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.

Senior Systems Engineer – VDI and Virtualization

Company: Interactive Brokers

Location: Chicago, IL

Posted Jan 23, 2025

Interactive Brokers Group Inc, a global financial services company, is seeking a hybrid role for a Global Windows Platform and Services team member. The role involves planning, designing, automating, orchestrating, and implementing VMware and HPE solutions in data centers. The ideal candidate should have extensive experience in designing and implementing virtual desktop environments using industry-standard on-prem and cloud virtualization technologies. They should also have advanced knowledge of VMware Horizon View, vSphere, and high-availability environments, as well as expert understanding of networking concepts, data backup, recovery, and replication. Proficiency in PowerShell, PowerCLI, Python, Terraform, Ansible, and cloud platforms like Azure and AWS is required. The role offers a competitive salary, bonuses, stock grants, retirement plans, health benefits, paid time off, and learning opportunities.

Shift Lead

Company: Walgreens

Location: Arlington Heights, IL

Posted Jan 23, 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 Arlington Heights, IL, with a salary range of $17 - $19 hourly.

CDL A Local Delivery Driver- Freeport

Company: Sysco

Location: Freeport, IL

Posted Jan 23, 2025

Sysco Baraboo, LLC is seeking full-time CDL A Delivery Truck Drivers. The role involves safely operating a tractor-trailer and manually delivering various products to customer locations. Drivers build relationships with customers and are expected to be flexible for overtime, weekends, and holidays. Benefits include excellent pay, paid vacation, ongoing training, career growth opportunities, comprehensive healthcare, and retirement benefits. Sysco is the global leader in foodservice distribution with over 71,000 colleagues and 333 distribution facilities worldwide.

Transportation Clerk

Company: Sysco

Location: Danville, IL

Posted Jan 23, 2025

Product Owner - Business Intelligence

Company: Coca-Cola

Location: Rosemont, IL

Posted Jan 23, 2025

The Product Owner - Business Intelligence role is responsible for maximizing the value of Business Intelligence and Analytics solutions. This involves aligning the team's technical direction with business strategies and goals, prioritizing work, and creating product roadmaps. The role also includes educating stakeholders about Agile and SCRUM practices, evangelizing BI solutions, and maintaining transparent communication with business partners. The position may also involve participating in a discretionary incentive program.

Paid Social Marketing Manager

Company: Walgreens

Location: Chicago, IL

Posted Jan 23, 2025

The job involves managing a multimillion-dollar paid social marketing budget, developing strategies to support sales efforts, and driving customer acquisition and retention. The role requires a strong technical background, experience in digital marketing, and the ability to analyze data and A/B test. The individual will lead internal social teams, manage agency relationships, and stay updated on industry trends. They will also work cross-functionally to support key initiatives and product launches.

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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