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.

Enterprise Sales Manager

Company: Taboola

Location: Chicago, IL

Posted Jan 23, 2025

Taboola, the world's number 1 discovery platform, is seeking an Enterprise Advertising Sales Manager for its Chicago team. The role involves building and managing long-term strategic partnerships with Tier 1 Brands and agencies across the midwest. Key responsibilities include prospecting, networking, pipeline development, new client acquisition, client retention, and achieving revenue goals. The ideal candidate should have a Bachelor's degree, 4+ years of digital advertising sales experience, existing relationships in Financial Services, Health, Home and Garden, Auto, Retail, and Tier I Agencies, deep knowledge of advertising and technology, strong business acumen, and emotional intelligence. Taboola offers a collaborative, high-growth environment with competitive benefits.

Shift Lead

Company: Walgreens

Location: Chicago, 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 Chicago, IL, with a salary range of $17 - $19 per hour.

PPC Specialist

Company: NinjaHoldings

Location: Chicago, IL

Posted Jan 23, 2025

NinjaHoldings, founded in 2017, is seeking a skilled PPC Specialist to join their dynamic team. The role involves developing, implementing, and optimizing paid advertising strategies across various digital platforms. The ideal candidate should have 3+ years of hands-on experience in PPC campaigns, preferably within the financial services sector. They should possess expertise in platforms like Google Ads, Microsoft Ads, and Facebook Ads Manager, along with strong analytical skills and a deep understanding of CRO principles. The company offers a competitive salary, flexible remote work, and a dynamic startup culture.

Principal Data Science

Company: Discover

Location: Riverwoods, IL

Posted Jan 23, 2025

Banking Management Consulting Manager - Credit / nCino

Company: Accenture

Location: Chicago, IL

Posted Jan 23, 2025

Accenture Consulting is a leading global professional services company, offering a wide range of services in strategy, consulting, technology, and operations. They are currently seeking a Manager within the Banking Credit Consulting practice, focusing on Business Transformation within the commercial lending industry. The role involves developing world-class solutions, conducting assessments, leading process design, and participating in business development. The ideal candidate should have 4+ years of relevant project delivery experience, industry experience in lending segments, and demonstrated business expertise across the commercial lending lifecycle. Skills in nCino and Salesforce.com are preferred. Accenture offers comprehensive training, a team-oriented environment, and opportunities for career growth.

Strategy and Analytics Manager

Company: Walgreens

Location: Deerfield, IL

Posted Jan 23, 2025

Manager, Information Technology

Company: Caterpillar

Location: Peoria, IL

Posted Jan 23, 2025

Caterpillar Inc. is seeking a Manager of Information Technology to lead a global team of project managers, team leads, architects, and IT analysts. The role involves managing various Center of Expertise (COE) teams, including Robotic Process Automation (RPA), Power Platform, Business Process Automation (BPA), Process Discovery and Mining (PDM), and offshore resources. The candidate will work closely with business units, Group CIO organizations, and other IT organizations to implement business objectives and promote best practices. Key responsibilities include direct management of a global team, planning and managing multiyear budgets, maximizing the value of existing tooling and technology, and leading the enterprise-level low-code/no-code tooling technology vision. The ideal candidate will have a Bachelor's degree in computer science, information systems, or a related field, extensive IT experience, and strong leadership and management skills. Caterpillar offers a total rewards package, including medical, dental, vision, 401K, and potential annual bonuses.

Wealth Management-Chicago-Administrative Assistant- Support

Company: Goldman Sachs

Location: Chicago, IL

Posted Jan 23, 2025

The Goldman Sachs Group, Inc., a renowned global investment firm, is seeking an administrative professional for a senior role in Chicago. The position involves providing complex support to executives, coordinating meetings, managing travel, and handling sensitive information. The ideal candidate should possess excellent communication skills, high attention to detail, and strong organizational abilities. A minimum of 3-5 years of experience is preferred. The salary range is $70,000-$110,000, with potential for a discretionary bonus. Goldman Sachs offers competitive benefits and a positive work environment.

Digital Tech Support Analyst

Company: Caterpillar

Location: Peoria, IL

Posted Jan 23, 2025

Caterpillar Inc. is seeking a Telematics Product Expert for its digital and technology arm, Cat Digital. The role involves providing worldwide support for the Cat Digital portfolio, managing cases for a seamless customer experience, and serving as a primary point of contact for Tier 1 support. The ideal candidate should have a college degree, technical certification, or equivalent experience, along with at least 2 years of experience in infrastructure system administration or equivalent support work. Strong understanding of telematics systems, engine control panels, and experience with tools like Salesforce and ServiceNow are required. The position offers a competitive salary range of $87,480 - $131,280, along with comprehensive benefits and opportunities for career development. The role can be based out of either the Chicago or Peoria IL offices with a flexible hybrid work environment, and travel up to 10% may be required.

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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