The Official SaaStr Podcast: SaaS | Founders | Investors SaaStr 816: PLG to Enterprise to SMB: Insights from Calendly's CEO
38 snips
Aug 20, 2025 
Tope Awotona, CEO and founder of Calendly, shares his journey in the product-led growth space. He discusses the balance between self-serve and enterprise sales strategies while navigating user engagement and customer acquisition costs. Tope highlights how Calendly is perceived in IT departments, managing the stigma of being a 'rogue app'. The conversation also touches on how AI innovations are set to enhance productivity in scheduling, promising exciting developments for future users. It's a treasure trove of insights for anyone in the SaaS landscape!
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Measure True Activation, Not Just Signups
- Calendly measures virality by tracking meetings→signups and signups→activation to capture meaningful growth signals.
- They define activation as five scheduled meetings to mark repeatable habit formation.
Small Footprint Grew Into A Million-Dollar Deal
- A large financial services customer began with a small footprint and expanded to a seven-figure account after a consultative sales process.
- The expansion took several months and required IT and contracting involvement.
Test Sales Expansion Before You Scale It
- Test and analyze hybrid PLG-to-sales motions with holdout groups before scaling a sales org.
- Use rigorous experiments to avoid cannibalizing cheaper self-serve growth with expensive sales efforts.