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.

Practice Architect, Retail/Consumer Packaged Goods, Google Cloud

Company: Google

Location: Chicago, IL

Posted Jul 14, 2025

You will orchestrate across contributing teams including solutions, services, partners, product engineering, marketing, and GTM stakeholder organizations in…

Artificial Intelligence Tech Lead - Remote Work

Company: BairesDev

Location: Chicago, IL

Posted Jul 14, 2025

You'll establish and document best practices, transfer knowledge across teams, serve as a point of contact for upper management, and interact with key…

Customer Retention Manager

Company: Neretva Group

Location: Chicago, IL

Posted Jul 14, 2025

This position involves developing and implementing strategies that foster long-term relationships with clients, ensuring their needs are met, and addressing any…

Entry Level Retail Sales Associate

Company: ASAP Business Resolutions

Location: Des Plaines, IL

Posted Jul 14, 2025

In this role, you will be responsible for driving sales and providing excellent customer service in a retail environment.

Unarmed Security Officer #247

Company: Stark Security Inc

Location: Chicago, IL

Posted Jul 14, 2025

Make guests aware of rules that must be adhered to. Occasional – reaching, stooping, climbing, balancing, driving, bending, twisting, handling paperwork.

Construction Crew Lead

Company: ALFF CONSTRUCTION LLC

Location: Chicago, IL

Posted Jul 14, 2025

Have own tools for routine tasks. Strong hands-on skills in at least two trades: HVAC, refrigeration, plumbing, electrical, or carpentry.

Insider Threat Hunt Analyst

Company: Northern Trust Corp.

Location: Chicago, IL

Posted Jul 14, 2025

Strong technical background in log analysis, data correlation, and behavioral analytics. Bachelor's degree in Computer Science, Information Security, or related…

Accountant

Company: Corporate Leadership Center, NFP

Location: Chicago, IL

Posted Jul 14, 2025

Assist with the annual audit, including preparing supporting information, answering questions and reviewing annual reports and Form 990.

Data Analyst

Company: HAVI Logistics GmbH

Location: Chicago, IL

Posted Jul 14, 2025

Bachelor’s degree in Engineering, Computer Science, Business, Analytics, or closely related field. Document current state and work and identify and plan the…

CNC Machine Operator I-Second Shift

Company: Dynamic Manufacturing

Location: Hillside, IL

Posted Jul 14, 2025

Prolonged periods of sitting at a desk and working on a computer. The CNC Machine Operator is responsible for the manufacture of parts per plant.

Manager, Loyalty Partnerships

Company: paypal

Location: Chicago, IL

Posted Jul 14, 2025

Engage closely with product, engineering, and architecture teams to drive the architectural runway and determine the best technical implementation/design.

PRN Retail Pharmacist (Howard Brown CHC)

Company: Cardinal Health

Location: Chicago, IL

Posted Jul 14, 2025

Participates in supervision of technical staff. Immunization Certification or willing to become a certified immunizer within 90 days of hire.

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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