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.

Actuarial Analyst

Company: Argo Group

Location: Chicago, IL

Posted Jan 23, 2025

Automation Mechanic - 3rd Shift

Company: CVS Health

Location: Mount Prospect, IL

Posted Jan 23, 2025

Senior Financial Analyst

Company: Addison Group

Location: Chicago, IL

Posted Jan 23, 2025

A client in Downers Grove, Illinois is looking for a Financial Analyst with technical and analytical skills. The role involves database management, financial analysis, and database maintenance for the retail division. Essential qualifications include Visual Basic experience, a Bachelor's Degree in Finance or Accounting, advanced Microsoft Excel skills, 4+ years of financial analysis experience, and SQL experience. The position is initially a contract-to-hire role.

Commercial Real Estate Senior Lead Transaction Manager

Company: Wells Fargo

Location: Chicago, IL

Posted Jan 23, 2025

Wells Fargo is seeking a CRE Lead Transaction Manager with 7+ years of Capital Markets Document Negotiation experience. The role involves strategic planning, problem-solving, and leadership. Key responsibilities include advising senior leadership, leading complex challenges, delivering long-term solutions, and managing legal agreements. The ideal candidate should have a strong understanding of lending products, loan lifecycles, and deal structures. They must be process-focused, proactive, adaptable, and capable of collaborating with senior management. The position offers a competitive salary range of $144,400 - $300,000 and comprehensive benefits.

Business Strategy Insurance Manager

Company: Accenture

Location: Chicago, IL

Posted Jan 23, 2025

Accenture Strategy offers an opportunity to transform leading organizations globally, with a focus on innovation and growth. The role involves developing operational and growth strategies, managing client engagements, and delivering value at the intersection of business and technology. Accenture invests heavily in training and development, fostering a team-oriented environment and promoting diversity. The Insurance Strategy Manager will work closely with senior clients, shaping business strategies, and managing transformation engagements. Bonus points for candidates with an MBA and relevant industry experience.

Payments Tech Lead Software Engineer - Java

Company: JPMorgan Chase

Location: Chicago, IL

Posted Jan 23, 2025

JPMorgan Chase is offering a Lead Software Engineer position in the Payments Technology team. The role involves working in an agile team to enhance, build, and deliver trusted market-leading technology products. Key responsibilities include executing creative software solutions, developing secure high-quality production code, and leading evaluation sessions with external vendors. The ideal candidate should have formal training in software engineering, 5+ years of applied experience, and advanced skills in Core Java, Object Oriented, RDBMS (Oracle), SQL, Spring, and Unix Scripts. Familiarity with container-based development, orchestration, and microservices frameworks is advantageous. JPMorgan Chase offers a competitive total rewards package, comprehensive health care coverage, and a diverse and inclusive work environment.

Training Specialist

Company: Black Mountain

Location: Chicago, IL

Posted Jan 23, 2025

Pharmacy Technician

Company: CVS Health

Location: Chicago, IL

Posted Jan 23, 2025

CVS Health emphasizes its commitment to human-centric health care, guided by a single purpose: 'Bringing our heart to every moment of your health.' The company aims to deliver enhanced, personalized, convenient, and affordable health care solutions. Pharmacy Technicians play a crucial role in this mission, supporting pharmacy teams to ensure smooth operations, accurate prescription fulfillment, and exceptional patient service. Technicians are expected to demonstrate empathy, genuine care, and a growth mindset, contributing to a safe, inclusive, and engaging team dynamic. They must comply with all relevant laws and regulations, and complete necessary training and certification requirements.

Workday (Certified) Project Manager

Company: Accenture

Location: Bloomington, IL

Posted Jan 23, 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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