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.

Employment Attorney Sr. Manager- HYBRID Chicago

Company: Allstate

Location: Chicago, IL

Posted Jan 24, 2025

Allstate, a company with over 90 years of experience, is seeking an Employment Senior Counsel. The role involves providing legal advice and counsel on employment laws, managing complex disputes, and conducting training for HR and business units. The ideal candidate will have 10+ years of experience, preferably in employment litigation and international employment law. The position offers a competitive salary and opportunities for professional growth. Allstate values diversity and inclusivity, and the role involves working in a flexible environment that encourages innovation and impact.

Director, Branch Network - East

Company: Grainger

Location: Lake Forest, IL

Posted Jan 24, 2025

Assistant Store Leader

Company: Kroger

Location: Carbondale, IL

Posted Jan 24, 2025

Senior Manager - Finance and HR Compensation

Company: Allstate

Location: Chicago, IL

Posted Jan 24, 2025

Allstate is seeking a Senior Manager - Finance and HR Compensation to serve as a strategic business advisor, bridging Finance Shared Services and HR functions. The role involves designing and analyzing compensation programs, providing strategic financial support, and leading a team. The ideal candidate should have strong business acumen, advanced financial modeling skills, and leadership abilities. The position offers a competitive salary and opportunities for professional growth in a supportive, inclusive environment.

Service and Engagement Team Leader

Company: Target

Location: Joliet, IL

Posted Jan 24, 2025

Target is offering a competitive pay range of $23.75 - $40.40 per hour, with additional benefits such as health insurance, 401(k), employee discount, and paid time off. The role of a Service and Engagement Team Leader involves guest service, team management, and business operations. Target values diversity, equity, and inclusion, and provides opportunities for career growth. The job requires strong communication, leadership, and problem-solving skills, with a flexible schedule including weekends and holidays.

Intern, US Property Tax

Company: CN

Location: Homewood, IL

Posted Jan 24, 2025

PT Member Specialist

Company: Walmart

Location: Rockford, IL

Posted Jan 24, 2025

Research & Development Intern

Company: Thermo Fisher Scientific

Location: Rockford, IL

Posted Jan 24, 2025

Thermo Fisher Scientific is offering a summer internship for undergraduate students in Engineering or Life Sciences. The internship, starting on either May 12th or June 16th, 2025, lasts for 10-12 weeks. Interns will work on strategic projects, learn continuous improvement methodologies, and align with company safety, training, and quality regulations. The compensation includes an hourly rate between $21.50 - $28.75 and a $5,000 relocation stipend if necessary. Thermo Fisher values integrity, innovation, involvement, and intensity, and offers comprehensive Total Rewards package including medical, dental, vision plans, retirement savings programs, and more.

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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