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.

IT Systems and Support Administrator

Company: Kalderos

Location: Chicago, IL

Posted Feb 01, 2025

Kalderos is seeking an IT Systems and Support Administrator to provide top-tier technical support to over 115 internal employees, ensuring smooth operations in a mixed Mac and Windows environment. The role involves critical thinking, troubleshooting, and collaboration with the Director of Information Technology to improve systems and processes. The candidate will also work with the Information Security team to ensure system security and act as a technical mentor to Level 1-2 technical support analysts. The ideal candidate will have 5+ years of experience, excellent technical skills, and a customer service mindset. Relevant certifications, experience in startup environments, and familiarity with Okta, Google Workspace, cloud infrastructure, and compliance standards are preferred. The position offers a competitive salary range, flexible PTO, and a range of benefits, including medical, dental, vision, 401k, and opportunities for growth. Kalderos values collaboration, feedback, and continuous learning, and is committed to equal opportunity.

Scala Software Engineer

Company: Rewards Network

Location: Chicago, IL

Posted Jan 31, 2025

Rewards Network, a company celebrating 40 years in business, is seeking a Scala Software Engineer for a hybrid position in Chicago. The role involves working with a team to build out new business areas and improve the rewards platform using the latest technologies. The company offers a competitive benefits package, including a comprehensive health plan, 401k with company match, and a flexible working environment. Requirements include a degree in Computer Science, 2+ years of development experience, and proficiency in Scala or other functional languages.

Manager, Solutions Architect - Oracle Cloud ERP & Integrations

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Feb 01, 2025

McDonald's is accelerating its growth strategy, focusing on enhancing the customer experience through Delivery, Digital, and Drive-Thru. The company is investing in transformative technology, including AI and robotics, to digitize its operations and improve efficiency. The role of Manager, Solutions Architect, is crucial in designing and maintaining solutions for Oracle Cloud ERP, ensuring scalability, security, and resilience. The ideal candidate should have extensive experience in solution architecture, particularly in large-scale global technology environments, and a strong understanding of Oracle Cloud ERP, DevOps, Security, and Systems Performance.

Software Engineer Team Lead - DevEx (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Jan 31, 2025

Enova International is seeking a Software Engineering Team Lead with 5+ years of full stack development experience. The role involves designing and implementing technical solutions, collaborating with engineers, mentoring junior developers, and managing agile scrum teams. The ideal candidate should have expertise in enterprise architecture, API integration, and automated testing. The position offers a competitive salary range of $116,000 to $160,000, along with comprehensive benefits and a flexible hybrid work model. Enova is a values-driven organization committed to creating accessible credit for millions through its AI-powered Colossus platform.

Nutanix Business Development Manager - Commerical

Company: CDW

Location: Chicago, IL

Posted Feb 01, 2025

CDW, a Fortune 200 leader, offers a Business Development role with a focus on accelerating growth within the Corporate segment. The role involves targeting high visibility corporate accounts, understanding client needs, and providing solutions. Key responsibilities include project management, coordination with sales, and developing long-term pipelines. The ideal candidate should have a Bachelor's degree or 6 years of experience in technical sales, marketing, or business development, with a proven track record in the Corporate Sales marketplace. Strong customer-facing skills, excellent communication, collaboration, and problem-solving abilities are required. The role involves significant travel and offers a pay range of $63,000 - $75,000, an annual bonus target of 100%, and comprehensive benefits.

