Learning Specialist Jobs in Chicago, IL
Learning Specialist jobs in Chicago are concentrated in the Loop, River North, and the Medical District, driven by demand across corporate training, higher education, and healthcare. Employers hiring right now include IXL Learning, Katten, and Prizmah. Find a role that fits below and apply directly.
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Company
Shared ServicesArgo and Farm Family are specialty property and casualty insurance brands whose underwriting companies are wholly-owned subsidiaries of Clearbrook Holdings Inc. Argo and Farm Family partner with agents and brokers to provide insurance solutions that enable businesses to manage risks with confidence.
Job Description
The Learning and Development Specialist will implement and support enterprise-wide learning and development (L&D) programs with a key focus on cohesive and integrated learning processes for a high-performance and inclusive culture. Collaborate with business leaders, HR business partners, subject matter experts and colleagues to identify needs and skills gaps, explore options, design planning and execute effective learning solutions to support the business to achieve strategic goals. This position will manage large-scale projects and deliver engaging, creative, and impactful virtual, in-person, and blended programs to improve individual and organizational performance and development.
This is a 100% in-office position. Candidates must be able to work on-site at a designated company office during standard business hours.
Essential Responsibilities:
- Establish a strategic roadmap for L&D programs, including manager/leadership development, interpersonal and values-based skills development, and applicable compliance training programs.
- Lead design, development, implementation, communication and sustainability of centralized learning programs consistent with industry best practices.
- Build and implement strategies focused on change management and application of the new skills, behaviors or habits.
- Determine training content for key compliance training needs and ensure the L&D roadmap aligns with state, local, or audit requirements and policies.
- Assess organizational and functional needs, co-create solutions, and ensure alignment with organizational priorities.
- Write, edit, and coordinate development of course catalogs, promotional materials, training manuals, reference guides, visuals/handouts, and/or training presentations, as appropriate to the program.
- Establish and manage a robust succession planning framework for key roles across the organization. Partner with HR Business Partners and Senior Leadership to regularly review and update succession plans to ensure readiness for future leadership transitions.
- Develop metrics to evaluate and measure program performance, learner outcomes, productivity and satisfaction of learning solutions; leverage data to drive, modify and create future learning offerings.
- Evaluate program effectiveness utilizing data and gathering feedback and apply insights to improve experiences, outcomes, and business value.
- Manage end-to-end program delivery from content development to vendor management to budget oversight. Provide support for various strategic and special projects as needed, including performance and talent management initiatives.
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Qualifications / Experience Required:
- Bachelor’s degree with a concentration in Human Resources Management or related field.
- 7+ years of experience in financial services.
- Facilitation and training experience.
- Knowledge of learning needs analysis; instructional/program design, development and evaluation; adult learning concepts and learning methodologies.
- Project management of multiple and complex HR projects.
- Experience in implementing leadership and talent management capability review and development initiatives, competency frameworks, performance management, change management, career development, talent management and succession processes.
- Ability to execute high-impact learning strategies that enhance people and business performance.
- Results focused; a consultative leadership style that builds high-performing teams across multi-disciplined projects that consistently meet targets and realize organizational benefits.
- Ability to collaborate with all levels throughout an organization.
- Excellent interpersonal, organizational and influencing skills and ability to facilitate across all levels of business.
- Strong written and verbal communication skills.
- Strong presentation skills.
- Experience with e-learning systems.
- Experience with vendor management. Occasional travel required.
Preferred Qualifications:
- Advanced degree in HR, Organizational Development or Education, a plus.
- Specialty insurance, a plus.
- Workday experience a plus Certification(s) in various training programs, a plus.
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Chicago Pay Range: $120,000 - $150,000
PLEASE NOTE:
Applicants must be legally authorized to work in the United States. At this time, we are not able to sponsor or assume sponsorship of employment visas.
If you have a disability under the Americans with Disabilities Act or similar state or local law and you wish to discuss potential reasonable accommodations related to applying for employment with us, please contact our Benefits Department at 210-321-8400.
Benefits and Compensation
We offer a competitive compensation package, performance-based incentives, and a comprehensive benefits program—including health, dental, vision, 401(k) with company match, paid time off, and professional development opportunities.
Core Values
At Clearbrook our Core Values are Integrity, Collaboration, Pursuit of Excellence and Forward Thinking. These values reflect who we are today and who we aspire to be - guiding how we work, how we lead and how we succeed.
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Find Learning Specialist JobsLearning Specialist Job Market in Chicago
Who's Hiring


Top Industries Hiring
- Education
- Technology & Software
Learning Specialist Jobs in Chicago: Frequently Asked Questions
How do I get a learning specialist job in Chicago?
Target Chicago's strongest hiring sectors: large corporate headquarters in the Loop, health systems in the Medical District, and universities along the lakefront. Candidates who combine instructional design skills with familiarity in e-learning platforms like Articulate or Adobe Captivate stand out locally. Networking through Chicago-area ATD chapter events and applying directly to healthcare and financial services employers gives you a concrete edge in this market.
Which companies hire learning specialists in Chicago?
Employers hiring learning specialists in Chicago right now include IXL Learning, Katten, and Prizmah, based on current listings on Migrate Mate as of November 2026. Chicago's mix of Fortune 500 headquarters, major health systems, and large universities means hiring comes from a wide range of employer types across the city.
Are there remote learning specialist jobs in Chicago?
Yes, though availability depends on the role: curriculum design and e-learning development work is often remote-eligible, while facilitation and onboarding roles typically require in-person attendance. About 71% of learning specialist openings tied to Chicago are remote or hybrid as of November 2026, reflecting broader flexibility in the instructional design side of the field. Corporate and technology employers in Chicago tend to offer the most remote-friendly arrangements.
How can I get a learning specialist job in Chicago with little or no experience?
The most realistic entry path in Chicago is through training coordinator or learning and development assistant roles at large healthcare systems or financial services firms, which regularly hire candidates with relevant coursework rather than years of direct experience. Community colleges and Chicago Public Schools also offer entry points for those with an education background. Volunteering with workforce development nonprofits on the South and West Sides builds a local portfolio that resonates with Chicago employers.
Which industries hire the most learning specialists in Chicago?
Chicago learning specialist roles concentrate in Education and Technology & Software, based on current listings on Migrate Mate as of November 2026. Chicago's density of corporate headquarters, major academic medical centers, and flagship universities creates consistent local demand across all three sectors throughout the year.
See All 27 Learning Specialist Jobs in Chicago
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