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.

Consulting, Senior Consultant

Company: Deloitte

Location: Chicago, IL

Posted Jan 24, 2025

Pharmacy Technician

Company: CVS Health

Location: Upper Alton, IL

Posted Jan 24, 2025

General Manager 5 - Food

Company: Sodexo

Location: Chicago, IL

Posted Jan 24, 2025

Pharmacy Technician

Company: CVS Health

Location: Peoria, IL

Posted Jan 24, 2025

CVS Health emphasizes its commitment to human-centric health care, guided by the purpose of 'Bringing our heart to every moment of your health'. The company aims to deliver enhanced, personalized, convenient, and affordable health care solutions. Pharmacy Technicians play a crucial role in this mission, supporting pharmacy teams to ensure smooth operations, accurate prescription fulfillment, and exceptional patient service. They are expected to demonstrate empathy, genuine care, and a growth mindset, contributing to a safe, inclusive, and engaging team dynamic. The role involves completing basic inventory activities, delivering additional health care services, and adhering to all relevant laws and regulations.

Lead Architect

Company: CVS Health

Location: Springfield, IL

Posted Jan 24, 2025

CVS Health is seeking an experienced Enterprise Architect to join their team, driving innovation and collaboration for their platform. The role involves defining and creating roadmaps, architectures, standards, and best practice documents. The ideal candidate should have 10+ years of relevant experience, including expertise in architectural methodologies, design patterns, and best practices. They should also possess a diverse technical background with depth in AI/ML, cloud, data platforms, and hybrid solutions. The role offers a competitive pay range, comprehensive benefits, and opportunities for professional growth.

Principal Product Owner (Backend Platform)

Company: Discover

Location: Riverwoods, IL

Posted Jan 24, 2025

Discover is offering a Product Professional role with a collaborative culture, opportunities for growth, and the chance to make a significant impact at a leading digital banking and payments company. The role involves partnering with stakeholders to define product vision, assess product performance, and develop strategic product plans. Key responsibilities include building product backlogs, aligning with compliance and quality standards, and collaborating with cross-functional teams to develop go-to-market strategies. The ideal candidate should have a Bachelor's degree in a relevant field and 6+ years of experience in Product Management or Engineering in Financial Services or Tech Industry. Bonus points for knowledge of APIs, Microservices, Datadog or Instana, and Agile certifications.

Backroom Coordinator

Company: The TJX Companies, Inc.

Location: Peoria, IL

Posted Jan 24, 2025

Marshalls, a retail store, is seeking a team player with 1 year of retail experience and 6 months of leadership experience. The role involves executing receiving and merchandising standards, ensuring a clean and organized store, and providing excellent customer service. The company offers a flexible schedule, competitive pay, and comprehensive benefits including associate discount, 401(k), health insurance, and more. Marshalls emphasizes a culture of honesty, integrity, and continuous change, encouraging employees to 'Discover Different' every day.

Store Manager

Company: The TJX Companies, Inc.

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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