Vice President, Digital Engineering Health100

CVS Health • Boston, MA

1d

About The Position

Health100 is recruiting a Vice President of Digital Engineering to lead cross-functional engineering capabilities for its platform, including digital identity and account management, payments, solutions engineering, and AI solutions. This strategic and highly technical leader will manage teams delivering new features, guide architectural direction and digital best practices, and help future-proof the platform. The role partners closely with Product leadership to co-own the roadmap and capability definition, while delivering solutions with urgency and ownership in an enterprise-scale, regulated healthcare environment.

The VP will lead engineering for digital account and profile capabilities, including registration, authentication, identity verification, profile and preference management, and consent and privacy controls. The role also owns digital payments engineering, including premium and copay flows, HSA/FSA integration, and payment processor and billing integrations, with an emphasis on PCI-DSS compliance and reliability. Other responsibilities include leading Solutions Engineering and AI Solutions, overseeing production reliability and operability, and coordinating integrations with CVS Health businesses such as Caremark, Aetna, and CVS Specialty.

The leader will manage and support a large engineering organization, foster a culture of ownership and product-based delivery, help experienced employees transition to new delivery methodologies, and track financial, operational, and organizational goals. The position is full-time and includes eligibility for a CVS Health bonus, commission or short-term incentive program, an equity award target, and a comprehensive benefits package.

Requirements

• 15+ years of experience in digital software development and engineering.
• 10+ years in a technology leadership position, including management of financials, goals, and operational metrics.
• Earlier-career experience as a hands-on software engineer or architect, with continued fluency in code and system design.
• Experience leading multiple engineering teams totaling 100+ resources.
• Experience coding, architecting, and leading large teams of technologists across multiple time zones and cultures.
• Track record of partnering closely with Product to shape roadmaps and capability strategy, rather than only executing a fixed backlog.
• Demonstrated ability to deliver and iterate quickly in tight cycles.
• Deep expertise in software architecture, APIs, microservices, cloud-native platforms, and DevSecOps.
• Experience designing, architecting, and engineering highly available, resilient, scalable systems, including cloud architectures.
• Experience building enterprise transaction-based systems focused on security, reliability, scalability, performance, and modern CI/CD techniques.
• Experience owning production reliability at enterprise scale, including defining and meeting SLOs/SLAs, leading incident response, and building observability practices.
• Experience with digital identity and account management systems such as OAuth 2.0/OIDC or equivalent.
• Experience with digital payments systems and PCI-DSS compliance.
• Experience delivering AI, ML, or Generative AI solutions in enterprise software environments.
• Experience with LLM evaluation frameworks, RAG architecture, agent orchestration platforms, model governance, and responsible AI practices.
• Experience supporting digital platforms with 1M+ visits per day.
• Experience translating high-level enterprise strategy and blueprints into system-level delivery plans.
• Experience in a fast-paced, dynamic environment, adapting to change and leading through ambiguity.
• Demonstrated success driving innovation and continuous improvement.
• Strong interpersonal and communication skills, including communicating effectively with executive leaders and internal and external stakeholders.

Nice To Haves

• Startup, high-growth, or 0-to-1 product-building experience, ideally 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

• Partner with Product leadership to define and shape the Health100 roadmap, capabilities, sequencing, and priorities.
• Lead cross-functional engineering capabilities supporting the Health100 member experience, including digital accounts and profiles, payments, solutions engineering, and AI solutions.
• Own engineering for registration, authentication, identity verification, profile and preference management, and consent and privacy controls, including CCPA/CPRA opt-out flows for authenticated and unauthenticated users.
• Own digital payments engineering, including premium and copay flows, HSA/FSA integration, and third-party payment processor and billing system integrations; ensure PCI-DSS compliance and transaction reliability.
• Lead Solutions Engineering by translating product and business requirements into technical designs, cross-team integration patterns, and reusable frameworks and accelerators.
• Lead AI Solutions engineering, including development and scaling of Generative AI and agentic capabilities such as conversational assistants and intelligent workflow automation.
• Own production reliability and operability across the portfolio; define SLOs/SLAs, lead incident response and on-call practices, and support performance and resiliency against enterprise uptime targets.
• Promote rapid iteration, lean processes, and pragmatic build-versus-buy decisions while meeting the requirements of a regulated healthcare environment.
• Collaborate with engineering leaders across CVS Health businesses, including Caremark, Aetna, and CVS Specialty, to support platform integrations.
• Manage and support a large team of engineering resources; build a culture of ownership, urgency, and product-based delivery, and help tenured resources transition to new delivery methodologies.
• Track and adhere to financial, operational, and other organizational OKRs and goals.

Benefits

• Medical coverage
• Dental coverage
• Vision coverage
• Paid time off
• Retirement savings options
• Wellness programs
• Other resources supporting physical, emotional, and financial well-being, based on eligibility
• Eligibility for a CVS Health bonus, commission, or short-term incentive program
• Equity award program target

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed