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.

Head of Customer Service

Company: Double Good

Location: Chicago, IL

Posted Jan 24, 2025

Double Good is a company that creates joy through its delectable popcorn, easy-to-use fundraising platform, and Kids Foundation. They are seeking a Head of Customer Service to lead their growing team, focusing on strategic ownership, customer advocacy, and cross-functional partnerships. The role involves managing SaaS and BPO vendors, ensuring a safe work environment, and developing future leaders. The company offers competitive compensation, benefits, and a positive work culture.

Partner Investment Specialist

Company: CDW

Location: Chicago, IL

Posted Jan 24, 2025

Diesel Fleet Technician I

Company: Sysco

Location: Park Ridge, IL

Posted Jan 24, 2025

Sysco Chicago, Inc. is seeking a Fleet Technician Apprentice to assist Fleet Technicians II and III in maintaining safe, reliable, and cost-efficient vehicles. The role involves learning to perform preventive maintenance inspections and repairs, diagnosing malfunctions, and performing quality repairs under guidance. The ideal candidate should have medium/heavy duty truck technical training, basic knowledge of vehicle systems, and computer skills. No experience is required, but a valid driver's license (CDL preferred) is necessary. The job involves regular physical activities, non-traditional hours, and occasional travel.

Product Manager- Microsoft, Azure

Company: CDW

Location: Chicago, IL

Posted Jan 24, 2025

Sr Relationship Manager II - Client Onboarding Operations

Company: Merrill

Location: Chicago, IL

Posted Jan 24, 2025

Bank of America is seeking a Sr Relationship Mgr II for onboarding and strategic account management of Institutional clients across Fixed Income and Equity products. The role involves providing client relationship management services, documenting LOB processes, and analyzing opportunities to drive operational excellence and efficiency. The candidate should have 2-3 years of onboarding experience, working knowledge of AML/KYC and Regulatory requirements, and strong written and verbal communication skills. The position offers a competitive salary range of $89,500.00 - $225,000.00 annualized, along with benefits and opportunities for growth.

Senior Manager of Hardware Engineering

Company: Eaton

Location: Bolingbrook, IL

Posted Jan 24, 2025

Veterinarian

Company: Banfield Pet Hospital

Location: Vernon Hills, IL

Posted Jan 24, 2025

Banfield, a leading general veterinary care practice in America, is offering full-time and part-time positions for veterinarians in Vernon Hills, Gurnee, and Kildeer. They are providing a generous sign-on bonus and relocation assistance. The anticipated starting base salary ranges from $102,000 to $170,000 per year, plus production. Banfield values work-life balance and offers a comprehensive benefits package including medical, dental, vision insurance, paid time off, 401(k) savings plan, mental health support, and opportunities for growth and leadership roles. They are open to hiring veterinarians with diverse perspectives and experiences.

GM and Food (General Merchandise, Closing, Fulfillment, Inbound, Food and Beverage , Food Service, Starbucks) (T0838)

Company: Target

Location: Wheaton, IL

Posted Jan 24, 2025

Target, a Fortune 50 company, is seeking a General Merchandise Expert. The role involves creating a welcoming experience for guests, ensuring product availability, accurate pricing, and presentation. Responsibilities include executing daily workload, managing inventory, and maintaining a safe, compliant work environment. The ideal candidate should possess a welcoming attitude, communication skills, attention to detail, and ability to work in a fast-paced environment. Target offers training and competitive benefits.

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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