Lead DevOps Engineer

Post Date

Feb 09, 2026

Location

Chicago,
Illinois

ZIP/Postal Code

60607
US
Apr 12, 2026 Insight Global

Job Type

Perm

Category

Programmer / Developer

Req #

CHI-a6dfc88c-f17e-4821-8cd7-24ad30157b54

Pay Rate

$150k - $180k (estimate)

Job Description

This financial services company is looking for a Lead DevOps Engineer to join their Modern Engineering group and drive an enterprise DevSecOps transformation. This role owns the strategy and execution plan for their Azure DevOps → GitHub migration, modernization of CI/CD, and defining enterprise‑wide standards for pipeline templates, IaC, Kubernetes, and security gates.

The Lead will design the roadmap and reusable patterns, supervise day‑to‑day pipeline and container operations, and partner across development, security, and architecture teams to uplift engineering practices. This role is hands‑on but not heads‑down—Sr. DevOps Engineers handle most implementation while the Lead defines direction, ensures adoption, mentors engineers, and embeds AI‑enabled SDLC practices.

Successful candidates are broad DevOps leaders,not just cloud or security SMEs, who have driven modernization at scale in regulated environments.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

Required Skills & Experience

7+ years of Software Engineering & DevOps experience
Includes hands-on technical work plus strategic roadmap responsibilities
Cloud background across AWS & Azure
Strong Pipeline Design & Deployment experience:
Azure DevOps > GitHub Migration
Building enterprise CI/CD strategy & standards
Strong DevSecOps experience (SAST/SCA/DAST, IaC scanning, container security)
Docker & Kubernetes experience (ECS & EKS preferred)
Programming background with Python & C++
Experience with optimizing observability tools (DataDog preferred)
Database experience:
SQL (MySQL, PostgreSQL)
NoSQL (DynamoDB, MongoDB)
Graph DB (Neo4J, Neptune)
IaC experience with Terraform, Ansible, and/or Chef for infrastructure automation and configuration
Excellent communication skills to present roadmap, strategy, and processes across IT & Business Teams

Nice to Have Skills & Experience

Experience in highly regulated financial environments
Experience contributing to Centers of Excellence or engineering roadmaps

Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.