RemoteLeaf Logo
Log in Sign up

Director, Customer Education

58 minutes 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 16

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

Similar Roles

Quantum-Si

Senior Customer and Technical Support Manager

Quantum-Si 51-250 Pharmaceuticals

Quantum-Si is hiring a Senior Customer and Technical Support Manager to lead global technical support, commercial training, and customer knowledge operations that improve issue resolution, field readiness, and product feedback loops.

United States Full-time Senior Training Manager
$135k-$160k
58 minutes ago
Databricks

Senior Customer Enablement Architect

Databricks 1K-5K IT Services

Databricks is seeking a US-based Customer Enablement Architect to lead enterprise training and enablement efforts across the Americas, helping customers turn their data and AI initiatives into measurable adoption, retention, expansion, and growth outcomes.

United States Full-time Senior Sales Enablement Training Manager
$115k-$198k
Apache Spark Databricks MLflow
1 hour, 13 minutes ago
SmithRx

Customer Trainer

SmithRx 1K-5K Pharmaceuticals

SmithRx is seeking a Client Training and Enablement professional to develop and deliver training programs that help brokers, partners, and customer success teams understand and adopt its pharmacy benefits platform.

Anywhere Full-time Senior Training Manager Training Specialist
1 hour, 41 minutes ago
Culligan

Director of Training and Onboarding

Culligan 1K-5K Beverages

Culligan Quench is hiring a Director of Training and Onboarding to lead the indirect dealer onboarding process from initial signup through launch and early revenue generation.

United States Full-time Lead Customer Success Manager Training Manager
$100k-$120k
1 hour, 58 minutes ago

You're on a roll! Sign up now to keep applying.

Sign Up

Already have an account? Log in

Used by 14,729+ remote workers