Product Design Lead, Contractor Experience

About Rippling Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system. Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds. Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes. We prioritize candidate safety. Please be aware that all official communication will only be sent from @ Rippling.com addresses. About the role At Rippling, design is core to our mission of freeing smart people to tackle hard problems. One of those problems is how companies pay and support contractors—the millions of people around the world who work for companies without being full-time employees. They might be software developers in Eastern Europe, designers in Latin America, customer support staff in Asia, or nurses picking up shifts across the U.S. Paying and managing them sounds simple, but it isn’t. Every country has different rules. Payments cross currencies and banking systems. Invoices and tax documents need to be tracked and reconciled. Identity checks and fraud controls add friction. Admins get stuck in the middle, and contractors are often left waiting, confused about when or how they’ll actually get paid. As Product Design Lead for Contractor Experience, you’ll take on this challenge directly. You’ll shape the entire lifecycle—from onboarding to invoicing, payouts, and tax documentation. You’ll help create a seamless experience where contractors get paid reliably and transparently, admins have clarity and control, and compliance needs are met globally. This is the opportunity to reimagine contractor payments and workflows end-to-end, making them trusted and effortless for millions of people worldwide. The scope is massive: designing how contractors are onboarded, how invoices and payments are managed across multiple rails and currencies, and how tax and compliance documents are surfaced at the right time. You’ll deliver competitive wins like faster payouts, smoother invoicing, debit card access, and earned wage advances. You’ll build trust at scale by making payments reliable and transparent, while reducing admin overhead and support tickets. Most importantly, you’ll shape a strategic product that is central to Rippling’s global expansion. What you will do Own the end-to-end design for Rippling’s contractor experience, spanning payments, invoicing, payment lifecycle management, and tax/compliance documentation Get close to admins and contractors, uncover where workflows break down, and translate those insights into designs that drive clarity, trust, and speed Anticipate global needs and edge cases as we expand into new markets, currencies, payment rails, and compliance regimes, future-proofing the contractor experience for scale Design capabilities and systems that support both admins and contractors, ensuring experiences are consistent and reliable across Rippling’s platform Work closely with Product, Engineering, Risk, Compliance, and Support partners to plan, design, and ship features that compete head-to-head with the best offerings in the market Deliver precise designs and prototypes that communicate complex concepts and interactions clearly to engineering teams and stakeholders What you will need 6+ years of professional product design experience with a track record of shipping complex, high-impact products end to end, from planning to QA Proven ability to transform complexity into elegant simplicity, whether in fintech, enterprise