Tope Awotona

11 statements across 4 episodes · 6 bullish · 1 bearish · 3 people on the record · first statement Nov 11, 2019 by David Cummings · said 14 times in 3 episodes since 2019 · across every show →

On the record as a speaker too: Tope Awotona's record, appearances and statements → this page counts the times other people say the name.

Mentions by year

brought up most by David Cummings (8), Jason Lemkin (5)

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every mention, scene by scene, with the transcript →

Everything said about Tope Awotona, oldest first

Nov 11, 2019 positive
Disclosure
Cummings: Invested $350K as sole pre-revenue investor in Calendly on the spot
“And right there on the spot, I wrote him a check for 350,000 dollars as the sole pre-revenue investor, and today Calendly is used by millions and millions of people around the world.”
David Cummings Nov 11, 2019 ▶ 5:19 7 Lessons Helping Start Pardot, SalesLoft, and Calendly
Nov 10, 2021 bullish
Disclosure
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 Awotona Nov 10, 2021 ▶ 14:10 Demystifying the Unicorn Buzz with the CEOs of Calendly, Algolia, and Contentful
Nov 10, 2021 positive
Disclosure
Awotona: Calendly CEO conducts at least one customer interaction every week
“So for me, in my case, for example, till today I still make sure that I have at least one customer interaction every single week.”
Tope Awotona Nov 10, 2021 ▶ 40:55 Demystifying the Unicorn Buzz with the CEOs of Calendly, Algolia, and Contentful
Nov 10, 2021
Insight
Awotona: Category creators can always borrow playbooks from indirect predecessors
“In almost every single thing you're looking to do, somebody has done it before. Maybe not directly in your category, maybe not directly in your space, but there's a very, very clear example that, ah, that you can follow. And so I would look for those parallels…”
Tope Awotona Nov 10, 2021 ▶ 20:27 Demystifying the Unicorn Buzz with the CEOs of Calendly, Algolia, and Contentful
Nov 10, 2021 positive
Assertion Not checkable as stated
Awotona: Calendly closes enterprise deals worth hundreds of thousands of dollars
“Our customers range from individuals all the way to through large enterprises that, you know, do business with us to the tunes of hundreds of hundreds of thousands of dollars.”
Tope Awotona Nov 10, 2021 ▶ 1:48 Demystifying the Unicorn Buzz with the CEOs of Calendly, Algolia, and Contentful
Aug 25, 2025
Disclosure
Awotona: About 90% of Calendly's revenue is self-serve
“It has evolved a lot during the course of our business, but today about 90% of our revenue is self-serve.”
Tope Awotona Aug 25, 2025 ▶ 6:10 From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
Aug 25, 2025 negative
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 Awotona Aug 25, 2025 ▶ 8:27 From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
Aug 25, 2025 bullish
Assertion Not checkable as stated
Awotona: A Few Hundred Million Unique People Have Used Calendly
“But a few hundred million unique people have used their product by now.”
Tope Awotona Aug 25, 2025 ▶ 4:20 From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
Aug 25, 2025
Insight
Awotona: External-Facing Roles Make Up About 25% of Business Headcount
“And globally, that looks like, you know, 25% of the, typically, you know, about 25% of the headcount in a business is doing those activities.”
Tope Awotona Aug 25, 2025 ▶ 3:28 From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
Aug 25, 2025 neutral
Disclosure
Awotona: Calendly routes leads between sales and self-serve by company size
“What we essentially use the size of the company to approximate like what we think the total opportunities is within that account. And that's really how we determine, maybe I'm sharing too much about how we route deals between self-serve and to into the sales t…”
Tope Awotona Aug 25, 2025 ▶ 14:55 From PLG to Enterprise to SMB: Insights from Calendly's CEO Tope Awotona
Aug 27, 2025 positive
Assertion Supported
Lemkin: Calendly is well over $200 million in revenue
“When you heard him say multi-product, they're well over two hundred million. I don't know where they are. I don't know if they're past 300, but they're well over two hundred million.”
Jason Lemkin Aug 27, 2025 ▶ 23:38 What Happens When AI Kills Your SaaS Growth? Live Q&A with SaaStr CEO and Founder Jason Lemkin
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