“From, I would say maybe from twenty-twenty to, twenty-twenty onwards, we made that asymmetric, so we allocated a lot more to that enterprise. Then we did PLG.”
quote is from the automated transcript, cleaned for reading:
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More from Tope Awotona
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Awotona: Calendly's top sales competition is its own free plan
“If you talk to a sales rep at Calendly, Their number one competition is not, you know, any of the competitors that they mentioned, it's the free.”
Tope AwotonaAug 25, 2025▶ 27:10From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
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Awotona: Calendly will stay single-product for a long time
“In our case, like, you know, we have a single product and we'll, we will for a very long time, and part of the reason that we've been able to do that and still grow and become a unicorn and still, like, grow at a pretty fast pace is really expanded the types o…”
Tope AwotonaNov 10, 2021▶ 14:10Demystifying the Unicorn Buzz with the CEOs of Calendly, Algolia, and Contentful
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Awotona: Calendly defines user activation as five completed bookings
“I start sending my links to people to schedule with me. And five people have scheduled with me is what we define as activated.”
Tope AwotonaAug 25, 2025▶ 5:16From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
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Awotona: Calendly's viral conversion rates declined at scale
“We've definitely seen the, yes, you see the, those conversion rates decline. But the good thing is like the top line, the denominator is getting bigger.”
Tope AwotonaAug 25, 2025▶ 5:39From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
Disclosure
Awotona: Expanding Calendly's enterprise sales team initially cannibalized its self-serve business
“We expanded that sales team greatly and sure enough, revenue grew. The number of accounts over a hundred K in revenue in revenue also grew, but what we found was the growth in our customer acquisition costs outpaced the incremental revenue growth. And so essen…”
Tope AwotonaAug 25, 2025▶ 8:27From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
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Awotona: Calendly spends almost zero dollars on marketing campaigns
“We spend almost zero dollars on, we have headcount in marketing, but we have almost zero dollars in marketing campaigns.”
Tope AwotonaAug 25, 2025▶ 26:22From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
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