Description
We are 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 will develop the content, learning modules, and programs that support a high-velocity sales organization serving sellers with different needs, experience levels, and business types.
Responsibilities:
- 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.
Requirements:
- 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 ability to lead complex programs across teams without direct reporting authority, make decisions independently, and align senior stakeholders.