Vice President, Digital Engineering Health100

CVS Health•Boston, TX

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. 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.

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

Nice To Haves

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

Responsibilities

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.