Director, Customer Education

About This Role

Calendly is seeking a Director, Customer Education to define and lead a full-funnel educational content strategy that spans product demos, feature education, the Calendly Learning Hub, and Help Center content. This is a high-impact leadership position for a strategic thinker who sees customer education as a lever for activation, adoption, and long-term retention. You will report to the Vice President, Brand & Product Marketing and lead a dedicated team of content specialists, owning both strategy and execution while building systems and capabilities to deliver education at scale.

Why Join Calendly?

Millions of people already rely on Calendly, and the company is in the midst of exciting product growth. This is an ideal time to join a fast-moving organization where your work will accelerate your career. You'll collaborate with talented professionals across Product, Sales, and Customer Success while maintaining a strong focus on quality and ambition. Calendly's Marketing team—encompassing brand, product marketing, and customer education—works in close partnership to shape how customers discover, understand, and derive value from the platform.

Key Responsibilities

• Define and Evolve Strategy: Establish Calendly's Customer Education strategy with a clear vision for how educational content—including 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: Build and mentor a team of education specialists and multimedia content producers. Set clear goals, provide coaching, and create an environment where team members can do their best work. Hold the team accountable to outcomes while advocating for necessary resources.
• Product Launch Partnership: Work closely with Product Marketing to embed education content in every product launch. Develop Help Center articles, demo videos, feature walkthroughs, and in-product guidance that enable customers to understand and rapidly adopt new capabilities.
• Cross-Functional Collaboration: Partner with Customer Success, Product, and Sales teams to ensure education content aligns with customer needs, pain points, and journey milestones. Serve as a key stakeholder in product decisions that impact how customers learn.
• Content Scalability: Build scalable systems, templates, and workflows that allow your team to produce high-quality educational content efficiently. Establish metrics and frameworks for measuring content effectiveness and customer outcomes.
• Learning Hub Ownership: Own the strategy and execution of Calendly's Learning Hub, ensuring courses are current, engaging, and aligned with product roadmaps and customer education goals.

What You Bring

You are an experienced leader with a proven track record in customer education, content strategy, or marketing leadership. You understand the full customer lifecycle and can translate product complexity into clear, engaging educational experiences. You excel at building and motivating teams, thinking strategically about impact, and executing flawlessly. You're comfortable with cross-functional collaboration, data-driven decision-making, and iterating based on customer feedback. Your passion for helping customers succeed is evident in everything you do.

Impact & Growth Opportunity

As education becomes central to Calendly's growth strategy, this role offers significant opportunity to shape how millions of customers engage with the platform. You'll work alongside top talent, contribute to strategic product decisions, and build a world-class education function from the ground up. Your leadership will directly influence customer activation, adoption rates, and long-term retention.

💰 Compensation not publicly listed. Market estimate for similar roles: from $200K, varying by experience and location.