Head of Self-Service Onboarding, Sales

About the Role

<p><span style="font-size: 10pt;">Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.</span><br><br><span style="font-size: 10pt;">So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.</span><br><br><span style="font-size: 10pt;">Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.</span></p> <h2><strong>About the role</strong></h2> <p>We’re looking for an expert in customer education and digital onboarding to build self-service learning programs that help sellers start transacting with confidence on Square.&nbsp;</p> <p>You’ll develop the content, learning modules, and programs that support a high-velocity sales organization serving sellers with different needs, experience levels, and business types. You’ll also guide the development of a new self-service onboarding portal, shaping product and operational decisions alongside Product, Design, and Engineering.</p> <p>We’re looking for someone who combines deep instructional design expertise with strong product judgment and execution skills. You know how to turn complex setup tasks into useful learning experiences, build content programs that scale, and measure whether customers can apply what they’ve learned.</p> <p>Reporting to the Head of Global Onboarding Operations, this is a senior individual contributor role. You’ll lead through expertise and influence, working across teams to take programs from concept through launch and ongoing improvement.</p> <h2><strong>What you’ll do</strong></h2> <h3><strong>Build self-service learning programs</strong></h3> <ul> <li>Define the learning strategy for seller onboarding, connecting seller needs with clear learning objectives, content, and measures of success.</li> <li>Design and launch modular learning paths, short-form videos, interactive tutorials, setup guides, webinars, and on-demand courses.</li> <li>Adapt learning paths to different business types, products, roles, and levels of technical experience.</li> <li>Stay close to the work: develop outlines, scripts, storyboards, and sample modules while guiding contributors and production partners.</li> </ul> <h3><strong>Shape the self-service onboarding portal</strong></h3> <ul> <li>Guide product and operational decisions for a portal that brings onboarding guidance, learning resources, and progress tracking into one experience.</li> <li>Translate seller research and learning needs into requirements for navigation, content discovery, guided setup, and personalized recommendations.</li> <li>Partner with Product, Design, and Engineering to prioritize features, evaluate tradeoffs, test prototypes, and launch improvements.</li> <li>Define how sellers move between independent learning, live education, and assisted onboarding when they need additional help.</li> <li>Establish ownership for publishing, maintaining, and improving the portal after launch.</li> </ul> <h3><strong>Connect learning to