Time is the ultimate flex, and wasting it is no longer an option. Endless back-and-forth emails, missed calls, and double-booked calendars were once unavoidable hassles.
Tope Awotona saw this chaos and refused to accept it. Instead, he turned frustration into innovation, building Calendly, the scheduling powerhouse trusted by over 20 million users worldwide. What began as one man’s pain point has become a global tool reshaping how workforces take control of their day.
Roots of Resilience
Awotona’s story begins in Lagos, Nigeria. Raised in a family of ambition, he faced tragedy early when his father was killed in a carjacking. At just 12 years old, he inherited more than grief; he inherited resolve. That moment set the stage for a future where discipline and focus became his armor.
At 15, his family relocated to Atlanta, Georgia, and by 2002, he graduated from the University of Georgia with a degree in Management Information Systems. While the classroom sharpened his skills, it was his drive that sharpened his vision.
From Sales Routes to Scheduling Roots
Before Calendly, Awotona walked the grind many men know well, long days in sales, chasing quotas at IBM, Dell EMC, and Perceptive Software. Along the way, he tried and failed with a dating site and an e-commerce projector store. Those failures weren’t setbacks; they were learning lessons that paved the road for what was to come.
Failure taught him that success only sticks when you solve a problem you truly understand.
Going All-In on a Solution
In 2013, Awotona hit his breaking point. He was tired of losing time to messy scheduling, and no tool on the market could fix it. So he made a decision that few would dare, he went all in. He poured his life savings and maxed out his credit cards to build Calendly. No investors. No safety net. Just vision, grit, and risk.
That same year, he joined Atlanta Tech Village, a hub for founders, and later secured $550,000 in seed funding. Calendly bootstrapped its way to profitability, becoming a rare tech unicorn born from hustle, not hype. By 2021, a $350 million investment valued the company at $3 billion.
Crafting the Tool
Calendly isn’t just software; it’s a power move. The platform integrates seamlessly with Google and Outlook, automates reminders, handles group scheduling, and scales for enterprise use. Its freemium model turned users into believers because when something saves time, people share it.
By 2023, Calendly employed more than 650 people and generated over $276 million in revenue. Awotona’s bet on himself paid off.
Recognition, Reputation & Responsibility
Awotona’s leadership earned him induction into the Georgia Technology Hall of Fame in 2025, celebrating his impact on the state’s tech landscape. Under his stewardship, Calendly employed over 650 people by 2023 and reached revenues of around $276 million, proving that purpose-driven scaling can sustain both growth and vision.
Tope Awotona is one of only a handful of Black tech founders to helm a business valued at $1 billion, showcasing the powerful intersection of tenacity, authenticity, and tech leadership.
