Director Engineering Jobs in Madison, WI (NOW HIRING)

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.

CVS Health is looking for a dynamic and driven Engineering Delivery Leader to work with cross-functional engineering teams tasked with creating best in class experiences focused on identifying, prioritizing, and shaping complex enterprise initiatives. In this role, you will be working across multiple engineering teams accountable for building and executing fast-paced Retail Front Store Modernization technology strategies for the Front Store Merchandising value streams. This leader will join forces with other value stream Leaders to plan, build, execute and deliver a roadmap for accelerated transformations and AI enabled modernizations which will drive our front store merchandising business and technology strategy forward.

The Lead Director should have the ability to prioritize well, communicate clearly, have a consistent track record of execution and accelerated delivery as well as possessing excellent software engineering skills. A successful candidate will be a highly motivated, collaborative individual; motivated to achieve results in a fast-paced environment.

• Lead transformation and modernization roadmaps to support Retail Front Store Value streams

• Drive AI enabled transformations and execution strategies

• Identify and manage risks, engage teams to drive towards resolution

• Identify and manage cross-workstream technical dependencies

• End-to-End Program Plan and timely tracking and reporting

• Manage program level status reporting and communication to stakeholders

• Define, measure and track metrics and KPIS to measure success and Business Outcomes for the FS merchandizing portfolio

• Drive and establish AI adoption and best practices for technical execution and delivery

• Build and cultivate strong relationships with Business, Product and Technology partners and vendors to support the delivery roadmap

• 10+ years working as a Technology Program Delivery leader or software engineering role leading the full cycle of large software engineering programs, managing stakeholders, Risk Mitigation, Issue Resolution, developing KPIs and Status Reporting to Senior Leaders

• 8+ years leading teams in a matrix organization

• 4+ years partnering with architecture, product and PMO teams to influence product development assisting or improving products

• 2+ years in a leadership role, coordinating across software cross-functional teams

• Experience working with distributed teams, working across multiple time zones and geographies

• Ability to determine strategy along with the plans, which need to be implemented to meet the end goal, evaluating situations, decisions, and issues in the short, medium, and long term

• Experience with Scrum/Agile development methodologies

• Individually motivated to be able to see the big picture and prioritize their work to make the largest impact on the business and customers vision and requirements

• Influence and persuade - able to present sound and well-reasoned arguments to convince others. Adapt to the situation and can draw from a range of strategies to persuade people in a way that results in agreement or behavior change

• Strong understanding of delivery practices

• Performance / people management experience

• Experience leading large program with responsibility of end to end planning

• Strong facilitation and presentation skills

• Experience working with technology vendors

• The candidate will have a strong work ethic, be a self-starter, and be able to be highly productive in a dynamic, collaborative environment

Bachelor’s degree or, equivalent experience (HS diploma + 4 years relevant experience)

Bring your heart to CVS Health Every one of us at CVS Health shares a single, clear purpose: Bringing our heart to every moment of your health. This purpose guides our commitment to deliver enhanced human-centric health care for a rapidly changing world. Anchored in our brand — with heart at its center — our purpose sends a personal message that how we deliver our services is just as important as what we deliver. Our Heart At Work Behaviors™ support this purpose. We want everyone who works at CVS Health to feel empowered by the role they play in transforming our culture and accelerating our ability to innovate and deliver solutions to make health care more personal, convenient and affordable. We strive to promote and sustain a culture of diversity, inclusion and belonging every day. CVS Health is an affirmative action employer, and is an equal opportunity employer, as are the physician-owned businesses for which CVS Health provides management services. We do not discriminate in recruiting, hiring, promotion, or any other personnel action based on race, ethnicity, color, national origin, sex/gender, sexual orientation, gender identity or expression, religion, age, disability, protected veteran status, or any other characteristic protected by applicable federal, state, or local law. We proudly support and encourage people with military experience (active, veterans, reservists and National Guard) as well as military spouses to apply for CVS Health job opportunities.

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 that they belong.

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 (https://learn.bswift.com/cvshealth-mainland) .

We anticipate the application window for this opening will close on: 11/27/2026

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

CVS Health is an equal opportunity/affirmative action employer, including Disability/Protected Veteran — committed to diversity in the workplace.