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 Architect

Company: CNA

Location: Chicago, IL

Posted Jan 27, 2025

CNA is seeking an Enterprise Architect to join as an individual contributor, responsible for the overall architecture of the Scaled Agile aligned portfolio. The role involves aligning business strategy with technology vision, driving innovative solutions for complex business problems, and leading architectural advancement through enabler initiatives. The ideal candidate should be a strategic and innovative leader with proficiency in agile methodologies and enterprise architecture principles, and a strong understanding of contemporary technology and business trends.

Application Security Engineer Intern

Company: iManage

Location: Chicago, IL

Posted Jan 27, 2025

iManage U is offering a paid internship program for students to experience a dynamic technology company firsthand. The program, based in downtown Chicago, will run from June 2nd to August 8th. Interns will work with the Application Security Team, contributing to threat modelling, risk analysis, security reviews, and vulnerability investigations. The role requires a Bachelor's degree in Computer Science or a related field, web technology experience, understanding of web protocols, and fundamental security concepts. iManage values diversity and encourages applications from individuals with a growth mindset.

Customer Experience Operations Intern

Company: iManage

Location: Chicago, IL

Posted Jan 27, 2025

iManage U offers a paid internship program for students to gain hands-on experience in a dynamic technology company. The program, based in downtown Chicago, runs from June 2nd to August 8th and focuses on project-based activities, problem-solving, team building, and fun experiences. Interns will support the Customer Experience Operations Team, responsible for operational excellence, CX data management, reporting, service configuration, and process optimization. The ideal candidate is passionate about technology, has strong communication skills, and can manage competing priorities. iManage values diversity and encourages applications from individuals with a growth mindset.

Customer Success Manager

Company: Zadara

Location: Chicago, IL

Posted Jan 27, 2025

The job posting is for a Cloud Customer Success Manager role in the Central USA Time Zone. The role involves building strong relationships with clients, guiding them through adoption, ongoing support, and growth. The goal is to drive customer satisfaction, retention, and expansion. The role requires 5+ years of experience in customer success account management, strong technical aptitude, and excellent communication skills. The company offers benefits such as medical, dental, vision insurance, 401k plan with matching, and more.

Systems Administrator Sr

Company: BAE Systems, Inc.

Location: Chicago, IL

Posted Jan 27, 2025

BAE Systems is offering a System Administrator position with an attractive salary range of $92,290 to $156,860. The role involves providing onsite technical support, troubleshooting hardware and software issues, and implementing solutions. Superior interpersonal skills are required for daily interaction with customer management, technical, and operator personnel. The ideal candidate should have a high school degree with 8+ years of experience in client-server LAN/WAN systems, Windows system administration, and Active Directory GPO configuration. A BS degree in Information Systems or Computer Science with 4 years of related experience is preferred. BAE Systems offers comprehensive benefits including health, dental, and vision insurance, a 401k savings plan, and disability coverage. The company is dedicated to improving national security with breakthrough technology and intelligence solutions.

Customer Success Intern

Company: iManage

Location: Chicago, IL

Posted Jan 27, 2025

iManage U offers a paid internship program in their downtown Chicago office, starting June 2nd and ending August 8th. The program focuses on project-based activities, business fundamentals, problem-solving, team building, and social events. Interns will support the iManage Cloud Customer Lifecycle, ensuring successful delivery of products and maintaining strategic partnerships with clients. Responsibilities include verifying customer contacts, managing tickets, reviewing interactions, identifying advocates, and writing communications. iManage values passion for learning, self-starting attitude, adaptability, attention to detail, and strong communication skills. They encourage applications from diverse backgrounds, including those who may not meet all qualifications.

Intern, Marketing

Company: Strata Decision Technology

Location: Chicago, IL

Posted Jan 27, 2025

Strata's 10-week paid internship program during the Summer of 2025 is open to students pursuing a bachelors degree or higher, based in the Chicago area. The program offers onboarding training, meaningful work, networking opportunities, and a chance to experience the company's culture. Interns will work with the Marketing team, analyzing campaign performance, designing email campaigns, managing data, and maintaining webpages. Strata values diversity and inclusion, with core values of positive intent, helpfulness, ownership, continuous improvement, and humility.

Senior Associate Data Engineer

Company: Discover

Location: Chicago, IL

Posted Jan 27, 2025

Discover is offering a Senior Associate Data Engineer position with a competitive salary range of $73,500 to $124,300. The role involves designing, developing, maintaining, and testing data solutions using enterprise frameworks. The company values unique skills and offers opportunities for growth and making a difference. The ideal candidate should have a Bachelor's degree in Computer Science, 1+ years of experience in Data Platform Administration/Engineering, and a technical proficiency rating of Advanced Beginner. Bonus points for knowledge of SQL, ETLELT tools, cloud-based warehousing solutions, and understanding of data modeling. Discover offers a range of benefits including paid parental leave, 401k plan, medical/dental/vision, and more. The company is committed to a diverse and inclusive workplace.

Principal Technical Architect

Company: Discover

Location: Chicago, IL

Posted Jan 27, 2025

Discover is offering a job opportunity for a data architect with expertise in NoSQL databases, Go programming, and enterprise architecture frameworks. The role involves designing technology strategies, managing implementation of best practices, and serving as a thought leader in the domain. The company values diversity and inclusion, and offers competitive compensation and benefits. The ideal candidate should have a Bachelor's degree in Computer Science, 8+ years of software development experience, and a technical proficiency rating of expert on the Dreyfus architecture scale.

Program Manager - Fixed Income

Company: Morningstar

Location: Chicago, IL

Posted Jan 27, 2025

Morningstar is seeking a Program Manager for the Fixed Income Data and Analytics Team. The role involves managing multiple projects using Agile tools, serving as Scrum Master, leading communication and planning activities, coordinating with stakeholders, and managing project risks. The ideal candidate should have a Bachelor's degree in a tech or finance field, at least 7 years of relevant experience, and knowledge of software development processes and Agile methodologies. The role is based in Chicago with a hybrid work environment. Morningstar offers comprehensive benefits including financial, physical, emotional, and social health programs, a competitive salary range, and a flexible work environment.

Cloud Operations Intern

Company: iManage

Location: Chicago, IL

Posted Jan 27, 2025

iManage U offers a paid internship program in their downtown Chicago office, starting June 2nd and ending August 8th. The program includes project-based activities, team building, and learning opportunities. Interns will work on the SRE team, collaborating with remote teams, improving CI/CD systems, and ensuring reliable applications. iManage values diversity and encourages applications from those who may not meet all qualifications. The company is dedicated to making knowledge work and solving complex professional challenges.

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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