SaaStr 816: PLG to Enterprise to SMB: Insights from Calendly's CEO

In this SaaStr podcast episode, Jason Lemkin interviews Tope Awotona, the CEO and Founder of Calendly, in a Q&A format. They discuss Calendly's product-led growth (PLG) strategy, the balance between self-serve and sales-led approaches, and the importance of not diminishing the value of the free plan. Awotona shares insights on how Calendly manages its sales team, avoids cannibalizing its PLG business, and adapts to competition from built-in calendar systems. They also explore the future of AI in scheduling and how Calendly plans to integrate AI to enhance productivity and customer acquisition. The conversation touches on pricing strategies, feature differentiation for sales motions, and the evolving needs of enterprise customers versus individual users.