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: Villa Park, IL

Posted Jan 24, 2025

Food Safety and Quality Assurance Technician

Company: Sysco

Location: West Dundee, IL

Posted Jan 24, 2025

Sysco Specialty Meat and/or Seafood Company is seeking a Food Safety & Quality Assurance professional with 1-3 years of meat/seafood industry experience. The role involves monitoring FSQA programs, assisting in employee training, and implementing independent FSQA audit programs. The candidate should have formal training in TQM principles, SPC, HACCP concepts, and FDA/CFIA regulations. They must be able to write reports, handle basic business correspondence, and use various equipment. The position requires frequent interaction with various departments and external personnel. Sysco offers a dynamic work environment with opportunities for growth and professional development.

Gastroenterology Opportunities

Company: Northwestern Medicine Regional Medical Group

Location: Chicago Northwest Suburbs

Posted Jan 24, 2025

Northwestern Medicine is actively recruiting board-certified Gastroenterologists for inpatient and outpatient opportunities in the northwest suburbs of Chicago. The position offers competitive compensation, comprehensive benefits, and access to advanced diagnostic techniques. The medical group emphasizes physician leadership, wellness, and work-life balance. The location provides excellent communities with good schools, parks, and amenities, and easy access to downtown Chicago. The salary range is $300,000 - $560,000 annually.

Emerging Store Manager

Company: Walgreens

Location: Evanston, IL

Posted Jan 24, 2025

Shift Lead

Company: Walgreens

Location: Chicago, IL

Posted Jan 24, 2025

Pharmacy Operations Manager

Company: Walgreens

Location: West Dundee, IL

Posted Jan 24, 2025

Senior Product Manager, AdTech

Company: Walgreens

Location: Deerfield, IL

Posted Jan 24, 2025

Shift Lead

Company: Walgreens

Location: Oak Park, IL

Posted Jan 24, 2025

Shift Lead

Company: Walgreens

Location: Chicago, IL

Posted Jan 24, 2025

The role involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Key responsibilities include managing deliveries, processing returns and refunds, maintaining store cleanliness, and assisting with pharmacy tasks. The position requires leadership experience, fluency in English, and knowledge of store systems. The role is based in Chicago, IL, with a salary range of $17 - $19 per hour.

Pharmacy Manager

Company: Walgreens

Location: Chicago, IL

Posted Jan 24, 2025

The job involves providing pharmacy consulting services with empathy to patients, ensuring effective medication usage and awareness of drug interactions. The role includes offering preventive and clinical healthcare services such as immunizations, diagnostic testing, and patient outcomes services. Key responsibilities encompass patient experience, operations, and people & performance management. The pharmacist engages patients, resolves issues, and models customer service best practices. They counsel patients on medication usage, side effects, interactions, and privacy, and perform pharmacist tasks like compounding and drug therapy reviews. The role also involves maintaining pharmacy operations in accordance with regulations, collaborating on business opportunities, and ensuring accurate insurance claim processing. Clinical and wellness services, such as immunizations and diagnostic testing, are also part of the role. The pharmacist manages staff performance, maintains records, and promotes community health awareness.

Shift Lead

Company: Walgreens

Location: Chicago, 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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