Head of Customer Self-Service Onboarding, Sales

This is a fully remote position, open to applicants in California.

📋 Description

• Establish the learning strategy for seller onboarding, aligning seller requirements with defined learning goals, content, and success metrics.

• Create and implement modular learning pathways, short videos, interactive tutorials, setup guides, webinars, and on-demand courses.

• Tailor learning paths to suit various business types, products, roles, and levels of technical expertise.

• Develop outlines, scripts, storyboards, and sample modules while providing guidance to contributors and production partners.

• Direct product and operational choices for a self-service onboarding portal.

• Convert seller research and learning requirements into specifications for navigation, content discovery, guided setup, and personalized recommendations.

• Collaborate with Product, Design, and Engineering teams to prioritize features, assess tradeoffs, test prototypes, and implement enhancements.

• Define the transitions for sellers between independent learning, live education, and assisted onboarding.

• Assign responsibilities for publishing, maintaining, and enhancing the portal post-launch.

• Work with Sales and Onboarding teams to integrate relevant learning throughout the purchasing, setup, and first-use experiences.

• Create recommendations, communications, and reminders to assist sellers in completing critical tasks.

• Develop scalable live training initiatives, including webinars and group sessions.

• Monitor setup progress, time to first use, product adoption, seller confidence, and demand for assisted support.

• Utilize learning analytics, seller research, support inquiries, and experiments to pinpoint areas where sellers encounter challenges.

• Test and refine content formats, learning paths, and portal experiences.

• Assess AI-assisted guidance and content tools with criteria for accuracy, privacy, and human oversight.

⛳️ Requirements

• Significant experience in developing customer education, digital learning, or self-service onboarding programs at scale.

• Experience within a high-velocity sales organization is preferred.

• Proven history of taking customer-facing learning programs from concept through launch, showcasing improvements in onboarding or product adoption.

• In-depth knowledge of instructional design, adult learning principles, curriculum development, and task-based learning strategies.

• Practical experience in creating modular courses, video tutorials, interactive learning, webinars, and written documentation.

• Familiarity with learning management systems, digital authoring tools, content management platforms, and learning analytics.

• Strong product acumen and experience collaborating with Product, Design, and Engineering on customer-facing portals or digital learning environments.

• Experience in establishing content production and maintenance workflows, including quality review, accessibility, localization, and version control.

• Analytical capabilities to link learning engagement with customer behavior and business results.

• Excellent writing and storytelling skills, with the ability to convey complex concepts in a clear and actionable manner.

• Capability to lead complex programs across teams without direct reporting authority, make independent decisions, and align senior stakeholders.

🏝️ Benefits

• Remote work options.

• Medical insurance coverage.

• Flexible time off policies.

• Retirement savings plans available.

• Modern family planning assistance.

• Reasonable accommodations throughout the recruitment process.