Engineering Director, Business Applications

Clasp

ENGINEERING DIRECTOR, 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 for 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 Clasp is searching for an Engineering Director to own the technical heart of Clasp Finance. This is a fun role: you will lead a small, high-impact engineering team, drive technical debt resolution, and hold the long-term health of the platform to a high standard. We’re looking for a hands-on modern technical leader who leverages AI to ship meaningful improvements, can evaluate and implement tooling across various technical stacks, and remains close enough to the work to earn respect from their teammates. While they can be doers, their real leverage is the team around them. They grow people deliberately, partner genuinely with others, and move on good ideas without waiting for permission. You will be embedded in the Clasp Finance business line, working directly with our Senior Product Manager for Lending to build an enterprise-grade loan origination platform, as well as partnering directly with stakeholders on critical data pipelines, and servicing and collections efforts. You will report to Engineering Leadership and have a dotted reporting line to the GM of Clasp Finance. We want someone who is excited by fintech and the unique challenges that the lending industry affords; they are willing to lean into hard problems and work with others to deliver meaningful features for internal and external stakeholders. We need someone who is a deep systems thinker and who loves to develop talent to asymmetrically scale teams and their impact. What You'll Do * Own the Technical Roadmap: Define and drive the engineering strategy for Clasp Finance in close partnership with the GM and Product Manager, and cross-functional stakeholders across lending operations, compliance, and sales. Translate business priorities into a sequenced technical plan – balancing new feature delivery against platform investment and regulatory requirements. * Lead and Grow the Team: Manage a small engineering team, setting clear goals, running effective 1:1s, and creating an environment where engineers do their best work. Partner with the Engineering Leadership on development, leveling, and team structure as Clasp Finance scales. Be a hands-on contributor where it matters — code reviews, architecture decisions, and unblocking the team on hard problems. * Partner Cross-Functionally: Work closely with compliance and legal to ensure the platform holds up under regulatory scrutiny. Understand our internal customer needs to streamline operations. * Think in Multipliers: You'll be working with a lean team against a big surface area. That means constantly asking where AI, automation, contracted staffing and tooling can create leverage and building the systems that make each engineer on your team significantly more productive than they'd be anywhere else. * Scale the Platform: Collaborate with Clasp Talent engineering leadership to detangle co-mingled codebases across business lines, align on shared services, and maintain a coherent overall technical architecture. Make principled trade-offs between build vs. buy, and communicate cost implications clearly to leadership. Ensure the loan origination system, credit model tooling, and school-facing administrative platform are reliable, scalable, and auditable. What You'll Need * Experience in Engineering Leadership: Experience managing engineers in a fintech, lending, or regulated domain environment. This role is not for first-time managers as it will require you to hit the ground running, juggling stakeholder management, technical execution, and people management. * Technical Depth: 5+ years of hands-on software engineering experience, with recent and meaningful depth in Python, JavaScript and/or TypeScript. Experience with Next.js and modern state management patterns. You can credibly review code, diagnose architectural problems, and make technology choices your team will trust. * Cloud & Architecture Experience: Experience working with cloud-based applications and infrastructure. Our platform leverages Firebase and Firestore, so experience with NoSQL document modeling is strongly preferred. Familiarity with GCP is a plus, though equivalent experience in AWS or Azure environments is also valued. * 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 school customers. * Strategic Thinking: Ability to leverage both qualitative and quantitative data to inform all decisions, and to make confident calls under uncertainty. 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 $200,000 to $210,000 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 engineering leader with deep fintech expertise and 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.

Gitlab

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 the Director, Enterprise Architecture and AI Intelligent Automation (IA), you will define and govern how GitLab's internal systems connect, integrate, and evolve to support our rapidly scaling business. Reporting to the VP, Business Systems, you will lead our Enterprise Architecture, Integration, & RPA teams, setting the architectural standards, governance frameworks, and strategic vision that keep our technology landscape coherent, scalable, and aligned with business objectives. This role is both deeply strategic and hands-on: you will shape the long-term architecture while staying close enough to the work to guide critical technical decisions across teams. As the architectural leader for GitLab's internal technology ecosystem, you will establish and lead our Architecture Review Board, partnering early and often with system owners so architecture becomes an enabler rather than a gate. You will rationalize our automation and integration landscape, clarify when to use AI, RPA, or traditional integration, reduce shadow IT and software sprawl, and drive clear patterns for data flows and system-of-record designations.  What you'll do * Define and drive GitLab's enterprise architecture strategy, setting clear principles and patterns for how internal systems connect, integrate, and scale across platforms like Salesforce, NetSuite, Zuora, Workato, and other core business applications. * Establish and lead GitLab's Architecture Review Board, engaging early with system owners and project teams to shape technical approaches, guide integration patterns, and ensure architectural decisions align with enterprise standards and business objectives including applying business capability & EA framework such as TOGAF * Design and govern integration architectures and data flow patterns, including API-first approaches, point-to-point integrations, and data warehouse and reverse ETL models, in close partnership with Data Governance and other cross-functional stakeholders. * Create and execute a cohesive automation strategy that spans agentic AI, robotic process automation (RPA), and traditional integration technologies, rationalizing existing investments and defining clear decision frameworks for tool selection. * Lead efforts to reduce shadow IT and software sprawl by implementing software governance processes, partnering with system owners to centralize fragmented solutions, eliminate redundant capabilities, and reduce technical debt and unnecessary spend. * Ensure enterprise, integration, and IA architectures meet SOX compliance and security requirements, including robust access controls, data governance, and audit-ready integration patterns that balance risk management with business agility. * Align decentralized system roadmaps with enterprise architecture strategy, systematically identify and address technical debt, and provide hands-on technical leadership and mentorship to Integration, RPA, and IA Engineering teams to elevate architectural thinking and execution. WHAT YOU'LL BRING * Extensive experience defining and governing enterprise architecture in complex, matrixed organizations, including leading architecture strategy across core business systems such as ERP, CRM, CPQ, billing, and financial platforms. * Deep technical background across integration, automation, and AI, with the ability to step into Architecture, Integration, RPA teams and contribute meaningfully to design discussions and problem solving. * Expert-level knowledge of data modeling, integration architecture patterns, and API design, microservices architecture, including experience designing integration strategies that support both operational and analytical use cases. * Strong experience establishing and leading architecture review boards or similar governance frameworks, balancing partnership-oriented engagement with clear, enforceable standards. * Demonstrated success reducing shadow IT and software sprawl through thoughtful software governance, portfolio rationalization, and roadmap alignment with enterprise architecture principles. * Deep understanding of SOX compliance, internal controls, and security architecture for business applications, with experience designing audit-ready integration and automation patterns. * Exceptional communication and influencing skills, with the ability to engage VP and C-level stakeholders, translate complex architectural concepts into clear business language, and drive alignment across decentralized teams. The Enterprise Architecture team at GitLab is responsible for designing, governing, and evolving the internal technology landscape that powers our business. We define how our core systems connect, integrate automation and AI into everyday workflows, and ensure our architecture is scalable, secure, and aligned with company priorities. Composed of experienced architects and engineers across integration, RPA, and AI, we operate asynchronously and partner closely with system owners in functions such as Sales, Finance, Customer Success, and Operations. We focus on setting clear architectural standards, rationalizing tools and automation, and guiding teams in using modern AI technologies to deliver measurable business impact while maintaining strong compliance and security practices. For more on how we work, see the Enterprise Applications Team Handbook Page. 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 $153,000—$287,000 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.

