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.

Executive Director, Digital Engineering

Health100 is an AI‑native health technology platform that unifies pharmacies, providers, insurers, PBMs, and digital health solutions into a single, consumer‑focused ecosystem. Health100 is reimagining how members engage with their health — combining AI-powered assistance, personalized care navigation, and seamless digital experiences to improve outcomes at scale. As 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 Health100 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.

Engineering Delivery & Execution

• Own sprint planning, delivery tracking, and release readiness across Health100 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.

Leadership and Team Oversight

• 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 Health100's engineering practices — not just headcount.
• Identify and escalate resourcing gaps proactively — through hiring, vendor engagement, or reallocation.
• Actively develop engineers on the team — providing technical mentorship, feedback, and growth opportunities.

Technical Leadership

• 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.

Cross-Functional Collaboration

• 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 tradeoffs clearly.
• Escalate issues proactively — with context, a point of view, and a recommended path forward, not just a problem.

Required Qualifications

• 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 record of iterative, fast-paced delivery — shipping frequently and improving based on real usage data.
• Experience leading large-scale, globally distributed teams, and ensuring the health and stability of production operations.
• Technical expertise in triaging, understanding, and solving complex challenges across various technology stacks, enterprise integrations, and vendor platforms.

Preferred Qualifications

• Experience building member- or patient-facing health applications; working knowledge of FHIR, HL7, or health data interoperability standards.
• Familiarity with AI/ML integration in production apps — particularly conversational AI, health assistants, or recommendation systems.
• Exposure to cloud-native architectures (AWS, Azure, or GCP) in an enterprise environment.
• Background working with software development vendors as delivery partners — including SOW management, onboarding, and performance accountability.

Education:

• Bachelor’s Degree

Pay Range

The typical pay range for this role is:

$175,100.00 - $334,750.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls.  The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors.  This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above.  This position also includes an award target in the company’s equity award program. 
 

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 10/31/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.