Director Software Development Jobs in Milton, DE

CVS Health Digital is looking for hands-on, passionate people who want to join a high energy and growing team to make a difference in customers' lives and who want to be on the forefront of digital innovation that aims to reinvent what a pharmacy and a health care company can be in the digital world. Currently, we are seeking Senior Manager - Software Development Engineering who will lead and manage a team of software engineers, providing hands-on technical direction, architecture guidance, and mentorship while establishing measurable engineering goals aligned with business outcomes. This Senior Engineer also will drive technical strategy and execution for software initiatives by defining system requirements, architecture, timelines, and deliverables.

Expectation For The Role:

• Own risk mitigation and production stability by proactively identifying system vulnerabilities, leading root cause analysis, and driving timely resolution of complex production issues to ensure high availability and minimal downtime


• Oversee the full software development lifecycle (SDLC), including requirements engineering, system design, development, testing, and deployment, ensuring adherence to modern engineering standards, secure coding practices, and scalable architecture principles


• Collaborate cross-functionally with Product, Data, Infrastructure, and business stakeholders to translate functional requirements into technical solutions, align priorities, and resolve dependencies while maintaining efficient delivery pipelines


• Continuously evaluate and adopt emerging technologies, frameworks, and engineering best practices, leading innovation through proof-of-concepts and informed technology selection to enhance system performance and developer productivity


• Build and develop high-performing engineering teams by hiring top talent, conducting technical performance evaluations, and fostering a culture of continuous improvement, technical excellence, and knowledge sharing

• 7+ years of overall software engineering experience with at least 5+ years of experience of leading projects or managing directs


• 7+ years of experience using and/or managing projects using Java, Spring boot, Kafka to build/deploy, and maintain software applications using cloud platforms


• 3+ years of experience leading cross-functional teams without direct authority, including documented collaboration with engineering, architecture, security, and business stakeholders in a matrixed organization


• 3+ years of experience defining technology strategy and leading the adoption and operationalization of technologies such as AI/ML, cloud services, automation, and developer productivity tools in a large-scale enterprise environment with evidence of measurable impact (e.g., reduction in MTTR, cost savings, efficiency gains, or adoption KPIs)


• Strong expertise in cloud platforms, distributed systems, APIs, microservices, and modern software development practices

• Experience with retail or health care industry with background in fulfillment, dispensing & delivery


• Experience with developing in AWS or GCP or Azure or similar public cloud environments (GCP preferred)


• Proven success driving technical strategy, engineering excellence, and organizational transformation


• Excellent communication, stakeholder management, and cross-functional collaboration skills


• Experience managing multiple teams and developing engineering leaders


• Ability to balance technical depth with business outcomes and strategic decision-making


• Ensured code quality and technical excellence through reviews, testing strategies, and debt management


• Owned system reliability and operational performance, including monitoring, incident management, and SLAs

Bachelor's degree or equivalent experience (High School Diploma and 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:

$106,605.00 - $284,280.00

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.

We anticipate the application window for this opening will close on: 08/21/2026

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