Lead Director – Observability Engineering

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.

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 Engineering and Infrastructure, 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 collection, consolidation, and analysis of metrics, events, logs & traces, generate performance and stability insights, and forecast system and environmental capacity needs as part of the broader Enterprise 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.

Responsibilities

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 technology enablement for the transition of services from numerous legacy platforms, improving operational visibility and predictability. This involves designing and implementing complex solutions to collect, process, and manage structured and unstructured data at massive scale, optimizing built and purchased platforms to ensure efficient and performant operations, 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 team members, assigning tasks, and ensuring projects are on track. Foster collaboration and knowledge sharing within the team.

Architecture and Design : Help define the overall architecture of the Observability environment, including observability standards, data models, integrations, and security controls. ensure our platforms are scalable, reliable, and aligned with best practices. Leverage open source and commercial software to deliver and maintain resilient, reliable, cost-effective platforms tailored to the needs of CVS Health.

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.

Required Qualifications

10+ years of experience Leading Software Development teams developing and managing applications for IT operations, SRE, logging and / or observability, with at least 5 years in a leadership role within a large enterprise (Fortune 100).

10 + years' of experience designing, developing, and implementing observability systems for large-scale, distributed systems, encompassing legacy and modern technologies; Experience leading a major logging and observability platform migration. Demonstrable experience building custom monitoring solutions.

Proven experience building and implementing operational data models. Experience designing and deploying data lakes and data pipelines at massive scale in an enterprise environment. Experience with enterprise demand analysis, capacity planning, and performance engineering.

Deep knowledge of, and experience with 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.

Proven experience developing automation solutions and workflows for deployment, event correlation, and incident remediation.

Experience and / or expertise with the following :

Core Platforms & Languages : Python, Java, Javascript, XML, JSON - 5 years

Application Programming Interfaces (API) : REST, SOAP - 5 years

Source Control : Github / GitOps - 5 years

Data Engineering, Data Lifecycle management, Big Data architectures -5 years

Preferred Qualifications

Proven ability to own problems end-to-end, willingness to obtain any required knowledge to get the job done.

Exceptional project and program management skills, with a proven track record of managing and prioritizing multiple simultaneous initiatives to successful completion.

Outstanding communication and interpersonal skills, with the ability to effectively engage and influence stakeholders across all levels of the organization; Must be able to set goals and participate in strategic initiatives for a team

Extensive experience developing high performing teams and interfacing with all levels of the organization; Ability to participate in development of resource plans and structures, and influence organizational priorities.

Knowledge of the healthcare industry's regulatory landscape, particularly in the context of data security and privacy, is desirable.

Education-

Bachelor degree from accredited university or equivalent work experience (HS diploma + 4 years relevant experience)

BUSINESS OVERVIEW

Bring your heart to CVS Health Every one of us at CVS Health shares a single, clear purpose : Bringing our heart to every moment of your health. This purpose guides our commitment to deliver enhanced human-centric health care for a rapidly changing world. Anchored in our brand — with heart at its center — our purpose sends a personal message that how we deliver our services is just as important as what we deliver. Our Heart At Work Behaviors support this purpose. We want everyone who works at CVS Health to feel empowered by the role they play in transforming our culture and accelerating our ability to innovate and deliver solutions to make health care more personal, convenient and affordable. We strive to promote and sustain a culture of diversity, inclusion and belonging every day. CVS Health is an affirmative action employer, and is an equal opportunity employer, as are the physician-owned businesses for which CVS Health provides management services. We do not discriminate in recruiting, hiring, promotion, or any other personnel action based on race, ethnicity, color, national origin, sex / gender, sexual orientation, gender identity or expression, religion, age, disability, protected veteran status, or any other characteristic protected by applicable federal, state, or local law. We proudly support and encourage people with military experience (active, veterans, reservists and National Guard) as well as military spouses to apply for CVS Health job opportunities

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.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

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 : 12 / 31 / 2025

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.

We are an equal opportunity and affirmative action employer. We do not discriminate in recruiting, hiring, promotion, or any other personnel action based on race, ethnicity, color, national origin, sex / gender, sexual orientation, gender identity or expression, religion, age, disability, protected veteran status, or any other characteristic protected by applicable federal, state, or local law.

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