Technical Lead Jobs in Chicago, IL
Technical Lead jobs in Chicago are concentrated in the Loop, River North, and the Fulton Market district, with strong hiring across enterprise software, fintech, and healthtech. Employers actively filling roles include Capgemini, United Airlines, and Huron Consulting. See the openings below and apply to the ones that match your experience.
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As Humana continues its transformation into an AI-first enterprise, we are looking for a hands-on, technically proficient Lead Product Manager to lead the design, prototyping, and scaling of AI solutions across our business. You will work with cross-functional teams of engineers, designers, data scientists, and business stakeholders to build AI-powered solutions that solve real enterprise problems. You will lead and drive a complex product area within our AI portfolio, define what success looks like, build and develop with the team, and drive results across the organization, moving from deeply understanding a business challenge to prototyping an AI solution, to proving its value, to delivering it through Humana's enterprise AI governance process.What you will own
Strategy and roadmap: Define the vision, strategy, and roadmap for a complex AI product area. Decide what to build and why, prioritize across competing opportunities, and adapt as the model landscape and the business change.
Business discovery: Partner directly with business units to map their operations end to end (service design), then translate ambiguous business problems into clearly scoped AI use cases with a clear value proposition, business case, and ROI justification.
Hands-on prototyping: Build working prototypes and demos yourself using agentic coding and AI tools (for example, Claude Code, Cursor, OpenAI Codex) to test feasibility and value before committing a full team.
Requirements and scoping: Turn validated use cases into clear, buildable requirements, user stories, acceptance criteria, edge cases, and success metrics, so engineers, data scientists, and designers know exactly what "done" and "good" mean. Shape the end-to-end user experience with design, since enterprise adoption lives or dies on usability.
Delivery and execution: Drive the build from prototype to production and own the backlog, sequence the work, make scope and tradeoff calls as models and constraints shift, unblock the team, and keep momentum from first demo through launch and iteration.
Evaluation and quality: Own how quality is defined and measured. Build golden sets and ground truth, run offline and live (production) evals, choose appropriate metrics (accuracy, precision, recall, F1, task success, hallucination rate), apply LLM-as-judge where it has been validated, and turn results into launch decisions and readouts for leadership.
Support Solution architecture: Support high-level architecture and feasibility discussions with engineering, while owning the required prompt engineering and/or skill creation components of the AI harness.
Cross-functional leadership: Lead engineers, data scientists, designers, and business partners without direct authority. Author reusable playbooks, skills, and solution patterns that make AI delivery faster and more consistent across the organization.
Governed delivery: Move solutions through Humana's enterprise AI governance (AIRB, LRC, Responsible AI Council), owning the product documentation, scorecards, and stage-gate reviews.
Communication and mentorship: Communicate strategy, requirements, roadmap, ROI, and eval results clearly to executive and technical audiences. Mentor product managers and raise the team's standard for building with AI.
Staying current: Track advances in models, agents, evals, and emerging techniques (agent harness, loop, and graph / GraphRAG approaches) and apply them in your portfolio.
Use your skills to make an impact
Required Qualifications
B.S. or M.S. in Computer Science, Engineering, or a related field (or equivalent experience)
7+ years of product or related experience, including 4+ years in product management, with AI/ML or GenAI products shipped to production.
Hands-on building: You use AI tools regularly and can articulate specifically what you would change about a model's behavior and why. You prototype your own ideas.
Evaluation experience: You have built evals, including golden sets, ground truth, and offline and live evals, and used precision- and recall-based metrics to make product decisions.
Systems thinking: When you find a problem, you build the infrastructure that prevents the whole class of problem.
Communication across domains: You move between business and technical concepts, with a track record of business cases, ROI models, and roadmaps that inform investment decisions.
AI knowledge: A working understanding of modern AI/ML and GenAI (LLMs, agents, RAG, prompt engineering, and Evaluation methodology) and how it applies to enterprise problems.
Preferred Qualifications
Experience in healthcare, insurance, or another regulated industry.
A well-supported point of view on where agentic AI, evals, and AI-native product development are headed.
Hands-on experience with agent frameworks, GraphRAG / knowledge graphs, and reusable skills / plugins.
Comfort with ambiguity and a fast pace, working from first principles.
Additional Information
All AI solutions must comply with Humana’s Enterprise AI Governance Framework and undergo full review at designated stage gates.
Work Style: This position follows a hybrid work schedule, requiring employees to work three days per week in the office and the remaining days remotely. Qualified candidates must currently reside within, or be willing to relocate to, a commutable distance from one of the talent markets listed below.
Office Location Options:
Louisville, KY
Chicago, IL
New York, NY
Dallas, TX
Boston, MA
Washington, DC
Scheduled Weekly Hours
Pay Range
The compensation range below reflects a good faith estimate of starting base pay for full time (40 hours per week) employment at the time of posting. The pay range may be higher or lower based on geographic location and individual pay will vary based on demonstrated job related skills, knowledge, experience, education, certifications, etc.$151,600 - $208,400 per year
This job is eligible for a bonus incentive plan. This incentive opportunity is based upon company and/or individual performance.
