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.

Senior Manager of Growth Marketing and ABM

Company: Smartly.io

Location: Chicago, IL

Posted Sep 09, 2023

Smartly.io is seeking a Senior Manager of Growth Marketing and ABM with 8+ years of B2B marketing experience in tech companies, preferably SaaS products. The role involves leading ABM efforts, designing and implementing marketing programs, managing a team, and collaborating with various departments. The company offers a competitive benefits package, flexible hybrid work options, and a global, inclusive culture.

Desktop Support Specialist

Company: SDI Presence

Location: Chicago, IL

Posted Sep 09, 2023

SDI Presence LLC, a 25-year-old IT consultancy and managed services provider, seeks a Desktop Support Specialist. The role involves installing, configuring, troubleshooting, and maintaining Microsoft Windows desktop and notebook computers. The candidate must have 5+ years of desktop hardware knowledge, understanding of PC imaging and cloning, and familiarity with Active Directory. A+ certification is a plus. The role requires strong multitasking skills, ability to work independently and as part of a team, and the capacity to perform routine and emergency PC maintenance during non-business hours.

Administrative Assistant

Company: DRW

Location: Chicago, IL

Posted Sep 09, 2023

DRW is a diversified trading firm with over 3 decades of experience, operating globally and leveraging technology and expertise to expand into various asset classes. They value autonomy, respect, and innovation, and are currently looking for an Accounting/Administrative Assistant to join their Family Office team.

System Administrator I

Company: SDI Presence

Location: Chicago, IL

Posted Sep 09, 2023

SDI Presence LLC, an IT consultancy and managed services provider, is seeking a System Administrator with 5 years of experience in managing Windows servers, laptops, and desktops. The role involves day-to-day administration, designing and configuring servers, maintaining patches, administering user access, and documenting procedures. The candidate should have experience with Hyper-V, Data Protection solutions, Meraki firewalls, and scripting languages like PowerShell. Excellent communication and problem-solving skills are required. The company is committed to diversity and inclusion.

Fraud Investigation/Research Analyst

Company: Interactive Brokers

Location: Chicago, IL

Posted Sep 09, 2023

Interactive Brokers LLC is seeking a Client Operations - Fraud Investigation/Research Analyst with a background in financial services and information security. The ideal candidate should have 2+ years of experience in fraud prevention, proficiency in Windows/macOS, and strong communication skills. Responsibilities include handling client inquiries, managing security protocols, and tracking fraud trends. The company offers competitive benefits, a dynamic work environment, and opportunities for growth.

Desktop Engineer

Company: OppFi

Location: Chicago, IL

Posted Sep 09, 2023

OppFi, a leading financial technology platform, is seeking a tech-savvy professional to design, build, and manage a workstation configuration management platform. The role involves packaging, testing, and deploying applications and configurations across the enterprise, deploying Windows and Mac OS, and remediating vulnerabilities on workstations. The ideal candidate should have 5+ years of experience in scripting (preferably PowerShell), building and managing SCCM, Intune, NinjaRMM, Kaseya, or Jamf, and standardizing and managing Windows and Mac systems. The role also includes mentoring junior engineers, developing policies, procedures, and best practices for the Service Desk, and participating in cross-team projects with Security and Platform Engineering. OppFi offers a flexible remote environment, 401(k) matching, and comprehensive benefits, including medical, dental, vision, tuition reimbursement, and wellness programs.

Fund Custody Specialist (Hybrid)

Company: Millennium Trust Company

Location: Chicago, IL

Posted Sep 09, 2023

Millennium Trust Company is inviting applications for a Fund Custody Specialist position. The role involves managing relationships with advisors and clients, processing fund subscriptions and redemptions, and executing various transactions. The company values diversity, fosters a collaborative environment, and offers opportunities for career development. Millennium Trust has experienced significant growth and has been recognized for its culture and benefits.

