Student Loan Payment Reimbursement Jobs in Chicago, IL

21,535 open positions · Updated daily

Looking for Student Loan Payment Reimbursement jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Student Loan Payment Reimbursement position in the Chicago, IL area.

Special Education Teacher (SPED) - High School - Full Time

Company: Invo Healthcare - Family of Companies

Location: Chicago, IL

Posted Apr 18, 2025

Hold a bachelor’s degree. This position may appeal to you if you have previously worked as a registered behavior technician, preschool employee, daycare worker…

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Carpenter

Company: Oak Park Elementary School District 97

Location: Oak Park, IL

Posted Apr 14, 2025

Build, set decoration and possible painting – design, organization of materials (building, painting, dressing). Middle School- Grades 6-8.

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Data Analyst - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

You can work on your own schedule. You will measure the progress of these AI chatbots, evaluate their logic, and solve problems to improve the quality of each…

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Database Developer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

A bachelor’s degree (completed or in progress). Proficiency in at least one of the following programming languages or frameworks: JavaScript, TypeScript, Python…

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Web Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

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travel health savings account life insurance

Travel Interventional Radiology Technologist - $2,967 per week

Company: Host Healthcare

Location: Chicago, Illinois

Posted Apr 15, 2025

View Details Apply on healthecareers.com

Full Stack Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

View Details Apply on SimplyHired
staffing agency contract travel

Travel Interventional Radiology Technologist - $2,735 per week

Company: MedPro Healthcare Allied Staffing

Location: Chicago, Illinois

Posted Apr 20, 2025

View Details Apply on healthecareers.com

Business Diversity Analyst

Company: Chicago Public Schools

Location: Chicago, IL

Posted Apr 17, 2025

Bachelor’s degree in Business Administration, Finance, Information Technology, or a related field of study from an accredited college or university.

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Back End Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

View Details Apply on SimplyHired
contract travel license reimbursement

Travel Physical Therapist - $2,610 per week

Company: Vibra Travels

Location: East Chicago, Indiana

Posted Apr 14, 2025

View Details Apply on healthecareers.com

Front-End Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 2025

A bachelor’s degree (completed or in progress). Proficiency in at least one of the following programming languages or frameworks: JavaScript, TypeScript, Python…

View Details Apply on SimplyHired

Frequently Asked Questions

What are typical salary ranges by seniority for Student Loan Reimbursement roles?
Entry‑level Loan Service Specialists earn $60,000–$80,000 annually; mid‑level Compliance Analysts or Program Coordinators range from $80,000–$110,000; senior positions such as Reimbursement Program Managers or Directors command $110,000–$150,000 plus performance bonuses tied to repayment metrics.
What skills and certifications are required for these positions?
Candidates should master loan‑servicing platforms like SLSP (Student Loan Servicing Platform), possess strong SQL and Python for data extraction, and be proficient with FICO Score integration. Certifications such as Certified Loan Servicer (CLS) or Certification in TRID Compliance are highly valued, along with experience in API development for USDA Direct Loan integration.
Is remote work available in Student Loan Reimbursement roles?
Yes, many employers offer fully remote or hybrid schedules. Remote positions typically require secure VPN access, proficiency with cloud‑based workflow tools (e.g., Salesforce, ServiceNow), and strong communication skills for cross‑functional teams spanning education, finance, and government agencies.
What career progression paths exist in this field?
A common trajectory starts with a Loan Service Specialist, moves to a Compliance Analyst or Reimbursement Coordinator, then to a Reimbursement Program Manager, and ultimately to Director of Student Loan Reimbursement or Chief Financial Officer for a lending institution. Each step adds responsibility for policy development, technology integration, and strategic partnership with federal agencies.
What are the current industry trends affecting Student Loan Reimbursement jobs?
The industry is pivoting to digital servicing, leveraging AI for credit scoring and automated repayment suggestions. Recent federal student‑loan forgiveness initiatives are reshaping program design, while regulatory changes under TRID and the new Student Loan Forgiveness Act increase demand for compliance expertise. Employers are investing in data‑analytics platforms and blockchain for transparent repayment tracking, creating new roles focused on fintech integration.

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