Repayment Operations Manager at Clasp

Location: Boston, MA (Hybrid — 2 days per week in office)

About Us

Clasp is a venture-backed, mission-driven startup transforming access to education and career pathways. We are revolutionizing the way employers attract and retain critical talent, while simultaneously tackling the student debt crisis. (Yep, we think BIG.) Our innovative platform meaningfully connects employers, educational institutions, and diverse talent to drive mutual benefit—using accessible education financing as the thread. We like to think of ourselves as more than a fintech; we’re a catalyst for economic mobility.

A Forbes Fintech 50 company, portfolio company of SHRM (Society of Human Resource Management — the largest HR organization out there!) and recipient of “43 Start Ups to Bet Your Career On in 2025” by Business Insider, Clasp is driven by our commitment to social impact and innovation. We are reshaping the future of the workforce one opportunity at a time. Join us on our journey to give power to learners and unlock fulfilling careers that drive positive change in their communities and beyond.

What We Need

We are hiring a Repayment Operations Manager to lead the end-to-end operations that power Clasp’s education repayment programs. You will own the systems, processes, and communications that ensure our repayment cycles run accurately, efficiently, and compliantly. This includes managing operational workflows, coordinating with financial partners, handling edge cases, and supporting automation and scalability as we 10x our repayment volume over the next year.

This role will be instrumental in ensuring flawless repayment execution for our employer partners and their employees while continuously improving the infrastructure that supports it. Occasionally, this role will provide support coverage alongside our Customer Experience team to stay close to the employee journey and identify friction points that impact repayment performance.

What You’ll Do

• Own the full repayment operations lifecycle – from roster validation and repayment scheduling to invoicing, reconciliation, and confirmation.
• Execute and optimize monthly repayment cycles: QA repayment schedules, validate employee eligibility, and ensure accurate invoicing and disbursement of employer funds.
• Manage repayment exceptions and escalations: Track failed transactions, reversals, and manual payments (e.g., pay-by-phone with loan servicers) to resolution, identifying root causes and designing prevention mechanisms.
• Develop and maintain operational playbooks for repayment workflows, exception handling, and compliance procedures.
• Partner with Finance and external payment partners (e.g., Dwolla) to reconcile transactions, confirm disbursements, and ensure regulatory compliance.
• Collaborate with Product & Engineering to drive automation of repayment workflows, improve error handling, and enhance visibility into repayment data.
• Support Partner Success in resolving employer-related repayment inquiries and ensuring smooth fund transfers.
• Monitor and report repayment performance metrics, highlighting trends, risk factors, and opportunities for process improvement.
• Ensure compliance with industry and regulatory standards governing education finance and payments.
  
  

What You’ll Need

• 3–5 years of experience in repayment operations, financial operations, payments, or benefits administration.
• High attention to detail with a strong commitment to accuracy and data integrity.
• Familiarity with payment operations tools (e.g., ACH processing, reconciliation workflows, or payment platforms like Dwolla, Plaid, or similar).
• Strong process management skills – comfortable managing recurring cycles with precision and accountability.
• Analytical mindset with proficiency in Excel/Google Sheets for data validation and reconciliation.
• Excellent communication skills – able to translate complex operational issues clearly across technical and non-technical stakeholders.
• Experience in regulated industries (fintech, benefits, or financial services) and a willingness to become a subject matter expert in repayment and compliance.
• Bias toward action and ownership – able to balance strategic thinking with hands-on execution.
  
  

Bonus:

• Experience with loan servicing, employer benefits, or education finance ecosystems.
• Exposure to ACH payments, bank partnerships, or student loan servicers.
• Familiarity with API-driven payment integrations or automation tools.
  
  

What We Give In Return

• Competitive cash and equity compensation
• Health benefits (health, dental, & vision)
• 401k with match
• Commuter benefits
• Flexible PTO policy
• Opportunities to grow and perform in a fast-paced environment alongside a stellar team.
  
  

Salary

The salary range for this position is competitive and will be commensurate with the candidate's experience, qualifications, and industry knowledge, ranging between $100,000-$130,000 annually. In addition to the base salary, we offer an attractive equity component as part of our compensation package, providing an opportunity for eligible employees to share in the success and growth of our company. We are committed to offering competitive compensation and benefits packages to attract and retain top talent.

Closing

If you are a highly driven individual with a passion for technology, and you thrive in a dynamic and fast-paced environment, we want to hear from you! Join us in revolutionizing the workforce solution industry and making a meaningful impact on businesses worldwide. Apply now to be a part of our growing team!

We are committed to creating a diverse and inclusive workplace where all employees feel valued, respected, and empowered to contribute their unique perspectives and talents. Clasp is an equal opportunity employer and prohibits discrimination and harassment of any kind. We embrace diversity and are dedicated to providing equal employment opportunities to all individuals regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.