Description of Benefits
Humana, Inc. and its affiliated subsidiaries (collectively, “Humana”) offers competitive benefits that support whole-person well-being. Associate benefits are designed to encourage personal wellness and smart healthcare decisions for you and your family while also knowing your life extends outside of work. Among our benefits, Humana provides medical, dental and vision benefits, 401(k) retirement savings plan, time off (including paid time off, company and personal holidays, paid parental and caregiver leave), short-term and long-term disability, life insurance and many other opportunities.
About Us
About Humana: Humana Inc. (NYSE: HUM) is a leading U.S. healthcare company. Through our Humana insurance services and our CenterWell healthcare services, we make it easier for the millions of people we serve to achieve their best health – delivering the care and service they need, when they need it. These efforts are leading to a better quality of life for people with Medicare and Medicaid, families, individuals, military service personnel, and communities at large. Learn more about what we offer at Humana.com and at CenterWell.com.
Equal Opportunity Employer
It is the policy of Humana not to discriminate against any employee or applicant for employment because of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or protected veteran status. It is also the policy of Humana to take affirmative action, in compliance with Section 503 of the Rehabilitation Act and VEVRAA, to employ and to advance in employment individuals with disability or protected veteran status, and to base all employment decisions only on valid job requirements. This policy shall apply to all employment actions, including but not limited to recruitment, hiring, upgrading, promotion, transfer, demotion, layoff, recall, termination, rates of pay or other forms of compensation and selection for training, including apprenticeship, at all levels of employment.
Become a part of our caring community
As Humana continues its transformation into an AI-first enterprise, we are looking for a hands-on, technically proficient Lead Product Manager to lead the design, prototyping, and scaling of AI solutions across our business. You will work with cross-functional teams of engineers, designers, data scientists, and business stakeholders to build AI-powered solutions that solve real enterprise problems. You will lead and drive a complex product area within our AI portfolio, define what success looks like, build and develop with the team, and drive results across the organization, moving from deeply understanding a business challenge to prototyping an AI solution, to proving its value, to delivering it through Humana's enterprise AI governance process.What you will own
Strategy and roadmap: Define the vision, strategy, and roadmap for a complex AI product area. Decide what to build and why, prioritize across competing opportunities, and adapt as the model landscape and the business change.
Business discovery: Partner directly with business units to map their operations end to end (service design), then translate ambiguous business problems into clearly scoped AI use cases with a clear value proposition, business case, and ROI justification.
Hands-on prototyping: Build working prototypes and demos yourself using agentic coding and AI tools (for example, Claude Code, Cursor, OpenAI Codex) to test feasibility and value before committing a full team.
Requirements and scoping: Turn validated use cases into clear, buildable requirements, user stories, acceptance criteria, edge cases, and success metrics, so engineers, data scientists, and designers know exactly what "done" and "good" mean. Shape the end-to-end user experience with design, since enterprise adoption lives or dies on usability.
Delivery and execution: Drive the build from prototype to production and own the backlog, sequence the work, make scope and tradeoff calls as models and constraints shift, unblock the team, and keep momentum from first demo through launch and iteration.
Evaluation and quality: Own how quality is defined and measured. Build golden sets and ground truth, run offline and live (production) evals, choose appropriate metrics (accuracy, precision, recall, F1, task success, hallucination rate), apply LLM-as-judge where it has been validated, and turn results into launch decisions and readouts for leadership.
Support Solution architecture: Support high-level architecture and feasibility discussions with engineering, while owning the required prompt engineering and/or skill creation components of the AI harness.
Cross-functional leadership: Lead engineers, data scientists, designers, and business partners without direct authority. Author reusable playbooks, skills, and solution patterns that make AI delivery faster and more consistent across the organization.
Governed delivery: Move solutions through Humana's enterprise AI governance (AIRB, LRC, Responsible AI Council), owning the product documentation, scorecards, and stage-gate reviews.
Communication and mentorship: Communicate strategy, requirements, roadmap, ROI, and eval results clearly to executive and technical audiences. Mentor product managers and raise the team's standard for building with AI.
Staying current: Track advances in models, agents, evals, and emerging techniques (agent harness, loop, and graph / GraphRAG approaches) and apply them in your portfolio.
Use your skills to make an impact
Required Qualifications
B.S. or M.S. in Computer Science, Engineering, or a related field (or equivalent experience)
7+ years of product or related experience, including 4+ years in product management, with AI/ML or GenAI products shipped to production.
Hands-on building: You use AI tools regularly and can articulate specifically what you would change about a model's behavior and why. You prototype your own ideas.
Evaluation experience: You have built evals, including golden sets, ground truth, and offline and live evals, and used precision- and recall-based metrics to make product decisions.
Systems thinking: When you find a problem, you build the infrastructure that prevents the whole class of problem.
Communication across domains: You move between business and technical concepts, with a track record of business cases, ROI models, and roadmaps that inform investment decisions.
AI knowledge: A working understanding of modern AI/ML and GenAI (LLMs, agents, RAG, prompt engineering, and Evaluation methodology) and how it applies to enterprise problems.
