Engineering Director, Lending (Clasp Finance)

Clasp

SENIOR FULLSTACK ENGINEER, LENDING (CLASP FINANCE) Remote (ET & CT time zones only – some travel required) 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 and the way colleges and universities support their students through education financing — all while tackling the student debt crisis. (Yep, we think BIG.) 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 "Startup of the Year" by StartUp Boston, Clasp is driven by our commitment to social impact and innovation. Our work spans two business lines: Clasp Talent helps healthcare employers attract and retain critical talent by connecting them with diverse candidates and using student loan repayment as a powerful recruiting and retention tool. We meaningfully connect employers, educational institutions, and learners to drive mutual benefit. Clasp Finance equips colleges and universities with lending technology to launch and operate their own private student loan programs, enabling schools to step in and support their students directly with financial aid. Recent federal financial aid changes are reshaping how institutions think about supporting their students, and Clasp Finance is poised to meet this moment. 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're looking for a Senior Software Engineer to join the Clasp Finance engineering team, a small, high-impact group working at the intersection of financial operations, product, and data. You will report to the Engineering Director, Lending and work directly with your teammates and stakeholders to build a resilient, highly available, and compliant workbench for Clasp Lending. This is not a role for someone who just ships features and moves on. You'll own hard problems end-to-end, building the operational tooling, data pipelines, and product features that make a lending platform run. You use AI tools deliberately and creatively to move faster than a team twice your size. You have strong opinions about software quality, are relentlessly detail-oriented, and thrive in ambiguous, high-ownership environments. We want someone who looks at a hard codebase and is excited to tactically and surgically work on improving the application in every interaction. WHAT YOU'LL DO * Design, build, and maintain features across the loan origination platform, ranging from application intake and decisioning logic through servicing and collections workflows. * Build and maintain internal operational tooling that empowers the Clasp Finance team to manage loans, configure programs, run reports, and respond to school and borrower needs with precision. * Participate in architecture decisions, code reviews, and technical design discussions that shape the long-term health of the platform. * Apply AI-assisted development techniques (code generation, test writing, refactoring, documentation) to asymmetrically scale your impact and ship higher-quality software faster. * Collaborate with compliance and legal to implement regulatory requirements (TILA, ECOA, fair lending, state licensing) as first-class engineering constraints — not afterthoughts. * Develop and instrument data pipelines alongside the data team that power credit modeling, compliance reporting, and school-facing portfolio analytics — treating data accuracy as non-negotiable. * Engage occasionally with school and university technical stakeholders to understand integration needs and build confidence in the platform's reliability. * Contribute to a culture of continuous learning, high standards, and direct, low-ego feedback. WHAT YOU'LL NEED * 5+ years of professional software engineering experience with strong fluency in Python and TypeScript/JavaScript. You write clean, maintainable code and understand the tradeoffs and appropriate use cases for each language. * Experience building operational and/or internal tooling for fintech, lending, or another regulated domain. * AI-native in your workflow where you are using coding tools (Cursor, Copilot, Claude, etc.) as a genuine force multiplier, not just for autocomplete or review. The goal here is not to just check the box but to be a leading member of the team who is genuinely excited about what AI can unlock for Engineering. * Familiarity with Django (or a comparable Python web framework) and React — enough to build full-stack features and understand the full request lifecycle. * Hands-on experience with cloud/serverless infrastructure (AWS Lambda, GCP Cloud Functions, or equivalent) and modern deployment practices. * Strong written and verbal communicator to explain technical decisions to non-engineers and write documentation others actually want to engage with, not just AI fluff. * We are looking for someone who cares about building technology that expands access to education and economic mobility, and that shows in how you work and persevere through the challenges of this changing industry. NICE TO HAVE * Any prior exposure to fintech, payments, banking, or financial services — even adjacent experience counts. * Experience designing and building data pipelines, ETL workflows, or event-driven systems that need to be reliable, observable, and correct. * Familiarity with TILA, ECOA, or state lending regulations and their technical implications. * Prior experience working in a startup environment where you've worn multiple hats. * Experience integrating with loan servicers, payment processors, or financial data providers. WHAT WE GIVE IN RETURN * Competitive cash and equity compensation * Health benefits (health, dental, & vision) * Student loan repayment benefits * 401k matching * 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 $135,000 - $165,000 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 driven engineer with a passion for building systems that meaningfully serve the people who rely on them, we want to hear from you. Join us in reshaping how schools support their students and making a lasting impact on the future of higher education financing. Apply now to be 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.

