CEO of  Calendly

Country: Nigeria

Sector: Technology

Tope Awotona is the founder and CEO of Calendly, a simple and beautiful scheduling tool that helps you schedule meetings without all the back and forth emails. After building 3 startups that failed, he finally built a $30 million successful business at the age of  40


Early Life and Education

Babatope Awotona was born in Lagos, Nigeria, in the year 1981 into a middle-class family. Both Parents were scientists, his dad was a microbiologist, and his mum was a pharmacist. His father was murdered in a carjacking. He has since recalled how a group of men followed his father home and demanded the keys to his car. They shot him at point-blank range after he threw the keys at them. Tope Awotona witnessed the entire thing. After his father’s death, his family moved to the US  when he was 15. And in 1996, he finished high school in the US. And then, I went to college at the University of Georgia. After finally leaving school, he studied management information systems at the University of Georgia.


His first job was actually in high school before college, and he worked at a fast food place for like two weeks, then went to CBS from there. But Tope’s first job in college was a job at a call center, and it was cold calling people requesting donations.

Tope said, “it is one of the most difficult things that you can do. After you get the initial shock of people saying no to you, you actually fall in love with you fall in love with being able to persuade people to give you their money”. This prompted him to work sales jobs in college.

He did the call center job, after which he started selling alarm systems door to door. He said while working those jobs, he found them interesting, and although he didn’t know it at the time, the experience completely changed his career.

He studied computer science at the University of Georgia, then switched to business and management information.  He said he loved coding, but it was too monotonous for him. He feels he is too extroverted to be a coder.

Instead, he sold software for tech companies, including Perceptive Software, Vertafore, and EMC (since acquired by Dell). He also founded a few businesses on the side: a dating website, a company that sold projectors, and another that sold garden tools. All three were flops.

At the age of 18, Awotona made her first journey into business. He invented a function for registers that allowed them to employ optical character recognition to determine which bills were being used and distributed after noting how the cash register he used at his part-time job in a drugstore didn’t add up properly. He approached NCR, the largest cash registry business at the time, to pitch his invention after patenting it. They were blown away. Awotona, on the other hand, froze. He refused NCR’s offer to buy his patent and abandoned his ambitions after being caught off guard by how swiftly things were moving. After years of tossing around various business concepts.

Calendly was unusual because his frustrations inspired it as a salesperson scheduling meeting, a chore that may take dozens of emails and days to complete. He explains, “The obvious assumption to me was that scheduling is broken.”

He then launched the company from Atlanta Tech Village, an entrepreneur co-working space. The 424-person company now works entirely remotely, a decision Awotona took last summer. Calendly was founded by him in Atlanta Tech Village, a coworking space for entrepreneurs, in 2013. He dipped into his 401(k) and maxed up his credit cards to pay for it. Calendly was founded by Awotona, who invested his whole life savings of $200,000 before quitting his job selling software for EMC.

“It could’ve gone horribly wrong,” he admits. “I hedged my bets with my past firms and gave myself a way out.” I flew into a battle zone with Calendly and threw everything I had into it. You have to go all-in if you’re going to do something.”
He hired the Ukrainian firm Railsware for programming assistance. Eight years ago, Awotona was in Kyiv as demonstrators fought government forces in the streets. Calendly has assisted its ten Ukraine-based contract developers in migrating to Railsware and has provided financial support to them and their families in the midst of the turmoil.

Awotona had a marketable product by late 2013 but no funds. With a half-million-dollar investment, seed investors led by Cummings came to the rescue.

Individual users can use Calendly for free, while businesses normally pay $25 per month. “Employees using the products sing praises to their superiors, and it surges up, and That’s how they have been able to break into companies through the Trojan horse.”
Customers in the enterprise may create bespoke landing pages, assign meetings to specific groups of employees, and integrate Calendly with other products like Salesforce, Stripe, Zoom, and Hubspot.
Calendly’s large customers, defined as those who pay more than $100,000 per year, have increased tenfold in the last year as the company has ramped up its internal sales team. Since joining Calendly in May, CarGurus, a publicly-traded vehicle-purchasing website, has arranged over 2,000 sales meetings with its dealers.

According to CarGurus senior digital strategist Michael Riley, who spearheaded the Calendly deployment, this has saved employees 500 hours.
Calendly was introduced to 100 people who work with independent eateries, largely mom-and-pop stores, by US Foods, a significant food supplier situated south of Chicago, in June.
Thanks to the agreement, US Foods created customized meeting templates in both English and Spanish and included new sales and other outcomes into its strategic planning.
According to David Eschler, vice president of restaurant operations at US Foods, “that visibility was a key selling point for entering an enterprise partnership with Calendly.” Calendly’s cost, according to Awotona, is more than offset by increased productivity for its business customers.

Calendly’s power dynamics can be complicated—who invites, who accepts—especially in professions where this kind of thing is critical, such as venture capital. This winter, Awotona, who claims that this hasn’t been an issue for the average recruiter or salesperson, watched in awe as his company became the target of a Twitter war.
On January 26, Slow Ventures VC Sam Lessin tweeted about his dislike for Calendly, calling it “the rawest/naked display of social capital dynamics in business.”
Dustin Moskovitz, the wealthy Facebook cofounder whose project management company, Asana, is a Calendly customer, retorted, “Who hurt you, Sam?” “Notice with immediate effect: Anyone who disregards my Calendly connections will be fired,” VC Marc Andreessen (net worth $1.7 billion) said in a since-deleted tweet.

Thousands of new users signed up as a result of the uproar. Now, Awotona, who made the 424-person firm totally remote last summer, is planning new capabilities to push Calendly even deeper into what has to happen before and after meetings (such as attaching candidates’ résumés to recruiters’ calendar invitations) (such as increased analytics).
He’s also thinking about expanding internationally, noting that the pain of scheduling is felt in all cultures and languages.

“We’re about making each meeting efficient and achieving its stated purpose,” adds Awotona, who admits to spending 25 hours in meetings per week on average. “We view meeting scheduling as an opportunity to set up for success—how the meeting is scheduled, simpler preparation, and follow-up.” That is our big picture.”



In 2007 he received the Top Performer Award during the Tivoli Top Gun Training from IBM. In that same year, he received the First Line Manager Award for Sales Excellence from IBM.

He is one of the speakers of AAE Speakers. AAE Speakers is a full-service speakers bureau and talent booking agency dedicated to meeting the needs of event professionals to book the best keynote speakers for their live and virtual events.

Awotona was listed as one of Atlanta’s 25 Most Influential People by Atlantan on 21 October 2020, and Atlanta Business Chronicle listed Awotona as one of their 40 Under Forty winners on 02 November 2020. Dream Financial Planning was also listed as one of the five Black corporate business leaders to watch in 2021 on 05 April 2021.



According to Forbes, Tope Awotona is worth 1.4 billion USD as of 2022.



(Forbes, Bellanaija, Saasclub)