Student Loan Payment Reimbursement Jobs in Chicago, IL

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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.

IT Systems and Support Administrator

Company: Kalderos

Location: Chicago, IL

Posted Feb 01, 2025

Kalderos is seeking an IT Systems and Support Administrator to provide top-tier technical support to over 115 internal employees, ensuring smooth operations in a mixed Mac and Windows environment. The role involves critical thinking, troubleshooting, and collaboration with the Director of Information Technology to improve systems and processes. The candidate will also work with the Information Security team to ensure system security and act as a technical mentor to Level 1-2 technical support analysts. The ideal candidate will have 5+ years of experience, excellent technical skills, and a customer service mindset. Relevant certifications, experience in startup environments, and familiarity with Okta, Google Workspace, cloud infrastructure, and compliance standards are preferred. The position offers a competitive salary range, flexible PTO, and a range of benefits, including medical, dental, vision, 401k, and opportunities for growth. Kalderos values collaboration, feedback, and continuous learning, and is committed to equal opportunity.

Client Account Executive

Company: Morningstar

Location: Chicago, IL

Posted Feb 01, 2025

Morningstar is seeking a sales-minded individual to join their Client Account Executive team. The role involves enhancing the experience of Advisor Workstation clients, driving value, and expanding business opportunities. The successful candidate will be responsible for managing a portfolio of clients, identifying growth opportunities, and achieving sales and retention goals. The position requires at least 2 years of sales experience, strong organizational skills, and a consultative selling approach. Morningstar offers a competitive total cash compensation, comprehensive benefits, and a hybrid work environment.

Scala Software Engineer

Company: Rewards Network

Location: Chicago, IL

Posted Jan 31, 2025

Rewards Network, a company celebrating 40 years in business, is seeking a Scala Software Engineer for a hybrid position in Chicago. The role involves working with a team to build out new business areas and improve the rewards platform using the latest technologies. The company offers a competitive benefits package, including a comprehensive health plan, 401k with company match, and a flexible working environment. Requirements include a degree in Computer Science, 2+ years of development experience, and proficiency in Scala or other functional languages.

Senior Applied Machine Learning Scientist- AI Agents

Company: Grainger

Location: Chicago, IL

Posted Feb 02, 2025

Grainger, a leading industrial distributor, is seeking a Senior Applied ML Scientist to drive cutting-edge generative AI solutions. The role involves building and maintaining Agentic processes, working closely with other ML scientists, engineers, and product managers, and designing robust data pipelines. The company offers competitive compensation, comprehensive benefits, and a commitment to equal employment opportunity. The position is part of Grainger's Product Discovery team, which aims to enable customers to find what they need when they need it.

IT Support Analyst

Company: Kalderos

Location: Chicago, IL

Posted Feb 01, 2025

Kalderos is a healthcare technology company focused on pharmaceutical pricing transparency, trust, and equity. They are seeking an IT Support Analyst to provide top-tier technical support to their 115+ internal employees in a fully remote environment. The role involves troubleshooting technical issues, collaborating with the IT team, and assisting with IT projects. The company values collaboration, feedback, and growth, offering competitive benefits and a dynamic work environment.

Principal Card Disputes Strategy

Company: Discover

Location: Chicago, IL

Posted Feb 01, 2025

Discover offers a bright future with meaningful work from day one. The Principal Card Disputes Strategy position is responsible for providing strategic direction for operational activities, ensuring efficient and compliant servicing operations for US Card Billing Disputes. The role involves collaborating with business partners, managing risk, and developing new controls. The candidate will also be responsible for authoring new controls and securing resources to comply with biyearly Network releases. The job requires a Bachelor's degree in Business Administration and Management or related field, along with 6+ years of experience in customer service, financial services, or related operations.

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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