Learning Specialist Jobs in Illinois
Learning Specialist jobs in Illinois are active across a wide range of sectors, with consistent demand from K-12 school districts, higher education institutions, corporate training departments, and healthcare systems at levels from entry-level instructional assistant through senior learning and development director. Chicago, Springfield, and Naperville anchor the largest concentrations of openings, where employers such as Allstate, University of Illinois, and Chicago Public Schools maintain ongoing needs. The most in-demand specialties include instructional design, e-learning development, and workplace learning and performance. 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.
See All 27 Learning Specialist Jobs in Illinois
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Find Learning Specialist JobsLearning Specialist Jobs by City in Illinois
Where Illinois roles are concentrated, by current openings.
Learning Specialist Job Market in Illinois
A snapshot from current Illinois openings, updated as new roles post.
Who's Hiring


Top Industries Hiring
- Education
- Technology & Software
What Illinois Employers Look For
The qualifications that appear most often in learning specialist jobs across Illinois.
- Bachelor's degree in education, instructional design, or a closely related field required
- Illinois Professional Educator License or equivalent state-recognized teaching credential preferred
- Experience designing and facilitating adult learning programs or K-12 curriculum strongly preferred
- Proficiency with learning management systems such as Canvas, Blackboard, or Cornerstone
- Strong communication and presentation skills for both in-person and virtual delivery
- Familiarity with needs assessment, instructional design models such as ADDIE, and learner evaluation methods
Learning Specialist Jobs in Illinois: Frequently Asked Questions
How do you become a learning specialist in Illinois?
Most learning specialist roles in Illinois require at least a bachelor's degree in education, instructional design, curriculum and instruction, or a related field. Roles within Illinois public schools typically require an Illinois Professional Educator License, issued through the Illinois State Board of Education. Corporate and healthcare learning roles generally do not require state licensure but often favor candidates with a master's degree or a recognized credential such as the ATD Certified Professional in Talent Development.
Which companies hire learning specialists in Illinois?
Employers hiring learning specialists in Illinois right now include Naperville Community Unit School District 203, IXL Learning, and West Chicago Elementary School District #33, based on current listings on Migrate Mate as of November 2026. Illinois's mix of Fortune 500 headquarters, large public school districts, and major health systems means demand is spread across corporate, education, and healthcare sectors.
Which Illinois cities have the most learning specialist jobs?
Chicago, Naperville, and West Chicago have the most learning specialist openings in Illinois. Chicago dominates due to its concentration of corporate headquarters, large nonprofit organizations, and one of the largest public school districts in the country, while suburban hubs like Naperville and Schaumburg draw demand from major employers and regional healthcare networks anchored outside the city core.
Are there remote learning specialist jobs in Illinois?
Yes, and more than many fields. Instructional design and e-learning development are among the more remote-friendly specialties because the work centers on building digital content and coordinating asynchronously. About 56% of learning specialist openings tied to Illinois are remote or hybrid as of November 2026, reflecting strong employer comfort with distributed learning teams. Roles requiring direct facilitation, classroom support, or on-site coaching are typically in person.
How can I get hired as a learning specialist in Illinois with little or no experience?
The most realistic entry path is through a paraprofessional or instructional aide role in an Illinois public school district, which provides classroom exposure while you complete a degree or earn an Illinois Professional Educator License. Chicago Public Schools and large suburban districts in Cook and DuPage counties regularly hire for these positions. For corporate learning roles, transitioning from a training coordinator or HR generalist position at a large Illinois employer is a common route, and building a portfolio of sample instructional materials or completing an ATD credential strengthens applications significantly.
Where can I find and apply to learning specialist jobs in Illinois?
You can find and apply to learning specialist jobs in Illinois on Migrate Mate, which lists current Illinois openings across school districts, corporations, healthcare systems, and nonprofits. Find roles that fit your background and apply directly to the employers posting them.
See All 27 Learning Specialist Jobs in Illinois
Find roles in Illinois that match your experience and apply in just a few clicks.
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