Director, Customer Education
Leads Customer Education strategy and team to create full-funnel content (demos, tutorials, Learning Hub) driving activation, adoption, and retention. Partners cross-functionally with Product, Marketing, Success; requires 15+ years experience scaling B2B SaaS education.
Responsibilities
- Define and evolve Calendly's Customer Education strategy across video demos, self-serve tutorials, Help Center articles, Learning Hub courses, and live programming, mapped to customer segments, product surfaces, and lifecycle stages.
- Lead and develop a team of education specialists and multimedia content producers, setting goals, providing coaching, and ensuring accountability.
- Partner with Product Marketing to embed education content in product launches, including Help Center articles, demo videos, and feature walkthroughs.
- Collaborate with Customer Success and Support to identify content gaps, reduce support volume, and build proactive educational materials.
- Build and scale the Calendly Learning Hub with curriculum strategy, course development, and content roadmap.
- Raise multimedia content quality standards, partnering with creative teams for compelling demo videos and tutorials.
- Establish KPIs (e.g., feature activation, Help Center deflection, engagement) and reporting to measure impact and improve strategy.
- Build operational systems for content planning, review, localization, and maintenance.
Requirements
Basic Qualifications
- 15+ years in customer education, content strategy, instructional design, or related field; 3+ years in director-level leadership managing teams.
- Track record building and scaling full-funnel customer education in B2B SaaS/tech.
- Experience with education content across video/multimedia, written documentation, and structured programs.
- Cross-functional partnership with Product, Product Marketing, Customer Success.
- Proven team leadership and development.
- Excellent editorial judgment for content quality and brand consistency.
- Data-driven with KPI establishment and insights for decisions.
Preferred Qualifications
- Experience at multi-product SaaS across product lines/segments.
- Familiarity with LMS, knowledge bases (e.g., Zendesk Guide, Guru), video production.
- Instructional design/curriculum development for adult learners.
- Multimedia/video production oversight.
- Brand/marketing organization experience.
- Familiarity with Calendly/scheduling products.
Compensation
Tier 1: $203,141—$253,926 USD
Tier 2: $186,212—$232,765 USD
Tier 3: $169,284—$211,605 USD
Base salary plus Top Performer Bonus, equity, benefits (full-time 30+ hours/week).
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