Principal IT Systems Administrator

Cargurus

Who we are At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact, we’re the largest and fastest-growing automotive marketplace, and we’ve been profitable for over 15 years. What we do The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus—our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride! Role Overview CarGurus is transforming how the company operates by embedding AI into workflows across every function — product, engineering, revenue, finance, support. It’s a software engineering role where the domain is the entire business. You’ll work directly with teams across the org to understand how work actually gets done, identify where AI can change the unit of work or shift where judgment lives, and build the systems that make it real. Some of that is agent-based automation. Some of it is workflow redesign. All of it requires someone who can architect and ship production-quality software, not stitch together SaaS integrations. This is not a Salesforce developer, Boomi connector, or low-code/no-code position, nor is it an enterprise architect or ML model training role. This is a small, high-autonomy team reporting to the Head of AI Solutions. You’ll have outsized influence on how a publicly traded company with ~$1B in revenue adopts AI — not as a pilot or a demo, but as a structural change in how the business runs. You will be successful here if you are a product-caliber engineer who finds internal workflow transformation genuinely interesting — not a consolation prize, but the most leveraged place to be right now. You’d rather build something real that 200 people use tomorrow than something polished that ships in 6 months. WHAT YOU’LL DO * Design and build AI-powered workflows and agent-based systems that transform how teams operate across the company. * Partner directly with stakeholders in revenue, product, engineering, finance, and operations to gather requirements, map existing workflows, and identify high-leverage opportunities for AI. * Build end-to-end — from scoping and architecture through implementation and deployment. This team ships, it doesn’t hand off specs. * Work with AI APIs and platforms (Anthropic/Claude, AWS Bedrock, and others) to build agentic systems, automation pipelines, and intelligent tooling. * Operate across a messy, heterogeneous environment — AWS infrastructure, Salesforce, internal services — without waiting for everything to be clean before you start building. * Help shape the technical strategy and standards for AI Solutions as a function. WHAT YOU’LL BRING Must-haves: * 8+ years of relevant software engineering experience (no degree required; equivalent experience is fully accepted). * Strong software engineering fundamentals — you’ve built and shipped production systems, not just prototypes. * Proficiency in Python as the primary language for this work; comfort with additional languages is a plus. * Experience designing APIs, services, and data pipelines. You think in systems, not scripts. * AWS fluency — you’re comfortable working within AWS infrastructure and services. * Hands-on experience building with LLM APIs, agent frameworks, or AI-powered applications — not just experimentation, but something that ran in production or was used by real people. * Ability to operate with high autonomy. You’ll scope your own work, make architectural decisions, and own outcomes. * Willingness to work across the full stack of a business — including systems like Salesforce that aren’t glamorous but are where the high-impact problems live. Nice-to-haves: * Experience with workflow orchestration or automation at scale. * Familiarity with Salesforce APIs and integration patterns (not Salesforce administration). * Background in recommendations, search, data science, or ML engineering. * Experience working cross-functionally with non-technical stakeholders. The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position. On-Target Earnings (OTE) is inclusive of base salary and on-target commission earnings, which applies exclusively to sales roles. Individual pay within this range is determined by work location and other factors such as job-related skills, experience, and relevant education or training. This annual base salary forms part of a comprehensive Total Rewards Package. In addition to benefits, this role may qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs). Position Pay Range $144,000—$172,000 USD Working at CarGurus We reward our Gurus’ curiosity and passion with best-in-class benefits and compensation, including equity for all employees, both when they start and as they continue to grow with us. Our career development and corporate giving programs, as well as our employee resource groups (ERGs) and communities, help people build connections while making an impact in personally meaningful ways. A flexible hybrid model and robust time off policies encourage work-life balance and individual well-being. Thoughtful perks like daily free lunch, a new car discount, meditation and fitness apps, commuting cost coverage, and more help our people create space for what matters most in their personal and professional lives. CarGurus may require in-person interviews as part of our hiring process, particularly for positions based in our Boston and Dublin offices. Candidates selected for an in-person interview will be notified in advance. Please be aware that travel expenses are the responsibility of the candidate. We welcome all CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potential—starting with our hiring process. We do not discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. We foster an inclusive environment that values people for their skills, experiences, and unique perspectives. That’s why we hope you’ll apply even if you don’t check every box listed in the job description. We also encourage you to tell your recruiter if you require accommodations to participate in our hiring process due to a disability so we can provide the appropriate support. We want to know what only you can bring to CarGurus. #LI-Hybrid

