Observability and Automation Engineer

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Chicago, IL
In-Office
125K-145K Annually
Insurance
The Role

ABOUT US 

At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. 

HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions. 

ABOUT THE ROLE

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.

Core Responsibilities for this Role:

Observability Engineering:

  • 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.

Automation Engineering:

  • 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.

Collaboration & Enablement:

  • 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.

REQUIRED QUALIFICATIONS

  • 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.

PREFERRED QUALIFICATIONS

  • Familiarity with cloud platforms (AWS, Azure, GCP) and modern cloud-native observability and automation practices.
  • Familiarity of On-Prem virtualization technologies.

JOIN OUR TEAM 

Do you believe in the power of innovation, collaboration, and transformation?  Do you thrive in a supportive and client focused work environment?  Are you looking for an opportunity to help build and drive change in a rapidly growing and evolving organization?  When you join HUB International, you will be part of a community of learners and doers focused on our Core Values: entrepreneurship, teamwork, integrity, accountability, and service. 

Disclosure required under applicable law in California, Colorado, Illinois, Maryland, Minnesota, New York, New Jersey, and Washington states: The expected salary range for this position is $125K to $145K and will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. If you believe that your qualifications and experience surpass the minimum requirements for this role, we encourage you to submit your application. By doing so, we will be able to keep your application on file for consideration for potential future positions within our organization. HUB International is proud to offer comprehensive benefit and total compensation packages which could include health/dental/vision/life/disability insurance, FSA, HSA and 401(k) accounts, paid-time-off benefits such as vacation, sick, and personal days, and eligible bonuses, equity and commissions for some positions.   

Department Information Technology

Required Experience: 7-10 years of relevant experience

Required Travel: Negligible

Required Education: Bachelor's degree (4-year degree)

HUB International Limited is an equal opportunity employer that does not discriminate on the basis of race/ethnicity, national origin, religion, age, color, sex, sexual orientation, gender identity, disability or veteran's status, or any other characteristic protected by local, state or federal laws, rules or regulations.

E-Verify Program

We endeavor to make this website accessible to any and all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please contact the recruiting team [email protected]. This contact information is for accommodation requests only; do not use this contact information to inquire about the status of applications.

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The Company
HQ: Chicago, IL
10,055 Employees
Year Founded: 1998

What We Do

Hi, we’re HUB.

We advise businesses and individuals on how to reach their goals. When you partner with us, you’re at the center of a vast network of risk, insurance, employee benefits, retirement and wealth management specialists that bring clarity to a changing world with tailored solutions and unrelenting advocacy.

So you’re ready for tomorrow.


About Hub International
Headquartered in Chicago, Illinois, Hub International Limited (Hub) is a leading full-service global insurance broker providing property and casualty, life and health, employee benefits, investment and risk management products and services. From offices located throughout North America, Hub’s vast network of specialists provides peace of mind on what matters most by protecting clients through unrelenting advocacy and tailored insurance solutions.

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