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 Analyst

Company: Discover

Location: Riverwoods, IL

Posted Jan 22, 2025

Consulting, Specialist Master

Company: Deloitte

Location: Chicago, IL

Posted Jan 22, 2025

Deloitte Consulting LLP is seeking a Consulting, Specialist Master in Chicago, Illinois and various unanticipated Deloitte office locations and client sites nationally. The role involves managing IT projects for software testing and implementation services across multiple industries. Key responsibilities include managing test estimation, planning, design, execution, and reporting, coordinating testing across all phases, and serving as a technical liaison between business, project team, and developers/testers. The role also involves managing day-to-day interactions with executives, coaching staff, and improving internal processes. A Master's degree or foreign equivalent in a relevant field with 3 years of related work experience is required. The position offers a competitive salary and benefits, with 50% travel required nationally.

Content Design Senior Associate

Company: JPMorgan Chase

Location: Chicago, IL

Posted Jan 22, 2025

JPMorgan Chase is seeking a Content Design Senior Associate to join the Corporate & Investment Bank Payments Team. The role involves creating and structuring product content within a user experience design framework, collaborating with cross-functional teams, and developing content strategies. The ideal candidate should have 3+ years of experience in content design, expertise in digital products, and understanding of accessibility guidelines. The company offers competitive total rewards, diverse talent opportunities, and a global presence in investment banking and securities services.

Systems Engineer / Architect

Company: Leidos

Location: O'Fallon, IL

Posted Jan 22, 2025

Solutions Architect III

Company: Grainger

Location: Lake Forest, IL

Posted Jan 22, 2025

Store Executive Intern (Store Leadership Intern)-Broadview, IL (Starting Summer 2025)

Company: Target

Location: North Riverside, IL

Posted Jan 22, 2025

Target is offering a paid 40-hour-per-week Stores Executive Leadership Internship. This program aims to provide a realistic job preview of an Executive Team Leader (ETL) role, teaching skills such as guest service fundamentals, retail business acumen, team management, and business strategy development. Interns will work closely with mentors, learn to lead a team, drive sales, and provide exceptional guest service. The role involves leading daily operations, addressing team member concerns, and participating in developmental activities. Target values leaders who are adaptable, have strong communication skills, and demonstrate a commitment to ethical conduct and safety.

Cybersecurity Analyst ( Cyber Assessment)

Company: Discover

Location: Riverwoods, IL

Posted Jan 22, 2025

Discover is offering a job opportunity for a Cybersecurity professional with deep expertise in governance, risk management, and alignment to industry frameworks like NIST CSF 2.0. The role involves ensuring compliance with cybersecurity policies, validating security controls, and driving continuous improvement. The company values unique qualities and encourages growth, offering a chance to make a difference at a leading digital banking and payments company. The position requires a Bachelor's Degree in a relevant field and 4+ years of experience in Information Security or related fields. Bonus points for certifications like CISSP and CISM. The base pay ranges from $91,000.00 to $153,400.00, with additional incentives possible. Discover is committed to a diverse and inclusive workplace.

Director, Data Science

Company: West Monroe

Location: Chicago, IL

Posted Jan 22, 2025

Veterinarian

Company: Banfield Pet Hospital

Location: Chicago, IL

Posted Jan 22, 2025

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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