Clasp

SENIOR PRODUCT MANAGER — CANDIDATE & RECRUITER PLATFORM Remote (ET & CT time zones only – some travel required) 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 and the way colleges and universities support their students through education financing — all while tackling the student debt crisis. (Yep, we think BIG.) 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 "Startup of the Year" by StartUp Boston, Clasp is driven by our commitment to social impact and innovation. Our work spans two business lines: Clasp Talent helps healthcare employers attract and retain critical talent by connecting them with diverse candidates and using student loan repayment as a powerful recruiting and retention tool. We meaningfully connect employers, educational institutions, and learners to drive mutual benefit. Clasp Finance equips colleges and universities with lending technology to launch and operate their own private student loan programs, enabling schools to step in and support their students directly with financial aid. 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 Clasp is looking for a Senior Product Manager to own the candidate and recruiter experience within Clasp Talent — the end-to-end product that helps healthcare students find jobs with student loan repayment and gives employers the platform they trust to build long-term clinical pipelines. You will own a two-sided product. On the candidate side, you will drive activation, conversion, and retention across the applicant journey — from a candidate's first discovery of Clasp through onboarding, application, and offer signing. On the employer side, you will own the platform that healthcare employers rely on every day to source candidates, move them through pipelines, and build the talent pipelines that solve their hardest staffing challenges. Both sides are critical. Candidates are the users whose experience defines the product; employers are the customers whose trust drives the business. The Senior Product Manager in this role will care deeply about funnel mechanics and activation while building the platform depth that makes employer teams' daily work better. You will report to the Director of Product, who oversees product across Clasp Talent and Clasp Finance. You will partner closely with leaders in marketing, partner success, design, and engineering, as well as your product teammate who owns the experience that begins after a candidate signs an offer. What You'll Do * Own the Candidate Funnel: Drive activation, conversion, and retention across the entire applicant journey — discovery, account creation, profile completion, application, interview, and offer signing. Set funnel metrics, instrument what matters, and run the experiments that move the needle. * Own the Employer Platform: Own the platform experience that healthcare employers use to source, screen, and place candidates. Recruiters log in every day and their workflow efficiency directly impacts our business. * Build the Network Effect: Identify and ship the features that make each new student more likely to fulfill a commitment to an open role and each new employer more valuable to students. * Deeply Understand Your Users: Spend real time with healthcare students and the recruiters who hire them. Learn what students actually want from their careers and what they fear about the job search. Watch recruiters work and understand the pressures they're under to fill critical roles. Build from what you hear, not from what you assume. * Partner with Marketing: Work closely with student marketing on top-of-funnel performance — landing pages, conversion paths, channel-specific experiences — and own how acquisition handoffs into product. We believe the line between marketing and product should feel seamless. * Collaborate with Partner Success: Work closely with partner success to understand how employers actually use the platform, where they get stuck, and what they need to be successful. Translate employer feedback into product investment. * Run a Disciplined Experimentation Program: Help mature the testing, instrumentation, and analysis practices that allow the team to learn fast and make informed decisions. Bring rigor to how the team measures success. * Champion the Candidate Experience: Represent the candidate's voice in every product decision. Healthcare students deciding whether to commit to an employer are making a meaningful career and financial decision; the experience should reflect that gravity while removing every unnecessary friction. What You'll Need * Experience: 4+ years in product management, with significant time spent on consumer growth, onboarding, activation, and/or two-sided marketplace products. You have shipped work that materially moved a funnel or an activation curve. * Growth Pattern Recognition: You understand funnel mechanics, conversion optimization, experimentation, and instrumentation. You can look at a flow and identify where users drop off, why, and what to test. You have run real experimentation programs, not just one-off A/B tests. * Two-Sided Product Sensibility: You have either worked on a marketplace or platform with two distinct user types, or you have a strong instinct for how to balance competing needs across them. You understand that the user and the customer are not always the same person. * Customer Obsession: