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: Tinley Park, 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 complying with company policies. The role requires leadership experience, fluency in English, and knowledge of store systems. Preferred qualifications include experience with store inventory control.

Technical Consultant

Company: SUSE

Location: Chicago, IL

Posted Jan 23, 2025

SUSE is a global leader in open source solutions, with over 60% of the Fortune 500 relying on their services. They are expanding their consulting team, seeking experienced Linux consultants with strong technical skills and interpersonal abilities. The role involves designing, reviewing, and implementing Linux environments, working closely with customers, and collaborating with SUSE's engineering and support teams. SUSE values inclusivity, empowerment, and integrity, offering a dynamic environment for career growth. The company is committed to equal opportunity and encourages applicants from diverse backgrounds.

Shift Lead

Company: Walgreens

Location: Skokie, IL

Posted Jan 23, 2025

The role involves managing store operations, including opening and closing the store, handling cash, managing inventory, and ensuring a positive customer experience. Key responsibilities include managing deliveries, processing returns and refunds, maintaining store cleanliness, and assisting with pharmacy tasks. The position requires leadership experience, fluency in English, and knowledge of store systems. The role is based in Skokie, IL, and the salary range is $17 - $19 hourly.

Outside Sales Rep Now 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.

Field Sales Representative – Hiring Immediately

Company:

Location: Downers Grove, 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. The company stands out due to its fully staffed departments, allowing sales reps more time for tasks. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with a 4% employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing new sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Outside Sales Representative

Company:

Location: Oak Park, IL

Posted Jan 23, 2025

Product Support Advisor Supervisor

Company: Sysco

Location: Arlington Heights, IL

Posted Jan 23, 2025

Sysco, the global leader in foodservice distribution, is seeking a candidate for a supervisory role. The position involves overseeing Product Support Advisors, providing coaching, mentoring, and career development. Key responsibilities include creating and delivering presentations, driving specialty and sales initiatives, and resolving customer escalation issues. The ideal candidate should have 2-3 years of food sales or customer service experience, along with strong communication, organization, and problem-solving skills. Sysco offers opportunities for personal and professional growth, and is committed to equal opportunity employment.

Shift Lead

Company: Walgreens

Location: Arlington Heights, IL

Posted Jan 23, 2025

Management & Sales Training Program (Madison/Rockford)

Company:

Location: Sterling, IL

Posted Jan 23, 2025

The Sherwin-Williams Management & Sales Training Program is an 18-24 month entry-level position designed to prepare individuals for a Store Management role. The program includes 6-8 weeks of intensive training, followed by a typical 44-hour workweek. Participants will collaborate with store management, oversee a million-dollar business, and learn all aspects of operations, sales, and strategy. The training equips participants with skills for a successful career in management and professional sales, offering limitless career opportunities and leadership development. Sherwin-Williams values diversity and inclusivity, encouraging applications from all backgrounds.

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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