Technical Leadership Jobs in Chicago, IL

41,758 open positions · Updated daily

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.

Operations Manager

Company: CVS Health

Location: South Elgin, IL

Posted Jan 22, 2025

CVS Health is seeking an Operations Manager to lead a store team, driving execution and performance while enhancing customer service. The role involves overall store management, sales and inventory management, employee staffing and development, and financial management. The ideal candidate will have strong leadership, communication, and analytical skills, and be able to work flexible hours. CVS Health offers competitive pay, comprehensive benefits, and opportunities for professional growth.

Sr Customer Success Consultant

Company: TransUnion

Location: Chicago, IL

Posted Jan 22, 2025

TransUnion is seeking a Senior Customer Success Consultant with a Bachelor's degree in business, finance, or computer science, and 5+ years of experience in consultancy, project management, implementation management, and/or fraud management. The role involves working with great people, pioneering products, and cutting-edge technology. The consultant will lead customer engagements across various industries, providing best-in-class insights and deliverables. They will own the operational relationship with high-level clients, positioning themselves as trusted advisors. The role is hybrid, involving regular virtual and in-person work at an assigned TransUnion office location. Benefits include flexible time off, health benefits, parental leave, tuition reimbursement, and more. The U.S. base salary range for this position is $82,700.00 - $120,000.00 annually.

Senior Manager Data Science

Company: Discover

Location: Riverwoods, IL

Posted Jan 22, 2025

Account Executive - Midwest (Field)

Company: BD

Location: Vernon Hills, IL

Posted Jan 22, 2025

BD, a leading global medical technology company, is seeking an Account Executive for Parata sales in the Midwest. The role involves achieving sales quotas, developing new business opportunities, and managing relationships with key decision-makers. The ideal candidate should have a Bachelor's degree, five years of capital pharma and/or medical device sales experience, and a strong knowledge of clinical practice workflow and financial operations. BD values collaboration, innovation, and effective problem-solving, and requires a minimum of 4 days of in-office presence per week. The company is an Equal Opportunity/Affirmative Action Employer.

Pharmacy Technician

Company: CVS Health

Location: Aurora, IL

Posted Jan 22, 2025

Director Security Solutions Sales

Company: Mastercard

Location: Chicago, IL

Posted Jan 22, 2025

Mastercard is seeking a Director of Sales for the North American Services Team. The role involves leading a portfolio of key accounts, developing sales strategies, and driving revenue growth. The ideal candidate should have extensive experience in sales, particularly in the banking industry, and a deep understanding of cybersecurity trends. They must possess excellent relationship management skills, sales performance analysis capabilities, and a track record of quota achievement. The position offers a competitive salary range of $139,000 - $222,000 along with comprehensive benefits.

Inland Marine Underwriter

Company: The Hartford

Location: Chicago, IL

Posted Jan 22, 2025

The Hartford is seeking an Inland Marine Underwriter with 3+ years of experience in commercial underwriting, particularly in construction, transportation, and renewable energy risks. The role involves building strong relationships with agents and brokers, managing the sales process, and developing cross-sell and up-sell opportunities. The company offers a collaborative environment, opportunities for career growth, and a hybrid work arrangement. Qualifications include a Bachelor's Degree, excellent communication skills, analytical thinking, and the ability to work in a fast-paced, changing business environment.

Lead Business Process Engineer

Company: Argo Group

Location: Chicago, IL

Posted Jan 22, 2025

Senior Manager, Business Architecture

Company: CVS Health

Location: Northbrook, IL

Posted Jan 22, 2025

CVS Health is seeking a Senior Manager, Business Architecture for its PBM Caremark division. The role involves leading strategic initiatives to ensure durability, sustainability, feasibility, reusability, reliability, and standardization within the organization's architecture. The Business Architect will develop business architecture blueprints, identify and catalog business capabilities, and apply techniques like Capability Modeling, Customer Journey Mapping, and Value Stream analysis. Required qualifications include 2+ years of experience in business capability modeling and value stream analysis, 5+ years in architecture/management consultancy, and 2+ years of experience with enterprise Architecture frameworks. The role offers a competitive pay range and comprehensive benefits, including medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, and PTO.

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.

Related Pages