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Director, Customer Education

1 month, 2 weeks ago
United States
Full-time
Executive
Content Strategist
Marketing and Growth
Apply Now
Calendly

Calendly

Calendly offers a modern scheduling platform that simplifies the process of finding meeting times, allowing users to eliminate the hassle of back-and-forth communication and enhance productivity through automated scheduling features.

Internet Software & Services
251-1K
Founded 2013
$351M raised
View All Jobs 14

Description

  • Define and evolve Calendly’s customer education strategy across demos, tutorials, Help Center content, Learning Hub courses, and live programming.
  • Lead, coach, and develop a team of education specialists and multimedia content producers.
  • Partner with Product Marketing to embed education content into every product launch.
  • Work with Customer Success and Support to identify customer pain points, content gaps, and churn risks.
  • Build and scale the Calendly Learning Hub as a self-serve education destination.
  • Raise the quality of multimedia educational content, including demo videos and feature tutorials.
  • Establish KPIs and reporting to measure education impact and communicate results to senior leadership.
  • Create operational systems and workflows for planning, review, localization, and content maintenance.
  • Ensure education content supports the full customer lifecycle from onboarding through deep feature adoption.
  • Collaborate cross-functionally with Product, Product Marketing, and Customer Success on customer journeys and launches.

Requirements

  • 15+ years of progressive experience in customer education, content strategy, instructional design, or a related field.
  • At least 3 years of director-level or equivalent senior leadership experience managing teams.
  • Proven experience building and scaling a full-funnel customer education function in a B2B SaaS or technology environment.
  • Experience developing education content strategy across video, multimedia, written documentation, and structured learning programs.
  • Strong cross-functional experience partnering with Product, Product Marketing, and Customer Success.
  • Track record of leading, coaching, and developing high-performing direct reports.
  • Excellent editorial judgment across written and multimedia content with a high bar for quality, clarity, and brand consistency.
  • Data-driven approach with experience establishing KPIs and measuring business impact.
  • Authorization to work lawfully in the United States; Calendly does not provide immigration sponsorship.
  • Preferred: Experience at a multi-product SaaS company across multiple product lines or customer segments.
  • Preferred: Familiarity with Learning Management Systems (LMS), knowledge base platforms such as Zendesk Guide or Guru, and video production workflows.
  • Preferred: Background in instructional design or curriculum development for adult learners.
  • Preferred: Experience building or overseeing a multimedia or video production function.
  • Preferred: Experience working within a brand and marketing organization.
  • Preferred: Familiarity with Calendly’s product and the scheduling, calendar management, or meeting intelligence category.

Benefits

  • Annual base salary range of $169,284 to $253,926 USD, depending on location tier.
  • Top Performer Bonus program for eligible full-time employees.
  • Equity awards as part of total rewards.
  • Competitive benefits package.
  • Remote work location-based pay zones.
  • Reasonable accommodation support during the application or recruiting process.
  • Potential occasional travel for company events, team collaboration, or offsites.

Interested in this position?

Apply directly on the company website

Apply Now

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