General Counsel

Company: SDI Presence

Location: Chicago, IL

Posted Sep 09, 2023

SDI Presence LLC, a 25-year-old IT consultancy and managed services provider, is seeking a Corporate Counsel with 5+ years of legal experience. The role involves negotiating and drafting complex commercial contracts, ensuring compliance with governmental contracting regulations, and advising on legal risks and opportunities. The ideal candidate should have extensive experience in technology and commercial contracting, a J.D. from an accredited law school, and strong collaboration and analytical skills. SDI Presence is an equal opportunity employer committed to diversity and inclusion.

Application Security Engineer (Chicago Remote)

Company: Motorola Solutions

Location: Chicago, IL

Posted Sep 09, 2023

Motorola Solutions is seeking a Lead Application Security Analyst to enhance their Enterprise Application Security process, mold security processes within their CI/CD pipeline, and improve their Application Security Maturity level. The role involves running application penetration tests, guiding developers, and collaborating with peers to improve the security of business applications. The candidate will drive changes in organization culture to include application security as an integrated mature process through automation, advanced tools, and creativity. The ideal candidate should have a Bachelor's degree in a related field, experience in leading application security peers, knowledge of common application vulnerabilities, and proven experience in web application penetration testing.

Reinsurance Analyst

Company: CNA

Location: Chicago, IL

Posted Sep 10, 2023

CNA is seeking a Reinsurance Analyst for their Corporate Reinsurance organization. The role involves analyzing, reconciling, and paying premium under various reinsurance treaties. The candidate will work on ceded reinsurance premiums, research coverage and liability issues, and assist with reinsurance balance recovery. The position offers a hybrid work schedule and a comprehensive benefits package. CNA values employee development and aims to create a culture where employees feel valued and their abilities are fully utilized.

Client Executive - Financial Services

Company: TransUnion

Location: Chicago, IL

Posted Sep 09, 2023

TransUnion is currently offering a fully virtual recruitment and new hire experience due to health and wellness priorities. The role involves managing relationships with assigned accounts, leading business reviews, and facilitating sales meetings. The company values diversity and offers flexible benefits including tuition reimbursement, parental leave, and retirement contributions. The ideal candidate should have 5+ years of sales experience, strong communication skills, and expertise in credit risk and marketing analytics.

Actuarial Analyst

Company: GoHealth

Location: Chicago, IL

Posted Sep 09, 2023

GoHealth, a leading health insurance marketplace and Medicare-focused digital health company, is seeking an Actuarial Analyst. The role involves using Medicare experience and actuarial techniques to build revenue forecasts, policy reporting, and commission payment reporting. The successful candidate will work with business stakeholders and data engineers to solve business problems, provide insights through analytics, and stay current with data analytics tools. GoHealth offers a remote position with comprehensive benefits, including an open vacation policy, 401k program, employee stock purchase program, and professional growth opportunities.

Frequently Asked Questions

What are typical salary ranges by seniority in Student Loan Payment Reimbursement roles?
Entry‑level analysts earn $55k–$70k annually, mid‑level specialists command $70k–$90k, and senior or lead positions range from $90k to $120k, often including a performance bonus tied to program metrics.
What skills and certifications are required for Student Loan Payment Reimbursement positions?
Strong Excel and Power BI skills for data reporting; proficiency in HRIS platforms like Workday, SAP SuccessFactors, or ADP; knowledge of federal student loan regulations and tax implications; and certifications such as SHRM‑CP, Certified Benefits Professional (CBP), or Certified Payroll Professional (CPP).
Is remote work available in this category?
Yes, many roles—especially Benefits Analysts and Program Managers—offer fully remote or hybrid arrangements. Employers require secure VPN access, two‑factor authentication, and compliance with data‑privacy protocols for handling employee loan information.
What are the career progression paths within Student Loan Reimbursement?
Typical progression follows: Junior Benefits Analyst → Senior Benefits Analyst → Benefits Manager → Director of Benefits → VP of HR or Chief Benefits Officer, with opportunities to specialize in HRIS or compliance leadership.
What industry trends are shaping Student Loan Payment Reimbursement?
Increasing employer‑sponsored repayment plans, new federal loan forgiveness initiatives, AI‑driven enrollment assistance, integration with fintech payment platforms, and evolving data‑privacy laws are redefining how organizations structure and manage loan‑reimbursement programs.

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