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.

District Support Pharmacist - PT

Company: CVS Health

Location: Danville, IL

Posted Jan 24, 2025

CVS Health emphasizes its purpose of delivering enhanced, human-centric health care through its Heart At Work Behaviors. District Support Pharmacists (DSPs) play a crucial role in this mission by modeling genuine care, setting high standards, and supporting safe and accurate prescription practices. They also contribute to positive patient experiences, maintain inventory, and stay updated with clinical skills. The role requires flexibility, strong communication, and problem-solving skills.

Senior Internal Auditor

Company: Discover

Location: Riverwoods, IL

Posted Jan 24, 2025

Lead Data Engineer (AWS, Azure, GCP)

Company: CapTech

Location: Chicago, IL / Remote

Posted Jan 24, 2025

(USA) Forklift-Merchandising Associate

Company: Walmart

Location: Calumet City, IL

Posted Jan 24, 2025

The job involves complying with company policies, operating a forklift, completing work assignments, providing member service, maintaining facility safety, and ensuring sales floor presentation. The role requires handling inventory, operating forklifts, and using technology to assist customers. Leadership expectations include respect for individuals, acting with integrity, serving the customer, striving for excellence, and maintaining a positive work environment. Benefits include competitive pay, health benefits, financial benefits, paid time off, and other perks. Minimum qualifications include 90 days of prior forklift experience and being 18 years or older.

Sr Manager, Information Security

Company: Grainger

Location: Lake Forest, IL

Posted Jan 24, 2025

Grainger, a leading industrial distributor, is seeking a Senior Manager of Security Engineering for a hybrid role based in Lakeforest, IL or Jacksonville, FL. The role involves leading teams of engineers to implement and operate enterprise-wide security services, driving the security engineering roadmap, and aligning security initiatives with business objectives. The ideal candidate should have 8+ years of information security experience, deep expertise in security domains, and a track record of delivering enterprise-scale security transformation initiatives. Grainger offers competitive benefits including medical, dental, vision, life insurance, a 401(k) plan, employee discounts, parental leave, tuition reimbursement, and more. The company is committed to equal employment opportunity and fostering an inclusive environment.

Retail Sales Associate - 3416 N Southport

Company: Gap Inc.

Location: Chicago, IL

Posted Jan 24, 2025

Gap, an iconic American brand, seeks a Brand Associate to provide excellent customer service, educate customers about loyalty programs, and drive sales through suggestive selling. The role involves maintaining a clean work environment, handling customer interactions professionally, and executing operational processes efficiently. Gap values communication, customer focus, problem-solving, flexibility, and retail technology skills. Benefits include merchandise discounts, competitive Paid Time Off, volunteer time, extensive 401(k) plan, and health insurance. Gap is committed to diversity and inclusion.

Patient Care Technician

Company: DaVita

Location: Calumet City, IL

Posted Jan 24, 2025

DaVita, an Italian term for 'giving life', is recruiting a Patient Care Technician for an outpatient dialysis center. The role involves direct patient care, technician duties, and building relationships with patients. No dialysis experience is required, and extensive paid training is provided. The position offers career advancement opportunities through DaVita's Clinical Ladders program and tuition assistance for those interested in becoming a DaVita RN. The work is physically demanding, requiring long hours on feet, and flexibility to work various shifts including mornings, evenings, weekends, and holidays.

Insurance Sales Associate

Company: Comparion Insurance Agency

Location: Orland Park, IL

Posted Jan 24, 2025

Liberty Mutual is hiring an Insurance Sales Associate for their Orland Park, IL office. The role involves working alongside a Comparion Insurance Sales Agent to drive new business sales and customer retention. Key responsibilities include utilizing consultative sales techniques, identifying cross-selling opportunities, and meeting monthly sales goals. The company offers comprehensive benefits, a supportive work environment, and opportunities for professional growth. A state insurance license is required or candidates must be willing to earn one with provided training.

Lead Director, Design Systems

Company: CVS Health

Location: Springfield, IL

Posted Jan 24, 2025

CVS Health is seeking a Lead Director, Design Systems to evolve and optimize their digital Pulse design system. This role involves leading the design system vision and strategy, ensuring quality of foundations, components, and documentation, and fostering strong partnerships with various teams. The ideal candidate should have extensive experience in digital design, product, or engineering, with a proven track record in leading enterprise design systems. They should possess excellent communication skills, the ability to interface with customers, and a record of delivering features on time with quality and value.

Shift Supervisor Trainee

Company: CVS Health

Location: Chicago, IL

Posted Jan 24, 2025

CVS Health is offering a Shift Supervisor Trainee position, an entry-level role designed to prepare employees for higher-level supervisory roles. The role involves working effectively with store management and crews, supervising activities, and ensuring smooth store operations. The company emphasizes a human-centric approach to healthcare, focusing on personal, convenient, and affordable solutions. Successful completion of the training program leads to eligibility for Operations Supervisor or Shift Supervisor positions, which involve leading store staff, driving store execution, and building customer loyalty through excellent service.

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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