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.

Training and Knowledge Specialist

Company: Caterpillar

Location: Peoria, IL

Posted Jan 29, 2025

Caterpillar Inc. is seeking a highly accountable individual with strong communication and organization skills for a role in their Digital and Data Technology area. The successful candidate will develop training materials, identify training needs, and lead training initiatives for the Cat Digital Support Center. They will also partner with third-party contact centers in launching new programs and ongoing operations. The role involves deploying various training methods, ensuring a seamless handoff of training and quality to third-party suppliers, and regularly reviewing curriculum materials. The position requires a college degree or equivalent experience in progressive training assignments, strong communication skills, and contact center experience. Caterpillar offers a flexible hybrid work environment, competitive compensation, and benefits, and is committed to a reduced-carbon future.

Senior Customer Success Leader - HCLS

Company: Qualtrics

Location: Chicago, IL

Posted Jan 29, 2025

Qualtrics is seeking a Senior Customer Success Leader to build and lead a team of Technical Success Managers. The role involves driving business value, ensuring top-tier customer management, and assisting customers throughout their lifecycle. The ideal candidate will have 8+ years of professional experience, 35 years of people leadership, and a proven track record of building scalable business operations. They should possess strong prioritization skills, data-driven communication abilities, and an entrepreneurial spirit. The role offers opportunities for growth, teamwork, and a supportive environment with various perks and benefits.

Executive Chef

Company: Aba

Location: Chicago, IL

Posted Jan 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

Senior Product Manager- Product strategy

Company: Ahold Delhaize USA

Location: Chicago, IL

Posted Jan 29, 2025

Ahold Delhaize USA is seeking a Product Strategy and Experimentation Manager for its Chicago office. The role involves driving strategic planning, managing the digital product roadmap, and leading a team of two product managers. The ideal candidate should have experience with agile development, cross-functional team leadership, and project management skills. The company offers a competitive salary range of $131,520 to $204,240 and values diversity, equity, inclusion, and wellness.

Applied AI Intern

Company: iManage

Location: Chicago, IL

Posted Jan 29, 2025

iManage offers a paid internship program for students interested in AI and data science. The program, based in Chicago, runs from June 2nd to August 8th and includes project-based activities, team building, and social events. Interns will work with a multidisciplinary team of AI engineers and data scientists, focusing on researching and applying cutting-edge Gen AI algorithms and NLP methods. The role involves performing exploratory data analyses, developing prompt engineering techniques, and conducting research experiments. Qualified candidates should have proficiency in data structures, algorithms, and statistics, current enrollment in a relevant graduate program, and experience with Python packages for text data analysis.

Operations Technology People Manager Manager

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 29, 2025

McDonald's is seeking a Service Delivery Manager to lead the Operations Technology People (OTP) Program, which supports the increasing technology footprint across nearly 14,000 McDonald's restaurants in the US. The role involves strategic leadership, program management, event management, communications, training, technology deployment, incident management, relationship management, budget management, project execution, and process improvement. The ideal candidate should have 10+ years of overall business experience, 5+ years of project management experience, exceptional communication skills, and proficiency in Microsoft Office Suite. The position offers health and welfare benefits, a 401k plan, educational assistance, flexible working arrangements, and time off policies.

Customer Success Manager II

Company: Tempus AI

Location: Chicago, IL

Posted Jan 29, 2025

Tempus, a company specializing in precision medicine, is seeking a dynamic leader for its customer success team. The role involves managing a team of professionals, driving strategic initiatives, and ensuring operational excellence. The company values a customer service culture rooted in servant-based leadership, empathy, and professionalism. The ideal candidate should have a background in healthcare, life sciences, or technology, with a proven track record in process improvements and cross-functional project management. The position requires travel up to 15% of the time and offers a salary range of $75,000 to $100,000 in Illinois.

Software Engineer (Chicago)

Company: Nextpoint

Location: Chicago, IL

Posted Jan 29, 2025

Nextpoint, an award-winning team, offers transformative software and services for law firms. They value innovation, creativity, diversity, and initiative, fostering a happy workplace. The Level 2 Support Engineer role involves creating and maintaining a high-performing, reliable environment for clients, collaborating with engineering and product teams, and continuously improving system performance. The ideal candidate has a Bachelor's degree in computer science, 2+ years of support engineering experience, and strong problem-solving skills.

Sr .NET Developer (Perm - Hybrid at our Chicago HQ near O'Hare Airport)

Company: Alliant Credit Union

Location: Chicago, IL

Posted Jan 29, 2025

This role involves designing, developing, and implementing platform solutions in an agile team, utilizing full stack development tools and technologies such as .NET, Web, and MuleSoft. The role requires a Bachelor's degree in Computer Science or related field and at least 3 years of experience in .NET APIs and Microservices application development. The position offers a competitive salary range, benefits including health care, 401k, and work from home options. The role also emphasizes adherence to Bank Secrecy Act policies and maintaining integrity and ethics in all actions.

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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