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.

Part-Time Stockroom Operations Associate

Company: Kohl's

Location: Champaign, IL

Posted Jan 22, 2025

The role involves delivering excellent customer service, managing store operations, and processing freight and replenishment. Key responsibilities include receiving and processing product, replenishing sales floor stock, engaging customers, and executing product protection standards. The role also involves participating in new hire training and adhering to company policies. Required skills include strong customer service, multitasking, attention to detail, and communication skills. No retail experience is required, but flexible availability is necessary. Preferred experience includes client-facing retail or service industry roles. The pay range is $15.00 - $21.65, with various benefits offered including work-life balance, health & wellness, savings & retirement benefits, insurance programs, and life events support.

Pharmacy Technician

Company: CVS Health

Location: Atlanta, IL

Posted Jan 22, 2025

Application Engineer

Company: Discover

Location: Chicago, IL

Posted Jan 22, 2025

Discover is offering a job opportunity for a seasoned IT professional with a bachelor's degree in a relevant field and 3+ years of experience. The role involves overseeing product design and implementation, guiding early-career engineers, and ensuring high-quality, reliable solutions. The successful candidate will contribute to technology communities of practice and enforce IT standards. Bonus points for experience with specific operating systems, databases, and programming languages. The position does not require travel and offers a competitive salary range along with comprehensive benefits.

Insurance Agent (Base salary + Uncapped commissions)

Company: Comparion Insurance Agency

Location: Hoffman Estates, IL

Posted Jan 22, 2025

Comparion Insurance Agency is hiring a Sales Agent in Hoffman Estates. The role involves building a local network, relationship building, and selling insurance products like Auto, Home, and Life. The compensation ranges from $55k - $75k initially, with potential for top performers to earn over $100k in the first year. Benefits include uncapped pay, recognition, paid training, sales support, comprehensive benefits, and more. Preferred qualifications include sales experience and a state insurance license.

Team Leader

Company: Crown Cork & Seal USA

Location: Tinley Park, IL

Posted Jan 22, 2025

Staff Security Engineer - External Attack Surface Management

Company: CVS Health

Location: Northbrook, IL

Posted Jan 22, 2025

CVS Health is seeking an External Attack Surface Management Staff Security Engineer to lead efforts in identifying, analyzing, and mitigating risks associated with the organization's external attack surface. The ideal candidate should have a strong technical background in cybersecurity, expertise in ASM tools and methodologies, and a proactive approach to risk management. Key responsibilities include attack surface discovery and inventory, vulnerability identification and remediation, risk assessment and threat analysis, incident response and escalation, tool management and automation, collaboration and stakeholder engagement, and policy and governance. Required qualifications include 7+ years in Cybersecurity roles with at least 3 years specializing in Attack Surface Management, 5+ years of experience with ASM Qualys, and 5+ years of experience with cloud platforms. The role offers a competitive pay range, comprehensive benefits, and opportunities for professional growth.

Automotive Technician

Company: CarMax

Location: Schaumburg, IL

Posted Jan 22, 2025

CarMax is currently hiring Automotive Technicians in Schaumburg, Illinois. The role involves diagnosing, repairing, and reconditioning vehicles to meet CarMax's high standards. Technicians work in a fast-paced environment, solving technical problems, and delivering great results. CarMax offers a range of benefits including paid time off, medical/dental coverage, 401k with company match, vehicle discount, tuition reimbursement, and more. The company is known for its commitment to training, diversity, and providing a supportive work environment. The hourly rate for this position is $19.80 - $38.90, with commission eligibility.

Assistant Store Leader

Company: Kroger

Location: Oak Park, IL

Posted Jan 22, 2025

The job description outlines responsibilities for a store manager role, including overseeing all departments, ensuring a positive customer experience, leading teams in merchandising initiatives, managing store operations, achieving sales and budget targets, promoting inclusive leadership, and maintaining compliance with laws and policies. The role requires retail management experience, staff supervisory experience, and a high school diploma or equivalent. Benefits include healthcare coverage, flexible scheduling, emotional and financial support, associate discounts, tuition reimbursement, and growth opportunities.

Principal - Dental SME- Healthcare

Company: Infosys

Location: Chicago, IL

Posted Jan 22, 2025

HealthcareInfosys Consulting is hiring a Principal Management Consultant with extensive experience in dental insurance. The candidate will lead a project team on a large core administrative platform implementation program, possessing solid knowledge in dental insurance operations, technology, and consulting. They should have 7+ years of experience with large Dental carriers and at least 5 years in advisory consulting. Key responsibilities include analyzing dental insurance products, developing recommendations for improvements, and implementing technology-enabled transformations. The ideal candidate should have an MBA or equivalent, strong client-facing skills, and experience with healthcare core administrative platforms like QNXT, Facets, and HealthRules Payer.

Analyst, Case Management (Field - Must reside in Winnebago/Jo Daviess County, IL or surrounding areas)

Company: CVS Health

Location: Rockford, IL

Posted Jan 22, 2025

CVS Health is seeking a Case Management Coordinator to collaborate and inform the case management process, facilitating appropriate healthcare outcomes for members. The role requires 2 years of experience in behavioral health, social services, or related fields. Key responsibilities include appointment scheduling, assisting with benefits, and using care management tools. The position offers a pay range of $21.10 - $44.99 and a comprehensive benefits package. CVS Health emphasizes a human-centric approach to healthcare, with a purpose to 'Bringing our heart to every moment of your health.'

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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