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 Manager - Aircraft Cybersecurity

Company:

Location: Chicago, IL

Posted Jan 22, 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. Key responsibilities include creating and implementing a cybersecurity strategy, managing aircraft cybersecurity processes, and coordinating with internal and external partners. United offers a competitive benefits package and values diverse experiences. Minimum qualifications include a STEM degree, aviation experience, and strong communication skills.

Shift Lead

Company: Banfield Pet Hospital

Location: Chicago, IL

Posted Jan 22, 2025

J.P. Morgan Wealth Management - Private Client Advisor - Chicago O'Hare / Cook County Northwest

Company: JPMorgan Chase

Location: Oakbrook, IL

Posted Jan 22, 2025

J.P. Morgan Chase is seeking a Private Client Advisor in Chase Wealth Management. The role involves offering comprehensive financial planning and advice to individuals and families, with a focus on relationship management rather than portfolio management. The ideal candidate should have at least 2 years of Financial Advisor experience, demonstrated success in client acquisition, and a commitment to goals-based planning. Required qualifications include valid Series 7, 66 (63/65), Life, Health, and Long Term Care Insurance licenses. Preferred qualifications include CFP® certification and a Bachelor's degree. The company offers a competitive total rewards package, extensive benefits, and a commitment to diversity and inclusion.

Pharmacy Technician

Company: CVS Health

Location: Decatur, IL

Posted Jan 22, 2025

Teachers at Woodridge North KinderCare

Company: KinderCare Learning Companies

Location: Bolingbrook, 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 emphasize building confidence in kids, families, and the future. The company values its teachers, center staff, and field leaders, providing them with comprehensive benefits and opportunities for career growth. They implement a curriculum tailored to each child's needs, fostering a safe, nurturing environment for learning and growth. KinderCare is committed to supporting its employees' mental health and personal growth, offering a range of benefits including discounted child care, medical, dental, and vision coverage, and wellness programs.

Site Reliability Engineer (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 22, 2025

Enova International is seeking a Site Reliability Engineer with 2+ years of experience in SRE, DevOps, Systems Administration, or Infrastructure Support. The role involves maintaining and improving the reliability of their consumer business, collaborating with various teams, and applying DevOps principles. The position offers competitive compensation, hybrid work model, and comprehensive benefits. Enova is committed to equal employment opportunities and fostering an inclusive work environment.

Senior Manager - Aircraft Cybersecurity

Company:

Location: Itasca, IL

Posted Jan 22, 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.

Principal Enterprise Risk Management, Risk Insights, Reporting, and Analytics

Company: Discover

Location: Riverwoods, IL

Posted Jan 22, 2025

Discover is offering a job opportunity for a professional with a background in Risk Management, Financial Services, or related fields. The role involves designing, developing, and maintaining the company's Enterprise Risk Management (ERM) Policy and Framework. The successful candidate will work collaboratively with business and risk partners, engaging in analytical and reporting initiatives, automation, and problem-solving. They will also develop reporting dashboards, provide tactical leadership in monitoring and reporting practices, and support enhancements to the New Initiatives and Change Management program. The position requires a Bachelor's Degree and 6+ years of relevant experience, with a preference for a Master's Degree and RIMS certification. The role involves indoor office work, with up to 10% travel. The base pay ranges from $91,000 to $153,400, with additional incentives possible. Discover offers a range of benefits and is committed to a diverse and inclusive workplace.

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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