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.

Lead Python Developer, Data Analytics

Company: CVS Health

Location: Springfield, IL

Posted Jan 22, 2025

CVS Health is seeking a Lead Python Developer with 3+ years of experience in software engineering with Python. The role is part of Aetna's Commercial's Sales Enablement department, focusing on designing and developing new Python code for healthcare analytics and reporting. Key responsibilities include creating business applications, refactoring legacy code, and communicating analytical findings to stakeholders. Required qualifications include proficiency in Python, Polars, NumPy, Pandas, XML, JSON, YAML, and Git. Preferred qualifications include experience with SQL, Plotly, Dash, front-end development, cloud computing providers, and specialized Python data management libraries.

Retail Sales Specialist - Part-Time -$18.00 per hour, plus commission and incentives!

Company: Spectrum

Location: Upper Alton, IL

Posted Jan 22, 2025

Spectrum, a leading TV, internet, and voice provider, is offering a part-time retail sales role with competitive earnings. The position involves selling wireless, TV, and internet products, with targeted hourly earnings of $22.50. Part-time employees working at least 20 hours per week are eligible for comprehensive benefits including insurance and discounted Spectrum services. The role is ideal for digitally savvy, competitive individuals with wireless sales experience. Spectrum provides extensive training, competitive base salary, and generous commission structure. Career advancement is achievable, with most managers having started as Retail Sales Specialists. The job requires thriving in a fast-paced environment, strong communication skills, and the ability to lift up to 35 lbs.

Electrical Engineer - Systems Test Equipment (Onsite)

Company: RTX

Location: Rockford, IL

Posted Jan 22, 2025

Collins Aerospace is seeking an experienced Electrical Engineer for an onsite role in Rockford, Illinois. The role involves designing, building, and testing electrical systems for aircraft power generation systems, contributing to the advancement of electric power technologies in aviation. Key responsibilities include evaluating test plans, designing harnessing and feeders, incorporating instrumentation into test setups, and coordinating the build, checkout, operation, maintenance, and troubleshooting of electrical systems. The ideal candidate should have a STEM degree with 5+ years of relevant experience or an advanced degree with 3+ years of experience. Preferred qualifications include experience in electrical design and integration, collaboration with test operators, and proficiency in LabView software development. Collins Aerospace offers a competitive benefits package, including medical, dental, vision insurance, generous vacation, a 401(k) plan, tuition reimbursement, and more. This role is also eligible for the Re-Empower Program, a 14-week initiative to help professionals rebuild capabilities and enhance leadership skills.

Senior Manager - Aircraft Cybersecurity

Company:

Location: Chicago, IL

Posted Jan 22, 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.

Teachers at Spring Street KinderCare

Company: KinderCare Learning Companies

Location: South Elgin, IL

Posted Jan 22, 2025

KinderCare Learning Companies, the first and only early childhood education provider recognized with the Gallup Exceptional Workplace Award, offers a variety of early education and child care options. They invest in teachers, center staff, and field leaders, who are considered the heart and soul of the business. The company provides comprehensive benefits, including discounted child care, medical, dental, and vision coverage, and employee assistance programs. KinderCare operates in more than 2,000 sites and centers across 40 states, committed to providing high-quality child care to all families, regardless of their background.

Restaurant Manager - Quarterly Bonus Available

Company:

Location: Carbondale, IL

Posted Jan 22, 2025

Chili's Managers are passionate about hospitality, connecting with team members and guests, and creating a fun work environment. They are responsible for ensuring a great guest experience, leading shifts, managing costs, and developing team members. Chili's values a culture of fun, teamwork, and accountability, with a focus on food perfection and inclusivity.

(USA) Area Manager - Maintenance (Fashion, Import, Print Solutions, Regional, Returns, Sam's, Wm.Com)-2

Company: Walmart

Location: Joliet, IL

Posted Jan 22, 2025

The role involves communicating with various individuals or groups, implementing business plans, managing staffing and scheduling, maintaining quality and safety standards, supervising and developing associates, managing maintenance department operations, and ensuring compliance with regulations. The leadership expectations emphasize respect for individuals, integrity, service to customers, striving for excellence, and competitive compensation including benefits like health, financial, and paid time off benefits.

Residential Lawn Specialist/Aerator

Company: TruGreen

Location: Plainfield, IL

Posted Jan 22, 2025

TruGreen, a leading lawn care company, is accepting applications on an ongoing basis. They emphasize the importance of every role in their company's success and offer a variety of positions including Lawn Specialists, Tree & Shrub Specialist, Aerator, Laborer, and Warehouse Technician. The job description highlights competitive wages, average income of $850 - $1,200/week, affordable health insurance, financial health resources, and training & development opportunities. TruGreen values its employees, customers, and the science of lawn care, promising a career full of new opportunities and pride in work. They also offer paid time off, sick leave, and a commitment to diversity and inclusion.

Payments Solutions Attorney -Vice President, Assistant General Counsel

Company: JPMorgan Chase

Location: Chicago, IL

Posted Jan 22, 2025

J.P. Morgan Payments Legal team supports a global, innovative payments business within Corporate and Investment Bank. The role of Payments Solutions Attorney - Vice President Assistant General Counsel involves working with a successful team of lawyers, collaborating with global business teams, and providing strategic legal advice. The Legal Department at JPMorgan Chase & Co. is a global team of 2,000 lawyers, known for thought leadership and best-in-class services. The successful candidate should have a JD, 5+ years of legal experience, strong interest in payments solutions, and excellent communication, drafting, and negotiation skills.

Retail Supervisor, Full Time, Product Operations - Eastland-Bloomington

Company: Gap Inc.

Location: Bloomington, IL

Posted Jan 22, 2025

Old Navy is a fashion retailer that aims to democratize style and make shopping enjoyable. Established in 1994, the company offers high-quality, affordable essentials for the whole family. The role involves supporting store leadership, modeling selling behaviors, and ensuring a positive customer experience. Key responsibilities include treating customers and employees with respect, promoting loyalty programs, and maintaining productivity. The ideal candidate is tech-savvy, flexible, and committed to continuous improvement. Old Navy offers competitive benefits, including merchandise discounts, paid time off, and a robust 401(k) plan.

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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