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.

Revenue Cycle Reporting & PB Contract Build Analyst

Company: Wolcott Wood and Taylor Inc.

Location: Chicago, IL

Posted Aug 01, 2025

Associate or bachelor’s degree in healthcare administration or finance related field. Intermediate to advanced skills in Microsoft Excel and data analytics…

Civil Engineering Project Manager

Company: Crescent Solutions, Inc.

Location: Chicago, IL

Posted Aug 01, 2025

Effective communication skills for working with personnel, clients, contractors, and regulatory agencies. Civil engineering: 8 years (Required).

Painter

Company: Potbelly

Location: Chicago, IL

Posted Aug 01, 2025

Travel occasionally for repairs, installations, or deliveries. Competitive pay with performance-based annual raises! FSA and HSA with Employer Contribution.

Registered Nurse

Company: Northwestern Medicine

Location: Chicago, IL

Posted Aug 02, 2025

Current State of Illinois, Registered Professional Nurse license. Based on the NMH framework for practice, the registered professional clinical nurse (RN) is…

Tax Accountant II

Company: Bank of America

Location: Chicago, IL

Posted Aug 02, 2025

Prepares complex federal and state individual income tax returns and gift tax returns. Job expectations include complying with client focused service standards,…

Special Agent: Mathematics/Data Expertise

Company: Federal Bureau of Investigation

Location: Chicago, IL

Posted Aug 01, 2025

Candidates must have a bachelor’s degree or higher (preferably in mathematics or a related field) from a U.S. accredited college or university.

2026 Data Science Analyst Program - Summer Analyst

Company: JPMorganChase

Location: Chicago, IL

Posted Aug 02, 2025

You will work on projects focusing on machine learning, business intelligence, data engineering, and visualization, combining your technical skills and…

HVAC Install Manager

Company: Precision Today

Location: Franklin Park, IL

Posted Aug 02, 2025

This includes creating project schedules, managing budgets, and coordinating with other contractors and suppliers.

Overnight Armed Field Supervisor

Company: Kates Detective Agency

Location: Chicago, IL

Posted Aug 02, 2025

Valid and current armed security license. Ensure all team members are in compliance with company policies and licensing requirements.

Mold Machine Operator

Company: S & C Electric Company

Location: Chicago, IL

Posted Aug 01, 2025

You will frequently use hand and power tools such as knives, scrapers, engravers and air-impact tools. Use hand tools like files, hammer, scrapper, air nozzle…

Digital Incentives Lead, Family Care

Company: Kimberly-Clark

Location: Chicago, IL

Posted Aug 02, 2025

This role will own and manage the Promotions Relationship within Family Care with cross functional stakeholders including KCNA brand and sector/business unit…

2025 Data for Good Hackathon - Data Science Analyst - Manhattan, New York

Company: JPMorganChase

Location: Chicago, IL

Posted Aug 02, 2025

You will work on projects focusing on machine learning, business intelligence, data engineering, and visualization, combining your technical skills and…

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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