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.

Customer Care Agent - Palmer House Hilton

Company: Hilton

Location: Chicago, IL

Posted Aug 07, 2025

As a Customer Care Agent you would be responsible for answering and responding to internal and external calls in the hotel's continuing effort to deliver…

Sr Data Scientist

Company: PayPal

Location: Chicago, IL

Posted Aug 07, 2025

Overall, this candidate will play a crucial role in shaping credit loss forecasting, ensuring compliance with regulatory requirements, and driving business…

Aging Program Specialist - Spanish Speaking (Exec I - SS)

Company: State of Illinois

Location: Chicago, IL

Posted Aug 07, 2025

Provides complex telephone assessment, face to face interviews, linkage to services, email responses, and correspondence following all Senior Helpline and…

Business Operations Analyst II

Company: ENGIE

Location: Chicago, IL

Posted Aug 07, 2025

Minimum of a Bachelor’s Degree in Business Analytics, Data Analytics, Operations, or a related field. ENGIE complies with all federal, state, and local minimum…

Manager, Project Manager - Community Impact and Investment Market Engagement

Company: Capital One

Location: Chicago, IL

Posted Aug 07, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

CONTRACTUAL WORKER

Company: State of Illinois

Location: Chicago, IL

Posted Aug 07, 2025

Requires a Bachelor’s degree in computer science, information technology, business or related field or equivalent work experience.

Security Operations Center Analyst

Company: iManage

Location: Chicago, IL

Posted Aug 06, 2025

End-user focused experience to investigate security issues and communicate risks clearly with technical and non-technical teams.

HVAC Service Technician

Company: Guardian Heating & Cooling Services LLC

Location: Chicago, IL

Posted Aug 06, 2025

Valid driver's license and insurable driving record. Service / maintenance / repair on residential heating and air conditioning systems.

IEP Specialist $10,000 Sign on bonus

Company: Specialized Education Services

Location: Chicago, IL

Posted Aug 07, 2025

Collaborate with school teams and families to offer personalized guidance and deliver SESI’s own evidence-based learning and instructional models, as well as…

Digital Forensic Analyst I

Company: Contact Government Services, LLC

Location: Chicago, IL

Posted Aug 07, 2025

Experience working with structured data exported from various platforms including analysis, custom scripting, and data manipulation to develop reports for…

Construction Site Plumber

Company: REI Plumbing & Construction INC

Location: Chicago, IL

Posted Aug 07, 2025

Reliable transportation and a valid driver’s license. Coordinate with project managers, contractors, and team members on job sites.

Dialysis Registered Nurse Float (M-F + 2 S) South Chicagoland Region

Company: Concerto Renal Services

Location: Chicago, IL

Posted Aug 06, 2025

The Dialysis Nurse supervises dialysis care in accordance with policy, procedure and training and in compliance with state and federal regulations.

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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