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.

Jr. Graphic Designer

Company: CannonDesign

Location: Chicago, IL

Posted Jul 29, 2025

Bachelor's degree in graphic design or a related field. 1+ years professional experience in a graphic design position, experience in the AE field is a plus but…

Customer Service Representative

Company: AZTECA FOODS, INC

Location: Chicago, IL

Posted Jul 28, 2025

*Provide sales, broker and customer support;* by answering incoming calls, and respond promptly to inquiries with professionalism and accuracy.

executive Chef

Company: Rosebud Restaurants

Location: Chicago, IL

Posted Jul 29, 2025

Candidates should be able to perform calmly and effectively in a fast-paced environment, be an efficient multi-tasker, maintain a positive attitude and friendly…

Project Manager - Multifamily - Downtown Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jul 29, 2025

Our client is an established growing general contractor/developer who specializes in luxury commercial, mid and high rise multifamily, mixed use, and various…

Journeyman Electrician - Chicago, IL

Company: Flock Safety

Location: Chicago, IL

Posted Jul 29, 2025

Valid driver's license and clean driving record. Familiarize with Support Tools and Processes: Learn the internal systems, tools, and methodologies used to…

Advanced Rail Technology, Director of Engineering - Uptime

Company: Progress Rail

Location: La Grange, IL

Posted Jul 29, 2025

5+ years of project and/or product management in a technical field. 10+ years of engineering leadership preferably in the software field.

Project Manager - Interiors - Chicagoland Construction

Company: Michael Page

Location: Chicago, IL

Posted Jul 29, 2025

Strong knowledge of project management tools and techniques. Proven experience managing interior construction projects.

Security Supervisor - 33885

Company: Harvard Protection Services, LLC

Location: Chicago, IL

Posted Jul 29, 2025

Assist in monitoring/developing staff performance to include supervision, evaluations, disciplinary matters, training, scheduling, callouts, assigning work.

Part-Time Public Area Attendant - The Ritz-Carlton, Chicago

Company: Sage Hospitality

Location: Chicago, IL

Posted Jul 29, 2025

At The Ritz-Carlton, Chicago, a luxury hotel set atop Water Tower Place in the historic Gold Coast, guests will have every chance to explore the city, from…

Field Security Supervisor

Company: GardaWorld Security Services U.S.

Location: Chicago, IL

Posted Jul 29, 2025

In addition, GardaWorld Security Services complies with applicable state and local laws governing nondiscrimination in employment. What’s in it for You.

Project Manager

Company: Duly Health and Care

Location: Downers Grove, IL

Posted Jul 29, 2025

Bachelor’s degree in Information Systems, Business, Healthcare Administration, or related field. These roles are critical to managing project lifecycles across…

Property Accountant

Company: Creative Financial Staffing

Location: Chicago, IL

Posted Jul 29, 2025

Bachelor’s degree in Accounting, Finance, or a related field. Oversee rent invoicing, collections, and vendor payments.

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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