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 PwC, Avanade, and Stantec. See the openings below and apply to the ones that match your experience.
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Responsibilities
- Leading Guidewire configuration workstreams across client engagements and aligning deliverables with business requirements
- Managing project plans, timelines, budgets, and team activities across PolicyCenter, BillingCenter, and ClaimCenter initiatives
- Coordinating solution design, configuration, and integration activities for Guidewire software implementations
- Reviewing technical deliverables, identifying system dependencies, and resolving complex configuration issues
- Coaching team members on Guidewire development approaches, delivery methods, and practical application of software tooling
- Supporting client discussions to clarify requirements, confirm scope, and translate business needs into platform solutions
- Overseeing testing activities, defect resolution, and deployment readiness across application releases
- Identifying opportunities to improve delivery methods, streamline configuration work, and strengthen operational efficiency
What You Must Have
- At least a Bachelor's degree
- At least 5 years of experience
What Sets You Apart
- Preference for a Master's or Masters of Business Administration degree in at least one of the following fields of study: Actuarial Science, Business Administration/Management, Business Analytics, Commerce, Computer and Information Science, Computer Applications, Computer Engineering, Computer Engineering & Accounting, Data Processing/Analytics/Science, Economics, Electrical Engineering, Engineering, Engineering and Business, Finance, Information Technology, Management Information Systems, Mathematics, Mechanical Engineering, Operations Management/Research, Risk Management, Software App, Statistics
- Demonstrating Guidewire configuration leadership across policy, billing, or claims
- Leading complex project planning, budgeting, execution, and delivery
- Mentoring teams through code reviews, issue resolution, and feedback
- Using Guidewire BillingCenter, ClaimCenter, or PolicyCenter configuration
- Translating business needs into system design and delivery priorities
The salary range for this position is: $99,000 - $232,000. Actual compensation within the range will be dependent upon the individual's skills, experience, qualifications and location, and applicable employment laws. All hired individuals are eligible for an annual discretionary bonus. PwC offers a wide range of benefits, including medical, dental, vision, 401k, holiday pay, vacation, personal and family sick leave, and more. To view our benefits at a glance, please visit the following link: https://pwc.to/benefits-at-a-glance
As PwC is an equal opportunity employer, all qualified applicants will receive consideration for employment at PwC without regard to race; color; religion; national origin; sex (including pregnancy, sexual orientation, and gender identity); age; disability; genetic information (including family medical history); veteran, marital, or citizenship status; or, any other status protected by law.
PwC does not intend to hire experienced or entry level job seekers who will need, now or in the future, PwC sponsorship through the H-1B lottery, except as set forth within the following policy: https://pwc.to/H-1B-Lottery-Policy.
Learn more about how we work: https://pwc.to/how-we-work
For only those qualified applicants that are impacted by the Los Angeles County Fair Chance Ordinance for Employers, the Los Angeles' Fair Chance Initiative for Hiring Ordinance, the San Francisco Fair Chance Ordinance, San Diego County Fair Chance Ordinance, and the California Fair Chance Act, where applicable, arrest or conviction records will be considered for Employment in accordance with these laws. At PwC, we recognize that conviction records may have a direct, adverse, and negative relationship to responsibilities such as accessing sensitive company or customer information, handling proprietary assets, or collaborating closely with team members. We evaluate these factors thoughtfully to establish a secure and trusted workplace for all.
Applications will be accepted until the position is filled or the posting is removed, unless otherwise set forth on the following webpage. Please visit this link for information about anticipated application deadlines: https://pwc.to/us-application-deadlines
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Find Technical Lead JobsTechnical Lead Job Market in Chicago
Who's Hiring



Top Industries Hiring
- Technology & Software
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 PwC, Avanade, and Stantec, per current listings on Migrate Mate as of November 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 93% of technical lead openings tied to Chicago are remote or hybrid as of November 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 Technology & Software, based on current listings on Migrate Mate as of November 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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