SaaStr 816: PLG to Enterprise to SMB: Insights from Calendly's CEO
Join us as Jason Lemkin, CEO, and Founder of SaaStr, sits down with Tope Awotona, CEO, and founder of Calendly for an insightful AMA session. They discuss Calendly's journey, their success in the Product-Led Growth (PLG) domain, and how it balances self-serve with enterprise sales strategies. Tope shares candid lessons learned from growing Calendly, from managing customer acquisition costs to aligning product development with customer needs. The conversation also delves into how Calendly plans to integrate AI to enhance user productivity and manage meetings more efficiently. This episode is packed with valuable insights for founders, CEOs, and anyone interested in SaaS growth strategies.
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Hey everybody, SaaStr Annual will be back in May of 2026.
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Lock in your spot today. Use my code JASON100 for exclusive savings. Get your tickets at podcast.saastrannual.com or use code JASON100 at checkout.
SaaStr Annual 2026. We'll see you there
Calendly: Tope Awotona (2020)
After emigrating from Nigeria to the US to attend college, Tope Awotona worked as a door-to-door salesman and eventually set out to become a tech entrepreneur. He launched a series of e-commerce businesses that quickly fizzled when he realized he had no passion for them. But then he landed on an idea he was truly excited about: designing software that would minimize the hassle and headache of scheduling meetings. In 2013, he cashed in his 401k and went into debt to build Calendly, a scheduling service reportedly doing over $100 million in revenue.
This episode was produced by Rachel Faulkner-White, with music by Ramtin Arablouei
Edited by Neva Grant, with research help from Daryth Gayles.
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Think like an outsider, w/Shellye Archambeau, Ellevest’s Sallie Krawcheck, and Calendly’s Tope Awotona
How do you evolve your greatest obstacle into your greatest superpower? Shellye Archambeau, Ellevest’s Sallie Krawcheck, and Calendly’s Tope Awotona discuss the hidden advantages of strategizing like an entrepreneurial outsider. Recorded live at the Masters of Scale Summit in San Francisco, they sit down with host Bob Safian to share lessons about questioning the status quo, maintaining confidence in the face of criticism, and orchestrating a cultural turnaround. Whether you’re a budding entrepreneur or firmly established in the C-suite, the outsider’s mindset has the power to inject counterintuitive creativity and dynamism into your leadership.
Read a transcript of this episode: https://mastersofscale.com/
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SaaStr 494: Demystifying the Unicorn Buzz with the CEOs of Calendly, Algolia, and Contentful
Reaching unicorn status is goal #1 for many startups. In this podcast, Tope Awotona, CEO at Calendly, Bernadette Nixon, CEO at Algolia, Steve Sloan, CEO at Contentful and by Casey Renner, Partner at OpenView discuss how high-growth companies can strive for profitability while growing responsibly to reach unicorn status.
Blog post and video: https://www.saastr.com/demystifying-the-unicorn-buzz-with-the-ceos-of-calendly-algolia-and-contentful/
Sponsors:
https://shortcut.com/saastr
https://www.litmus.com/saastr
https://flatfile.com/saastr/
Calendly: Tope Awotona
After emigrating from Nigeria to the US to attend college, Tope Awotona worked as a door-to-door salesman and eventually set out to become a tech entrepreneur. He launched a series of e-commerce businesses that quickly fizzled when he realized he had no passion for them. But then he landed on an idea he was truly excited about: designing software that would minimize the hassle and headache of scheduling meetings. In 2013, he cashed in his 401k and went into debt to build Calendly, a scheduling service expected to make about $60 million this year.
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SaaS Product Validation: 3 Failed Startups to Calendly
Three failed startups. A dating site, projectors, and grills. Tope Awotona spent years chasing money instead of solving real problems. Then he wasted an entire day scheduling a meeting and found what was missing. That problem became Calendly - now serving 4 million users at $30M ARR. In this episode, Tope shares the SaaS product validation lesson that changed everything.
Tope's approach to SaaS product validation was unconventional: he did not interview a single potential customer. Instead, he studied existing scheduling tools with paying customers as proof of demand, used those products himself to find gaps, and read user forums to understand what people loved and hated - a form of idea validation through market observation.
Calendly launched free by accident (they ran out of money before building billing) and became freemium by design. The viral nature of scheduling meant every invite exposed new users to the product, turning product-market fit and SaaS product validation into organic growth that reached 4 million users without traditional marketing.
🔑 Key Lessons
🎯 SaaS product validation requires passion, not profit motives: Tope's first three startups failed because he was chasing money. Calendly worked because scheduling pain was his own frustration from seven years in sales.
💡 Validate by observing behavior, not conducting interviews: Tope did not talk to a single customer. He validated demand by seeing existing tools with paying customers - a practical approach to startup validation.
🛠️ Optimize for the recipient's experience in SaaS product validation: Calendly won by reducing friction for invitees rather than only serving account holders. Fewer clicks and automatic timezone detection made scheduling effortless.
🚀 Freemium plus virality equals organic growth: Calendly launched free by accident and reached 4M users through viral sharing. Every meeting invite exposed new users to the product.
💰 Go all-in when SaaS product validation confirms product-market fit: After three part-time failures, Tope emptied his bank account, flew to Ukraine to hire engineers, and committed full-time to Calendly.
Chapters
Introduction
What Calendly does and who uses it
Growing up in Nigeria and moving to the US
Three failed startups before Calendly
Why the projector and grill businesses failed
Taking a sabbatical from entrepreneurship
How the idea for Calendly came about
Spending months on SaaS product validation
Idea validation without customer interviews
Emptying his bank account to go all-in
Hiring engineers in Ukraine
Differentiating on invitee experience
How Calendly got its first 1,000 users
The accidental freemium model
When Calendly started charging (and the mistake)
Reaching $30M ARR and 4 million users
The emotional rollercoaster of scaling
Hiring too fast vs hiring too slow
Lightning round
Resources
Full show notes: https://saasclub.io/213
Join 5,000+ SaaS founders: https://saasclub.io/email
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