Technical Lead, Observability Operations

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
We are currently seeking an experienced and highly skilled Technical Lead for our Observability Operations team. This critical role will drive the architecture, automation, and continuous advancement of enterprise-grade observability and event management platforms at scale. You will lead efforts to modernize telemetry collection, streamline observability-as-code practices, and embed AIOps capabilities into core operational workflows.

• Lead Automation-First Strategy:
  Define and execute a roadmap to automate observability deployment, configuration, and lifecycle management using infrastructure-as-code and observability-as-code principles.
• Streamline Operational Workflows:
  Eliminate manual processes by engineering intelligent workflows, including self-service provisioning, automated health checks, and event-driven incident remediation.
• Orchestrate Telemetry & Platform Modernization:
  Automate the ingestion, normalization, and correlation of telemetry data (metrics, logs, traces) across hybrid and multi-cloud environments. Transition legacy observability tooling to modern platforms through automated migration frameworks.
• Engineer Self-Healing Capabilities:
  Design and implement automated remediation and recovery actions for known failure scenarios using tools such as Ansible, SCCM, PowerShell, and ServiceNow workflows.
• Enable CI/CD and GitOps for Observability:
  Integrate observability deployment and configuration into CI/CD pipelines. Leverage Git-based workflows to support consistent, version-controlled platform management.
• Support Custom Solutions:
  Maintain and enhance homegrown observability tools and integrations, particularly those built in C# or other object oriented applications, ensuring they scale with business needs and integrate seamlessly into the automated ecosystem.
• Promote Observability as Code:
  Drive adoption of code-first observability strategies through reusable templates, automation libraries, and documentation. Embed instrumentation and alerting directly into the SDLC.
• Agile Collaboration:
• Utilize tools like Jira, Jira Align, and ServiceNow to manage sprints, backlogs, and releases. Track bugs, tasks and user stories to illustrate progress.
• Mentor and Influence Across Teams:
  Provide technical leadership to engineers and operational partners. Evangelize automation best practices and observability automation patterns across the organization.

• 7+ years of experience in automation engineering, observability, or SRE roles
• Strong expertise with automation tools such as Ansible, SCCM, Jenkins, Git, and scripting languages (Python, Bash, PowerShell)
• Demonstrate success engineering automation for telemetry collection, alerting, and event handling at scale
• 3+ years of experience with Observability / Log tools (example: AppDynamics, Splunk, etc)
• Hands-on experience supporting or extending homegrown tools in C# or similar object-oriented languages
• Deep understanding of infrastructure-as-code and GitOps principles in enterprise environments
• Strong knowledge of enterprise IT environments, including cloud, on-premises, and hybrid infrastructure
• Experience working in Jira, Jira Align, ServiceNow, and other collaboration tools.
• Excellent problem-solving skills and the ability to lead in high-urgency, high-complexity environments

• Enterprise-Scale Automation Experience:
  Proven track record of designing and implementing automation solutions across large-scale environments (e.g., 10,000+ servers, hybrid or multi-cloud infrastructure).
• CI/CD and GitOps Expertise:
  Experience integrating observability tooling and automation scripts into CI/CD pipelines (Jenkins, GitLab CI, Azure DevOps), and using GitOps frameworks for configuration and deployment management.
• Infrastructure as Code (IaC):
  Proficient in building infrastructure provisioning templates using Terraform or Ansible, with a focus on modular, reusable, and secure patterns.
• Advanced Scripting and Tooling:
  Strong programming or scripting ability in Python, PowerShell, or Go, with the ability to build automation frameworks, not just individual scripts.
• AIOps and Event Intelligence:
  Experience implementing AIOps tools (e.g., Servicenow ITOM) for automated event correlation, noise reduction, and predictive alerting.
• Cloud-Native Observability & Automation:
  Familiarity with Kubernetes observability (e.g., kube-prometheus-stack, FluentBit, Loki), cloud-native instrumentation via OpenTelemetry, and service mesh monitoring (e.g., Istio).
• Custom Solution Development:
  Experience supporting or enhancing custom-built internal observability platforms written in C#, or other object oriented languages, including integration with APIs, dashboards, and event pipelines.
• ITSM and Workflow Automation:
  Knowledge of ServiceNow or equivalent ITSM platforms, especially in automating incident creation, routing, and remediation using orchestration and playbooks.
• Security & Compliance Automation:
  Familiarity with integrating observability automation with compliance and audit requirements, including automated validation of logging, alerting, and retention policies.
• Cross-Functional Leadership:
  Ability to influence engineering, operations, and security teams to adopt automation-first approaches. Experience mentoring junior engineers and leading communities of practice is a plus.

• 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.