Lead Director of Software Engineering

Health100 is America’s trusted front door to health and care. The Health100 platform integrates any participating health plan, PBM, pharmacy (retail and specialty), provider, digital health point solution provider, and employer, and addresses the top health care challenges for the consumer.

We are looking for a hands-on, passionate engineering leader to join a high-energy, mission-driven team on the forefront of digital health innovation - reinventing how consumers engage with their health. As the Lead Director of Software Engineering, you will lead the strategic vision, development, and execution of our platform engineering 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 own integration strategy and execution across multiple domains, managing partner requirements, technical constraints, and external commitments while advancing platform modernization initiatives. You will partner closely with external stakeholders, understand their technical constraints and success criteria, and communicate risks and feasibility clearly in both technical and business terms.

Responsibilities:

• Strategic & technology roadmap ownership: Define and drive multi-team product and technical roadmaps, aligning engineering investments, architectural direction, and delivery priorities with business outcomes
• Engineering excellence & delivery governance: Establish scalable engineering standards, operational frameworks, and risk management practices to ensure quality, efficiency, and reliable execution across teams
• Organizational leadership & talent strategy: Lead, mentor, and grow engineering managers and senior engineers, owning hiring, performance management, career development, succession planning, and a culture of accountability and high performance
• Cross-functional and external stakeholder alignment: Partner closely with Product, Business, Architecture, Design, Security, and external partners to translate strategy into executable programs with clear milestones, accountable ownership, and measurable outcomes
• Technical complexity and ambiguity navigation: Own architecturally complex initiatives across multiple domains, guiding teams through evolving requirements, tight dependencies, and external commitments that require disciplined execution and sound technical judgment
• Resource scaling and innovation: Manage vendor and contingent workforce strategies while leading technology research across AI, cloud, and distributed systems to inform long-term platform investments, optimize integrations, and improve operational outcomes

• 12+ years of hands-on software engineering experience in large-scale distributed platforms, including complex integration and interoperability challenges; 5+ years of experience leading managers and senior engineers through complex technical initiatives
• Proven delivery of large-scale, multi-team engineering programs, owning strategy through execution across complex integrations, platform modernization, and cloud migrations in fast-paced digital or healthcare technology environments
• Strong technical depth in distributed systems and cloud-native architectures, including microservices (Java/Spring Boot, Python), DevOps (CI/CD, Kubernetes/Docker), and cloud platforms (GCP preferred)
• Executive-level communication and influence skills and demonstrated success building and scaling high-performing engineering organizations, including distributed teams and vendor partnerships
• Hands-on experience delivering AI-enabled or generative AI-integrated software solutions that produced measurable business or operational outcomes, * Proven experience hiring and leading high-performing, distributed engineering teams, including multi-site and fully remote models
• Demonstrated data-driven problem solving, using quantitative analysis to guide decisions and improve outcomes
• Hands-on experience defining, tracking, and analyzing KPIs to measure engineering productivity, delivery health, and project success
• Experience delivering healthcare or wellness technology solutions, working effectively with both onshore and offshore teams, * Bachelor’s degree in Computer Science, Information Systems, Engineering, related field, or equivalent experience (High school diploma plus 4 years relevant work experience), Architectural Design, Architectural Services, Artificial Intelligence (AI), Business Architecture, Business Operations, Career Development, Cloud Architecture, Cloud Computing, Computer Science, Continuous Deployment/Delivery, Continuous Integration, Cross-Functional, DevOps, Distributed Computing, Docker, Engineering, Engineering Management, Establish Priorities, GCP (Good Clinical Practices), Geography, Health Plan, Healthcare, Healthcare Providers, High School Diploma, Incentive Programs, Interoperability, Java, Leadership, Mentoring, Microservices, Offshoring, Operational Improvement, Operational Measurement, Performance Management, Performance Metrics, Pharmacy, Problem Solving Skills, Product Planning, Python Programming/Scripting Language, Quantitative Analysis, Requirements Management, Retail, Risk Management Framework (RMF), Safety/Work Safety, Software Engineering, Succession Planning, Systems Engineering, Team Lead/Manager, Technical Leadership, Technical Recruiting, Technical Research, Technical Strategy, Vendor/Supplier Management

$144,200.00 - $288,400.00

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.

CVS Health offers a world of promising job opportunities across a diverse range of careers in everything from corporate and pharmacy roles to retails positions. No matter where you work at CVS Health, your unique skills, talents and abilities are welcome and valued. We recognize and reward greatness and want our employees to know their work is making a difference in the lives of millions. Join us today. Together we can continue making innovative, high-quality health and pharmacy services safe, affordable and accessible - for all.

Company Size: 10,000 employees or more

Industry: Biotechnology/Pharmaceuticals