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.

Product Marketing Manager

Company: Expedia Group

Location: Chicago, IL

Posted Jul 30, 2025

With a deep knowledge of the Transport product space, you will champion customer-centric products and communicate the product vision, craft insights to help…

Department Manager - Plumbing

Company: American Vintage Home

Location: Chicago, IL

Posted Jul 30, 2025

Assist sales staff with design, layout, equipment, and material selections when needed. Identify technical weaknesses in trainees and provide support and…

Software Engineer

Company: Morningstar

Location: Chicago, IL

Posted Jul 30, 2025

You will be exposed to all aspects of product development: design of user experience, system architecture, model development, productionizing models, API/…

Project Manager, Supply Chain Continuity

Company: Ferrara Candy Company, Inc.

Location: Chicago, IL

Posted Jul 30, 2025

Financial analysis and/or cost accounting experience within a manufacturing business. Knowledge of technical functions such as planning, procurement,…

Service Technician Trainee Roofing

Company: Complete Bldg Maint Co

Location: Lombard, IL

Posted Jul 30, 2025

This entry-level position is ideal for individuals looking to develop their skills in the commercial roofing repair, and maintenance field.

Assistant Director, Event and Program Marketing

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

This position demands a blend of creativity, analytical skills, and project management expertise, with strong writing abilities to effectively promote topics…

Senior Income Tax Analyst

Company: Amrize Building Materials US

Location: Chicago, IL

Posted Jul 30, 2025

Working knowledge of federal and state corporate income tax compliance. The Senior Income Tax Analyst, Tax Reporting will play a key role in the preparation and…

Travel General Laborer Nights $18

Company: SPAR Inc.

Location: Chicago, IL

Posted Jul 30, 2025

Reliable transportation, valid driver’s license,. This role is made for road warriors — expect to be continuously on assignment outside your home state.

Ambulatory RN 2 - Adult and Pediatrics Population

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jul 30, 2025

Current license and credentials by the state they are assigned. 6.Utilizes evidence-based ambulatory care nursing interventions during clinical visits,…

Assistant Director, Content

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

Minimum requirements include a college or university degree in related field. Bachelor’s degree in a writing-related field such as journalism, English, or…

UN Swing Driver

Company: Lakeshore Recycling Systems LLC

Location: Chicago, IL

Posted Jul 30, 2025

Must not have any license suspensions within the last 2 years. The Swing driver collects and hauls waste, recycling materials or containers to a disposal site…

Artificial Intelligence/Machine Learning (AI/ML) Engineer

Company: The University of Chicago

Location: Chicago, IL

Posted Jul 30, 2025

Minimum requirements include a college or university degree in related field. Acts as a technical consultant and resource for faculty research, teaching, and/or…

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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