Lead Director – Observability Engineering 100% remote. 10% travel.

Job Description

This position is 100% remote in the USA. 10% travel will be expected.
Position Summary…
As CVS Health continues to grow, we are looking for experienced leaders to ensure our systems remain stable and performant as we scale. The Lead Director of Observability Engineering is a critical leadership role within Solutions Architecture and Infrastructure Platforms, reporting directly to the Executive Director of Observability and Performance. This position is responsible for leading a team of engineers focused on building next generation Observability systems to enable effective delivery and analysis of metrics, events, logging & tracing, generate performance and stability insights, and forecast system and environmental capacity needs as part of the broader Observability team. In addition to helping define the roadmap for the next 3-5 years, you will be interacting with many other managers and their teams at CVS Health, who rely on the Observability ecosystem to deliver stable and scalable services to our customers.
In This Role You Will:
Program Development and Modernization –Develop a plan to rationalize and modernize observability platforms, delivering an efficient observability ecosystem that meets the unique needs of CVS Health. Spearhead the transition of services from numerous legacy platforms, improving operational visibility and predictability. This involves designing and implementing complex solutions, configuring workflows, scripting, and making other adjustments to optimize platforms for specific business processes, and ensuring solutions align with the organization’s goals.
Team Leadership and Mentoring: Provide guidance and leadership to the Observability Engineering team. This involves hiring and developing talent, mentoring and supporting junior team members, assigning tasks, and ensuring projects are on track. Foster collaboration and knowledge sharing within the team.
Architecture and Design: Work on defining the overall architecture of the Observability environment, including observability standards, data models, integrations, and security controls. Validate that platforms are scalable, reliable, and aligned with best practices.
Project Management: Engage executives, department heads, and IT teams to plan, execute, and oversee Observability projects. This includes planning, coordinating, and overseeing systems implementation and service transition projects, managing project timelines and resources, and confirming that deliverables are met within budget and scope. This also involves communicating project progress to stakeholders.
Stakeholder Management – Cultivate and maintain relationships with application owners ensuring our observability standards, products, and services continue to meet their evolving needs. Establish partnerships to identify opportunities for automation, innovation, and operational excellence.
What You Are Known For:
• You are currently leading the Observability function for a Fortune 500 company.
• As the program manager, you maintain the financials, licensing management, and forecasting of operations work.
• You are considered the SME in leading and owning the observability, capacity planning, and the operational data store for your entire business. This includes ownership of all KPI’s and scorecards.
Required Qualifications
• 10+ years of experience in IT operations, systems engineering, DevOps, SRE, or a related field, with at least 5 years in a leadership role overseeing observability or similar functions within a large enterprise (Fortune 100).
• 8 years of experience designing and implementing observability frameworks for large-scale, distributed systems, encompassing legacy and modern technologies; Experience leading a major observability platform migration. Demonstrable experience building custom monitoring solutions.
• 5 years of experience building and implementing operational data models. Experience designing and deploying data lakes and data pipelines in an enterprise environment.
• 8 years of experience in on-premises infrastructure, cloud infrastructure, and application architectures; Strong background in cloud-native technologies and architectures (e.g., Kubernetes, Docker, microservices) and an understanding of the unique challenges they pose to observability.
• 5 years of experience in the development of high performing teams. You interface with all levels in your organization and influence organizational priorities.
• 5 years of experience and/or expertise with the following:
Core Platforms & Languages: Python, Java, Javascript, XML, JSON
Application Programming Interfaces (API): REST, SOAP
Source Control: Github/GitOps
Data Engineering, Data Lifecycle management, Big Data architectures
• 8 years of experience in a variety of observability tools and standards (e.g., App Dynamics, Prometheus, Grafana stack, ELK stack, Splunk, Dynatrace, OTEL).
• 5 years of experience developing automation solutions and workflows for deployment, event correlation, and incident remediation.
• 3 years of experience with enterprise demand analysis, capacity planning, and performance engineering.
Preferred Qualifications
Knowledge of the healthcare industry regulatory landscape, particularly in the context of data security and privacy.
Education
Bachelor’s degree from accredited university or equivalent work experience (HS diploma + 4 years relevant experience).
To Be Considered:
If you’d like to be at the center of helping millions of people on their path to better health every day, please apply via LinkedIn by including your resume and complete the introductory prequalification questions. We will contact individuals whose profiles most closely match the requirements of this leadership role.
No agency assistance is required to assist us in filling this role.
Pay Range
The typical pay range for this role is: $144,000.00 – $288,000.00
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

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