Lead Director - Software Engineering (Modernization & Reliability)

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

Job summary

CVS Health is seeking a Lead Director within the Caremark Adjudication Services Engineering group to partner with business and IT leaders. The role drives strategy, architecture, and delivery across legacy IBMi AS400 and modern cloud platforms, with a hands-on leadership style.

You will guide modernization, automation, and AI-enabled initiatives, set OKRs and KPIs, and ensure reliable CI/CD, observability, and strong vendor management across onsite and offshore teams in a healthcare context.

Qualifications

• 10+ years IT experience across various platforms including leadership and development management.
• 8+ years hands-on development across multiple platforms.
• 8+ years managing large or multiple application teams with onsite and offshore vendors.
• 8+ years experience managing customer expectations and building strong relationships.

Responsibilities

• Provide strategic engineering and architecture leadership with roadmaps and delivery plans.
• Oversee teams on IBMi AS400 and cloud platforms (GCP/Azure).
• Drive modernization and automation initiatives (APIs, platform migration).
• Define OKRs and KPIs, deliver reports on metrics and improve delivery.
• Collaborate with stakeholders to maintain an actionable engineering backlog.
• Ensure safe, automated, and scalable CI/CD pipelines with DevOps/Platform teams.

Skills

Leadership

Stakeholder communication

Program management

Budgeting & cost optimization

AI awareness

Education

Bachelor's degree or equivalent experience

Tools

IBMi AS400

GCP

Azure

Angular

Java

RPG

OpenAI

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 Overview

The Lead Director is a critical role, supporting a dynamic organization and partnering with both business and IT leaders. This position offers the opportunity to make a meaningful difference for customers utilizing Pharmacy Benefits. The ideal candidate brings a passion for organization, attention to detail, and the ability to facilitate the success of their unit while providing direct support to the Executive Director of Adjudication Services Engineering at Caremark.

This leadership position is essential within the adjudication technology organization, driving key transformation initiatives and fostering innovation through creative solutions. The Lead Director is expected to take a hands-on approach to managing engineering teams and to encourage out-of-the-box thinking to develop technical solutions for business processes. High standards will be set and maintained for the continuous improvement and development of both new and existing products and platforms within the adjudication ecosystem.

Key Responsibilities

• Provide strategic and tactical engineering and architecture leadership, including the creation of delivery and resource plans, generation of roadmaps, and driving operational excellence. Optimize operating costs and budgets by reducing technical debt, offering enhanced risk visibility through executive-level reporting, and coordinating all program-related activities.
• Oversee engineering teams operating on both legacy IBMi AS400 and modern cloud platforms such as GCP and Azure. Lead teams composed of engineering managers, engineers, product leads, and quality engineers, employing a player-coach leadership style.
• Drive modernization and automation initiatives (i.e. API, Platform Migration etc), conduct comprehensive analyses of business operations to identify opportunities for AI integration and automation.
• Provide strategic direction for the SRE function, aligning SRE strategies with enterprise goals. Develop strategies for observability, monitoring, automation, and reliability improvements across applications. Partner with DevOps and Platform teams to ensure safe, automated, and scalable CI/CD pipelines.
• 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 OKRs and KPIs, deliver reports on metrics, and make recommendations for improving delivery.
• Collaborate with business stakeholders to ensure a clear and actionable engineering backlog is created.
• Remove blockers and demonstrate engineering progress to senior leadership.
• Establish frameworks for consistent and effective software delivery practices.
• 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 deep understanding of, and provide guidance on, principles, practices, and techniques relevant to the application area and organization.
• Conduct periodic assessments of CVS and vendor resources.
• 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 both onsite and offshore vendors.
• Ensure that 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 in IT principles, development methodologies, and the use of platforms, applications, or software products.
• 8+ years of hands-on development experience across multiple technological platforms.
• 8+ years of experience leading large or multiple application teams to effectively deliver projects and initiatives including managing full-time employees, including their work and career development, as well as managing onsite and offshore vendor relationships.
• 8+ years of experience managing customer expectations and building strong relationships.

Preferred Qualifications

• Background in Health Care and Pharmacy Benefit Management (PBM).
• Experience with IBMi AS400 and GCP-Azure platforms, has led teams of full stack developers in Angular and Java and teams of RPG developers
• Strong foundational knowledge in AI, with hands-on experience using technologies such as OpenAI, Gemini, and Agentic AI automation.
• Ability to foster a collaborative team environment that encourages innovation and professional growth.

Education

Bachelor's degree or equivalent 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.

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 the 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.

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: 08/28/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.