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Tope Awotona

CEO and founder of Calendly, a popular scheduling platform. He has experience in product-led growth and balancing self-serve with enterprise sales strategies.

Top 3 podcasts with Tope Awotona

Ranked by the Snipd community
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38 snips
Aug 20, 2025 • 32min

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

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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21 snips
Jan 8, 2024 • 1h 10min

Calendly: Tope Awotona (2020)

Tope Awotona, Founder and CEO of Calendly, shares his inspiring journey from Nigeria to tech entrepreneurship. He recounts his many failed ventures before landing on the idea of simplifying scheduling through software. The discussion delves into personal tragedies and the resilience required to overcome them, alongside navigating the challenges of securing a technical co-founder. Tope reflects on the delicate balance of luck and hard work in business, ultimately showcasing Calendly's remarkable growth and the emotional facets of his entrepreneurial spirit.
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4 snips
Sep 14, 2020 • 1h 12min

Calendly: Tope Awotona

Tope Awotona, founder of Calendly, shares his inspiring journey from Nigeria to entrepreneurial success in the tech world. After early setbacks with e-commerce ventures, he found his passion in creating a scheduling tool that caters to the needs of busy professionals. He discusses the financial risks he took, including cashing in his 401k, and the challenges of developing a user-friendly product. Tope reflects on resilience through personal loss and how the pandemic accelerated Calendly's growth, marking it as a pivotal moment for the company.

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