Clasp

Lead the end-to-end operations of Clasp’s education repayment programs, ensuring accurate and compliant repayment cycles. Manage operational workflows, coordinate with financial partners, and continuously improve repayment infrastructure. | Candidates should have 3-5 years of experience in repayment operations or related fields, with a strong attention to detail and familiarity with payment operations tools. Excellent communication skills and a willingness to become a subject matter expert in repayment and compliance are essential. | Repayment Specialist 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 Specialist 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.

Manage end-to-end repayment operations including scheduling, invoicing, reconciliation, exception handling, and compliance while collaborating with finance, product, and external partners to optimize workflows and support scaling. | 3-5 years in repayment or financial operations with strong attention to detail, familiarity with payment tools, process management skills, analytical mindset, excellent communication, and experience in regulated industries. | Payment Operations Manager 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 Payment 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.

Manage and grow a portfolio of employer partners by driving engagement, strategic growth, onboarding, performance optimization, and cross-functional collaboration. | Experience in account management or customer success with strong problem-solving, communication, and collaboration skills, preferably with familiarity in education benefits or workforce development. | Partner Success Manager 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. The position will serve as both a strategic advisor and an enthusiastic champion for Clasp’s employer partners. This role blends deep knowledge of our creative work with inspiring communication and storytelling to build excitement, strengthen alignment, and drive long-term growth.You’ll own a portfolio of partners and go beyond traditional success management—immersing yourself in the details of our work, asking probing questions about partner goals, and shaping conversations that spark expansion opportunities. You’ll collaborate closely with Sales, Implementation, Product, Marketing, and Talent Fulfillment to ensure Clasp’s creativity shines and partners see measurable impact.If you’re excited about using education and technology to solve systemic problems in workforce development—and want to grow with a high-impact, high-growth team—we’d love to hear from you. What You’ll Do: Drive Enthusiasm and Advocacy: Deliver high-energy, compelling partner engagements—using storytelling, visuals, and real impact examples to make partners excited about Clasp’s creativity. Champion Strategic Growth: Push conversations beyond the present. Ask deeper questions about multi-year goals, hiring strategies, and industry shifts to uncover expansion opportunities. Know the Work: Stay fluent in the details of Clasp’s creative output, talent fulfillment roadmap, and performance metrics, so you can credibly advise partners. Facilitate Onboarding and Alignment: Partner with sales and implementation teams to streamline launches, ensuring clarity and consistency from pre-sale through steady state. Lead Technical Problem-Solving and Enablement: Guide partners through onboarding, scoping, and translating requirements into actionable builds; deliver training and change management support to ensure adoption and long-term impact. Monitor and Optimize Performance: Analyze partner metrics and feedback to identify risks and opportunities, balancing long-term strategy with responsive day-to-day support. Collaborate Cross-Functionally: Present materials developed by internal teams with authority and context, ensuring partners see the full value of Clasp’s work. Act as a Trusted Advisor: Serve as a subject matter expert, offering training and insights to maximize the value partners derive from Clasp’s services Partner Engagement: Conduct high-impact business reviews and regular touch points to enhance partner satisfaction and expand Clasp’s value What You’ll Need: Experience in account management, customer success, management consulting, or other client/customer-facing role Proven problem-solving and analytical skills to identify partner challenges and risks and design effective solutions Relationship-building and communication skills with the ability to foster trust, understanding, and alignment across diverse audiences Excellent communication skills and the ability to think strategically while executing tactically, balancing long-term goals with immediate partner and business needs Collaborative mindset with experience working across multiple departments to build cohesive strategies and implement cross-functional initiatives Adaptability and resilience to navigate the fast-paced, evolving landscape of a high-growth company Nice to Have: Familiarity with education benefits, workforce development, or upskilling programs Experience working with human resources and/or talent acquisition stakeholders Understanding of healthcare industry What We Give In Return Competitive cash and equity compensation Health benefits (health, dental, & vision), 401k 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 $110,000 to $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.

Manage and grow a portfolio of employer partners through strategic advising, onboarding, performance optimization, and cross-functional collaboration to drive long-term growth and partner satisfaction. | Experience in client-facing roles such as account management or customer success, strong problem-solving and communication skills, ability to collaborate across departments, and adaptability in a fast-paced environment. | Principal Partner Success Manager 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. The position will serve as both a strategic advisor and an enthusiastic champion for Clasp’s employer partners. This role blends deep knowledge of our creative work with inspiring communication and storytelling to build excitement, strengthen alignment, and drive long-term growth.You’ll own a portfolio of partners and go beyond traditional success management—immersing yourself in the details of our work, asking probing questions about partner goals, and shaping conversations that spark expansion opportunities. You’ll collaborate closely with Sales, Implementation, Product, Marketing, and Talent Fulfillment to ensure Clasp’s creativity shines and partners see measurable impact.If you’re excited about using education and technology to solve systemic problems in workforce development—and want to grow with a high-impact, high-growth team—we’d love to hear from you. What You’ll Do: Drive Enthusiasm and Advocacy: Deliver high-energy, compelling partner engagements—using storytelling, visuals, and real impact examples to make partners excited about Clasp’s creativity. Champion Strategic Growth: Push conversations beyond the present. Ask deeper questions about multi-year goals, hiring strategies, and industry shifts to uncover expansion opportunities. Know the Work: Stay fluent in the details of Clasp’s creative output, talent fulfillment roadmap, and performance metrics, so you can credibly advise partners. Facilitate Onboarding and Alignment: Partner with sales and implementation teams to streamline launches, ensuring clarity and consistency from pre-sale through steady state. Lead Technical Problem-Solving and Enablement: Guide partners through onboarding, scoping, and translating requirements into actionable builds; deliver training and change management support to ensure adoption and long-term impact. Monitor and Optimize Performance: Analyze partner metrics and feedback to identify risks and opportunities, balancing long-term strategy with responsive day-to-day support. Collaborate Cross-Functionally: Present materials developed by internal teams with authority and context, ensuring partners see the full value of Clasp’s work. Act as a Trusted Advisor: Serve as a subject matter expert, offering training and insights to maximize the value partners derive from Clasp’s services Partner Engagement: Conduct high-impact business reviews and regular touch points to enhance partner satisfaction and expand Clasp’s value What You’ll Need: Experience in account management, customer success, management consulting, or other client/customer-facing role Proven problem-solving and analytical skills to identify partner challenges and risks and design effective solutions Relationship-building and communication skills with the ability to foster trust, understanding, and alignment across diverse audiences Excellent communication skills and the ability to think strategically while executing tactically, balancing long-term goals with immediate partner and business needs Collaborative mindset with experience working across multiple departments to build cohesive strategies and implement cross-functional initiatives Adaptability and resilience to navigate the fast-paced, evolving landscape of a high-growth company Nice to Have: Familiarity with education benefits, workforce development, or upskilling programs Experience working with human resources and/or talent acquisition stakeholders Understanding of healthcare industry What We Give In Return Competitive cash and equity compensation Health benefits (health, dental, & vision), 401k 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 $110,000 to $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.

Manage end-to-end repayment operations lifecycle including scheduling, invoicing, reconciliation, exception handling, and compliance. | 3-5 years experience in repayment or financial operations, strong process and data management skills, familiarity with payment platforms, and excellent communication. | Repayment Operations Manager 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.