Position Overview

The Lead Director – AI Software Engineering is a pivotal role within a dynamic organization, serving as a key partner to both business and IT leaders. This position provides the opportunity to make a significant impact for customers utilizing Pharmacy Benefits. The ideal candidate possesses a passion for organizational excellence, attention to detail, and the ability to facilitate the success of their unit, while also providing direct support to the Executive Director of Adjudication Services Engineering at Caremark.

We seek an exceptionally skilled and motivated Lead Director – AI Software Engineering with a strong background in building and leading high-performing teams specializing in Testing, Automation, and Production Operations. The Lead Director is expected to actively manage engineering teams, foster innovative thinking, and develop technical solutions to optimize business processes. This role includes coaching and mentoring engineers to ensure the consistent delivery of high-quality products and services. Candidates who are passionate about quality engineering, automation, and operations leveraging the latest AI technologies, and who have a proven record of leading successful teams in fast-paced environments, are encouraged to apply.

Responsibilities

• 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, automation, and manual testing, driving consistent quality outcomes and timely release cycles.

• Oversee the development and adoption of AI-Driven Operations (AIOps) and Automation capabilities to enable proactive issue detection, alert noise reduction, and predictive failure prevention. Implement AI-assisted incident triage, automated runbooks, root-cause analysis, and self-healing systems. Collaborate with the AI Platform team to integrate Large Language Models (LLMs) and Machine Learning (ML) models into operational workflows, including log summarization, anomaly detection, and remediation.

• Champion modern testing and operational practices, as well as emerging technologies, including agile testing methodologies, automation frameworks, and AI-specific testing tools.

• Work closely with product, engineering, and leadership teams to identify quality risks, communicate insights and metrics, and proactively enhance the customer experience.

• 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, offering improved risk visibility through executive-level reporting, and coordinating all program-related activities.

• Guide the planning and execution of projects and programs, establish technical and functional standards and practices, and oversee processes, procedures, career development, and skillset mapping.

• Define objectives and key results (OKRs), return on investment (ROI), and key performance indicators (KPIs). Deliver reports on metrics and make recommendations for improved delivery.

• Collaborate with business stakeholders to ensure a clear and actionable engineering backlog. Remove blockers and showcase engineering progress to senior leadership.

• Facilitate communication between technical and non-technical stakeholders to ensure alignment on priorities and deliverables.

• Participate in annual budgeting, capital processes, and quality improvement activities for the organization.

• 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 onsite and offshore vendors.

• Ensure all teams adhere to the highest standards of integrity and the Code of Conduct.

Required Qualifications

• 10+ years of Information Technology experience across various technological platforms, including leadership and development management experience.

• 10+ years of experience translating complex testing and automation strategies into strategic business outcomes.

• 5+ years of experience leveraging AI technologies and testing and automation techniques for validating these technologies, including unit, integration, quality and model testing, regression, and performance validation. in a high-performance Agile environment.

• 5 years focused on cloud-native environments (i.e. IBMi AS400, GCP, and Azure highly preferred)

• 4+ years of hands-on development experience across multiple technological platforms.

Preferred Qualifications

• Executive-level communication skills with the ability to effectively articulate strategic concepts to multiple stakeholders.

• Background in Health Care and Pharmacy Benefit Management (PBM).

• Experience with IBMi AS400 and GCP-Azure platforms.

• Hands-on experience with Large Language Models (LLM) and their practical applications in AI.

• At least 7 years of experience with API testing tools such as Postman, Swagger, or similar tools.

Bachelor's degree or equivalent experience

Pay Range

The typical pay range for this role is:

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. 

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

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.

Additional details about available benefits are provided during the application process and on .