Tope Awotona: The Black Tech Founder Behind Calendly’s Scheduling evolution

Discover how Tope Awotona built Calendly, the billion-dollar scheduling tool, and transformed time management for businesses worldwide.

"If you're going to do something, you have to go all in. I spent just as much time looking to prove the idea as I did trying to disprove the idea”

Several people tell their inspiring journey in black tech but few stories are as inspiring as that of  Tope Awotona, the visionary founder of Calendly. From his humble beginnings in Lagos, Nigeria, he grew to lead a billion-dollar tech company in the United States. 

Tope's journey exemplifies perseverance, creativity, and ambition. Calendly has redefined scheduling meetings. Scheduling can sometimes be ignored to mean a small task, but when left unattended can turn into a real problem and even cause back and forth.

Calendly, being an automated platform streamlining scheduling is a powerhouse transforming how businesses and individuals manage their time.

The Man Behind the Mission: Tope Awotona's Early Life

Born and raised in Lagos, Nigeria, Tope Awotona  faced personal challenges and a tragedy when his father was killed during a robbery. That singular moment shaped his resilience and fueled his drive forever.

Despite his struggles, he excelled academically and developed passion for technology. To this end, he moved to the United States and studied computer science at the University of Georgia. But, Tope was not satisfied. He wanted to blend his passion for technology with entrepreneurship. He, therefore, changed from computer sciences to studying business and management information systems.

As early as the start of his career, Tope already saw himself working with big companies like IBM, Dell, and EMC. He knew working at such companies would gain him the necessary experience he needed in sales and software development but sadly, his passion for entrepreneurship would remain unfulfilled.. 

How Tope Awotona Built Calendly to Solve Scheduling Frustrations 

Calendly was born out of frustration - a suitable base for groundbreaking innovations. While working on a startup idea, Tope struggled to schedule client meetings. 

The back and forths were endless, calendars were conflicting, missed appointments. He was frustrated about this, especially because any one could easily point him out as being an inefficient businessman.

Tope didn't want that, so he invested his life savings, which was at the time reportedly $200,000, to find a solution to the problem he was facing. 

He went ahead to create a simple and easy-to-use scheduling tool. In 2013, he officially launched Calendly.

The major concept for Calendly was simple:

Users:

• Could sync their calendars with the platform,
• They could also set their availability and
• Create and share a personalized link for meetings

Recipients:

• Could select a time that worked for them and
• Automatically add the meeting to both parties' calendars.

With this, Tope successfully eliminated sharing emails, which could be exhausting, by turning scheduling into a streamlined, seamless, and automated process.

Scaling to Success: Calendly’s Rise to a $3 Billion Valuation

Success in any business doesn't come overnight and the story wasn't so different for Tope. He struggled to secure funding and get partnerships for his business especially because not so many investors and big companies saw the potential of a scheduling app or platform. 

Determined, Tope bootstrapped the company by focusing on brands without introductions. A brand that could and would stand individually on its own and still get the attention it deserves. A brand that would speak for itself.

Reflecting on the journey of building Calendly, Tope Awotona shared in an interview: "If you're going to do something, you have to go all in. I spent just as much time looking to prove the idea as I did trying to disprove the idea."

Unusually, Calendly grew steadily through word of mouth and customer satisfaction testimonials. Soon more professionals became convinced by how convenient it was after using it. Calendly's user base was pivoted exponentially. 

More and more companies began using Calendly to draft and coordinate internal meetings, schedule appointments, and manage remote jobs, partnerships, and collaborations. 

The platform's simple interface and navigation integrated well with apps like Zoom, Google, Calendar, and Microsoft Teams, making it indispensable and unignorable to any business, regardless of how big or small the company is. 

By 2021, Calendly had secured an Investment of $350 million from OpenView Venture Partners and Iconiq Capital, catapulting its value to $3 billion. This pushed Tope Awotona and set him in the spotlight as one of the most influential Black Tech founders to achieve business success and redefine black tech.

What Makes Calendly Stand Out Amongst Other Scheduling Software?

