Head of Customer Self-Service Onboarding, Sales

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. 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. 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. About the role 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. 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. 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. 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. What you’ll do Build self-service learning programs • Define the learning strategy for seller onboarding, connecting seller needs with clear learning objectives, content, and measures of success. • Design and launch modular learning paths, short-form videos, interactive tutorials, setup guides, webinars, and on-demand courses. • Adapt learning paths to different business types, products, roles, and levels of technical experience. • Stay close to the work: develop outlines, scripts, storyboards, and sample modules while guiding contributors and production partners. Shape the self-service onboarding portal • Guide product and operational decisions for a portal that brings onboarding guidance, learning resources, and progress tracking into one experience. • Translate seller research and learning needs into requirements for navigation, content discovery, guided setup, and personalized recommendations. • Partner with Product, Design, and Engineering to prioritize features, evaluate tradeoffs, test prototypes, and launch improvements. • Define how sellers move between independent learning, live education, and assisted onboarding when they need additional help. • Establish ownership for publishing, maintaining, and improving the portal after launch. Connect learning to the sales and onboarding journey • Design programs for a high-volume sales environment, where sellers need timely guidance without relying on one-to-one training. • Partner with Sales and Onboarding to introduce relevant learning at the right moments, from purchase through setup and first use. • Develop recommendations, communications, and reminders that help sellers start learning, complete key tasks, and stay on track. • Build scalable live training programs, including webinars and group sessions that complement on-demand content. Measure and improve outcomes • Define success beyond content views and course completion: measure setup progress, time to first use, product adoption, seller confidence, and demand for assisted support. • Use learning analytics, seller research, support questions, and experiments to identify where sellers get stuck. • Test and improve content formats, learning paths, and portal experiences based on evidence. • Evaluate AI-assisted guidance and content tools that improve learning and production efficiency, with clear standards for accuracy, privacy, and human review. What you’ll bring • Extensive experience building customer education, digital learning, or self-service onboarding programs at scale, ideally supporting a high-velocity sales organization. • A track record of taking customer-facing learning programs from concept to launch and demonstrating improvements in onboarding or product adoption. • Deep expertise in instructional design, adult learning, curriculum development, and task-based learning. • Hands-on experience producing modular courses, video tutorials, interactive learning, webinars, and written guidance. • Experience with learning management systems, digital authoring tools, content management platforms, and learning analytics. • Strong product judgment and experience partnering with Product, Design, and Engineering on customer-facing portals or digital learning experiences. • Experience building content production and maintenance processes, including quality review, accessibility, localization, and version control. • Analytical skills and the ability to connect learning engagement with customer behavior and business outcomes. • Strong writing and storytelling skills, with the ability to make complex concepts clear and actionable. • The abili