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 Customer Service Representative

Company: TruGreen

Location: St. Charles, IL

Posted Jan 22, 2025

TruGreen is hiring for a customer service role in West Chicago, Illinois. The position involves handling inbound calls to resolve customer issues, providing support to new hires, and assisting with onboarding and training. The ideal candidate should have 2-3 years of customer service experience, preferably in a call center environment. Knowledge of lawn care services and strong communication skills are required. TruGreen offers competitive pay, benefits, and a commitment to diversity and inclusion.

Pharmacy Technician

Company: CVS Health

Location: Calumet City, IL

Posted Jan 22, 2025

CVS Health emphasizes a heart-centric approach to healthcare, aiming to deliver personalized, convenient, and affordable services. The company's purpose is to bring heart to every moment of health, supported by their Heart At Work Behaviors™. Pharmacy Technicians play a crucial role in their retail locations, contributing to operational excellence, positive patient experiences, and a safe, inclusive culture. They are expected to complete a training program and meet state-specific licensing requirements. The role involves various responsibilities, including following SOPs, contributing to positive patient experiences, and potentially administering immunizations. CVS Health offers competitive pay, comprehensive benefits, and a supportive work environment.

Senior Director, Procurement - Technology and Marketing

Company: Walgreens

Location: Deerfield, IL

Posted Jan 22, 2025

The role involves developing strategy, leading change management, and directing a team of Directors, Category Managers, and Category Specialists. Key responsibilities include establishing objectives for spend categories, overseeing sourcing and procurement strategies, and driving cross-functional category teams in change management. The position requires managing approximately $2 Billion of Company resources, creating collaborative business plans with strategic vendors, and ensuring goods and services meet established standards and legal requirements. The ideal candidate should have a Bachelor's degree and at least 8 years of experience in strategic sourcing, with a proven track record in managing category spend in excess of $1B. Strong leadership, communication, and negotiation skills are essential, along with proficiency in Microsoft Office Suite.

Beauty and Wellness Consultant

Company: Walgreens

Location: Chicago, IL

Posted Jan 22, 2025

Info Systm Architect

Company: TIAA

Location: Chicago, IL

Posted Jan 22, 2025

The Information Systems Architect develops complex architectural guidelines, specifications, and technical standards for running end-user applications. They work under minimal supervision to convert end-user needs into technical solutions and design systems that integrate multiple platforms, operating systems, and applications across the enterprise.

Shift Supervisor Trainee

Company: CVS Health

Location: DeKalb, IL

Posted Jan 22, 2025

CVS Health is a company that values its employees and customers, offering various benefits such as medical, dental, and vision insurance, 401(k) retirement savings plan, and employee stock purchase plan. The Shift Supervisor Trainee role prepares an employee for higher-level supervisory responsibilities and provides opportunities for growth and development.

Solution Consultant e-invoicing

Company: Thomson Reuters

Location: Chicago, IL

Posted Jan 22, 2025

Thomson Reuters is seeking a Solutions Consultant to support sales and partner teams with expert knowledge in Thomson Reuters ONESOURCE Pagero services, industry, SAAS, competition, and general O2C and P2P markets. The role involves liaising with subject matter expert teams, directly with Pagero/TR customers and opportunities, and presenting the Pagero/TR suite of solutions. Key responsibilities include managing demo accounts, responding to commercial team questions, completing RFx and data security questionnaires, and maintaining data in Loopio. The role offers a competitive compensation package of $100,000-130,000 base salary and $20,000 variable compensation. Thomson Reuters provides a comprehensive benefits package including wellbeing, culture, learning & development, social impact, purpose-driven work, and work-life balance benefits.

Automation Mechanic - 2nd Shift

Company: CVS Health

Location: Mount Prospect, IL

Posted Jan 22, 2025

Pharmacy Technician

Company: CVS Health

Location: Plainfield, IL

Posted Jan 22, 2025

CVS Health emphasizes a heart-centric approach to healthcare, aiming to deliver personalized, convenient, and affordable services. The company's purpose is to bring heart to every moment of health, supported by their Heart At Work Behaviors™. Pharmacy Technicians play a crucial role in achieving this, ensuring smooth pharmacy operations, accurate prescription fulfillment, and exceptional patient experiences. They contribute to a safe, inclusive culture and are required to complete a training program and meet state-specific licensing and certification requirements.

Registered Manager Local Specialty

Company: Walgreens

Location: Rockford, IL

Posted Jan 22, 2025

The role involves directing a Walgreens Local Specialty Pharmacy, focusing on improving sales, profits, and image. Key responsibilities include managing personnel, building patient relationships, and overseeing clinical management. The individual is expected to model excellent customer service, respond to patient inquiries, and ensure compliance with regulations. They will also develop business plans, maintain inventory, and manage pharmacy operations, ensuring adherence to federal and state laws.

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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