Head of Customer Self-Service Onboarding, Sales

The role

You will build self-service learning programs and a new onboarding portal to help sellers start transacting on Square. You will develop content, learning modules, and programs for a high-velocity sales organization.

What you will do

• Define the learning strategy for seller onboarding.
• Design and launch modular learning paths, videos, tutorials, and courses.
• Guide product and operational decisions for a self-service onboarding portal.
• Partner with Product, Design, and Engineering to prioritize features and launch improvements.
• Design programs for a high-volume sales environment.
• Partner with Sales and Onboarding to introduce learning at relevant moments.
• Build scalable live training programs including webinars and group sessions.
• Measure setup progress, product adoption, and seller confidence.
• Use learning analytics and research to identify where sellers get stuck.
• Test and improve content formats and portal experiences.

Required qualifications

• Extensive experience building customer education, digital learning, or self-service onboarding programs at scale.
• Track record of taking customer-facing learning programs from concept to launch.
• 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.
• Experience building content production and maintenance processes.
• Analytical skills to connect learning engagement with customer behavior and business outcomes.
• Strong writing and storytelling skills.
• Ability to lead complex programs across teams without direct reporting authority.

Benefits

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

Before you apply

• Candidates may submit up to 9 active applications within a 60-day period.
• Reapplications to the same role are accepted 90 days after a previous application has been reviewed.
• Automated AI tools may be used to evaluate job applications.

About the company

Block, Inc. builds technology to increase access to the global economy through brands like Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto.