CVS Health
Lead Director, Software Development Engineering - SRE, Retail Pharmacy
CVS Health, Boston, Massachusetts, us, 02298
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.
Overview 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
Minimum Qualifications
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 methodologies
8+ 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
Preferred Qualifications
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 and feedback tools like Quantum Metrics, Medalia, Adobe analytics to understand business KPIs and customer metrics
Education
Bachelor’s degree in Computer Science, Engineering, or related field required
Master’s degree in Computer Science, Engineering, or related field preferred
Pay Range 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.
Benefits Great benefits for great people
We take pride in our comprehensive and competitive mix of pay and benefits – investing in the physical, emotional and financial wellness of our colleagues and their families to help them be the healthiest they can be. In addition to our competitive wages, our great benefits include:
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.
For more information, visit https://jobs.cvshealth.com/us/en/benefits
We anticipate the application window for this opening will close on: 03/02/2026
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.
#J-18808-Ljbffr
Overview 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
Minimum Qualifications
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 methodologies
8+ 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
Preferred Qualifications
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 and feedback tools like Quantum Metrics, Medalia, Adobe analytics to understand business KPIs and customer metrics
Education
Bachelor’s degree in Computer Science, Engineering, or related field required
Master’s degree in Computer Science, Engineering, or related field preferred
Pay Range 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.
Benefits Great benefits for great people
We take pride in our comprehensive and competitive mix of pay and benefits – investing in the physical, emotional and financial wellness of our colleagues and their families to help them be the healthiest they can be. In addition to our competitive wages, our great benefits include:
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.
For more information, visit https://jobs.cvshealth.com/us/en/benefits
We anticipate the application window for this opening will close on: 03/02/2026
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.
#J-18808-Ljbffr