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.

Thermoforming - Process Technician

Company: Pactiv Evergreen

Location: Bridgeview, IL

Posted Jul 09, 2025

Two or four year technical degree or certification. Partner with plant Training Coordinator to develop and conduct training programs for line operators and…

Senior Accountant

Company: Rosecrance Health Network

Location: Chicago, IL

Posted Jul 09, 2025

OR a Bachelor's Degree and a valid CPA (Certified Public Accountant) license. Master's Degree in Accounting, Business or a related field.

Founding Graphic Designer

Company: Bulqit

Location: Chicago, IL

Posted Jul 08, 2025

Have enough technical skill to collaborate with developers—or even build simple tools and automations yourself.

Business System Analyst, HRIS Data - National Office (Remote)

Company: YMCA of the USA

Location: Chicago, IL

Posted Jul 09, 2025

Excellent communication and interpersonal skills; ability to translate technical concepts for non-technical audiences. YMCA Team Leader certification preferred.

Manual Machinist

Company: Monarch Technical Search

Location: Burr Ridge, IL

Posted Jul 09, 2025

Strong mechanical knowledge with the ability to understand complex technical drawings. The ideal candidate will possess strong mechanical knowledge and…

Job Assistance Data Analyst

Company: Benda Infotech

Location: Chicago, IL

Posted Jul 09, 2025

Present findings in a clear and concise manner to technical and non-technical stakeholders. Bachelor’s or Master’s degree in Data Science, Statistics, Computer…

Union Carpenter Journeyman - Chicago, IL

Company: Turner Construction Company

Location: Chicago, IL

Posted Jul 09, 2025

Valid driver’s license preferred. Inspect all tools and power tools before use to ensure they are in safe and working condition.

Area Canvassing Sales Manager ($150k - $300k OTE)

Company: Zeo Energy

Location: Chicago, IL

Posted Jul 09, 2025

Our territory managers are responsible for generating leads inside their territory and maintaining business relationships with customers.

Senior Customer Support Specialist - Chicago, IL

Company: Uber

Location: Chicago, IL

Posted Jul 09, 2025

Facilitate driver sign-ups and communicating value proposition of driving with Uber, which may include proactive outreach.

Regional Marketing Associate - Student Housing Exp Required

Company: The Scion Group

Location: Chicago, IL

Posted Jul 09, 2025

Scion is paving a path in student living, and the Regional Marketing Associate is a crucial team member responsible for driving traditional marketing efforts…

Union Carpenter Foreman - Data Center Hot Aisle Containment

Company: Turner Construction Company

Location: Chicago, IL

Posted Jul 09, 2025

Supervise and develop trade employees, as assigned, including providing input on or completing performance appraisals. Address staff needs and resolve problems.

Oncology Infusion RN 2 - RUSH Cancer Center (Chicago) - Per Diem

Company: Rush Oak Park

Location: Chicago, IL

Posted Jul 09, 2025

Demonstrates accountability for own professional practice, including progress toward achievement of annual goals. Work Type: Restricted Part-Time (0. 1 FTE).

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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