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.

Software Engineer

Company: CACI

Location: Lisle, IL

Posted Jul 24, 2025

Participate in technical activities spanning multiple technical disciplines including security analysis, software/tool development, software test, development…

Director of Growth Marketing

Company: Four Seasons Heating And Air Conditioning Llc

Location: Bedford Park, IL

Posted Jul 23, 2025

As Director of Growth Marketing, you will own the strategy and execution of performance-driven acquisition channels—PPC, LSA, paid social, display/retargeting,…

Cloud Infrastructure Architect

Company: Sargent & Lundy

Location: Chicago, IL

Posted Jul 23, 2025

We are seeking a highly experienced and strategic Cloud & Infrastructure Architect to lead the design, governance, and implementation of enterprise-grade cloud…

AI Prompt Engineer

Company: ActiveCampaign

Location: Chicago, IL

Posted Jul 24, 2025

This is a hands-on role focused on prompt design, workflow implementation, and knowledge asset creation, with a goal of delivering repeatable, high-quality…

Manual Lathe Machinist II

Company: American Roller Company

Location: Chicago, IL

Posted Jul 24, 2025

Along the way, you’ll develop technical, mechanical, and problem-solving skills that open doors. Blueprint Reading: Interpret technical drawings and follow…

Area Marketing Manager, Premium Select Hotels

Company: First Hospitality

Location: Chicago, IL

Posted Jul 23, 2025

Oversee portfolio social media efforts, driving following and engagement, fostering collaboration amongst broader marketing strategies.

Data Analyst - Remote

Company: Guidehealth

Location: Chicago, IL

Posted Jul 23, 2025

Employees provide their own internet connection, capable of conducting video calls on camera and connecting to various internal and external systems.

Senior Manager, Organic Marketing

Company: Four Seasons Heating And Air Conditioning Llc

Location: Bedford Park, IL

Posted Jul 23, 2025

Coordinate with content team to develop service-specific blog posts, FAQs, landing pages, rich content, and CTAs that educate and drive action.

Sales Assistant Part Time

Company: Ralph Lauren

Location: Chicago, IL

Posted Jul 24, 2025

Interest in and appreciation for luxury and best-in-class service. Supports product pulls, fitting room setup & recovery, floor presentation standards and…

Senior Tax Analyst Indirect Tax

Company: Amrize Building Materials US

Location: Chicago, IL

Posted Jul 24, 2025

Manage state and local audits, working directly with auditors to provide required and requested data, and manage end to end audit process.

Retail Cosmetics Sales Associate - CHANEL Beaute, Orland Square - Full Time

Company: Macy’s

Location: Orland Park, IL

Posted Jul 24, 2025

Collaboration: Partnership with the total Beauty team to drive sales and deliver the customer experience. Use product knowledge to give expert guidance to each…

Unarmed Security Officer

Company: American Heritage Protective Services, Inc.

Location: East Chicago, IN

Posted Jul 23, 2025

Receive all emergency and non-emergency incoming calls to the dispatch center while soliciting descriptive information to determine the nature and urgency of…

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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