Billing Disputes Operations Strategy Intelligence Lead

Company: Discover

Location: Chicago, IL

Posted Feb 01, 2025

Discover is offering a job opportunity for a Billing Disputes Operations Strategy Intelligence Lead. The role involves implementing strategies and systems improvements to support business operations, utilizing data to identify opportunities for enhancement, fostering collaboration, and problem-solving issues. The candidate will be responsible for developing numerous business dashboards and scorecards, ensuring proper reporting and data collection. The position requires a Bachelor's degree in Business Administration, Management Engineering, Social Sciences, or related fields, along with 4+ years of customer service or financial services operations experience. The role is primarily performed indoors in an office setting, with the ability to operate office equipment and communicate verbally. Discover offers a competitive total compensation package, including benefits such as paid parental leave, paid time off, 401k plan, medical, dental, vision, and health savings account, STD, life, LTD, and AD&D, recognition program, education assistance, commuter benefits, family support programs, and employee stock purchase plan.

IT Support Analyst

Company: Kalderos

Location: Chicago, IL

Posted Feb 01, 2025

Kalderos is a healthcare technology company focused on pharmaceutical pricing transparency, trust, and equity. They are seeking an IT Support Analyst to provide top-tier technical support to their 115+ internal employees in a fully remote environment. The role involves troubleshooting technical issues, collaborating with the IT team, and assisting with IT projects. The company values collaboration, feedback, and growth, offering competitive benefits and a dynamic work environment.

Senior Software Engineer - Platform (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Feb 01, 2025

Enova International is seeking a Senior Software Engineer with 3+ years of full stack development experience. The role involves taking ownership of system development, collaborating with stakeholders, and mentoring team members. Preferred skills include proficiency in Ruby and Go, and experience in the Finance domain. The position offers a competitive salary range, comprehensive benefits, and a flexible hybrid work model. Enova is a values-driven organization committed to creating accessible credit for millions through its AI-powered platform.

Lead AI Software Engineer

Company: iManage

Location: Chicago, IL

Posted Feb 01, 2025

iManage offers a flexible working policy that supports employee wellbeing and work-life balance. The company values collaboration and learning from peers while providing necessary flexibility. The Lead AI Software Engineer role involves using cutting-edge research and technology to work on a wide range of AI problems, focusing on building systems for deploying, scaling, and monitoring NLP and Gen AI applications. The role requires a Masters or PhD in Computer Science, Machine Learning, Data Science, Artificial Intelligence, Statistics, or related field, along with 6+ years of experience in ML/AI engineering or software engineering with expertise in NLP. The role involves driving technical strategy, designing production-ready NLP applications, and collaborating with product and business stakeholders. iManage provides a supportive team, flexible work hours, and comprehensive benefits, including a market-competitive salary, health benefits, and a 401k retirement plan with a company match.

Contract Payroll Tax Analyst

Company: Revantage, a Blackstone Portfolio Company

Location: Chicago, IL

Posted Feb 01, 2025

Revantage, a Blackstone Real Estate portfolio company, is a global provider of corporate services. With a commitment to collaboration and inclusivity, Revantage delivers value-added services and world-class talent for Blackstone Real Estate portfolio companies across diverse asset classes. The company is seeking a Payroll Tax professional with minimum 5 years of experience in federal and multistate payroll tax, in-depth knowledge of multistate payroll tax laws, and experience in Workday and Smart Compliance. The role involves staying in compliance with Payroll Taxes, resolving payroll tax issues, and partnering with ADP to validate accuracy of periodic taxes. The company offers dynamic work, competitive compensation, benefits, and flexibility, and has earned numerous awards as a top employer.

Product Manager - LLM & NLP

Company: IMO Health

Location: Chicago, IL

Posted Feb 01, 2025

The role of a Product Manager involves driving the development and delivery of innovative products powered by large language models (LLM) and natural language processing (NLP). The individual will collaborate with cross-functional teams, including development and NLP/LLM engineering, to ensure product features align with business objectives and user needs. The role emphasizes strategic execution and hands-on collaboration across teams. Key responsibilities include driving the product roadmap, collaborating with clients, defining product strategies, managing the product backlog, and leading internal and external communication efforts. The ideal candidate should have 5+ years of product management experience in clinical AI, expertise in NLP and LLM technologies, a solid understanding of AI, experience in the healthcare industry, and strong communication skills.

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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