Observability and Automation Engineer

Hub International-posted 3 months ago
$125,000 - $145,000/Yr
Full-time • Mid Level
Chicago, IL
5,001-10,000 employees
Insurance Carriers and Related Activities
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We are seeking a skilled and innovative Observability and Automation Engineer to help advance our automation and monitoring capabilities during a period of rapid growth and transformation. This role is central to modernizing how IT delivers services by designing and implementing scalable, self-service automation solutions and integrating them into our observability platforms. You will work cross-functionally to identify and streamline manual processes, enhance operational visibility through metrics and telemetry, and ensure the reliability and performance of our hybrid cloud infrastructure. This position plays a key role in supporting the broader transition to a new Managed Service Provider (MSP) and the development of a 24/7/365 Operations Center.

  • Design, implement, and maintain observability integrations across hybrid environments (on-prem and cloud), including metrics collection, logging, alerting, and distributed tracing.
  • Support and extend centralized dashboards and alerting logic to provide actionable insights and reduce noise across platforms such as Dynatrace, ServiceNow ITOM, and LogicMonitor.
  • Integrate observability instrumentation into automation workflows and infrastructure deployments for real-time telemetry and proactive monitoring.
  • Provide support, root cause analysis, and iterative improvement for automation and observability incidents, acting as a bridge between engineering and operations.
  • Work cross-functionally to evaluate processes and procedures for automation opportunities. Identify process improvement opportunities to allow successful conversion to an automated process.
  • Define, implement, and manage toolsets required to enable self-service, service desk, and infrastructure automation.
  • Build, maintain, and extend reusable Ansible roles/playbooks and Terraform modules in alignment with enterprise Infrastructure as Code (IaC) standards and governance models.
  • Collaborate with Cloud, Infrastructure, and Network teams to automate full-stack lifecycle, from provisioning to decommissioning, using IaC and CI/CD pipelines.
  • Develop and manage Jenkins pipelines and other CI/CD automation tools to ensure reliable, test-driven deployment of automation artifacts.
  • Build and maintain automation APIs, CLI tools, and scripts to reduce manual work across infrastructure and operations.
  • Create framework for other IT teams to utilize in automating jobs, processes, and tasks. Act as consultant to those teams to train staff and define automation best practices.
  • Participate in code reviews, documentation, and knowledge sharing for new observability and automation capabilities across IT teams.
  • Experience working with observability and automation platforms, including ServiceNow ITOM, Dynatrace, and LogicMonitor, with a strong understanding of telemetry standards such as OpenTelemetry, SNMP, and WMI.
  • Experience with Microsoft Windows and Red Hat Enterprise Linux (RHEL) operating systems in hybrid cloud environments.
  • Proficiency with Infrastructure as Code (IaC) tooling such as Ansible, Terraform, and Jenkins, including hands-on experience creating reusable modules, libraries, and pipeline integrations.
  • Deep knowledge of CI/CD practices, with experience designing and managing pipelines that support infrastructure lifecycle automation and automated testing.
  • Proficiency in version control systems such as GitHub and Bitbucket, supporting secure, efficient collaboration and code lifecycle management.
  • Strong understanding of programming concepts and automation design, with experience building CLI tools and working with REST APIs.
  • Languages: Python, .NET, PowerShell, GoLang
  • Frameworks: Django, Flask, FastAPI
  • Concepts: Software Development Life Cycle (SDLC), Test Driven Development (TDD)
  • Experience with identity platforms including On-prem and Azure Active Directory and Office 365.
  • Excellent troubleshooting skills with a focus on documentation, collaboration, and continuous improvement across cross-functional teams.
  • Familiarity with cloud platforms (AWS, Azure, GCP) and modern cloud-native observability and automation practices.
  • Familiarity of On-Prem virtualization technologies.
  • Health, dental, and vision insurance
  • Life and disability insurance
  • Flexible spending accounts (FSA)
  • Health savings accounts (HSA)
  • 401(k) accounts
  • Paid-time-off benefits such as vacation, sick, and personal days
  • Eligible bonuses, equity, and commissions for some positions
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