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Tope Awotona: The Entrepreneur Who Turned Frustration Into A $3 Billion Scheduling Platform

Tope Awotona is not your typical tech founder. He was born in Lagos, Nigeria, and immigrated to the United States as a teenager. He did not study computer science or engineering, but business administration. He did not work for Google or Facebook, but for tech firms like EMC (now Dell EMC) as a salesperson. He did not raise millions of dollars from venture capitalists, but bootstrapped his company with his savings and a small-business loan.

But despite these unconventional credentials, Awotona has built one of the most successful and popular software products in the world: Calendly, a scheduling platform that simplifies the process of booking meetings and appointments. Calendly has over 30 million users worldwide, and is growing 100% year over year. In January 2021, Calendly raised $350 million from investors, valuing the company at $3 billion.

So how did Awotona turn his frustration with the hassle of scheduling into a multi-billion dollar business? Here is his story.

Tope Awotona | Calendly| The Business Aneceote

The Problem

Awotona's journey as an entrepreneur began with a problem he faced in his previous job as a salesperson. He had to schedule dozens of calls and demos with potential customers every week, but the process was tedious and time-consuming. He had to send multiple emails back and forth, check his calendar for availability, deal with time zones and conflicts, and confirm the meeting details. He estimated that he spent about 20% of his time on scheduling alone, which was a huge waste of productivity and opportunity.

He searched for a solution that could automate and streamline the scheduling process, but he was disappointed with the existing options. They were either too complex, too expensive, or too limited. He wanted a simple, elegant, and affordable tool that could integrate with his calendar, offer his availability to his prospects, and allow them to book a meeting with one click.

The Solution

Since he could not find a satisfactory solution, he decided to create one himself. He had some experience in starting businesses, but none of them were successful. He had sold projectors, garden tools, and even tried to launch a Groupon-like platform in Nigeria, but they all flopped. He realized that he needed to focus on solving a real pain point that he understood well, and that he had a unique insight into.

He quit his job and moved to Atlanta, where he joined the co-working incubator Atlanta Tech Village. He hired a Ukrainian firm, Railsware, to help him develop the software. He named it Calendly, a portmanteau of "calendar" and "easily". He launched the first version of the product in late 2013, as a freemium service for individual users.

The Growth

Calendly's growth was slow at first, but it soon picked up momentum. The product was simple, intuitive, and effective. It solved a common and universal problem that many people faced, not just salespeople, but also recruiters, consultants, teachers, doctors, and anyone who needed to schedule meetings. It integrated seamlessly with popular calendar services like Google and Outlook, and offered features like time zone detection, buffer times, round robin, and group scheduling. It also integrated with other tools like video conferencing and payment services.

Calendly's users loved the product and spread the word to their colleagues, friends, and contacts. The product had a viral effect, as every invitee who received a Calendly link could become a potential user. Calendly also benefited from positive reviews, media coverage, and word-of-mouth. By late 2014, Calendly added a premium version for individual users, and by 2016, it added a team version for organizations.

Calendly grew organically, without spending much on marketing or sales. It also grew profitably, without raising any external funding. Awotona bootstrapped the company for years, reinvesting the revenue into the product and the team. He was selective and careful about hiring, and maintained a lean and remote workforce. He also stayed focused on the core value proposition of the product, and resisted the temptation to add unnecessary features or expand into unrelated markets.

The Future

In January 2021, after seven years of bootstrapping, Awotona decided to take on a $350 million investment from OpenView Venture Partners and Iconiq, two prominent venture capital firms. The investment valued Calendly at $3 billion, making it one of the most valuable software companies in the world, and one of the few tech unicorns with a Black founder and CEO.

Awotona said that he took the investment to accelerate Calendly's growth, expand its global reach, and enhance its product offerings. He also said that he wanted to use the opportunity to inspire and support other aspiring entrepreneurs, especially those from underrepresented backgrounds. He said that he hoped to show them that they could achieve their dreams with hard work, perseverance, and passion.

Calendly's future looks bright, as the demand for its product continues to grow in the post-pandemic world, where remote work, online education, and digital communication are becoming the norm. Calendly's mission is to make scheduling easy and enjoyable for everyone, and to help people save time and focus on what matters most. As Awotona said,

"In my life, I've benefited from not taking the conventional wisdom. It's benefited me personally, and I think it has benefited the business."


(2) Calendly - Wikipedia.

(3) Tope Awotona - A Founder Story - Atlanta Tech Village.

(4) linkedin



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