Preferred Qualifications
Experience in healthcare, insurance, or another regulated industry.
A well-supported point of view on where agentic AI, evals, and AI-native product development are headed.
Hands-on experience with agent frameworks, GraphRAG / knowledge graphs, and reusable skills / plugins.
Comfort with ambiguity and a fast pace, working from first principles.
Additional Information
All AI solutions must comply with Humana’s Enterprise AI Governance Framework and undergo full review at designated stage gates.
Work Style: This position follows a hybrid work schedule, requiring employees to work three days per week in the office and the remaining days remotely. Qualified candidates must currently reside within, or be willing to relocate to, a commutable distance from one of the talent markets listed below.
Office Location Options:
Louisville, KY
Chicago, IL
New York, NY
Dallas, TX
Boston, MA
Washington, DC
Scheduled Weekly Hours
Pay Range
The compensation range below reflects a good faith estimate of starting base pay for full time (40 hours per week) employment at the time of posting. The pay range may be higher or lower based on geographic location and individual pay will vary based on demonstrated job related skills, knowledge, experience, education, certifications, etc.$151,600 - $208,400 per year
This job is eligible for a bonus incentive plan. This incentive opportunity is based upon company and/or individual performance.
Description of Benefits
Humana, Inc. and its affiliated subsidiaries (collectively, “Humana”) offers competitive benefits that support whole-person well-being. Associate benefits are designed to encourage personal wellness and smart healthcare decisions for you and your family while also knowing your life extends outside of work. Among our benefits, Humana provides medical, dental and vision benefits, 401(k) retirement savings plan, time off (including paid time off, company and personal holidays, paid parental and caregiver leave), short-term and long-term disability, life insurance and many other opportunities.
About Us
About Humana: Humana Inc. (NYSE: HUM) is a leading U.S. healthcare company. Through our Humana insurance services and our CenterWell healthcare services, we make it easier for the millions of people we serve to achieve their best health – delivering the care and service they need, when they need it. These efforts are leading to a better quality of life for people with Medicare and Medicaid, families, individuals, military service personnel, and communities at large. Learn more about what we offer at Humana.com and at CenterWell.com.
Equal Opportunity Employer
It is the policy of Humana not to discriminate against any employee or applicant for employment because of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or protected veteran status. It is also the policy of Humana to take affirmative action, in compliance with Section 503 of the Rehabilitation Act and VEVRAA, to employ and to advance in employment individuals with disability or protected veteran status, and to base all employment decisions only on valid job requirements. This policy shall apply to all employment actions, including but not limited to recruitment, hiring, upgrading, promotion, transfer, demotion, layoff, recall, termination, rates of pay or other forms of compensation and selection for training, including apprenticeship, at all levels of employment.
See All 38 Technical Lead Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Technical Lead JobsTechnical Lead Job Market in Chicago
Who's Hiring
Top Industries Hiring
- Consulting & Professional Services
- Technology & Software
- Renewable Energy
Technical Lead Jobs in Chicago: Frequently Asked Questions
How do I get a technical lead job in Chicago?
Focus your search on Chicago's strongest hiring sectors: enterprise software, financial technology, and healthcare technology. The Loop and Fulton Market district concentrate the largest share of openings, with additional demand from consulting firms along the Magnificent Mile corridor. Candidates who combine hands-on engineering depth with demonstrated team leadership stand out, and familiarity with agile delivery in large enterprise environments is a consistent differentiator in this market.
Which companies hire technical leads in Chicago?
Companies currently hiring technical leads in Chicago include Capgemini, United Airlines, and Huron Consulting, per current listings on Migrate Mate as of August 2026. Chicago's mix of large financial institutions, global consultancies, and a growing startup ecosystem in Fulton Market means openings exist across a wide range of company sizes and technical stacks.
Are there remote technical lead jobs in Chicago?
Yes, though availability depends on the role, because technical leads with team mentoring and architecture review duties are more often required on-site than purely individual-contributor engineers. About 64% of technical lead openings tied to Chicago are remote or hybrid as of August 2026, with the highest remote flexibility found in product-facing and platform engineering roles at software-first companies.
How can I get a technical lead job in Chicago with little or no experience?
The most realistic entry path in Chicago is moving into a senior engineer role at a mid-size software or fintech company, then taking on informal team lead responsibilities before stepping into the title formally. Chicago-based consultancies and enterprise technology teams frequently promote from within, so targeting companies with structured career ladders gives you the clearest route. Building experience leading sprint ceremonies or mentoring junior engineers in your current role strengthens any application significantly.
Which industries hire the most technical leads in Chicago?
Chicago technical lead roles concentrate in Consulting & Professional Services, Technology & Software, and Renewable Energy, based on current listings on Migrate Mate as of August 2026. Chicago's legacy as a financial and commodities trading hub, combined with its growing healthtech corridor and a dense base of enterprise software firms, sustains consistent demand for technical leads who can manage both complex systems and cross-functional teams.
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See All 38 Technical Lead Jobs in Chicago
Find roles in Chicago that match your experience and apply in just a few clicks.
Find Technical Lead Jobs