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.

Shift Lead

Company: Walgreens

Location: Chicago, IL

Posted Jan 24, 2025

Global Incident Response Manager

Company: Coca-Cola

Location: Rosemont, IL

Posted Jan 24, 2025

Summer Pharmacy Intern

Company: Walgreens

Location: Mount Prospect, IL

Posted Jan 24, 2025

Bid Desk Associate

Company: CDW

Location: Chicago, IL

Posted Jan 24, 2025

Territory Manager - Hampton Roads, Virginia

Company: iRhythm Technologies

Location: Deerfield, IL

Posted Jan 24, 2025

iRhythm Technologies is seeking a motivated Medical Territory Manager to expand the growth of the Zio Patch platform. The role involves prospecting, developing, and closing new business, building support from EP's, cardiologists, and other clinical stakeholders, and achieving territory sales goals. The company is passionate about delivering innovations that improve healthcare and patient experience. The ideal candidate should have a Bachelor's degree, at least 5 years of related sales experience, and a history of outstanding achievements. The compensation package includes excellent benefits and a competitive salary range of $76,300—$90,000 USD.

Staff Engineer - iOS

Company: CVS Health

Location: Buffalo Grove, IL

Posted Jan 24, 2025

CVS Health is seeking a Staff Engineer - iOS to join their team, responsible for advancing the architecture and Mobile Product. The role involves working with cross-functional teams to deliver great user experiences, mentoring team members, and improving foundational architecture. The ideal candidate should have 7+ years of software development experience, 5+ years in modern iOS development frameworks, and 3+ years in influencing large organizations on best practices in Mobile iOS development. The role is part of the fastest-growing business unit, the CVS Mobile App, with over a million daily average users. Responsibilities include developing iOS code, partnering with Product, UX, and Engineers, and maintaining CI and CD infrastructure.

Shift Lead

Company: Walgreens

Location: Arlington Heights, IL

Posted Jan 24, 2025

The job involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Responsibilities also include coaching team members, maintaining store cleanliness, and complying with company policies. The role requires leadership experience, fluency in English, and knowledge of store systems. Preferred qualifications include experience with store inventory control.

Beauty and Wellness Consultant

Company: Walgreens

Location: Villa Park, IL

Posted Jan 24, 2025

Pharmacy Manager

Company: Walgreens

Location: Aurora, IL

Posted Jan 24, 2025

Technical Development Program, Liquid

Company: Diageo

Location: Plainfield, IL

Posted Jan 24, 2025

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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