Modulr

Are you curious, excited by experimentation and always looking for a better way of doing things? * Do you want to keep learning and developing whilst getting hands-on experience working in the embedded payments space? * Do you want to have the opportunity to be a key member of our automation team? If so, we would love to connect and collaborate! We want to hire ambitious, and value-adding talent into Modulr, one of the fastest growing payments businesses in the UK and Europe. Modulr is experiencing significant growth, and in this role you will work in a cross-functional team who are asked to solve a problem, rather than be handed a task to do. This is an excellent opportunity to work in a high-growth environment with a fast-paced and collaborative culture where you will have great opportunities to work on challenging problems. About us At Modulr, our vision is a world where all businesses are powered by embedded payments. Modulr enables businesses, from SMEs to Enterprise, initially across the UK and Europe to efficiently pay-in, collect and disburse funds instantly via a range of payment schemes, accounts, and card products. We have created an industry-leading API platform with comprehensive online tools and access, to meet the demands of daily business payments. We have two routes to market. Our Core Business Payments product allows customers in any sector to connect to us and our expanding network of accounting and payroll platforms, including Sage, Xero, BrightPay and IRIS to automate payments. Our Vertical Solutions targets a growing range of industry verticals which directly connect their IT platforms to our APIs and webhooks. We solve complex payment problems for hundreds of clients in a range of industries, including Travel, Lending, Wage Advance, and Investment & Wealth. We are deeply integrated into the payment eco-system. In the UK, we are direct participants of Faster Payments and Bacs. Modulr hold settlement accounts at the Bank of England. Our payment network connectivity includes CHAPS, Open Banking, SEPA, SWIFT and account issuance in multiple currencies. We are principal issuing members of Visa and Mastercard schemes across UK and Europe. Our regulatory permissions and governance structure are the foundations of our business. We are regulated and supervised as an Authorised Electronic Money Institution (AEMI) in the UK by the Financial Conduct Authority and in the Netherlands by De Nederlandsche Bank. Our founding team has a wealth of experience in the payments industry and growing successful businesses. Modulr is backed by the venture arms of payments giants PayPal and FIS, as well as growth investors Blenheim Chalcot, General Atlantic, Frog Capital and Highland Europe. Modulr now has over 400 employees spread globally across offices in London, Edinburgh, Amsterdam, and Mumbai. Modulr values •Building the extraordinary; going that extra mile. •Owning the opportunity; be passionate and proud of the time you invest. •Move at pace; reach goals faster whilst supported on your career journey. •Achieve it together, working collaboratively and being a Modulite. The Team At Modulr we are focused on building autonomous squads that are focused on working in the best possible way. We operate in a tribes and squad model with each area focused on a particular growth area. Each squad is small and cross-functional. We have big ambitions and have many interesting challenges ahead. Our strategy is to provide our customers with seamless connectivity into payment schemes both domestically and overseas no matter where they're based. Specific duties Depending on the project, you will need to be comfortable doing the following: •Delivery of enhancements and configuration changes; understanding requirements, coding, testing and implementing these to broaden the usage of Salesforce. •Supporting, maintaining and improving the working of existing Salesforce environment for optimal functionality. •Creating and maintaining integrations with other applications and systems using web services and APIs. •Ensuring compliance with security and development standards of Salesforce. •Develop and maintain custom solutions on the Salesforce platform using Apex, flows and other technologies. •Work collaboratively with technical teams to deliver business requirements. •Develop and maintain Salesforce integrations and third-party applications. •Participate in code reviews to ensure that the best practices for the existing and new Salesforce solutions are implemented. •Stay updated with new Salesforce features & functionalities and recommend best practices to enhance the existing Salesforce implementations. About you •Proficient understanding of CRM administration/customisation, including Salesforce lightning framework, Salesforce Sales cloud and Salesforce Community cloud. •Practical knowledge of automation with AI tools in the CRM space. E.g., Agentforce •5-8 years’ experience of Apex, LWC, Aura, flows, DevOps and continuous integration/deployment (CI/CD) processes. •In depth understanding of Salesforce data model, including standard and custom objects, relationships and fields. •Salesforce certifications like Platform Developer I or II, App Builder, Administrator, JavaScript. •Experience in a Robust communication skills to work in a fast-paced environment. •Knowledge of HTML, CSS, JavaScript and jQuery. ModInclusion At Modulr, we are working hard to build a more positive diverse and inclusive culture that helps everyone to feel they belong and can truly bring their whole self to work. Not only is it the right thing to do for everyone in the Modulr team, it’s also the right thing to do for our business, the community we operate in and attracting future talent. As part of our approach, we actively welcome applications from candidates with diverse backgrounds.

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.