You have a track record of getting close to your users — talking to them directly, sitting alongside them as they use your product, and translating that contact into product decisions. You build for real people, not personas in a deck. * Engineering Partnership: You have deep experience partnering with engineering teams. You collaborate with engineers on trade-offs and planning rather than throwing requirements over the wall. * Data Fluency: You are comfortable with funnel analytics, cohort analysis, and experiment design. You can work with data teams to define the right metrics and hold yourself accountable to them. * Cross-Functional Leadership: You partner naturally with marketing, customer success, design, engineering, and analytics. You can align stakeholders with different incentives around shared product goals. * Communication Skills: Strong verbal and written communication, with the ability to explain complex ideas to both technical and non-technical stakeholders, including executive leadership and external partners. * Healthcare experience is not required but is a nice-to-have. What We Give In Return * Competitive cash and equity compensation * Health benefits (health, dental, & vision) * Student loan repayment benefits * 401k matching * Commuter benefits * Flexible PTO policy Salary The salary range for this position is competitive and will be commensurate with the candidate's experience, qualifications, and industry knowledge, ranging between $105,000 to $120,000 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. Remote Policy To ensure smooth collaboration with the Boston-based team, we are limiting to Eastern/Central timezones with the expectation that it will be Boston hours. Additionally, they must be within 1 hour of a medium hub/ large airport with multiple daily flights to Boston. We are targeting the broader New England area to start as we expect that the candidate to have frequent travel to Boston for onboarding and ongoing collaboration. Closing If you are a driven product manager who obsesses over user experience, runs disciplined experiments, and knows how to build trust with both consumer users and B2B power users, we want to hear from you. Join us in connecting healthcare students with meaningful careers and the financial benefits that change their lives. 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.

Clasp

PRINCIPAL PRODUCT DESIGNER REMOTE (ET & CT TIME ZONES ONLY — SOME TRAVEL REQUIRED) 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 and the way colleges and universities support their students through education financing — all while tackling the student debt crisis. (Yep, we think BIG.) 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 world's largest HR professional society), and one of Business Insider's "43 Start-Ups to Bet Your Career On in 2025," Clasp is driven by our commitment to social impact and innovation. What We Need Clasp is looking for a Principal Product Designer to define design, brand, and taste across all of our user interactions.. This is a foundational, strategic hire — the person who sets the bar for how Clasp looks, feels, and earns trust, from the first marketing touchpoint a candidate ever sees through the products our users rely on every day. You will own design as a discipline at Clasp. That means more than shipping screens: it means establishing the visual language, the design culture, and the standard of craft that everything else is measured against. You'll work across both our product surfaces and our marketing site, making sure a student who first encounters Clasp in an ad, lands on our site, signs an offer, and becomes an employee receiving their first repayment feels like they're moving through one coherent, considered, trustworthy experience. This is a green-field mandate. You are not inheriting a mature design org or a rigid system to maintain — you are defining what design at Clasp is. You'll set the direction, build the foundations, and make the high-leverage calls about brand and product identity that we don't have anyone to make today. It's also a hands-on role: at this stage, you'll design and ship the work yourself while laying the groundwork for the design function to grow around you. You'll partner directly with the Founder & CEO and the Director of Product on the vision for the company and the product, and work closely with the Product Managers on Clasp Talent and leaders in Marketing, Partner Success, and Engineering to bring it to life. What You’ll Do * Define Design and Brand at Clasp: Own the visual identity, design language, and standard of taste across the company. Make the foundational decisions about how Clasp looks and feels — and set the bar everyone else builds toward. * Own the Full Experience, Product to Marketing Site: Design across consumer acquisition flows, the marketing site, recruiter platforms, employee benefits experiences, and employer admin tooling — moving fluidly between brand-led marketing surfaces and operations-heavy fintech workflows so the whole journey feels like one product. * Own and Evolve the Design System: Take ownership of our existing design system — maturing components, patterns, and principles so they scale with the company. Evolve what's working, and if you believe a deeper rethink is warranted, make the case for it. Either way, you own the