Engineering Director, Lending (Clasp Finance)

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.

GitLab is the intelligent orchestration platform for DevSecOps. GitLab enables organizations to increase developer productivity, improve operational efficiency, reduce security and compliance risk, and accelerate digital transformation. More than 50 million registered users and more than 50% of the Fortune 100* trust GitLab to ship better, more secure software faster. The same principles built into our products are reflected in how our team works: we embrace AI as a core productivity multiplier, with all team members expected to incorporate AI into their daily workflows to drive efficiency, innovation, and impact. GitLab is where careers accelerate, innovation flourishes, and every voice is valued. Our high-performance culture is driven by our values and continuous knowledge exchange, enabling our team members to reach their full potential while collaborating with industry leaders to solve complex problems. Co-create the future with us as we build technology that transforms how the world develops software. *Fortune 500® is a registered trademark of Fortune Media IP Limited, used under license. Claim based on GitLab data. Fortune 100 refers to the top 20% ranked companies in the 2025 Fortune 500 list, published in June 2025. Fortune and Fortune Media IP Limited are not affiliated with, and do not endorse products or services of GitLab. AN OVERVIEW OF THIS ROLE As an AI Engineer at GitLab, you'll help build the foundation for GitLab's transformation into an AI-first company. Reporting to the Director, Enterprise AI, you'll be a hands-on technical leader responsible for delivering internal AI-powered solutions that drive measurable business outcomes. Building fast matters, but it's not enough on its own. This role starts with understanding the real problem: mapping how work moves across teams, tools, and handoffs, identifying the true constraint, and validating whether AI is the right solution before you begin development. From there, you'll take ownership from discovery through deployment, combining strong engineering skills with systems thinking and business understanding. Your initial focus will span Sales, Marketing, and Customer Support, where you will embed AI solutions into key systems and workflows. This role offers the opportunity to shape how GitLab team members work, improve flow across the organization, and help advance our mission in a remote, asynchronous, and values-driven environment. WHAT YOU'LL DO * Diagnose business problems before building solutions. Map workflows, identify constraints, and confirm whether AI is the right intervention. Be prepared to say "this doesn't need AI" when that's the honest answer. * Own AI initiatives end-to-end, from stakeholder discovery and technical design through implementation, deployment, and iteration. * Design, develop, and ship AI-powered solutions quickly, delivering working prototypes in days, not months, with a focus on practical outcomes and measurable business value. * Improve organizational flow by building solutions that reduce bottlenecks, shorten lead times, and increase throughput. Measure success using flow metrics alongside adoption and ROI. * Integrate AI capabilities into existing systems and workflows using APIs, orchestration tools, and modern AI platforms, including GitLab Duo Agent Platform, where appropriate. The right tool wins, whether that's custom code, a platform, or a well-crafted prompt. * Be Customer Zero: leverage and showcase GitLab's AI offerings wherever possible, feeding real-world usage insights back to R&D. * Partner closely with stakeholders across functions to understand the real constraints. Ask the right questions, bridge technical and non-technical perspectives, and align on outcomes before jumping to solutions. * Define and track success through business metrics, flow metrics, and feedback loops that make performance visible and actionable. * Contribute to technical direction by evaluating tools, documenting patterns, and creating reusable foundations that help the team scale its impact. WHAT YOU'LL BRING * A Technologist at Heart - Genuinely invested in technology, the foundational and the cutting-edge in equal measure. You're as energised by a well-designed API integration as you are by the latest foundation model release. You reach for the simplest solution that solves the problem well, rather than forcing new technology when proven approaches would do. AI is a powerful part of your toolkit, but it sits on top of solid engineering fundamentals, not in place of them. * Competent, Confident Coding Skills - You can build working solutions end-to-end, write clean and maintainable code, and debug effectively. Whether your skills were honed in a traditional engineering role, through building automations, or shipping side projects, what matters is that you can deliver production-quality work independently. * AI & LLM Technical Depth - Strong proficiency in at least one modern scripting language (Python, JavaScript/TypeScript, or similar) and a solid understanding of REST APIs, GraphQL, and integration patterns. Deep, practical experience with modern AI technologies, specifically: Prompt engineering as a core discipline: designing effective system prompts, managing context windows, structuring multi-turn interactions, evaluating output quality, and iterating systematically on prompt design. * Model selection and cost-performance trade-offs: understanding when a smaller fine-tuned model outperforms a general-purpose large one, when RAG is the right architecture versus expanding the context window, and how to make principled decisions about capability versus cost. * Agentic architecture patterns: tool use, multi-agent orchestration, human-in-the-loop designs, guardrails, evaluation frameworks, and production-grade reliability patterns.Practical fluency