How Tope Awotona built Calendly to Simplify Scheduling, One Meeting at a Time.
How a Nigerian immigrant Tope Awotona living in the United States created a $Billion Company.
Calendly: Simplifying Scheduling, One Meeting at a Time
Company Name: Calendly
Founded Date: January 2013
Founder: Tope Awotona
Headquarters: Atlanta, Georgia, USA
The Beginning: A Frustration Turned Opportunity
In 2013, Tope Awotona, a Nigerian immigrant living in the United States, was working as a successful sales executive. Like many in sales, Tope spent hours each week coordinating meetings with clients, often exchanging countless emails to find a time that worked for everyone.
Frustrated by this inefficient process, Tope began searching for a solution. He wanted a tool that could simplify scheduling—allowing people to book meetings without back-and-forth emails. When he couldn’t find one that met his needs, he decided to create it himself.
The Leap of Faith
Tope had dabbled in entrepreneurship before but hadn’t found lasting success. This time, he went all in. He emptied his life savings, around $200,000, to start Calendly, betting everything on his vision.
Unlike many tech founders, Tope wasn’t a programmer. To bring his idea to life, he hired a team of developers, working closely with them to design a simple, user-friendly platform. The goal was clear: Calendly should allow users to set their availability, share a link, and let others choose a time for meetings.
The Early Struggles
Calendly’s early days weren’t easy. Tope’s decision to self-fund the business meant he had to be resourceful, balancing costs while ensuring the product was built to the highest standard. He also faced skepticism—some people questioned whether a simple scheduling tool could become a profitable business.
Tope focused on building a product that delivered real value. His background in sales helped him understand what users wanted, and he made sure Calendly was easy to use, with a clean interface and seamless integrations with popular calendars like Google and Outlook.
The Breakthrough
Calendly launched in 2013, and the response was overwhelmingly positive. Professionals across industries—from salespeople to recruiters—embraced the tool as a way to save time and reduce scheduling headaches.
Key milestones included:
2014: Calendly reached $1 million in annual recurring revenue (ARR), a significant milestone for a self-funded startup.
2017: The company introduced premium features like team scheduling and advanced analytics, attracting business clients and driving revenue growth.
2020: The COVID-19 pandemic accelerated Calendly’s adoption, as remote work made efficient scheduling more important than ever.
Scaling the Business
Tope’s decision to bootstrap Calendly for its first eight years paid off. By focusing on profitability from the start, he retained full control of the company’s vision and avoided the pressures of venture capital.
In 2021, Calendly raised $350 million from investors, including OpenView Venture Partners, valuing the company at $3 billion. This funding allowed Calendly to expand its team, improve its product, and explore new features.
Today, Calendly is used by over 10 million people worldwide, including professionals at major companies like Lyft, LinkedIn, and Zendesk.
Lessons from Calendly’s Journey
Solve a Common Problem: Calendly addressed a universal pain point—scheduling meetings—and became indispensable for professionals.
Bet on Yourself: Tope Awotona risked everything to start Calendly, showing that belief in your vision can pay off.
Start Simple, Then Expand: By focusing on a single, well-executed feature (scheduling), Calendly built a loyal user base before adding advanced capabilities.
Bootstrapping Works: Tope’s decision to self-fund Calendly allowed him to grow sustainably and maintain control over the company’s direction.
What We Can Learn from Calendly
Turn Frustration into Innovation: Like Tope, many people face daily frustrations. These challenges can inspire solutions that become successful businesses.
You Don’t Need a Tech Background to Succeed: Tope wasn’t a programmer, but he hired the right team and focused on his vision.
Start Small, Think Global: Calendly began as a simple tool but is now a global brand, showing that Nigerian entrepreneurs can create solutions that resonate worldwide.
Tope Awotona’s journey from a frustrated salesperson to the founder of a billion-dollar company is a testament to resilience, vision, and the power of solving everyday problems.
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