standard everyone builds toward. * Shape Product Direction, Not Just Execution: Bring a strong point of view to what we build and why, not only how it looks. Partner with the founder and Product on strategy, framing problems and proposing directions rather than waiting for fully specified requirements. * Make Complex Workflows Feel Simple: Bring clarity to the genuinely hard surfaces — HRIS integration setup, flow-of-funds visibility, invoice and credit reconciliation, benefit administration. Make data-rich, compliance-sensitive interfaces feel calm, legible, and trustworthy. * Get Close to Users: Partner with Product to run qualitative and quantitative research — usability testing, interviews, data-driven insights. Spend real time with healthcare students, recruiters, employees, and employer-administrators, and translate that contact into design decisions. * Elevate the Craft: Raise the bar for clarity, quality, and cohesion across everything Clasp ships. Healthcare students deciding whether to commit to an employer, and employees relying on this benefit to repay their loans, are making meaningful career and financial decisions; the experience should reflect that gravity while removing every unnecessary friction. * Infuse Delight and Personality: Introduce moments of engagement, warmth, and humanity that make the product feel trustworthy and memorable, not transactional — even (especially) on the operational surfaces. * Leverage AI Workflows: Explore and responsibly apply emerging AI tools to accelerate research, ideation, and design production — making your process smarter, faster, and more scalable. What You’ll Need * Principal-Level Design Experience: 8+ years of product design experience, including time spent setting design direction — not just executing within someone else's system. You've owned the visual language, brand, or design practice for a product or company, and have the case studies to show how you did it. * Strategic Range: You think beyond the screen. You can hold the company's goals in your head, form a point of view on what matters, and make foundational calls about brand and product identity with limited direction. * Brand and Product Fluency: Comfort moving between brand-led marketing surfaces (a marketing site, a landing page, a campaign) and data-dense product tooling (an invoice reconciliation screen, an admin dashboard) — and bringing craft to both. * Systems Thinking: Ability to hold a large, interconnected ecosystem in your head and design experiences that scale. You understand how a change in one persona's flow ripples across the others, and you build systems, not one-offs. * Design System Ownership: You've owned or substantially shaped a production design system — evolving components, patterns, and principles, and balancing flexibility with consistency as a product grows. You know when to refine what exists and when to argue for a rebuild. * Strong Visual Craft: A refined sense of typography, layout, color, and visual hierarchy, with awareness of modern product aesthetics and the instinct for when to break convention. * Fluency in Figma: Deep experience with components, variables, auto layout, and prototyping. You understand how your designs map to code and collaborate effectively with engineers. * Multi-Persona Product Sensibility: Comfort designing for products with multiple distinct user types — where each persona has different goals, contexts, and constraints. Bonus if you've worked on products where the user and the customer aren't the same person. * Research Competency: Comfort partnering with Product on qualitative and quantitative research — usability tests, interviews, analytics reviews — and incorporating insights into your design process. * AI Curiosity: Hands-on experience experimenting with AI tools in your workflow, and excitement about applying them responsibly to accelerate output and explore new interaction models. * Remote Collaboration: You're effective working remotely with a distributed team. You're proactive about communication, comfortable shaping ideas in writing as well as in real time, and willing to travel occasionally for in-person sessions when it matters. * Healthcare, health-tech, fintech, or HR-tech experience is a plus but not required. What We Give In Return * Competitive cash and equity compensation * Health benefits (health, dental, & vision) * Student loan repayment benefits * 401k matching * 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 $155,000 to $190,000 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. Remote Policy To ensure smooth collaboration with the Boston-based team, we are limiting to Eastern/Central timezones with the expectation that it will be Boston hours. Additionally, they must be within 1 hour of a medium hub/ large airport with multiple daily flights to Boston. We are targeting the broader New England area to start as we expect that the candidate to have frequent travel to Boston for onboarding and ongoing collaboration. Closing If you are a senior designer who cares about craft, thinks in systems, and wants to anchor design for a mission-driven company at a real inflection point, we want to hear from you. Join us in connecting healthcare students with meaningful careers and the financial benefits that change their lives. 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.