across the LLM ecosystem: hands-on experience with models from Anthropic, OpenAI, open-source alternatives, and the judgment to know which to reach for and when. * AI Safety & Risk Awareness - You think critically about how the solutions you build could be exploited, misused, or produce unintended consequences. You know how to design appropriate guardrails (input validation, output filtering, access controls, prompt injection defences, and data leakage prevention) and you treat these as first-class engineering concerns. * Systems Thinking & Diagnostic Rigour - The ability to look at a complex process and see the constraint. Comfortable mapping how work flows end-to-end, identifying bottlenecks, and tracing problems to root causes before proposing solutions. You instinctively ask "what's actually blocking flow here?" before asking "what model should I use?" * Business System Expertise - Familiarity with the landscape of enterprise business systems, CRM (Salesforce), marketing automation (Marketo), support platforms (Zendesk), integration and orchestration tools (Workato), AI platforms (Relevance AI), and enterprise search and knowledge tools (Glean). You don't need deep experience with all of these, but to understand what they do, how they fit together, and be willing to build with and across them. A strong understanding of enterprise data models and workflows is essential. * Broad Functional Understanding - Ability to have meaningful conversations with stakeholders across diverse domains and quickly understand their unique needs. * End-to-End Ownership - Track record of owning complex initiatives from discovery through delivery. Comfortable operating with ambiguity and driving to measurable outcomes independently. * Product Mindset - Ability to scope MVPs, prioritise ruthlessly, and deliver iteratively. In addition, consider adoption, user experience, and business outcomes.   Preferred requirements * Experience with GitLab platform and CI/CD workflows * Background in consulting, solutions engineering, or customer-facing technical roles * Familiarity with value stream mapping, flow metrics, or Theory of Constraints thinking * Experience with low-code/no-code orchestration tools (n8n, Make, Workato) alongside custom development * Previous startup or high-growth company experience * Experience mentoring or leading technical projects with junior engineers ABOUT THE TEAM You will join the Enterprise Technology & AI team. We're the backbone of the organisation, driving transformation in how GitLab team members make decisions, operate at scale, and deliver results for our customers. We believe the best AI solutions start with understanding the system, not the technology. We value people who think in constraints and flow, who build with conviction, and who never stop learning. We work in an all-remote, asynchronous setting, guided by GitLab's values of collaboration, results, efficiency, diversity, inclusion and belonging, iteration, and transparency. The base salary range for this role’s listed level is currently for residents of the United States only. This range is intended to reflect the role's base salary rate in locations throughout the US. Grade level and salary ranges are determined through interviews and a review of education, experience, knowledge, skills, abilities of the applicant, equity with other team members, alignment with market data, and geographic location. The base salary range does not include any bonuses, equity, or benefits. See more information on our benefits and equity. Sales roles are also eligible for incentive pay targeted at up to 100% of the offered base salary. United States Salary Range $108,400—$129,600 USD HOW GITLAB SUPPORTS FULL-TIME EMPLOYEES * Benefits to support your health, finances, and well-being * Flexible Paid Time Off  * Team Member Resource Groups * Equity Compensation & Employee Stock Purchase Plan * Growth and Development Fund * Parental Leave  Please note that we welcome interest from candidates with varying levels of experience; many successful candidates do not meet every single requirement. Additionally, studies have shown that people from underrepresented groups are less likely to apply to a job unless they meet every single qualification. If you're excited about this role, please apply and allow our recruiters to assess your application. ---------------------------------------------------------------------------------------------------------------------------------- Country Hiring Guidelines: GitLab hires new team members in countries around the world. All of our roles are remote, however some roles may carry specific location-based eligibility requirements. Our Talent Acquisition team can help answer any questions about location after starting the recruiting process.   Privacy Policy: Please review our Recruitment Privacy Policy. Your privacy is important to us. GitLab is proud to be an equal opportunity workplace and is an affirmative action employer. GitLab’s policies and practices relating to recruitment, employment, career development and advancement, promotion, and retirement are based solely on merit, regardless of race, color, religion, ancestry, sex (including pregnancy, lactation, sexual orientation, gender identity, or gender expression), national origin, age, citizenship, marital status, mental or physical disability, genetic information (including family medical history), discharge status from the military, protected veteran status (which includes disabled veterans, recently separated veterans, active duty wartime or campaign badge veterans, and Armed Forces service medal veterans), or any other basis protected by law. GitLab will not tolerate discrimination or harassment based on any of these characteristics. See also GitLab’s EEO Policy and EEO is the Law. If you have a disability or special need that requires accommodation, please let us know during the recruiting process.