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.

Associate Business Systems Analyst

Company: CSC

Location: Buffalo Grove, IL

Posted Jan 22, 2025

CSC is seeking a motivated individual for a remote Associate Tax Research Specialist position in the Americas. The role involves researching tax form changes, interpreting tax code updates, and providing guidance to programmers. The ideal candidate will have 2-5 years of experience in corporate or pass-through income tax compliance or programming, and a degree in Accounting, Computer Science, or a related field. CSC offers a diverse and growth-oriented environment with excellent benefits and opportunities for career advancement.

VP, Brand Strategy

Company: Merge (mergeedu)

Location: Chicago, IL

Posted Jan 22, 2025

MERGE is a company that merges storytelling and technology to help clients solve business challenges and rise to the top. They have enduring partnerships with major brands like American Express, T-Mobile, and Adobe. MERGE promotes health, wellness, and happiness by partnering with purpose-driven clients in healthcare, life science, and consumer products. They offer a superior work experience where talented individuals can grow and do their best work. The VP Brand Strategy role involves sparking new ways of thinking, driving creative solutions, and leading brand strategy for life sciences clients. The ideal candidate should have 12+ years of relevant experience, be a proven thought leader, and have a strong understanding of brand strategy and marketing models.

Customer Experience Coordinator

Company: The TJX Companies, Inc.

Location: Peoria, IL

Posted Jan 22, 2025

Marshalls, a retail store, is seeking a team leader to contribute to the growth of their career. The role involves promoting an excellent customer experience, overseeing a team of associates, and maintaining a clean and organized store. The company values change, encourages teamwork, and provides opportunities for career advancement. Benefits include an associate discount, 401(k) contributions, and various insurance options. The starting pay range is $16.00 to $16.50 per hour.

Director of Technology

Company: tastylive

Location: Chicago, IL

Posted Jan 22, 2025

The Small Exchange is seeking an experienced Director of Technology for their CFTC-regulated designated contract market. The role involves leading technology risk management, policy development, vendor management, and leadership of internal technology staff. The ideal candidate should have 7+ years of technology management experience, strong understanding of futures trading technology, and proven track record in managing complex technology projects and vendor relationships. The company offers competitive benefits including performance bonuses, stock purchase options, and a full kitchen with snacks and beverages. The salary range is $130,000 - $150,000, based on the candidate's experience and qualifications.

Director of Technology

Company: tastytrade/ tastylive/ tastyfx/ tastycrypto

Location: Chicago, IL

Posted Jan 22, 2025

The Small Exchange is seeking an experienced Director of Technology for their CFTC-regulated designated contract market. The role involves leading technology risk management, policy development, vendor management, and leadership of internal technology staff. The ideal candidate should have 7+ years of technology management experience, strong understanding of futures trading technology, and proven track record in managing complex technology projects and vendor relationships. The company offers competitive benefits including performance bonuses, stock purchase options, and a full kitchen with snacks and beverages. The salary range is $130,000 - $150,000, based on the candidate's experience and qualifications.

Principal Technical Architect

Company: Discover

Location: Riverwoods, IL

Posted Jan 22, 2025

Discover is offering a job opportunity for a data architect with expertise in NoSQL databases, particularly MongoDB. The role involves designing technology strategies, managing implementation of best practices, compliance standards, and security controls. The company values unique skills and encourages growth. Bonus points for experience in Go programming language, infrastructure as code, and enterprise architecture frameworks like TOGAF. The position requires excellent communication and collaboration skills, and a track record in managing technology lifecycle and delivery.

Senior Data Science Analyst

Company: Discover

Location: Riverwoods, IL

Posted Jan 22, 2025

Discover is offering a job opportunity for an analytical professional to work closely with management, solving business problems using techniques like segmentation, optimization, and machine learning. The role involves creating reports and dashboards, managing risks, and collaborating with cross-functional teams. The ideal candidate should have a Bachelor's degree in Analytics, Engineering, Statistics, or related field, and 2+ years of experience in relevant fields. The position offers a competitive salary, benefits, and opportunities for growth and development.

DELI/COFFEESHOP BARISTA

Company: Kroger

Location: Chicago, IL

Posted Jan 22, 2025

The job description outlines responsibilities for a customer service role at Mariano's, a grocery store chain in Chicago. Key duties include exceeding service standards, demonstrating company values, promoting initiatives, maintaining cleanliness, preparing beverages, and adhering to store policies. The role requires a high school diploma or equivalent, six months of customer service experience, and the ability to work weekends and overtime. Desired qualifications include knowledge of company policies and industry terms. Mariano's, part of the Kroger family, offers comprehensive benefits including healthcare, flexible scheduling, emotional and financial support, associate discounts, tuition reimbursement, and growth opportunities.

Patient Care Technician

Company: DaVita

Location: Rock Island, IL

Posted Jan 22, 2025

(USA) Merchandising Lead

Company: Walmart

Location: Aurora, IL

Posted Jan 22, 2025

VP, Media

Company: Merge (mergeedu)

Location: Chicago, IL

Posted Jan 22, 2025

MERGE is a company that merges storytelling and technology to help clients solve business challenges. They have long-term partnerships with major companies like American Express, T-Mobile, and Adobe. MERGE is committed to promoting health, wellness, and happiness through partnerships in healthcare, life science, and consumer products. They offer a superior work experience for talented individuals, encouraging them to think higher and feel deeper. The VP Media role involves developing media plan recommendations for pharmaceutical advertising clients, overseeing the media planning process, and leading a team of media professionals. MERGE values transparency, equity, and diversity, offering competitive salaries and benefits. They are an Equal Opportunity Employer.

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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