Health100 is recruiting for a VP, Digital Engineering to lead cross-functional engineering capabilities for the Health100 platform, spanning digital identity and account management, payments, solutions engineering, and AI solutions. This is a highly technical and strategic leadership role where this leader will not only manage the teams delivering new features and capabilities but also guide architectural direction and digital best practices to future-proof the platform. The ideal candidate operates as a true partner to Product - co-owning the roadmap and capability definition in addition to executing against it. This leader brings a builder's instinct for moving fast, cutting through ambiguity, and shipping solutions. We're looking for someone who can bring a startup-caliber sense of urgency and ownership to an enterprise-scale platform, positioning Health100 as an industry-leading consumer health experience. You will make an impact by: • Partnering directly with Product leadership to define and shape the Health100 roadmap and capability set - not just receiving requirements, but co-driving what gets built, in what sequence, and why. • Leading a portfolio of cross-cutting engineering capabilities that underpin the Health100 member experience, including digital account and profile management, digital payments, solutions engineering, and AI solutions. • Owning engineering for digital account and profile capabilities - registration, authentication, identity verification, profile and preference management, and consent/privacy controls (including CCPA/CPRA opt-out flows across authenticated and unauthenticated users) - ensuring a secure, unified member identity experience. • Owning digital payments engineering across Health100, including premium and copay payment flows, HSA/FSA integration, and third-party payment processor and billing system integrations, with a strong focus on PCI-DSS compliance and transaction reliability. • Leading the Solutions Engineering function: translating product and business requirements into technical designs, cross-team integration patterns, and reusable frameworks/accelerators that let feature teams ship consistently and quickly across Health100. • Leading AI Solutions engineering for Health100 - building and scaling Generative AI and agentic capabilities (conversational assistants, intelligent workflow automation) designed to be incremental and invisible in the member experience rather than disruptive. • Owning production reliability and operability across the portfolio - defining SLOs/SLAs, leading incident response and on-call practices, and ensuring performance and resiliency against enterprise uptime targets across identity, payment, and AI transaction volumes. • Driving a bias toward action: favoring rapid iteration, lean process, and pragmatic build/buy decisions over lengthy planning cycles, while still meeting the rigor a regulated healthcare environment demands. • Working closely with other engineering leaders across CVS Health's vertically integrated ecosystem (Caremark, Aetna, CVS Specialty) to ensure Health100 capabilities integrate cleanly with adjacent platforms over time. • Managing and supporting a large team of engineering resources, building a culture of ownership, urgency, and product-based delivery, and helping tenured resources transition to new delivery methodologies. • Tracking and adhering to financial, operational, and other OKRs/goals within and across the organization. . Requirements • 15+ years of experience in digital software development and engineering • 10+ years overall in a Technology leadership position, including managing financials, goals, and operational metrics • Background as a hands-on software engineer or architect earlier in career, with continued fluency in code and system design • Experience leading multiple engineering teams totaling 100+ resources • Experience in coding, architecting and leading large teams of technologists across multiple time zones and cultures • Track record of partnering closely with Product to shape roadmap and capability strategy, not just execute against a fixed backlog • Demonstrated ability to drive fast, high-quality execution - shipping and iterating in tight cycles rather than over-planning • Deep expertise in software architecture, APIs, microservices, cloud-native platforms, and DevSecOps • Previous experience in design, architecture, and engineering of highly available, resilient, scalable systems, including cloud architectures • Experience building enterprise transaction-based systems with focus on security, reliability, scalability, performance, and modern CI/CD techniques • Experience owning production reliability at enterprise scale - defining and meeting SLOs/SLAs, leading incident response, and building strong observability practices • Experience with digital identity and account management systems (OAuth 2.0/OIDC or equivalent) • Experience with digital payments systems and PCI-DSS compliance • Experience delivering AI, ML, or Generative AI solutions within enterprise software environments • Experience with LLM evaluation frameworks, RAG architecture, and agent orchestration platforms, including model governance and responsible AI practices • Experience supporting digital platforms with large daily visitor volumes (1M+ visits/day) • Demonstrated experience in taking high-level enterprise strategy and blueprints and converting them into system-level deliverables for delivery • Experience working in a fast-paced, dynamic environment, with the ability to adapt to change and lead through ambiguity • Demonstrated success in driving innovation and continuous improvement • Strong interpersonal and communication skills, effectively communicating key messages to executive leaders and internal/external stakeholders Preferred Qualifications • Startup, high-growth, or 0-to-1 product-building experience, ideally brought into and adapted for a large enterprise setting • Healthcare, pharmacy, payer, provider, or digital health experience • Experience with LLMs, agentic architecture, conversational AI, and intelligent workflow automation 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. 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: 10/12/2026