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.

Manager - Digital Content Strategy

Company: United Airlines

Location: Chicago, IL

Posted Jul 10, 2025

Leads content strategy, content governance, content management strategy, and content best practices, including search engine optimization.

Ammonia Technician

Company: JTM FOODS LLC

Location: Chicago, IL

Posted Jul 09, 2025

Troubleshoot and repair mechanical, electrical, hydraulic, pneumatic, and plumbing systems. Knowledge of mechanical systems, electrical distribution, and safety…

ETL/SQL Data Analyst

Company: Magnifact

Location: Chicago, IL

Posted Jul 09, 2025

Bachelor’s Degree in Business, Computer Science, Information Systems, or related field. Leverage tools such as Jenkins for automating ETL processes within a…

Executive Chef

Company: Levy Sector

Location: Chicago, IL

Posted Jul 09, 2025

Holiday Time Off (varies by site/state). Associates may also be eligible for paid and/or unpaid time off benefits in accordance with applicable federal, state,…

Senior Manager, Software Engineering, Full Stack (Python, GoLang, Java, AWS)

Company: Capital One

Location: Chicago, IL

Posted Jul 10, 2025

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

Sous Chef (Earn up to $75k+/yr + Bonus Structure)

Company: Gilt Bar

Location: Chicago, IL

Posted Jul 09, 2025

Communicate professionally and confidently with guests, employees, vendors, and leadership. 2 years of experience as a Sous Chef or other kitchen leadership…

Installer/Plumber

Company: Legendary Service

Location: Chicago, IL

Posted Jul 10, 2025

Valid driver's license with a clean driving record. Clearly explain diagnoses and repair or installation options to customers in a professional, polite manner.

Sous Chef (Earn up to $75k+/yr + Bonus Structure)

Company: Armitage Alehouse

Location: Chicago, IL

Posted Jul 09, 2025

Communicate professionally and confidently with guests, employees, vendors, and leadership. 2 years of experience as a Sous Chef or other kitchen leadership…

Entry Level Sales Associate

Company: Customer Sales Representative

Location: Burr Ridge, IL

Posted Jul 10, 2025

Learn and implement sales scripts, client product information, and promotional strategies. Track and achieve weekly and monthly sales goals.

Sous Chef (Earn up to $75k+/yr + Bonus Structure)

Company: Bavette's

Location: Chicago, IL

Posted Jul 09, 2025

Communicate professionally and confidently with guests, employees, vendors, and leadership. 2 years of experience as a Sous Chef or other kitchen leadership…

Master Plumber

Company: Leaf Home

Location: Chicago, IL

Posted Jul 10, 2025

Train, coach and develop installation employees and contractors both in the office and in the field. Must hold a valid driver's license.

Machinist II

Company: Dart Container

Location: Chicago, IL

Posted Jul 10, 2025

Ability to obtain and maintain powered industrial truck (PIT) license. Read blueprints, schematics, specifications, bills of material, and various technical…

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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