Executive Director - Site Reliability Engineering - Retail Pharmacy

CVS Health•Woonsocket, RI

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. At CVS Health, Site Reliability Engineering (SRE) is fundamental to delivering the reliable, secure, and scalable technology experiences that support millions of patients, customers, pharmacists, and healthcare professionals every day. Our SRE organization drives operational excellence across critical healthcare and retail platforms through innovation, automation, observability, and engineering best practices. The Executive Director, Site Reliability Engineering serves as the strategic leader responsible for the reliability, resilience, and performance of CVS Health's retail and pharmacy technology ecosystem. This executive will define and execute a comprehensive reliability strategy, oversee large global engineering teams, and establish a long-term vision for observability, automation, and operational excellence across thousands of store locations. Working closely with senior business and technology leaders, the Executive Director will champion modern SRE practices, accelerate incident response capabilities, and deliver real-time operational visibility that enables proactive issue prevention and exceptional customer and patient experiences.

Requirements

15+ years of progressive technology leadership experience across infrastructure, operations, software engineering, or related disciplines.
Significant experience leading Site Reliability Engineering, production operations, platform engineering, or large-scale reliability programs.
Proven success managing complex, distributed technology environments, preferably in retail, healthcare, pharmacy, or other multi-site enterprise operations.
Deep expertise in incident management, observability, automation, resiliency engineering, and operational excellence methodologies.
Strong understanding of retail technology ecosystems, including POS systems, pharmacy applications, handheld devices, store servers, and network infrastructure.
Demonstrated ability to lead enterprise-wide transformation initiatives and influence executive stakeholders.
Exceptional communication, strategic thinking, decision-making, and problem-solving skills.
Experience leading large-scale global teams and managing enterprise technology programs.
Strong commitment to collaboration, inclusion, innovation, and team development.
Bachelor's degree in Computer Science, Engineering, Information Technology, or a related technical field preferred.

Nice To Haves

Experience leading large SRE, infrastructure, or technology operations organizations within retail, healthcare, pharmacy, or similarly complex environments.
Advanced knowledge of cloud platforms including AWS, Microsoft Azure, and Google Cloud Platform (GCP).
Expertise with containerization and orchestration technologies such as Kubernetes and OpenShift.
Hands-on familiarity with leading observability and monitoring platforms including Splunk, Dynatrace, Datadog, Prometheus, and Grafana.
Strong understanding of regulatory and compliance requirements, including HIPAA, PCI DSS, and ADA standards.
Proven experience leveraging AI and machine learning to enhance monitoring, automation, predictive operations, and incident management.
Experience utilizing customer experience and digital analytics platforms such as Quantum Metric, Medallia, and Adobe Analytics to connect technology performance with business outcomes and customer experience metrics.
Advanced degree (MBA, Master's, or equivalent) and/or relevant industry certifications are highly desirable.

Responsibilities

Define and lead the enterprise-wide Site Reliability Engineering strategy supporting CVS Health's retail and pharmacy operations.
Align reliability and operational objectives with broader business and technology priorities.
Develop and execute a multi-year roadmap focused on observability, automation, platform resiliency, and operational excellence.
Influence technology investment decisions and architectural direction to advance reliability capabilities across the enterprise.
Serve as the executive sponsor and trusted advisor for store reliability, partnering with retail, pharmacy, digital, and corporate leadership.
Establish and govern Service Level Objectives (SLOs), Service Level Agreements (SLAs), and error budgets for mission-critical store applications and services.
Drive continuous improvements in availability, performance, scalability, and resilience across distributed technology environments.
Lead enterprise major incident management activities, ensuring rapid detection, effective escalation, root-cause analysis, and lasting remediation.
Foster a culture of accountability, operational excellence, and continuous improvement across engineering organizations.
Establish comprehensive observability capabilities, including advanced monitoring, logging, metrics collection, event correlation, and distributed tracing.
Deliver end-to-end visibility into the health and performance of retail and pharmacy systems across thousands of locations.
Drive automation initiatives that reduce manual effort, eliminate operational toil, and enable self-healing operational capabilities.
Leverage AI and machine learning technologies to improve monitoring, predictive analytics, operational insights, and incident prevention.
Champion modern cloud, edge computing, and distributed systems architectures that enhance reliability and scalability.
Partner with Product Engineering, Architecture, Infrastructure, Security, and Operations teams to embed reliability practices throughout the software development lifecycle.
Ensure technology operations remain secure, compliant, and aligned with healthcare and retail regulatory requirements.
Lead, mentor, and inspire large global teams of Site Reliability Engineers and engineering leaders.
Build a high-performing, inclusive engineering culture focused on innovation, collaboration, and customer outcomes.
Develop workforce planning strategies and talent pipelines to attract, retain, and grow world-class engineering talent.
Promote leadership development and succession planning across the organization.