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.

Center Director

Company: KinderCare Learning Companies

Location: Homewood, IL

Posted Jan 21, 2025

KinderCare Learning Companies, the first early childhood education provider to receive the Gallup Exceptional Workplace Award, is seeking a Center Director. This role involves hiring, engaging, and developing a team of educators, partnering with parents, and cultivating positive relationships with families, teachers, and community partners. The Center Director will use their business, sales, and marketing skills to grow KinderCare's presence in the community. Benefits include discounted child care, medical, dental, and vision coverage, mental health support, health and wellness programs, and more. KinderCare is committed to providing high-quality child care to all families, regardless of their background.

Senior Manager - Aircraft Cybersecurity Operations

Company:

Location: Itasca, IL

Posted Jan 21, 2025

United Airlines is inviting applications for a Senior Manager of Aircraft Cybersecurity Operations. The role involves leading a team to ensure United's aircraft-related products comply with cybersecurity regulations. Responsibilities include managing cybersecurity processes, administrative tasks, and collaborating with internal and external partners. The ideal candidate should have a technical background, aviation experience, and strong communication skills. A master's degree and certifications in cybersecurity are preferred but not mandatory. United offers competitive benefits and a remote work option. The salary range is $126,225 - $185,130.

Financial Services Security Manager-Northeast

Company: Accenture

Location: Chicago, IL

Posted Jan 21, 2025

Accenture offers diverse career opportunities in Consulting, Technology, Operations, and Corporate Functions. Consulting professionals design strategies to enhance business performance, while Security professionals protect enterprise systems, applications, and data. The company values diversity, inclusion, and equal employment opportunities, and is committed to providing reasonable accommodations for employees and applicants with disabilities or religious observances.

Shift Lead

Company: Walgreens

Location: Chicago, IL

Posted Jan 21, 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 Chicago, IL, with a salary range of $17 - $19 per hour.

Application Engineer (AbInitio)

Company: Discover

Location: Riverwoods, IL

Posted Jan 21, 2025

Discover is inviting applications for a role in the Business Technology Finance Corporate Services Team. The position involves providing technical leadership for ETL pipeline applications, developing data-driven solutions, and ensuring high-quality production. The ideal candidate will have excellent communication skills, be able to manage risks, and mentor early-career engineers. Knowledge of AWS, Data Warehouse technology, and ETL migration is a plus. The role requires a bachelor's degree in a relevant field, 3+ years of IT or engineering experience, and the ability to work in a stationary position. The base pay ranges from $89,000 to $150,200 with additional incentives. Discover offers a range of benefits and is committed to a diverse and inclusive workplace.

Sales Management Trainee Internship - Peoria, IL - Summer 2025

Company: Enterprise Mobility

Location: Peoria, IL

Posted Jan 21, 2025

The Enterprise Management Internship offers university/college students a 90-day paid opportunity to gain real-world business and leadership skills. Interns will work alongside full-time professionals, handling tasks such as fleet management, customer service, marketing strategies, and relationship building. The internship includes corporate training, friendly competition, and potential performance incentives. Eligibility requires current student status, a valid driver's license, and U.S. work authorization.

Teachers at Rockford KinderCare

Company: KinderCare Learning Companies

Location: Rockford, IL

Posted Jan 21, 2025

KinderCare Learning Companies, the leading early childhood education provider, offers a variety of child care options including KinderCare Learning Centers, Champions, and Crème de la Crème. They emphasize building confidence in kids, families, and the future. The company values its teachers and staff, providing a supportive environment and opportunities for career growth. Benefits include discounted child care, health insurance, mental health support, and more. KinderCare operates in over 2,000 sites across 40 states, committed to providing high-quality child care to all families, regardless of background or location.

Sr Software Development Engineer - Full Stack Java

Company: CVS Health

Location: Buffalo Grove, IL

Posted Jan 21, 2025

CVS Health is seeking a Java Software Engineer for their Platform Innovation team in Buffalo Grove, IL. The role involves working in an eXtreme Programming (XP) environment, building high-quality products, and maintaining a user-centered approach. The ideal candidate should have 5+ years of experience in enterprise solution delivery, preferably in a J2EE environment, and 2+ years of Java development experience. Knowledge of Spring Boot, Spring MVC, NodeJS, Angular, or React is beneficial. The position requires experience in Agile-based development, including CI/CD and TDD. CVS Health offers a competitive pay range, comprehensive benefits, and a culture that values diversity, inclusion, and belonging.

Emerging Store Manager

Company: Walgreens

Location: Hoffman Estates, IL

Posted Jan 21, 2025

Senior Manager - Aircraft Cybersecurity Operations

Company:

Location: Evanston, IL

Posted Jan 21, 2025

United Airlines is inviting applications for a Senior Manager - Aircraft Cybersecurity Operations role. This position involves leading a team of cybersecurity engineers to ensure end-to-end security architecture of United's aircraft-related products. The role requires aviation experience, strong technical communication skills, and experience in risk management. United offers a competitive benefits package and values diverse experiences. The ideal candidate will have a STEM or Engineering degree, 9+ years of related experience, and knowledge of aviation cybersecurity and IT security best practices.

GM and Food (General Merchandise, Closing, Fulfillment, Inbound, Food and Beverage , Starbucks) (T0893)

Company: Target

Location: Itasca, IL

Posted Jan 21, 2025

Target, a Fortune 50 company, is offering a General Merchandise Expert position with a starting hourly rate of $16.50 USD. The role involves creating a welcoming experience for guests, ensuring product availability, and maintaining accurate pricing and signing. The team leads inbound, outbound, replenishment, inventory accuracy, presentation, pricing, and promotional signing processes. Target values team members' growth and offers opportunities for skill development. The job requires a welcoming attitude, ability to communicate on multiple frequency devices, and capacity to work in varying temperatures.

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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