks early and proposing pragmatic solutions.
• Own technical debt management: identify what slows the team down, prioritize remediation, and advocate for engineering time to address it.
• Ensure compliance, PHI safeguards, and security best practices are embedded in engineering workflows, not treated as afterthoughts.
• Drive integration quality with health data systems - including FHIR‑based APIs, lab data, and benefits platforms.

• Partner closely with product managers and designers to refine requirements, assess feasibility, and sequence delivery effectively.
• Represent engineering in cross‑functional feature reviews and planning sessions - communicating progress, risks, and trade‑offs clearly.
• Escalate issues proactively - with context, a point of view, and a recommended path forward, not just a problem.

• 15+ years of software engineering experience, with 5+ years in engineering management or technical leadership roles.
• Proven track record delivering full‑stack digital products at scale.
• Strong full‑stack technical foundation - you can credibly lead engineers across frontend (Flutter, React, mobile), backend (APIs, microservices), and data integration layers.
• Track…