Lead Director Engineering, SRE - Retail & Pharmacy

At CVS Health, we're building a world of health around every consumer and surrounding ourselves with dedicated colleagues who are passionate about transforming health care.As the nation's leading health solutions company, we reach millions of Americans through our local presence, digital channels and more than 300,000 purpose-driven colleagues - caring for people where, when and how they choose in a way that is uniquely more connected, more convenient and more compassionate. And we do it all with heart, each and every day.The Lead Director Engineering - SRE, Retail & Pharmacy provides leadership in ensuring the reliability, availability, observability, and scalability of distributed store technology - including pharmacy platforms, Point of Sale (POS) systems, handheld devices, store servers, dispensing locations and connectivity infrastructure. This role requires strong leadership, strategic planning, and technical expertise in managing complex systems, incident response, compliance, and creating a culture of continuous improvement. This role is also responsible for coordinating with stakeholders to drive operational excellence, modernize monitoring and automation capabilities, and establish real-time visibility into store health, enabling proactive incident prevention and rapid resolution.What You Will Do:

• Lead a global team of technical professionals, providing guidance, mentorship, and support to ensure their success and professional growth
• Align SRE strategies with enterprise goals, delivering resilient technology that enables world-class customer and patient experiences
• Execute on a multi-year roadmap for observability, automation, and reliability improvements across distributed store environments
• Define and implement standardization and process improvements across the SRE organization
• Define and maintain Service Level Indicators (SLIs), Service Level Objectives (SLOs), and business KPIs to measure and enhance system reliability for critical store applications
• Build and optimize dashboards, visualizations, and alerting systems to enable real-time insights and rapid incident response for edge nodes and remote facilities
• Provide weekly and monthly reporting on KPIs and other operational-based metrics to cross-functional teams and senior leadership
• Develop and implement strategic communication plans to support organizational goals, ensuring alignment with business objectives and stakeholder needs
• Reduce operational costs and increase efficiency through automation and platform engineering to reduce toil and enable self-healing capabilities across thousands of locations
• Lead major incident management, ensuring rapid detection, root-cause analysis, and resolution in collaboration with business and technology partners
• Champion modern cloud, edge, and AI-driven monitoring solutions for store technology
• Partner with architects, product engineering, and infrastructure teams to embed reliability practices throughout the software lifecycle
• Represent CVS Health as a thought leader in SRE and operational resilience, both internally and externally
• Mentor the SRE and technical teams on building, scaling, and operating highly available systems
• Foster a culture of ownership, honesty, accountability, and continuous improvement within the organization
• Contribute to long-term planning, technology adoption strategies, and innovation initiatives to drive digital modernization efforts

• 10+ years of experience with cloud platform technologies such as: AWS, Microsoft Azure, Google Cloud
• 8+ years of experience in a technical leadership or people management role, with a proven ability to lead and grow technical teams, particularly within SRE or large-scale reliability organizations
• 8+ years of experience leading complex technical initiatives using Agile/continuous improvement methodologies8+ years of managing distributed technology environments (retail, healthcare, or other multi-site operations strongly preferred)
• 5+ years of experience in container orchestration (Kubernetes) and using monitoring tools (Dynatrace, AppDynamics, Prometheus, Splunk, Grafana, etc.)
• Strong understanding of cloud infrastructure components (compute, storage, networking, security)
• Strong knowledge of Point of Sale (POS), pharmacy systems, handheld devices, store servers, and network infrastructure
• Exceptional communication, decision-making, and problem-solving skills, with demonstrated ability to influence senior executives and cross-functional teams (technical and non-technical)
• Experience leading performance reviews, career development planning, and team capacity management
• Mastery of incident management, observability, automation, and operational excellence practices
• Adept at resource planning, program delivery, and change leadership at enterprise scale
• Adept at collaboration, teamwork, and fostering an inclusive engineering culture

• Experience leading large SRE or operations functions in a retail, healthcare, or pharmacy environment
• Expertise in cloud platforms (AWS, Azure, GCP), containerization (Kubernetes, OpenShift), and distributed systems
• Strong understanding of compliance and regulatory requirements (HIPAA, PCI DSS, ADA)
• Demonstrated ability to deliver transformation at scale, leveraging AI/ML for monitoring, automation, and operational insights
• Experience in using experience, feedback tools like Quantum Metrics, Medalia, Adobe analytics to understand business KPIs customer

• Bachelor's degree in Computer Science, Engineering, or related field required
• Master's degree in Computer Science, Engineering, or related field preferred

• Affordable medical plan options, a 401(k) plan (including matching company contributions), and an employee stock purchase plan.
• No-cost programs for all colleagues including wellness screenings, tobacco cessation and weight management programs, confidential counseling and financial coaching.
• Benefit solutions that address the different needs and preferences of our colleagues including paid time off, flexible work schedules, family leave, dependent care resources, colleague assistance programs, tuition assistance, retiree medical access and many other benefits depending on eligibility.