Gitlab

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 the Director of Engineering, Growth and Monetization, you will lead the engineering strategy and execution behind the systems and product experiences that help customers adopt, buy, and expand with GitLab. This role focuses on the full monetization journey, including self-service experiences, quote-to-cash systems, billing, usage, budgeting, entitlements, and account management. You will help GitLab evolve toward usage- and impact-based pricing by building modular, scalable platforms that support seamless customer workflows and reliable business operations. In this role, you will guide multiple teams through managers and partner closely with Product, Design, Finance, Legal, Sales, and Enterprise Applications to deliver customer-centered, compliant, and resilient systems. You will shape the technical direction for an API-first monetization platform and raise the bar for architecture, execution quality, and platform resilience. Over your first year, your work will center on aligning engineering strategy across the monetization journey, strengthening core systems and integrations, and helping the organization support new pricing and packaging models with confidence. You will report into engineering leadership and play a key role in connecting customer experience, platform architecture, and business outcomes. * Some examples of our projects: Building end-to-end workflows across quoting, ordering, provisioning, billing, invoicing, entitlements, renewals, and expansion * Some examples of our projects: Integrating AI and machine learning into monetization platforms for predictive pricing, usage forecasting, and more personalized billing experiences WHAT YOU’LL DO * Lead the Growth and Monetization engineering organization with accountability for strategy, architecture, execution, and team health. * Drive the technical vision for self-service purchase, expansion, billing, usage visibility, budgeting, and account management experiences. * Build end-to-end workflows across quoting, ordering, provisioning, billing, invoicing, entitlements, renewals, and expansion. * Design an API-first monetization platform that is modular, scalable, and adaptable to evolving pricing and packaging models. * Develop systems that support usage- and impact-based products, including metering, rating, packaging, billing, and reporting. * Own and evolve integrations across monetization systems such as Zuora, Salesforce, and related enterprise platforms. * Partner with Enterprise Applications, Finance, Legal, Sales, Product, and Design to deliver compliant, scalable, customer-centered workflows. * Ensure high standards for reliability, auditability, controls, and operational rigor across monetization systems, including SOX-aware processes where needed. * Guide engineering initiatives that apply AI and machine learning to monetization use cases such as predictive pricing models, intelligent usage forecasting, and automated personalized billing experiences. WHAT YOU’LL BRING * Experience leading multiple engineering teams through managers in a director-level or comparable engineering leadership role. * Strong foundation in application development and distributed systems, with the ability to apply that depth to customer-facing monetization platforms. * Knowledge of billing architecture, usage metering, invoicing, entitlements, budgeting, and account lifecycle management. * Experience launching usage-based products or platforms and supporting changes in pricing models. * Understanding of API-first, modular, and scalable platform architecture. * Experience building systems that require strong controls, compliance, and auditability, including SOX-related considerations. * Ability to work effectively across Engineering, Enterprise Applications, Finance, Legal, Sales, and other cross-functional teams in a distributed environment. * Clear communication, organizational leadership, and execution skills, with openness to candidates who bring transferable experience from adjacent platform or SaaS domains. * Familiarity with SaaS monetization, self-service growth models, hybrid self-service and sales-assisted journeys, or tools such as Zuora and Salesforce is helpful. ABOUT THE TEAM The Growth and Monetization Engineering team owns the systems and product experiences that move users from acquisition to activation to purchase and ongoing expansion. The team builds self-service growth flows, billing and pricing platforms, entitlements, usage controls, and customer-facing workflows that make GitLab easier to adopt, easier to buy, and easier to scale. This work spans product and platform concerns and requires close asynchronous collaboration across regions and functions as the team solves for evolving pricing models, platform modernization, enterprise system integrations, and dependable customer experiences at scale. For more on how this team works, see the Growth team Handbook page.  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 $203,200—$345,600 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.