Vice President, Digital Engineering

This is a fully remote position, open to applicants in Illinois, +4 more states.

📋 Description

• Collaborate with Product leadership to define and refine the Health100 roadmap and capability offerings

• Oversee cross-functional engineering capabilities for the Health100 platform

• Manage digital account and profile functionalities, including registration, authentication, identity verification, profile and preference management, as well as consent/privacy controls

• Supervise digital payments engineering, covering premium and copay flows, HSA/FSA integration, along with third-party payment and billing integrations

• Lead Solutions Engineering by converting product and business requirements into technical designs, integration patterns, and reusable frameworks

• Direct AI Solutions engineering, which encompasses Generative AI and agentic capabilities

• Ensure production reliability and operability across the portfolio, focusing on SLOs/SLAs, incident response, and on-call practices

• Promote rapid iteration, lean processes, and pragmatic build/buy decisions while complying with regulated healthcare standards

• Collaborate with engineering leaders from Caremark, Aetna, and CVS Specialty

• Manage and support a substantial engineering team, fostering a culture of ownership, urgency, and product-based delivery

• Monitor and comply with financial, operational, and organizational OKRs and goals

⛳️ Requirements

• Over 15 years of experience in digital software development and engineering

• More than 10 years in a Technology leadership role, including management of financials, goals, and operational metrics

• Previous experience as a hands-on software engineer or architect, maintaining fluency in code and system design

• Proven ability to lead multiple engineering teams totaling over 100 resources

• Experience in coding, architecting, and managing large teams across various time zones and cultures

• A strong history of closely partnering with Product to influence roadmap and capability strategy

• Proven ability to drive rapid, high-quality execution

• Extensive expertise in software architecture, APIs, microservices, cloud-native platforms, and DevSecOps

• Experience in designing and engineering highly available, resilient, and scalable systems, particularly cloud architectures

• Proven track record in building enterprise transaction-based systems with a focus on security, reliability, scalability, performance, and modern CI/CD practices

• Experience with production reliability at an enterprise scale, including SLOs/SLAs, incident response, and observability

• Familiarity with digital identity and account management systems, including OAuth 2.0/OIDC or equivalent

• Knowledge of digital payments systems and PCI-DSS compliance

• Experience in delivering AI, ML, or Generative AI solutions within enterprise software environments

• Proficiency with LLM evaluation frameworks, RAG architecture, agent orchestration platforms, model governance, and responsible AI practices

• Background in supporting digital platforms with over 1 million daily visits

• Ability to translate enterprise strategy and blueprints into system-level delivery

• Experience in fast-paced, dynamic environments and leading through uncertainty

• Demonstrated success in driving innovation and continuous improvement

• Strong interpersonal and communication skills with executive leaders and internal/external stakeholders

• Preferred: experience in startups, high-growth environments, or 0-to-1 product development

• Preferred: background in healthcare, pharmacy, payer, provider, or digital health

• Preferred: expertise in LLMs, agentic architecture, conversational AI, and intelligent workflow automation

🏝️ Benefits

• CVS Health bonus, commission or short-term incentive program

• Award target in the company’s equity award program

• Medical coverage

• Dental coverage

• Vision coverage

• Paid time off

• Retirement savings options

• Wellness programs

• Additional resources supporting physical, emotional, and financial well-being, based on eligibility