Lead Director - Software Engineering (Health100 Platform)

CVS Health•Boston, MA

3d•$144,200 - $288,400

About The Position

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. Position Summary 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.

Requirements

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

Nice To Haves

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

Responsibilities

Define and drive multi-team product and technical roadmaps, aligning engineering investments, architectural direction, and delivery priorities with business outcomes
Establish scalable engineering standards, operational frameworks, and risk management practices to ensure quality, efficiency, and reliable execution across teams
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
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
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
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