Calendly's core advantage is its ability to solve global problems through seamless, Inclusive and elegant solutions. Some features that make Calendly stand out as a scheduling tool: 

1. Automation at its Best: Through calendar synching and automated scheduling, Calendly reduces manual tasks, thereby saving users countless hours.
2. Seamless Integrations: it integrates seamlessly with other notable apps like Zoom, Slack, and Salesforce, fitting effortlessly into existing workflows.
3. User-Centric Design: The play form has an interface with easy to use interface making it accessible for both tech-savvy professionals and those less familiar with digital tools.
4. Scalability: Whether you're a solopreneur, small business, or large enterprise, Calendly offers flexible plans to suit your needs.
5. Global Reach: With remote work rising, Calendly's ability to coordinate meetings across time zones has become invaluable.

Tope Awotona’s Impact on the Society 

Beyond his successful business career, Tope is determined to give back to his society. As the founder of Calendly, he has ensured and supported the donation of over $100,000 to organizations such as Black Girls Code and My Brother's Keeper to reflect his dedication to supporting marginalized communities in tech. 

Aside from this, during the Russian invasion of Ukraine, Tope facilitated the safety of his Kyiv-based development team. He showed that he is an exemplary leader and is human-centered.

Awards and Recognition 

Tope has reinvented scheduling through Calendly, earning him a top position in the tech industry.

Through different awards, each highlights the excellence and innovations that make Calendly stand out.

• In 2023, Calendly received the G2's Best Software Awards, ranking #36 in the "Top Collaboration and Productivity Products" category.

Interestingly, this singular recognition set Calendly on the same scale as global software leaders like Zoom and Google Workspace. Aside from that, G2 acknowledged Calendly's excellence in:

✔️Interview Scheduling Software (#1)

✔️Online Appointment Scheduling (#2)

✔️Business Scheduling (#2)

• Webby Award for Apps & Software Work & Productivity, which Calendly was honored with in 2023. 
• In 2024, SoftwareReviews recognized Calendly as a Data Quadrant Gold Medalist and an Emotional Footprint Champion. 

Product Hunt honored calendly's through special awards like :

• December 2, 2022, Calendly Meeting Polls ranked #5 Product of the Day 
• September 9th 2020, Calendly Workflows ranked #4 Product of the Day
• On May 11, 2019, Calendly Mobile ranked #2 Product of the Day
• In January 10th, 2018, Calendly for Chrome ranked #4 Product of the Day

Lessons from Tope Awotona: What Black Tech Entrepreneurs Can Learn

Tope Awotona's journey offers powerful lessons for aspiring entrepreneurs:

• Solve Real Problems

Every genuine startup must always solve a problem. Tope didn't want to create a flashy and inefficient app. He created something of value. One that solved and still solves real problems for millions of people daily. Problems that they face daily in their workplaces. Entrepreneurs must strive and focus on creating solutions to real, tangible problems.

• Resilience is Key

For Tope, his path was not rosy. No one ever hardly finds it smooth. He faced personal struggles, funding rejections, and even risked losing his life savings by investing in his startup. Yet, his belief and focus on his vision kept him moving forward. Persistence and resilience in the face of adversity are traits every entrepreneur must build. 

• Bootstrap When Necessary

The common thing for most early startups is to chase funding. However, for Tope, it wasn't so. He took his time to build a powerful tool, a strong project. By bootstrapping, he had enough time to define and redefine his brand. It enabled him to grow Calendly without external pressures from partners and investors. He proved that the best investment an entrepreneur can make is in himself.

• Leverage Word-of-mouth 

A global platform like Calendly in her early days grew organically. Satisfied customers recommended and shared testimonials and the tool with those they worked with. This fulfilled one of Tope's core goals: Creating a platform that markets and announces itself.

• Diversity and Representation Matter

As one of the few Black tech founders to achieve this height and status, Tope's success reminds us about the importance of diversity in tech. His story inspires marginalized entrepreneurs to pursue their ambitions, regardless of the biased systemic barriers they may face.

More Than Just a Scheduling Tool

Tope Awotona's journey is more than a story of a successful black man in tech; it highlights resilience, creativity, determination, and strategic thinking. Even though Calendly started as a simple scheduling app with zero fundings, it has grown exponentially into a platform that helps businesses manage time, boost productivity, and support remote jobs and partnerships.

Tope's story reminds us that innovation is not necessarily reinventing; it's taking and improving what already exists. Innovation is fixing the inefficiencies that most people will not think about fixing.

For every entrepreneur, especially black entrepreneurs, Tope's journey proves that hope, passion, and persistence can pivot one's seemingly small dream to a global audience.

So the next time you schedule a meeting with Calendly, remember: behind that sleek interface lies the story of a man who dared to dream big and changed how the world manages time.