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.

Pharmacy Technician

Company: CVS Health

Location: Ottawa, IL

Posted Jan 23, 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.

Shift Supervisor Trainee

Company: CVS Health

Location: Chicago, IL

Posted Jan 23, 2025

CVS Health is offering a Shift Supervisor Trainee position, an entry-level role designed to prepare employees for higher-level supervisory roles. The role involves working effectively with store management and crews, supervising activities, and ensuring smooth store operations. The company emphasizes a human-centric approach to healthcare, focusing on personal, convenient, and affordable solutions. Upon successful completion of the training, trainees can be considered for Operations Supervisor or Shift Supervisor positions. The role requires deductive reasoning, analytical skills, and computer skills, with a flexible schedule including early mornings, overnight, and weekend shifts. The company offers a comprehensive benefits package, including medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, education assistance, and a CVS store discount.

Outside Sales Professional

Company: Rentokil Terminix

Location: Marion, IL

Posted Jan 23, 2025

The text describes a job opportunity for a Residential Sales Specialist at Rentokil, a global leader in pest control. The role involves selling pest management services and products to new and existing residential customers, assessing their needs, and providing expert knowledge of the company's offerings. Benefits start on the first day with no waiting period. Rentokil is committed to professional growth, offering training, development programs, tuition reimbursement, and a comprehensive benefits package including health, dental, vision, disability, and life insurance. The company promotes from within, offers performance incentives, and prioritizes work-life balance.

Facilities Maintenance Electrician

Company: Advanced Technology Services

Location: Peoria, IL

Posted Jan 23, 2025

ATS, founded in 1985, is a global industrial maintenance company with operations in the US, Mexico, and the UK. They specialize in improving factory performance through expert break-fix and preventative maintenance. Key responsibilities include identifying and sourcing parts, performing maintenance according to industry standards, and utilizing predictive maintenance technologies. The role requires a high school diploma or equivalent, technical degree, and relevant industry experience. Physical demands include standing, walking, lifting, and working in a loud, potentially hazardous factory environment.

Career Educator Seneca Lane KinderCare

Company: KinderCare Learning Companies

Location: Bolingbrook, IL

Posted Jan 23, 2025

KinderCare Learning Companies, the first and only early childhood education provider recognized with the Gallup Exceptional Workplace Award, is seeking a Teacher to lead, coach, and mentor less experienced teachers. The role involves implementing KinderCare's curriculum, creating a nurturing environment, partnering with parents, and supporting the center's success. Benefits include discounted child care, medical, dental, and vision coverage, mental health support, and more. The company operates in over 2,000 sites across 40 states, committed to providing high-quality child care for all families.

Employer Brand Program Manager, Events & Partnerships, Americas

Company: Adyen

Location: Chicago, IL

Posted Jan 23, 2025

Adyen, a financial technology platform serving clients like Meta, Uber, H&M, and Microsoft, is seeking an Employer Brand Program Manager for the Americas. The role involves strategizing, planning, and executing high-visibility employer brand initiatives, managing events and partnerships, and collaborating with various teams. The ideal candidate should have 5+ years of events marketing experience, a strong track record of driving results, and passion for DEI. The role is based in Chicago and offers a salary range of $115,000-$160,000.

Strategic Account Associate

Company: Advanced Technology Services

Location: Peoria, IL

Posted Jan 23, 2025

ATS, founded in 1985, is a global industrial maintenance company with operations in the US, Mexico, and the UK. They specialize in improving factory efficiency. Key responsibilities include maintaining and growing account revenue, developing new business, and cultivating relationships with key decision-makers. The role requires a Bachelor's degree, relevant experience, and proven success in business development. Essential skills include negotiation, decision-making, and driving results. Physical demands involve standing, walking, and occasionally lifting heavy weights. ATS is committed to equal employment opportunities.

Art Director, Digital Product

Company: CapTech

Location: Chicago, IL

Posted Jan 23, 2025

Senior Analytics Engineer

Company: CVS Health

Location: Northbrook, IL

Posted Jan 23, 2025

Store Manager In Training

Company: CVS Health

Location: Rockford, IL

Posted Jan 23, 2025

CVS Health is offering a Store Manager In Training (SMIT) program, a 16-week development role designed to prepare individuals for a CVS Store Manager position. The program includes self-paced, collaborative training with virtual and hands-on learning experiences. Key responsibilities include effective communication, customer care, merchandising strategies, and inventory management. CVS Health supports growth with a team of leaders and offers a competitive pay range, comprehensive benefits, and opportunities for career advancement.

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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