Executive Director - Engineering, SRE - Retail, Pharmacy & Dispensing

CVS Health

6d

About The Position

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. A Brief Overview Provides strategic leadership and oversight of the Site Reliability Engineering (SRE) function supporting CVS Health’s retail and pharmacy store systems. This leader defines strategies, builds roadmaps, and directs large global teams focused on ensuring the reliability, availability, observability, and scalability of distributed store technology — including pharmacy platforms, POS systems, handheld devices, store servers, dispensing locations and connectivity infrastructure. The Executive Director partners closely with senior business and technology 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.

Requirements

• 15+ years of technology leadership experience in operations, infrastructure, or software engineering, with significant experience in SRE or large-scale reliability programs.
• Proven track record managing distributed technology environments (retail, healthcare, or other multi-site operations strongly preferred).
• Mastery of incident management, observability, automation, and operational excellence practices.
• Strong knowledge of 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.
• Adept at resource planning, program delivery, and change leadership at enterprise scale.
• Adept at collaboration, teamwork, and fostering an inclusive engineering culture.

Nice To Haves

• 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.
• Hands-on familiarity with observability tools (Splunk, Dynatrace, Datadog, Prometheus, Grafana, etc.).
• 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 customer experience, feedback tools like Quantum Metrics, Medalia, Adobe analytics to understand business KPIs

Responsibilities

• Provide strategic direction for the SRE function supporting CVS Health stores and pharmacies.
• Align SRE strategies with enterprise goals, delivering resilient technology that enables world-class customer and patient experiences.
• Develop and oversee a multi-year roadmap for observability, automation, and reliability improvements across distributed store environments.
• Lead initiatives to instrument all store systems with advanced monitoring, logging, metrics, and distributed tracing.
• Establish and manage Service Level Objectives (SLOs), Service Level Agreements (SLAs), and error budgets for critical store applications.
• Drive automation to reduce toil, improve efficiency, and enable self-healing capabilities across thousands of locations.
• Oversee 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.
• Ensure secure, compliant, and resilient operations aligned with healthcare and retail regulations.
• Serve as the executive leader for store reliability, partnering with pharmacy, retail operations, and digital leadership.
• Influence technology strategy and investment decisions to advance reliability and observability capabilities.
• Represent CVS Health as a thought leader in SRE and operational resilience, both internally and externally.
• Lead, mentor, and grow diverse global teams of site reliability engineers.
• Foster a culture of reliability, accountability, innovation, and continuous improvement.
• Develop organizational talent strategies to build and retain top-tier engineering and operational expertise.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive