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.

Senior Director Cybersecurity - IAM and Architecture

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 31, 2025

McDonald's is seeking a Senior Director of Identity and Access Management to lead the development and implementation of innovative IAM strategies and solutions. The role involves driving the creation of pioneering IAM strategies, developing a strategic vision for User Access Enforcement, leading large-scale IAM projects, and providing strong leadership to the IAM team. The ideal candidate should have 5+ years of experience leading IAM teams, proficiency in IAM technologies, and strong people leadership skills.

Senior Analyst, Liquidity and Funding Risk

Company: BMO US

Location: Chicago, IL

Posted Jan 30, 2025

Typically between 4 - 6 years of relevant experience and post-secondary degree in related field of study or an equivalent combination of education and…

Marketing Analytics Manager

Company: SpotHero

Location: Chicago, IL

Posted Jan 31, 2025

SpotHero, a rapidly growing parking industry technology company, is seeking a Marketing Analytics Manager. The role involves leading a team of analysts, developing a marketing analytics roadmap, and designing marketing models. The ideal candidate should have a minimum of 3 years of experience in marketing analytics leadership, strong SQL and Python skills, and a deep understanding of marketing attribution and ROI methodologies. SpotHero offers a competitive salary, excellent benefits, flexible PTO, and a supportive work environment.

Sr. Director, Cyber Business Office

Company: McDonald’s Global Technology

Location: Chicago, IL

Posted Jan 31, 2025

McDonald's is seeking a Sr Director Cyber Business Office to lead and oversee the execution of their Securing the Arches Strategy. The role involves implementing a comprehensive cybersecurity program, developing metrics and reporting frameworks, and collaborating with various teams. The ideal candidate should have experience leading sophisticated programs, influencing high-performing teams, and managing risks with a focus on security and compliance.

Senior Manager, Compensation and Benefits

Company: Point B

Location: Chicago, IL

Posted Jan 30, 2025

Point B is a business innovation firm that specializes in transformation, combining advanced technologies and industry expertise to help businesses reimagine their processes and stay ahead. They offer a world-class NPS score, proving their commitment to client success. The firm is seeking a Senior Compensation and Benefits Manager to lead their compensation and benefits programs, ensuring alignment with Point B's vision and competitive practices. The ideal candidate will have a strong analytical skill set, excellent communication skills, and a thorough understanding of compensation practices. Point B offers a career path based on expertise, a flexible lifestyle, and a comprehensive Total Rewards program. The estimated salary range for this role is $94,500 - $210,000 USD per year.

Senior Customer Success Manager

Company: Jobba Trade Technologies, Inc.

Location: Chicago, IL

Posted Jan 30, 2025

Jobba Trade Technologies is seeking a Senior Customer Success Manager to lead the successful transition from sale to client implementation, recommend workflows, develop and facilitate training, build trusted advisor relationships, and elevate the overall client experience. The role involves managing complex, valuable, and at-risk customers, developing processes and training programs, and coaching junior team members. Required skills include 57 years of experience in consulting services or software implementation, demonstrated success in driving product adoption, tech savviness, proactive client engagement, and business acumen. Preferred skills include a Bachelor's degree, construction or service industry experience, CRM ERP and client management experience, and curriculum and learning content development experience.

Project Manager - Construction [48023]

Company: Technology Resource Group

Location: Chicago, IL

Posted Jan 31, 2025

Collaborate with the quality assurance team to develop and implement quality control processes during production. Risk Management and Problem-Solving:

Product Manager (EMV Mobile Payments)

Company: Discover

Location: Chicago, IL

Posted Jan 30, 2025

Discover is offering a job opportunity for an EMV Mobile Payments Product Manager. The role involves developing and managing the Mobile DPAS product, which enables contactless payments using mobile devices. The successful candidate will be responsible for creating the product strategy, roadmap, and features based on client needs. They will also be accountable for achieving specific goals for each product, evaluating product performance, and identifying innovations to address customer needs. The ideal candidate should have a Bachelor's degree in a relevant field and at least 6 years of experience in Product Management. Bonus points for a Masters degree, experience in the payments industry, and knowledge of EMV specifications.

Senior Fundamental Research Analyst

Company: PEAK6

Location: Chicago, IL

Posted Jan 31, 2025

PEAK6 Capital Management, a 25-year-old proprietary options trading firm based in Chicago, is seeking a highly motivated Analyst for its growing trading team. The role involves conducting in-depth research, building financial models, performing valuation analysis, monitoring portfolio companies, generating investment ideas, and preparing presentations. The ideal candidate should have 5+ years of experience in a related field, excellent research and analytical skills, strong communication skills, and experience with financial modeling or valuation. PEAK6 offers a robust package of employee perks and benefits, including healthcare, competitive PTO, 401k match, and a paid subscription to the Calm app.

Principal Product Owner - Digital Experiences

Company: Discover

Location: Chicago, IL

Posted Jan 31, 2025

Discover is seeking a Principal Product Owner for Digital Experiences to lead the development of a new mobile application feature for cardmembers to manage transaction disputes. The role involves partnering with various teams, defining product vision, prioritizing tasks, and ensuring adherence to compliance and quality standards. The ideal candidate should have a background in digital, product management, and financial services, with 6+ years of experience. The position offers a competitive salary and benefits package, and Discover is committed to a diverse and inclusive workplace.

Sr. Technical Business Analyst

Company: NinjaHoldings

Location: Chicago, IL

Posted Jan 30, 2025

NinjaHoldings, founded in 2017, aims to revolutionize financial services for overlooked Americans through digital banking and lending products. The company's EDGE brand offers analytics services to businesses. The Sr Technical Business Analyst role involves leading strategic conversations, managing teams, and driving project planning. The ideal candidate should have extensive experience in business intelligence, a deep understanding of financial products, and strong leadership skills.

Consultant, Comparative Analytics

Company: Strata Decision Technology

Location: Chicago, IL

Posted Jan 31, 2025

The job posting is for a Comparative Analytics Consultant role in healthcare. The successful candidate will work with healthcare organizations to implement, optimize, and provide advisory services for Strata's financial and operational benchmarking software solution. Key responsibilities include working with a team to implement the software, defining user requirements, configuring the system, leading customer training, communicating with team members, contributing to growth projects, collaborating with other solution consultants, and using SQL, Excel, and Strata tools. The ideal candidate should have a data-driven mindset, relevant experience, strong customer service skills, understanding of financial concepts, ability to adapt to new challenges, self-motivation, and willingness to travel. Additional points for professional or academic background in SQL, healthcare finance experience, setting productivity standards, and software implementation experience. The company values collaboration, continuous learning, and diversity, with a focus on inclusion and equity.

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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