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.

Staff Accountant

Company: Hogsalt Headquarters

Location: Chicago, IL

Posted Jul 28, 2025

Prepare and file city and state monthly and annual sales tax returns. Compile and analyze financial information to prepare entries to accounts, such as general…

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Electrical Estimator/Project Manager

Company: Arrow Flow

Location: Elk Grove, IL

Posted Jul 25, 2025

The ideal candidate will possess a strong background in electrical estimating, engineering, and project management, ensuring that all projects are completed on…

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full time be or bc academic

Director of Clinical Operations UI Health

Company: UI Health

Location: Chicago, Illinois

Posted Jul 27, 2025

View Details Apply on healthecareers.com

CNC Machinist (Setup / Operator)

Company: Belden Universal

Location: Hillside, IL

Posted Jul 25, 2025

Maintains specifications by observing drilling, grooving, and cutting, including turning, facing, knurling and thread chasing operations; taking measurements;…

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Java Engineer - Kiosk Backend Services

Company: CoinFlip

Location: Chicago, IL

Posted Jul 25, 2025

Develop Modular Backend Services: Build and maintain robust, scalable Java components designed for plug-and-play integration into our backend server environment…

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Project Delivery Manager (Warehouse/Mfg Automation exp. req. $140K)

Company: #twiceasnice Recruiting

Location: Chicago, IL

Posted Jul 25, 2025

Lead end-to-end delivery of warehouse automation projects, from design to implementation. Technical/automation solutions implementation: 3 years (Required).

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Project Manager – Manufacturing and Technology

Company: Belden Universal

Location: Hillside, IL

Posted Jul 25, 2025

The Project Manager will lead and perform all phases of project management activities including scope management, requirements definition and analysis,…

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Project Manager Engineering

Company: CONAGRA

Location: Chicago, IL

Posted Jul 25, 2025

Have external interactions with, but not limited to, equipment vendors, construction contractors, engineering services contractors, local / state / federal…

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Centerless Grinding Machinist (Setup / Operator)

Company: Belden Universal

Location: Hillside, IL

Posted Jul 25, 2025

Sets up centerless grinding and honing equipment efficiently and effectively by entering instructions, including zero and reference points; setting tool…

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HVAC Service Technician- LEAD EXPERIENCE- SIGN ON BONUS

Company: Home Comfort Services, Inc.

Location: Des Plaines, IL

Posted Jul 25, 2025

Valid driver's license with a clean driving record; van driving experience preferred. Proven experience as an HVAC Service or similar role in the field service…

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Program Manager II, Legal Tooling, Global Affairs

Company: Google

Location: Chicago, IL

Posted Jul 26, 2025

Contribute to the development of tooling, solutions strategy and roadmap for Global Affairs stakeholders such as Legal and Risk Engineering, Privacy and Safety…

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Principal Solutions Architect, Banking & Capital Markets

Company: Chainlink Labs

Location: Chicago, IL

Posted Jul 25, 2025

Drive the successful adoption of Chainlink products in the capital markets industry by establishing strong relationships with key stakeholders, including major…

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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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