Director, Customer Education

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

We are the team behind how millions of people discover, understand, and get value from Calendly. Our Marketing team spans brand, product marketing, and customer education — working in close partnership with Product, Sales, and Customer Success to shape the story we tell and ensure customers have what they need to succeed. We move fast, think ambitiously, and care deeply about the quality of what we put into the world. As Calendly expands its product portfolio, education has never been more central to how we grow.

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.

• Define and evolve Calendly’s Customer Education strategy, setting a clear vision for how educational content — video demos, self-serve tutorials, Help Center articles, Learning Hub courses, and live programming — maps to customer segments, product surfaces, and lifecycle stages from onboarding through deep feature adoption.
• Lead and develop your team of education specialists and multimedia content producers, setting clear goals, providing coaching, and building an environment where each person can do their best work. Hold the team accountable to outcomes while advocating for the resources needed to execute.
• Partner closely with Product Marketing to ensure education content is embedded in every product launch — developing Help Center articles, demo videos, feature walkthroughs, and in-product guidance that help customers understand and adopt new capabilities quickly.
• Partner with Customer Success and Support to identify where customers are getting stuck, surface education content gaps that are contributing to support volume or churn risk, and build content that proactively answers the questions customers have before they need to ask.
• Build and scale the Calendly Learning Hub as a best-in-class self-serve education destination — developing a curriculum strategy, overseeing course development, and creating a content roadmap that keeps pace with Calendly’s product evolution.
• Raise the bar on multimedia content quality across the education function, partnering with your multimedia producer and the broader creative team to develop demo videos, feature tutorials, and educational experiences that are compelling, on-brand, and built for how customers actually learn.
• Establish KPIs and a reporting cadence to measure the impact of education content — tracking metrics like feature activation rates, Help Center deflection, Learning Hub engagement, and time-to-value for new users. Use data and insights to continuously improve strategy and communicate program effectiveness to senior leadership.
• Build the operational systems and workflows that allow your team to produce high-quality content at the speed of Calendly’s product cadence, including processes for content planning, review, localization, and maintenance.

• 15+ years of progressive experience in customer education, content strategy, instructional design, or a related field, with 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 — not just managing an existing content operation.
• Experience developing education content strategy across multiple formats, including video and multimedia, written documentation, and structured learning programs.
• Proven ability to partner cross-functionally with Product, Product Marketing, and Customer Success to align education content with product launches and customer lifecycle milestones.
• Strong track record of leading and developing direct reports, with experience building high-performing, accountable teams.
• Excellent editorial judgment across written and multimedia formats, with a high bar for content quality, clarity, and brand consistency.
• Data-driven mindset with the ability to establish KPIs, measure the business impact of education content, and translate insights into strategic decisions.
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time.

• 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), knowledge base platforms (e.g., Zendesk Guide, Guru), and video production workflows for educational content.
• Background in instructional design or curriculum development, with experience creating structured learning experiences for adult learners.
• Experience building or overseeing a multimedia or video content production function, including partnering with producers and creative teams to develop high-quality educational video at scale.
• Experience working within a brand and marketing organization, with an understanding of how education content fits into a broader go-to-market and brand strategy.
• Familiarity with Calendly’s product and the scheduling, calendar management, or meeting intelligence category.

This role may require occasional travel for company events, team collaboration, or offsites.