Technical Leadership Jobs in Chicago, IL

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Looking for Technical Leadership jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Technical Leadership position in the Chicago, IL area.

Maintenance Supervisor

Company: Servitas Management Group, LLC

Location: Chicago, IL

Posted May 27, 2025

During performance of duties, documents and reports items to Management requiring repair or any suspicious or unlawful items around the facility or students,…

AI Engineer (Associate) - Remote

Company: Huron Consulting Group Inc.

Location: Chicago, IL

Posted May 28, 2025

Ability to work on cross-functional teams, balance multiple projects, and communicate effectively with technical and non-technical audiences.

ERP Project Manager – PLEX

Company: Weiss-Aug – Elk Grove Village, IL

Location: Elk Grove Village, IL

Posted May 28, 2025

A bachelor’s degree in an information systems field, such as CIS, BIS or MIS degree and 5-10 years’ experience as a business analyst, software developer or…

Communications and Marketing Manager

Company: The University of Chicago

Location: Chicago, IL

Posted May 29, 2025

A bachelor’s degree from an accredited four-year college or university with a degree in journalism, communications, public relations, marketing, or related…

Pharmacist Centralized Services Work From Home - NY

Company: WALGREENS

Location: Deerfield, IL

Posted May 28, 2025

Current Pharmacist license as granted by the appropriate state licensing authority. Willing to travel up to 10% of the time for business purposes (within state…

Lead Software Engineer, Back End (Enterprise Platforms Technology)

Company: Capital One

Location: Chicago, IL

Posted May 29, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

Principal Platform Engineer

Company: Avant, LLC

Location: Chicago, IL

Posted May 28, 2025

As a team member, you will be developing tools to create and maintain cloud infrastructure, automate the management of complex service-oriented applications,…

Field Service Technician (Injection Molding)

Company: Accelera

Location: Elk Grove Village, IL

Posted May 27, 2025

Valid passport and driver's license with a clean driving record. Strong electrical and hydraulic troubleshooting skills; ability to read schematics.

Building/Refrigeration Engineer

Company: The University of Chicago

Location: Chicago, IL

Posted May 28, 2025

Current valid driver's license. In addition, this role is responsible for advanced installation, maintenance, repair, and operation of building equipment…

Security and Facilities Lead

Company: KITH

Location: Chicago, IL

Posted May 27, 2025

Handles undesired conduct, violations of building policy and civil laws as warranted for the security and safety of guests, employees, patrons, and property.

Senior Software Engineer, Full Stack

Company: Capital One

Location: Chicago, IL

Posted May 29, 2025

Collaborate with and across Agile teams to design, develop, test, implement, and support technical solutions in full-stack development tools and technologies.

Frequently Asked Questions

What are the typical salary ranges for Technical Leadership roles by seniority level?
Engineering Manager: $140k–$190k base, often topped with 10–20% bonus and 0.5–1% equity. Director of Engineering: $190k–$240k base, 15–25% bonus, 1–3% equity. VP/Head of Engineering: $240k–$320k base, 20–30% bonus, 3–7% equity. Adjustments for cost‑of‑living and company size apply; leaders in AI/ML or multi‑cloud sectors may see a 5–10% premium.
What core skills and certifications are essential for Technical Leadership positions?
Core skills: Kubernetes & container orchestration, Terraform or Pulumi for IaC, GitOps with Flux or ArgoCD, CI/CD pipelines (GitLab CI, Jenkins, CircleCI), cloud expertise (AWS, Azure, GCP), AI Ops (MLflow, Kubeflow), data platform architecture, security (CISSP, ISO 27001), cost‑optimization, and people management. Certifications that add credibility: Certified Kubernetes Administrator (CKA), Certified Kubernetes Application Developer (CKAD), AWS Solutions Architect Professional, Google Professional Cloud Architect, Certified DevOps Professional, and Scrum Master for cross‑functional leadership.
How common is remote work for Technical Leadership roles?
Approximately 65% of Technical Leadership openings allow full‑time remote work, 20% are hybrid (3–5 days on‑site), and 15% require on‑site presence. Remote roles often demand 24/7 coverage across time zones, so leaders use asynchronous OKR reviews, distributed retrospectives, and tooling like Slack, Zoom, Azure DevOps, and Jira to coordinate squads worldwide.
What are the typical career progression paths for Technical Leaders?
Typical trajectory: Engineering Manager → Director of Engineering → VP/Head of Engineering → Chief Technology Officer or Chief Architect. Lateral moves include Enterprise Solutions Lead, AI/ML Platform Lead, Technical Advisor, or Consulting roles. Advancement hinges on mastering cross‑functional strategy, earning advanced certifications, publishing technical roadmaps, and demonstrating measurable impact on product velocity and revenue.
What industry trends should Technical Leaders be aware of?
Key trends: AI/ML Ops integration for automated model deployment, serverless and Function‑as‑a‑Service for cost‑efficient scaling, multi‑cloud governance tools like Anthos or Terraform Enterprise, AI‑driven observability and predictive monitoring, edge computing for low‑latency services, data mesh and governance frameworks, automated security (SecOps), sustainability metrics for cloud usage, and remote‑first culture with distributed leadership practices. Leaders should adopt Kubernetes‑native ops, implement cost‑monitoring dashboards, and champion DevSecOps to stay competitive.

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