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.

Senior Manager Software Engineering, Full Stack (Java/Go, Angular/React, AWS)

Company: Capital One

Location: Chicago, IL

Posted Jun 27, 2025

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

Graphic Designer (Multimedia Focus)

Company: Daniels Health

Location: Chicago, IL

Posted Jun 25, 2025

Experience with project management and managing project timelines (not only your own, but also of any contractors).

Sr. Software Engineer

Company: Caterpillar

Location: Chicago, IL

Posted Jun 25, 2025

REQS: This position requires a bachelor’s degree, or foreign equivalent, in Computer Science, Computer Engineering, Performance, Information Management, or a…

Wound Care Treatment Nurse

Company: Wentworth Rehabilitation and Health Care Center Inc.

Location: Chicago, IL

Posted Jun 27, 2025

Must possess a current, unencumbered license to practice as a RN or LPN in the State of Illinois. Plan, develop, organize, implement, evaluate, and direct the…

Project Manager, Office of Equity

Company: Chicago Public Schools

Location: Chicago, IL

Posted Jun 26, 2025

Build and maintain strong partnerships with school leaders, educators, parents, community organizations, city/state agencies, and other stakeholders to create a…

SERVICE NOW ENGINEER - GLOBAL TECHNOLOGY SUPPORT (REMOTE OPPORTUNITY)

Company: Hyatt Corporate Office

Location: Chicago, IL

Posted Jun 26, 2025

Responsible for the design, implementation, and configuration of ServiceNow applications and modules aligned with ITSM processes.

Registered Nurse

Company: Pearl of Hinsdale

Location: Hinsdale, IL

Posted Jun 25, 2025

Prepare & administer medications as ordered by the physician. Admit, transfer and discharge residents as required. Current Illinois Nursing License (Required).

SOUS CHEF

Company: Hyatt Regency Chicago

Location: Chicago, IL

Posted Jun 27, 2025

At Hyatt, we believe our guests select Hyatt because of our caring and attentive associates who are focused on providing efficient service and meaningful…

Rough and Finish Carpenter , Deck experience

Company: NyJ Builders Inc

Location: Chicago, IL

Posted Jun 25, 2025

Utilize hand tools and power tools effectively for various tasks. Ability to read blueprints and technical drawings accurately. Job Types: Full-time, Part-time.

Project Manager - Multifamily - Downtown Chicago

Company: Michael Page

Location: Chicago, IL

Posted Jun 26, 2025

Bachelors degree in Construction Management or a related field is preferred. Train and develop the Project team and schedule project resources.

Registered Nurse 2, Antepartum/Postpartum

Company: Rush University Medical Center

Location: Chicago, IL

Posted Jun 26, 2025

17.Demonstrates accountability for own professional practice, including progress toward achievement of annual goals. 2.Maintain current BLS certification.

Senior Project Manager - Chicago

Company: Turner Construction Company

Location: Chicago, IL

Posted Jun 25, 2025

Work Environment: While performing the duties of this job, the employee regularly works on-site at the construction work site where the employee is exposed to…

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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