The Start

Tope Awotona, the founder of Calendly, was born in Lagos, Nigeria, and later moved to the United States. His background includes a blend of software sales and entrepreneurship.

Before founding Calendly, Tope worked for several tech companies, including IBM, Perceptive Software, and Dell EMC, gaining valuable experience in sales and understanding the pain points in business operations.

His journey in entrepreneurship began with various ventures that didn't take off, which only fueled his determination to find a successful niche.

Tope's frustration with the back-and-forth emails needed to schedule meetings led him to identify a gap in the market for a more efficient scheduling tool.

The Problem

Tope Awotona realized that scheduling meetings was a universally tedious task, often involving multiple emails and calendar checks to find a suitable time.

This inefficiency was not only time-consuming but also disruptive to productivity.

Seeing the potential to streamline this process, Tope envisioned a tool that would automate scheduling, eliminate the hassle of coordinating availability, and integrate seamlessly with existing calendar systems.

This problem, common to both individuals and businesses, provided the impetus for the creation of Calendly in 2013.

Tope's goal was to develop a solution that would simplify meeting scheduling and improve productivity, ultimately making Calendly a valuable asset for professionals worldwide.

Getting his first customers:

The first 10 users of Calendly were customer success agents at Bright Bytes, a data and analytics company in the education space.

Bright Bytes had contracted the same development shop as Calendly, and during a check-up meeting, the exec team at Bright Bytes learned about Calendly. They realized it solved a similar problem they faced.

Bright Bytes' customer success team began using Calendly to schedule calls with K-12 parents.

Some parents, who were clients of Bright Bytes, started using Calendly for parent-teacher conferences. Schools took notice and began officially running all their parent-teacher conferences on Calendly.

This led to other schools feeling FOMO and signing up to see what the hype was about.

Within less than a year, tens of schools and thousands of parents in the Atlanta area were using Calendly for their external meetings.

Tope, the founder, engaged with customers who requested features to understand their usage and needs. He targeted super users and used traditional sales tactics to expand within their domains.

This strategy resulted in gaining 10,000 users and raising $550k shortly after.

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