Customer Success Associate

Clasp; Boston (MA); On-site; USD 50,000 - 75,000; Full time

Job summary

A fintech startup is seeking a Customer Success Associate in Boston to guide employees through loan repayment and education benefits programs. This role combines customer service, operations, and issue resolution to enhance the talent experience across various employer offerings. Ideal candidates will have 2-3 years of experience in related fields and strong communication skills.

Benefits

Equity compensation

Health, dental, and vision insurance

401(k) and commuter benefits

Flexible PTO and remote-first flexibility

Qualifications

• 2-3 years in customer success, workforce development, education services, or employee benefits.
• Excellent written and verbal communication skills.
• Empathy and professionalism when working with employees.

Responsibilities

• Serve as the main point of contact for employees regarding loan repayment programs.
• Troubleshoot issues related to enrollment and documentation.
• Track and maintain accurate user records across systems.

Skills

Communication Skills

Attention to Detail

Problem Solving

Tools

Zendesk

HubSpot

Airtable

Job description

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.

We are looking for a Customer Success Associate to support the talent experience side of our operations. In this role, you'll be the first point of contact for employees participating in Clasp's employer loan repayment and education benefits programs. You’ll help guide them through eligibility, onboarding, and participation—ensuring a smooth, high-touch experience across a range of employer offerings. These offerings are meant to engage prospective employees and acquire hard to hire talent, as well as incentivize them to stay with our employers - as a retention strategy.

This is a cross-functional role that blends customer service, operational coordination, and issue resolution. You’ll communicate with employees via phone, email, and chat—while collaborating closely with internal teams to continuously improve the experience for learners and working professionals nationwide.

What You’ll Do:

• Talent Support & Success:
• Serve as the main point of contact for employees enrolled in Clasp’s employer loan repayment programs and education benefit offeringsAnswer questions via phone, email, and chat, providing clear, supportive guidance on program eligibility, participation steps, and ongoing requirements
• Troubleshoot issues related to enrollment, benefit timelines, documentation, and platform use with professionalism and empathyFollow up with employees who have not completed required steps and support them through to completion
• Communicate clearly with employees at all stages of their education and career journey
• Operations & Issue Resolution:
• Track and maintain accurate user records across systems and workflows
• Triage and help resolve escalations—including payment issues involving student loan servicers
• Support documentation collection and follow-up for employees where additional information is needed to process payments or verify eligibility
• Collaborate with partner success and implementation teams to flag blockers and ensure operational follow-through
• Provide feedback on tools, processes, and content to enhance the employee experience
  
  
  

What You’ll Bring:

• 2–3 years of experience in customer success, workforce development, education services, or employee benefits
• Excellent written and verbal communication skills with a service-oriented mindset
• Comfort working across multiple systems (e.g., Zendesk, HubSpot, Airtable) and triaging technical or process-related issues
• High attention to detail and ability to manage multiple work streams in a fast-paced environment
• Empathy and professionalism when working with employees managing loan repayment or education pathways
• Bonus: Prior exposure to working with loan servicers, student loan repayment, or financial aid workflows
  
  
  

What We Offer:

• Equity compensation: share in Clasp’s success and growth
• Health, dental, and vision insurance401(k) and commuter benefits
• Flexible PTO and remote-first flexibility
• A collaborative, mission-driven team committed to impact
  
  
  

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.