Technical Leadership Jobs in Chicago, IL

41,748 open positions · Updated daily

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.

Senior Tax Accountant

Company: Creative Financial Staffing

Location: Chicago, IL

Posted Aug 05, 2025

Support federal and state tax audits, providing documentation and follow-up. Conduct research across federal, state, estate/gift, and employment tax areas.

Regional Marketing Specialist

Company: Polsinelli PC

Location: Chicago, IL

Posted Aug 04, 2025

Experience managing budgets and driving cost-effective strategies. The successful candidate will work with the Senior Regional Marketing Manager and on the…

Marketing Analytics Manager

Company: Adtalem Global Education

Location: Chicago, IL

Posted Aug 05, 2025

Bachelor’s degree in marketing, business, statistics, or a related field; Master’s preferred. Our Talent Acquisition Team will be happy to answer any questions…

Project Manager II - Multifamily Projects - Chicago

Company: Michael Page

Location: Chicago, IL

Posted Aug 05, 2025

Ability to hire, train, develop and manage a team of Project Managers by providing intentional and proactive leadership. Travel to job site 1-2 days a week.

Software Development Engineer, Veteran Opportunity

Company: Amazon.com Services LLC

Location: Chicago, IL

Posted Aug 05, 2025

Strong knowledge of Computer Science fundamentals in object-oriented design, data structures, algorithm design, problem solving, and complexity analysis.

Carpenter

Company: Marriott International, Inc

Location: Chicago, IL

Posted Aug 05, 2025

Welcome and acknowledge all guests according to company standards, anticipate and address guests’ service needs, assist individuals with disabilities, and thank…

Glass Project Manager

Company: MTH Industries

Location: Hillside, IL

Posted Aug 05, 2025

This role requires strong technical knowledge, organizational skills, and the ability to coordinate teams across design, procurement, fabrication, and field…

Controller

Company: Creative Financial Staffing

Location: Chicago, IL

Posted Aug 05, 2025

Ensure compliance with all regulatory reporting requirements, including 990s, 1099s, state cost reports, and sales tax filings.

Customer Engineer III, Applied AI, Public Sector

Company: Google

Location: Chicago, IL

Posted Aug 05, 2025

Master's degree in Computer Science, Engineering, Mathematics, or a technical field. Identify and qualify business opportunities and key customer technical…

Part-Time Flex Officer

Company: Securitas

Location: Franklin Park, IL

Posted Aug 04, 2025

Valid driver's License and clear driving history. Provide high level of customer service to clients, employees, and guests. Prior security experience a plus.

State-Certified HVAC Contractor/Installer (Manual J Expert)

Company: Green Attic Insulation

Location: Mount Prospect, IL

Posted Aug 05, 2025

*Valid driver’s license* with a clean driving record. *State-approved HVAC certification/license.*. We are seeking a highly skilled and state-certified HVAC…

Trade Specialist I (Construction, Renovations, Plumbing, Electrical)

Company: Lessen

Location: Chicago, IL

Posted Aug 05, 2025

4+ years of experience in relevant field. Demonstrable experience of solving highly complex trade related technical issues. SME in a specific relevant trade.

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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