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.

Senior Software Engineer, Full Stack

Company: Capital One

Location: Chicago, IL

Posted May 23, 2025

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

View Details Apply on SimplyHired

Registered Nurse RN Home Health

Company: Elara Caring

Location: Chicago, IL

Posted May 23, 2025

Must have a dependable vehicle, valid driver’s license, and current auto insurance in accordance with state laws. 401(K) with employer match.

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Customer Support Product Support Consultant, gTech Ads

Company: Google

Location: Chicago, IL

Posted May 21, 2025

Experience in account/campaign management roles, technical troubleshooting, or technical customer support. Based on the evolving needs of our ads customers, we…

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full time

Chief - Section of Maternal Fetal Medicine

Company: The University of Chicago

Location: Chicago, Illinois

Posted May 25, 2025

View Details Apply on healthecareers.com

Chef De Cuisine - Sable at Navy Pier

Company: Sable at Navy Pier

Location: Chicago, IL

Posted May 21, 2025

Maintain food and labor cost controls while ensuring guest satisfaction and operational efficiency. Oversee the development and execution of seasonal menus that…

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Project Manager

Company: Keller North America, Inc.

Location: Chicago, IL

Posted May 24, 2025

Assembles proposals which includes performing risk assessment, evaluating opportunities to increase profit, estimating, engineering, technical writing, site…

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Project Superintendent #2080

Company: Pivotal Talent Search

Location: Chicago, IL

Posted May 22, 2025

Valid driver license and willingness to travel locally to job sites. Collaborate with project managers to manage change orders and resolve field-related issues.

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HVAC Service Technician

Company: R.A. SHAVITZ INC

Location: Skokie, IL

Posted May 21, 2025

Valid driver’s license with an insurable record. Certificate of completion from HVAC technical school. Year-Round Employment with guaranteed weekly hours.

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Senior Finance Analyst

Company: Expedia Group

Location: Chicago, IL

Posted May 21, 2025

Support, develop, and implement improved processes and controls to enable sustainable, profitable scaling of the PLS business.

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Software Engineer Manager (Hybrid or Remote Available)

Company: S&S Activewear LLC

Location: Bolingbrook, IL

Posted May 23, 2025

Partner with software engineering leaders to design and implement dev ops automation using target state CI/CD tools. Monday-Friday, Full-Time, Exempt.

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Welder/Fabricator

Company: ProFlow Pumping Solutions

Location: Alsip, IL

Posted May 22, 2025

Ability to read and understand technical drawings and mechanical layouts. Interpret and work from technical drawings, blueprints, and schematics.

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Facilities Painter

Company: The Resurrection Project

Location: Chicago, IL

Posted May 22, 2025

Access to a car, valid driver's license, and ability to travel within the metropolitan area and out of state. Access to a motor vehicle, valid driver’s license,…

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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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