Technical Leadership Jobs in Chicago, IL

41,750 open positions · Updated daily

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.

Multisite Plant Finance Manager

Company: Eaton

Location: Edwardsville, IL

Posted Jan 27, 2025

View Details Apply on The Muse

Shift Supervisor Trainee

Company: CVS Health

Location: Buffalo Grove, IL

Posted Jan 27, 2025

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Cyber Intelligence Analyst (TS/SCI with Poly Required)

Company: Deloitte

Location: Springfield, IL

Posted Jan 27, 2025

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Product Manager - Pangea (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 27, 2025

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Property Adjuster - Field Estimating – Chicagoland, IL

Company: Allstate

Location: Chicago, IL

Posted Jan 27, 2025

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District Support Pharmacist FT

Company: CVS Health

Location: Chicago, IL

Posted Jan 27, 2025

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Software Development Team Lead - Java

Company:

Location: Itasca, IL

Posted Jan 27, 2025

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Lead Operations Strategy - Dispute Policy and Compliance

Company: Discover

Location: Riverwoods, IL

Posted Jan 27, 2025

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leading financial technology company competitive salary range comprehensive benefits

Compliance Lead (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 26, 2025

Enova International is seeking a Compliance Lead with at least 5 years of experience in technology compliance or analytics. The role involves enhancing and overseeing internal control frameworks, advising business teams on control design, and leading training initiatives. The ideal candidate should have knowledge of US consumer financial regulations, strong analytical skills, and excellent communication abilities. Enova offers a competitive salary range of $80000 to $110000, along with comprehensive benefits including health, dental, and vision insurance, 401k matching, PTO, paid holidays, sabbatical program, and more. Enova is a values-driven organization committed to making accessible credit for millions and fostering an inclusive culture.

View Details Apply on BuiltIn

Software Development Team Lead - Java

Company:

Location: Lake Bluff, IL

Posted Jan 27, 2025

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Lead Machine Learning Engineer - Retail Analytics

Company: CVS Health

Location: Chicago, IL

Posted Jan 27, 2025

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Senior Manager, Mechanical Engineering - Locomotives

Company: CN

Location: Homewood, IL

Posted Jan 27, 2025

View Details Apply on The Muse

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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