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Head of Self-Service Onboarding

Location: Remote
Compensation: To Be Discussed
Reviewed: Thu, Oct 22, 2026
This job expires in: 26 days

Job Summary

To enhance seller confidence in transacting with Square, the full-time salaried Head of Self-Service Onboarding will develop and implement self-service learning programs, create a comprehensive onboarding portal, and connect educational resources to the sales journey.

Key responsibilities
  • Build self-service learning programs tailored to various seller needs and technical experiences
  • Guide the development of a self-service onboarding portal, ensuring effective navigation and content discovery
  • Measure and improve learning outcomes by analyzing seller engagement and onboarding success metrics
Required qualifications
  • Extensive experience in customer education or self-service onboarding programs, particularly in high-velocity sales environments
  • Proven track record of launching customer-facing learning programs that improve onboarding and product adoption
  • Deep expertise in instructional design, curriculum development, and task-based learning
  • Hands-on experience with digital learning tools and learning management systems
  • Strong analytical skills to connect learning engagement with customer behavior and business outcomes

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