Technology Lead Jobs in Chicago, IL
Technology Lead jobs in Chicago are in strong demand, concentrated in the Loop, River North, and the Fulton Market tech corridor, across fintech, healthcare technology, and enterprise software. Employers actively hiring include Avanade, JPMorganChase, and Wolters Kluwer. See the openings below and apply to the ones that match your experience.
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Build trusted AI experiences that help clinicians get from question to answer faster.
At Wolters Kluwer Health, the UpToDate suite supports millions of clinical decisions every day. As AI changes how clinicians search for, interpret, and apply clinical knowledge, we are building product experiences that make trusted guidance easier to access, understand, and use.
As Senior Product Manager, AI Clinical Decision Support, you will play a core role in developing AI-enabled experiences for UpToDate's core clinical decision support products. Working under product leadership, you will own discovery and delivery for defined capabilities that improve how users ask clinical questions, navigate evidence-based content, and engage with trusted answers.
This role focuses on building useful, responsible, and engaging AI product experiences that support clinical judgment and strengthen the core UpToDate experience.
What You'll Do
Drive discovery and delivery for defined AI-enabled clinical decision support capabilities.
Translate clinician, customer, and business needs into product requirements, experiments, roadmap priorities, and measurable outcomes.
Shape experiences that help clinicians ask questions, find relevant information, understand clinical context, and move from question to action with confidence.
Partner with engineering, design, clinical, content, analytics, customer-facing, and commercial teams from discovery through launch and iteration.
Define success metrics tied to adoption, engagement, trust, user satisfaction, workflow impact, and business value.
Use customer conversations, concept tests, analytics, and feedback to validate user needs and product direction.
Make product decisions that balance customer value, usability, clinical trust, technical feasibility, speed, cost, and responsible AI considerations.
Communicate roadmap priorities, rationale, risks, and tradeoffs clearly across teams and leadership.
What You'll Bring
5+ years of product management experience in healthcare, enterprise SaaS, content products, search, workflow, or data-driven products.
Strong product discovery and execution skills, including customer research, experimentation, roadmap development, and metrics-driven decision-making.
Experience translating complex customer problems into intuitive product experiences, clear requirements, and measurable outcomes.
Ability to partner closely with engineering, design, clinical, content, analytics, commercial, and customer-facing teams.
Strong communication, analytical thinking, stakeholder-management, and influencing skills.
Curiosity and learning agility around AI, automation, emerging technologies, and responsible product development.
Ability to operate in ambiguity and make sound product decisions in complex, regulated healthcare environments.
Preferred Background
Experience with AI-enabled, data-driven, search, content, knowledge, or decision-support products.
Practical understanding of generative AI, retrieval-based systems, recommendation systems, workflow automation, or applied machine learning concepts.
Experience with clinical decision support, healthcare content, point-of-care tools, or professional-information products.
Familiarity with human-in-the-loop workflows, responsible AI practices, model evaluation, or trust and safety considerations.
What Success Looks Like
AI-enabled CDS experiences help users get to relevant, trusted information faster.
New capabilities improve adoption, engagement, user satisfaction, and measurable customer value.
Product teams have clear priorities, validated learnings, and actionable success metrics.
AI experiences are designed with appropriate transparency, evidence grounding, and responsible use practices.
Our Interview Practices
To maintain a fair and genuine hiring process, we kindly ask that all candidates participate in interviews without the assistance of AI tools or external prompts. Our interview process is designed to assess your individual skills, experiences, and communication style. We value authenticity and want to ensure we’re getting to know you—not a digital assistant. To help maintain this integrity, we ask to remove virtual backgrounds and include in-person interviews in our hiring process. Please note that use of AI-generated responses or third-party support during interviews will be grounds for disqualification from the recruitment process.
Applicants may be required to appear onsite at a Wolters Kluwer office as part of the recruitment process.
Compensation:
This role is eligible for Bonus.
Compensation range listed is based on primary location of the position. Actual base salary offer is influenced by a wide array of factors including but not limited to skills, experience and actual hiring location. Your recruiter can share more information about the specific offer for the job location during the hiring process.
Additional Information:
Wolters Kluwer offers a wide variety of competitive benefits and programs to help meet your needs and balance your work and personal life, including but not limited to: Medical, Dental, & Vision Plans, 401(k), FSA/HSA, Commuter Benefits, Tuition Assistance Plan, Vacation and Sick Time, and Paid Parental Leave. Full details of our benefits are available upon request.
Build trusted AI experiences that help clinicians get from question to answer faster.
At Wolters Kluwer Health, the UpToDate suite supports millions of clinical decisions every day. As AI changes how clinicians search for, interpret, and apply clinical knowledge, we are building product experiences that make trusted guidance easier to access, understand, and use.
As Senior Product Manager, AI Clinical Decision Support, you will play a core role in developing AI-enabled experiences for UpToDate's core clinical decision support products. Working under product leadership, you will own discovery and delivery for defined capabilities that improve how users ask clinical questions, navigate evidence-based content, and engage with trusted answers.
This role focuses on building useful, responsible, and engaging AI product experiences that support clinical judgment and strengthen the core UpToDate experience.
What You'll Do
Drive discovery and delivery for defined AI-enabled clinical decision support capabilities.
Translate clinician, customer, and business needs into product requirements, experiments, roadmap priorities, and measurable outcomes.
Shape experiences that help clinicians ask questions, find relevant information, understand clinical context, and move from question to action with confidence.
Partner with engineering, design, clinical, content, analytics, customer-facing, and commercial teams from discovery through launch and iteration.
Define success metrics tied to adoption, engagement, trust, user satisfaction, workflow impact, and business value.
Use customer conversations, concept tests, analytics, and feedback to validate user needs and product direction.
Make product decisions that balance customer value, usability, clinical trust, technical feasibility, speed, cost, and responsible AI considerations.
Communicate roadmap priorities, rationale, risks, and tradeoffs clearly across teams and leadership.
What You'll Bring
5+ years of product management experience in healthcare, enterprise SaaS, content products, search, workflow, or data-driven products.
Strong product discovery and execution skills, including customer research, experimentation, roadmap development, and metrics-driven decision-making.
Experience translating complex customer problems into intuitive product experiences, clear requirements, and measurable outcomes.
Ability to partner closely with engineering, design, clinical, content, analytics, commercial, and customer-facing teams.
Strong communication, analytical thinking, stakeholder-management, and influencing skills.
Curiosity and learning agility around AI, automation, emerging technologies, and responsible product development.
Ability to operate in ambiguity and make sound product decisions in complex, regulated healthcare environments.
Preferred Background
Experience with AI-enabled, data-driven, search, content, knowledge, or decision-support products.
Practical understanding of generative AI, retrieval-based systems, recommendation systems, workflow automation, or applied machine learning concepts.
Experience with clinical decision support, healthcare content, point-of-care tools, or professional-information products.
Familiarity with human-in-the-loop workflows, responsible AI practices, model evaluation, or trust and safety considerations.
What Success Looks Like
AI-enabled CDS experiences help users get to relevant, trusted information faster.
New capabilities improve adoption, engagement, user satisfaction, and measurable customer value.
Product teams have clear priorities, validated learnings, and actionable success metrics.
AI experiences are designed with appropriate transparency, evidence grounding, and responsible use practices.
Our Interview Practices
To maintain a fair and genuine hiring process, we kindly ask that all candidates participate in interviews without the assistance of AI tools or external prompts. Our interview process is designed to assess your individual skills, experiences, and communication style. We value authenticity and want to ensure we’re getting to know you—not a digital assistant. To help maintain this integrity, we ask to remove virtual backgrounds and include in-person interviews in our hiring process. Please note that use of AI-generated responses or third-party support during interviews will be grounds for disqualification from the recruitment process.
Applicants may be required to appear onsite at a Wolters Kluwer office as part of the recruitment process.
Compensation:
This role is eligible for Bonus.
Compensation range listed is based on primary location of the position. Actual base salary offer is influenced by a wide array of factors including but not limited to skills, experience and actual hiring location. Your recruiter can share more information about the specific offer for the job location during the hiring process.
Additional Information:
Wolters Kluwer offers a wide variety of competitive benefits and programs to help meet your needs and balance your work and personal life, including but not limited to: Medical, Dental, & Vision Plans, 401(k), FSA/HSA, Commuter Benefits, Tuition Assistance Plan, Vacation and Sick Time, and Paid Parental Leave. Full details of our benefits are available upon request.
See All 19 Technology Lead Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Technology Lead JobsTechnology Lead Job Market in Chicago
Who's Hiring
Top Industries Hiring
- Consulting & Professional Services
- Fintech
- Law & Legal Services
- Technology & Software
- Banking & Financial Services
Technology Lead Jobs in Chicago: Frequently Asked Questions
How do I get a technology lead job in Chicago?
Start by targeting Chicago's strongest hiring sectors: fintech firms along LaSalle Street, health tech companies anchored near the Illinois Medical District, and enterprise software employers clustered in the Loop and Fulton Market. Candidates who stand out typically combine hands-on delivery leadership with stakeholder management experience. Familiarity with agile at scale and a local professional network built through Chicago tech meetups or industry groups gives a real edge.
Which companies hire technology leads in Chicago?
Chicago technology lead roles are posted by Avanade, JPMorganChase, and Wolters Kluwer and others right now, based on current listings on Migrate Mate as of August 2026. Chicago's market is particularly active among large financial institutions, mid-market consulting firms, and fast-growing health tech companies, all of which maintain substantial engineering and delivery teams in the city.
Are there remote technology lead jobs in Chicago?
Yes, though availability depends heavily on the role: technology leads in architecture and strategy tend to be more remote-friendly than those managing on-site delivery teams. About 75% of technology lead openings tied to Chicago are remote or hybrid as of August 2026, reflecting broader flexibility across the market. Hybrid arrangements are especially common at Chicago's larger financial services and consulting employers.
How can I get a technology lead job in Chicago with little or no experience?
The most realistic entry path is through a senior engineer or technical project lead role at a mid-size Chicago employer, where the step up to technology lead is a defined internal promotion. Chicago's fintech and health tech startups in Fulton Market and River North regularly hire engineers ready to take on team leadership. Building visibility through Chicago tech communities, local hackathons, or the Chicago CTO Club can accelerate that transition.
Which industries hire the most technology leads in Chicago?
Chicago technology lead roles concentrate in Consulting & Professional Services, Fintech, and Law & Legal Services, based on current listings on Migrate Mate as of August 2026. Chicago's position as a national hub for financial services, a growing center for health technology, and a longtime base for large consulting and managed services firms drives consistent, high-volume demand for experienced technology leads across those sectors.
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