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 Data Science Product Mgr

Company: Health Care Service Corporation

Location: Chicago, IL

Posted May 18, 2025

Bachelors degree and 5 years of work experience in a mathematical, statistical, computer science, engineering, physics, economics or related quantitative field…

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Senior Associate, Oracle ERP

Company: Options Clearing Corporation

Location: Chicago, IL

Posted May 15, 2025

You will be asked to define requirements, investigate and implement configuration changes, test, deploy, and lead efforts to implement cross-functional…

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Pet Insurance Sales Associate - Chicago, IL

Company: Fetch Pet Insurance

Location: Chicago, IL

Posted May 20, 2025

Active Property & Casualty (P&C) license or willing to obtain a P&C license at the expense of the Company within 30 days of employment (subject to state…

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Sr. Mgr, Software Engineering

Company: Capital One

Location: Chicago, IL

Posted May 19, 2025

Experience leading teams through ambiguity by driving technical design and delivery decisions. Capital One will consider for employment qualified applicants…

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Lead Software Engineer, Back End

Company: Capital One

Location: Chicago, IL

Posted May 15, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

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Risk Analytics Data Scientist

Company: PayPal

Location: Chicago, IL

Posted May 15, 2025

A master’s or advanced degree in a quantitative field such as statistics, mathematics, finance, or economics. We enable consumers to exchange funds more safely…

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Senior Manager, Software Engineer (People Leader)

Company: Capital One

Location: Chicago, IL

Posted May 19, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

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mentorship health system full time

UIC Physician Assistant (Orthopaedics)

Company: University of Illinois-Chicago

Location: Chicago, Illinois

Posted May 16, 2025

View Details Apply on healthecareers.com

Registered Nurse All Shifts

Company: Alden Lincoln Park Rehabilitation and Health Care Center

Location: Chicago, IL

Posted May 15, 2025

Must possess a current, unencumbered license to practice as a RN in the State of Illinois and/or Wisconsin. Plan, develop, organize, implement, evaluate, and…

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People Intelligence and Engagement Partner

Company: Chainlink Labs

Location: Chicago, IL

Posted May 16, 2025

Tuning into the Web 3 industry and business to keep abreast with trends to reflect in own workstreams. High proficiency in operational tools (e.g., Sheets,…

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Clinical Analyst

Company: JACKSON PARK HOSPITAL AND MEDICAL CENTER

Location: Chicago, IL

Posted May 16, 2025

Assist in the development and implementation of new digital tools and technologies to improve patient outcomes. Associates Degree Minimum, Bachelors preferred.

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Mgr Clinical Pharmacy

Company: Rush University Medical Center

Location: Chicago, IL

Posted May 20, 2025

> 6 years practice experience, Pharm.D. with PGY1 and PGY2 training (or equivalent experience), Illinois licensure, and board certification (specialty…

View Details Apply on SimplyHired

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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