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.

Shift Supervisor Trainee

Company: CVS Health

Location: Godfrey, IL

Posted Jan 23, 2025

(USA) Optometrist Pre-Grad Intern - Walmart

Company: Walmart

Location: Skokie, IL

Posted Jan 23, 2025

The role involves supporting optical care and services to customers, including obtaining measurements, verifying prescriptions, and counseling. Clinical care is provided by diagnosing customers and managing treatment of visual problems. The position also involves maintaining the optical area, ensuring it aligns with company policies and standards, and maintaining a safe work environment. Merchandise presentation is crucial, involving stocking, rotating, and organizing products. The role requires selling optical products and services, assisting customers with purchasing decisions, and completing eyewear/contact lens orders. Leadership expectations include respect for the individual, acting with integrity, serving the customer, and striving for excellence. Walmart offers competitive pay, health benefits, financial benefits, and other perks like PTO, disability benefits, and Live Better U education program.

Shift Supervisor Trainee

Company: CVS Health

Location: O'Fallon, IL

Posted Jan 23, 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 communicating information. The trainee will also learn about key business aspects and CVS/pharmacy culture. Upon successful completion, they can be considered for Operations Supervisor or Shift Supervisor positions. These roles involve leading store staff, ensuring smooth operations, and maintaining excellent customer service. The job requires deductive reasoning, analytical skills, computer skills, and advanced communication. The pay range is $16.00 - $24.00, and the company offers comprehensive benefits including medical, dental, vision, 401(k), life insurance, disability benefits, well-being programs, education assistance, and more.

Program Manager, New Hire Training

Company: Tempus AI

Location: Chicago, IL

Posted Jan 23, 2025

Tempus, a healthcare technology company, is seeking a New Hire Training Program Manager. The role involves managing onboarding and training for the sales team, ensuring a thorough understanding of Tempus' ecosystem and offerings. The ideal candidate should have a background in sales training, passion for education, and commitment to excellence. Key responsibilities include managing structured onboarding, facilitating engaging training sessions, collaborating with subject matter experts, and providing ongoing support to new hires. Qualifications include a bachelor's degree, minimum of 2 years of sales training experience, familiarity with Tempus' mission, strong project management skills, excellent communication skills, and proficiency in learning management systems. Preferred qualifications include sales training experience in the medical field, instructional design background, and experience with sales operations tools.

Pharmacy Technician

Company: CVS Health

Location: Rockton, IL

Posted Jan 23, 2025

Cycling Instructors, Chicago

Company: Equinox

Location: Chicago, IL

Posted Jan 23, 2025

Organizational Change Management Lead

Company: TransUnion

Location: Chicago, IL

Posted Jan 23, 2025

TransUnion is hiring for an Organizational Lead position, offering a dynamic work environment with opportunities for skill development and innovation. The role involves supporting TransUnion's growth strategy, focusing on change management, and equipping needs. The successful candidate will work with stakeholders, project teams, and HR partners to ensure benefit realization, value creation, and ROI. Key responsibilities include developing employee-centric strategies, improving adoption and proficiency of new tools or processes, and facilitating virtual and in-person trainings. The position offers a competitive salary range of $82,700.00 - $120,000.00 annually, along with comprehensive benefits and a commitment to diversity and equal opportunity.

Pharmacy Technician

Company: CVS Health

Location: Ottawa, IL

Posted Jan 23, 2025

CVS Health emphasizes its commitment to human-centric health care, guided by the purpose of '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. They are expected to demonstrate empathy, genuine care, and a growth mindset, contributing to a safe, inclusive, and engaging team dynamic. The role involves completing basic inventory activities, delivering additional health care services, and adhering to all relevant laws and regulations.

Staff Pharmacist

Company: CVS Health

Location: Marion, IL

Posted Jan 23, 2025

Store Manager in Training

Company: CVS Health

Location: Decatur, 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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