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 Lead

Company: Walgreens

Location: Crestwood, IL

Posted Jan 23, 2025

Pharmacy Intern

Company: Walgreens

Location: Chicago, IL

Posted Jan 23, 2025

The job involves learning to provide excellent patient experience by assisting pharmacists and team members, adhering to regulations. Key responsibilities include engaging customers, resolving issues, and maintaining a positive customer experience. The role also involves assisting in pharmacy operations, such as prescription processing, inventory management, and maintaining a clean, orderly pharmacy. The ideal candidate is a current pharmacy student, fluent in English, and willing to work flexible hours. Prior retail experience and good math skills are preferred.

Outside Sales Rep Now Hiring

Company:

Location: St. Charles, IL

Posted Jan 23, 2025

Supply Chain Analyst, Transportation Optimization

Company: Walgreens

Location: Deerfield, IL

Posted Jan 23, 2025

The Supply Chain Analyst on the last mile transportation team is responsible for conducting moderately complex analysis of information, problems, and data. This role involves working under general supervision, making recommendations for senior staff review, tracking and measuring the impact of implemented solutions, and communicating risks with mitigation recommendations. The analyst also builds internal/external relationships, resolves moderately complex issues, and recommends process improvements. Walgreens, the employer, is a leading healthcare, pharmacy, and retail company with a focus on community care and omnichannel experiences.

Shift Lead

Company: Walgreens

Location: Park Ridge, IL

Posted Jan 23, 2025

The job involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Responsibilities also include coaching team members, maintaining store cleanliness, and ensuring compliance with regulations. The role requires leadership experience, fluency in English, and knowledge of store systems. Preferred qualifications include experience with store inventory control.

Senior Knowledge Analyst - Loyalty & Subscription Program Strategy

Company: Boston Consulting Group (BCG)

Location: Chicago, IL

Posted Jan 23, 2025

BCG's Loyalty & Subscriptions business is expanding and seeks a Senior Knowledge Analyst. This role involves collaborating with consulting teams to deliver high-impact analyses for Loyalty program design and optimization. The ideal candidate will have strong analytical skills, an entrepreneurial mindset, and excellent networking abilities. They will augment consulting teams on casework, conduct in-depth analyses of client Loyalty programs, and develop strategies to improve customer retention and lifetime value. The role requires 3-6+ years of Loyalty program experience, strong financial analysis skills, and fluency in English.

Senior Consultant, NetSuite

Company: West Monroe

Location: Chicago, IL

Posted Jan 23, 2025

Roofing Sales Immediately Hiring

Company:

Location: Plainfield, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling sales reps to focus on selling. The company offers competitive compensation including draw against commission, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Sales reps are expected to prospect, qualify, and close new sales, manage territories, inspect properties for damage, and build relationships with homeowners. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and a smart phone. Industry knowledge and CRM experience are preferred.

Roofing Sales Immediately Hiring

Company:

Location: Oak Park, IL

Posted Jan 23, 2025

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects, offering them protection at reduced costs. The company stands out due to its fully staffed departments, enabling sales reps to focus on sales without administrative burdens. AmeriPro Roofing offers competitive compensation including a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. The role involves prospecting, qualifying, and closing new sales, managing a territory, conducting property inspections, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Inventory Control Coordinator

Company: CVS Health

Location: Mount Prospect, IL

Posted Jan 23, 2025

Beauty and Wellness Consultant

Company: Walgreens

Location: Skokie, IL

Posted Jan 23, 2025

The job description outlines responsibilities for a Beauty Consultant at Walgreens, focusing on maximizing sales and brand awareness through exceptional customer service. Key tasks include providing personalized advice, conducting mini-makeovers and skincare consultations, and leading in-store events. The role involves achieving sales targets, maintaining department standards, and engaging with customers through various channels. The ideal candidate should have retail sales experience, product knowledge, and relationship-building skills. Fluency in English is required, and a cosmetology or esthetician license is preferred. Walgreens, as a leading drugstore chain, offers a supportive work environment and opportunities for career growth.

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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