Lead Director AI Platform Enablement Automation

CVS Health; Chicago (IL); On-site; USD 144,000 - 288,000; Full time

Benefits offered by this job

Medical, dental, vision coverage

Paid time off and retirement options

Wellness programs

Job summary

CVS Health in Chicago seeks a Lead Director for AI Platform Enablement & Automation to own end-to-end integration, AI-assisted development, and scalable cloud platforms. You will drive platform modernization, automation, and proactive incident management using AI/ML within AIOps frameworks.

Lead engineering teams, set roadmaps, budget, and vendor partnerships while delivering high-quality, cost-optimized solutions aligned with business goals and customer experiences.

Qualifications

• 10+ years IT leadership across platforms.
• 5+ years AI technologies development, testing, and automation in Agile environments.
• 4+ years hands-on development across multiple technology platforms.
• 5+ years cloud-native experience (Azure, GCP, AWS).
• 10+ years translating testing and automation strategies into measurable outcomes.

Responsibilities

• Oversee end-to-end delivery for Pharmacy Segment and PCW lines.
• Lead teams across legacy middleware and modern cloud platforms (GCP, AWS, Azure).
• Drive modernization and automation initiatives via AI integration and automation.
• Define objectives, roadmaps, and budgets; drive operational excellence and ROI.

Skills

IT leadership

Automation strategy

AI technologies

Cloud platforms

Software development

Education

Bachelor's degree or equivalent experience

Tools

Kafka

APIM

Kong

LLMs

Job description

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 The Lead Director – AI Platform Enablement & Automation leads Integration Engineering with end-to-end ownership across PS, PCW, and Test Automation. This role ensures scalable, reliable, and high-quality delivery by embedding AIOps, and automation across product and operational lifecycles. It oversees AI assisted development, release quality, and proactive incident management through predictive analytics and anomaly detection, aligning outcomes with business objectives, customer experience goals, and executive KPIs/OKRs. The role leverages modern cloud-native and integration technologies, including Azure, AWS, and GCP, along with API-based service orchestration. It utilizes AI/ML and Large Language Models (LLMs) within AIOps frameworks to enable intelligent monitoring, and operational efficiency. Testing frameworks, CI/CD pipelines, and agile methodologies drive continuous quality and deployment velocity. Additionally, the role provides strategic leadership across engineering teams, overseeing budgeting, roadmap planning, and vendor partnerships while driving innovation, reducing technical debt, and enabling resilient, cost-optimized platforms through standardized engineering and automation practices.

Responsibilities

• Oversee end to end delivery of solutions for PS (Pharmacy Segment) and PCW (Pharmacy and Consumer Wellness) Lines of business.
• Oversee engineering teams operating on legacy middleware technologies and modern cloud platforms such as GCP, AWS and Azure.
• Lead teams composed of engineering managers, architects, engineers, product leads, and quality engineers.
• Drive modernization and automation initiatives (i.e. API Modernization, Platform Migration etc) by identifying opportunities for AI integration and automation.
• Work closely with product, engineering, and leadership teams to identify quality risks, communicate insights and metrics, and proactively enhance the customer experience.
• Oversee annual budgeting, capital processes, and quality improvement activities for the organization.
• Provide both strategic and tactical engineering and architecture leadership, including developing delivery and resource plans, creating roadmaps, and driving operational excellence.
• Optimize operating costs and budgets by reducing technical debt, improving risk visibility through executive-level reporting, and coordinating program-related activities.
• Lead a variety of testing and automation strategies across IT and business operations using AI platforms, ensuring high-quality, scalable delivery aligned with internal and external business objectives and customer experience goals.
• Own the end-to-end execution of quality assurance processes across AI model validation and automation, driving consistent quality outcomes and timely release cycles.
• Guide the planning and execution of projects and programs; establish technical and functional standards and practices; and oversee processes, procedures, career development, and skills mapping.
• Define objectives and key results (OKRs), return on investment (ROI), and key performance indicators (KPIs).
• Deliver metrics-based reports and make recommendations to improve delivery.
• Facilitate communication between technical and non-technical stakeholders to ensure alignment on priorities and deliverables.
• Demonstrate a thorough understanding of, and provide guidance on, principles, practices, and techniques relevant to the application area and organization.
• Provide formal and informal feedback to address performance gaps, including functional, technical, and soft skills.
• Actively participate in recruitment and selection processes for both CVS and vendor candidates, and lead relationships with on-site and offshore vendors.
• Ensure all teams adhere to the highest standards of integrity and the Code of Conduct.
• Drive skills transformation through upskilling plans focused on cloud, automation, and AI technologies.
• Lead hiring for full-time and contract roles and manage onshore/offshore vendor partnerships.

Required Qualifications

• 10+ years of information technology leadership experience across various platforms.
• 10+ years of experience translating complex testing and automation strategies into measurable business outcomes.
• 5+ years of experience leveraging AI technologies and development, testing, and automation techniques in a high-performance Agile environment.
• 5+ years of experience in cloud-native environments, including Azure, GCP and AWS.
• 4+ years of hands-on development experience across multiple technology platforms.

Preferred Qualifications

• Executive-level communication skills with the ability to articulate strategic concepts effectively to diverse stakeholders.
• Background in healthcare and Pharmacy Benefit Management (PBM).
• Experience with Kafka, APIM, and Kong platforms.
• Hands-on experience with Large Language Models (LLMs) and their practical application in software modernization, code generation, or refactoring initiatives.

Education

Bachelor’s degree or equivalent experience (Highschool diploma plus 4 years relevant work experience).

Pay Range

The typical pay range for this role is: $144,200.00 - $288,400.00 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: 12/31/2026

Our Work Experience is the combination of everything that's unique about us: our culture, our core values, our company meetings, our commitment to sustainability, our recognition programs, but most importantly, it's our people. Our employees are self-disciplined, hard working, curious, trustworthy, humble, and truthful. They make choices according to what is best for the team, they live for opportunities to collaborate and make a difference, and they make us the #1 Top Workplace in the area.