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

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

Author: SaaStr August 20, 2025 Duration: 31:48

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. 

The world's largest SaaS + AI gathering for executives. Just this May we hosted: 10,000 attendees with 68% VP-level and above, 36% CEOs and founders and a growing 25% were AI-first professionals. This is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. 

But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait.

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


Tune into The Official SaaStr Podcast: SaaS | Founders | Investors for direct conversations with the people building and funding the software-as-a-service industry. This isn't about abstract theory; it's the practical, often hard-won wisdom from prominent founders and seasoned investors who have navigated the path themselves. Each episode digs into the specific mechanics of scaling a SaaS business, focusing on the critical journey from zero to one hundred million dollars in annual recurring revenue. You'll hear founders break down what actually worked when it came to hiring key talent, entering new markets, and managing the immense pressure of hyper-growth. From the investor side, the discussions reveal how top venture capitalists evaluate potential, what metrics truly matter beyond the pitch deck, and their perspectives on sustainable company culture. Hosted by SaaStr, this podcast serves as an ongoing masterclass for operators and entrepreneurs who prefer learning through candid stories and detailed strategies rather than generic advice. The dialogue is always grounded in the fierce realities of the competitive tech landscape, making every interview a source of actionable insights you can apply to your own challenges.
Author: Language: English Episodes: 100

The Official SaaStr Podcast: SaaS | Founders | Investors
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