[Hiring] Director, Customer Education @Calendly

Role Description

We are looking for a Director, Customer Education who will define and lead a full-funnel educational content strategy for Calendly — one that spans product demos, feature education, the Calendly Learning Hub, and Help Center content. This is a high-impact leadership role for someone who thinks beyond content production and sees education as a strategic lever for customer activation, adoption, and long-term retention.

You will report to the Vice President, Brand & Product Marketing and lead a team of content specialists. You will be responsible for both the strategy and the execution — setting the vision for how Calendly educates its customers across the full lifecycle, and building the systems, content, and team capabilities to deliver it at scale. You will serve as a key cross-functional partner to Product Marketing, Product, and Customer Success, ensuring that education content is a core part of every product launch and customer journey.

On a typical day, you will:

• Define and evolve Calendly’s Customer Education strategy, setting a clear vision for how educational content maps to customer segments, product surfaces, and lifecycle stages.
• Lead and develop your team of education specialists and multimedia content producers, setting clear goals and providing coaching.
• Partner closely with Product Marketing to ensure education content is embedded in every product launch.
• Partner with Customer Success and Support to identify where customers are getting stuck and build content that proactively answers their questions.
• Build and scale the Calendly Learning Hub as a best-in-class self-serve education destination.
• Raise the bar on multimedia content quality across the education function.
• Establish KPIs and a reporting cadence to measure the impact of education content.
• Build the operational systems and workflows that allow your team to produce high-quality content.

Qualifications

• 15+ years of progressive experience in customer education, content strategy, instructional design, or a related field.
• At least 3 years in a director-level or equivalent senior leadership role managing teams.
• Demonstrated track record of building and scaling a full-funnel customer education function in a B2B SaaS or technology environment.
• Experience developing education content strategy across multiple formats.
• Proven ability to partner cross-functionally with Product, Product Marketing, and Customer Success.
• Strong track record of leading and developing direct reports.
• Excellent editorial judgment across written and multimedia formats.
• Data-driven mindset with the ability to establish KPIs and measure the business impact of education content.
• Authorized to work lawfully in the United States of America.

Requirements

• Experience at a multi-product SaaS company managing education content across more than one product line or customer segment.
• Familiarity with Learning Management Systems (LMS) and knowledge base platforms.
• Background in instructional design or curriculum development.
• Experience building or overseeing a multimedia or video content production function.
• Experience working within a brand and marketing organization.
• Familiarity with Calendly’s product and the scheduling, calendar management, or meeting intelligence category.

Benefits

• Base salary is just one component of Calendly’s total rewards package.
• All full-time (30 hours/week) employees are also eligible for our Top Performer Bonus program, equity awards, and competitive benefits.