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.

AI Platform Engineer (GCP) - Remote

Company: The Hartford

Location: Chicago, IL

Posted Jul 07, 2025

Bachelor's degree in Computer Science, Computer Engineering, or a technical field. Manage engineering tasks, driving execution, and optimizing workflows with…

Sales Associate

Company: Instacart

Location: Chicago, IL

Posted Jul 07, 2025

Familiarity with tools of the trade (eg. Microsoft Office, Excel, Google Drive, Salesforce). Act as a primary point of escalation for technical issues.

Senior Business Analyst – Data

Company: United Airlines

Location: Chicago, IL

Posted Jul 07, 2025

Training or certification in analytics tools used in financial analysis, such as Power BI or Oracle Analytics, is advantageous.

Customer Service Representative

Company: Van DerBosch Plumbing

Location: Chicago, IL

Posted Jul 07, 2025

Help the field team by taking detailed notes from customer calls and entering them into our system. Answer all incoming calls, as the initial point of contact.

Commercial HVAC Installer

Company: Forced Air Mechanical

Location: Elk Grove Village, IL

Posted Jul 07, 2025

Valid driver’s license with a clean, insurable record. Read and interpret blueprints and mechanical drawings. OSHA 30 certification (or willing to obtain).

Bathroom Remodeling Installer

Company: J. Blanton Plumbing

Location: Northbrook, IL

Posted Jul 07, 2025

Valid plumbing license or current apprenticeship status (apprenticeship sponsorship available). Read and interpret blueprints and technical drawings for…

Executive Chef

Company: Ambar Restaurant - Chicago

Location: Chicago, IL

Posted Jul 07, 2025

Strong leadership skills with a passion for training, developing, and elevating teams. Manage food and labor costs, inventory, vendor relationships, and kitchen…

Manager, Media Planning (Traditional and Digital)

Company: Rise

Location: Chicago, IL

Posted Jul 07, 2025

Develop and oversee media strategy, campaign creation, budget, optimization, and testing strategy(ies), as applicable, for full-funnel, multi-platform campaigns…

Senior Brand Manager - Cottonelle® Flushable Wipes

Company: Kimberly-Clark

Location: Chicago, IL

Posted Jul 06, 2025

Diverse income protection insurance options to protect yourself and your family in case of illness, injury, or other unexpected events. In this role, you will:

HVAC Service Technician

Company: Guardian Heating & Cooling Services LLC

Location: Chicago, IL

Posted Jul 07, 2025

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

Controller

Company: Housing Opportunity Development Corporation

Location: Skokie, IL

Posted Jul 07, 2025

Daily: Oversee invoice processing, check deposits, data entry, account reconciliation, and records filing. Education: Bachelor’s degree in finance, accounting,…

Permanent Substitute Teacher

Company: Oak Park Elementary School District 97

Location: Oak Park, IL

Posted Jul 06, 2025

They establish a positive rapport with students, motivating them to develop the skills, attitudes, and knowledge needed to pursue their full potential.

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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