Study playbooks

Get 3 new founder stories/playbooks to you inbox every Sunday. The #1 founder newsletter.

Tope Awotona's Calendly: A $3 Billion success story

Share this story

Table of contents

  • Company - Calendly
  • Founder - Tobe Awotona
  • Headquarters - Atlanta, USA
  • Founded in 2013
  • 10 million users
  • Revenue: US$276M (2023)
  • Employees: 650 (2023)

Early Life: Foundations of Resilience and Ambition

Overcoming early adversity in Lagos, Nigeria

Tope Awotona's story begins in the bustling metropolis of Lagos, Nigeria. Here, he was exposed to the harsh realities of life early on, most notably through the traumatic loss of his father at age 12. This event profoundly shaped his perspective, instilling in him a relentless drive and a desire to honor his father's entrepreneurial spirit.

Embracing opportunities in the United States

At 15, Tope's journey led him to the United States, marking a significant shift in his life. He pursued his education with zeal, initially diving into computer science at the University of Georgia before switching to business and management information systems, laying a solid foundation for his future business endeavors.

Building blocks of a future CEO

Cutting teeth in sales

Tope's career trajectory took him into the world of enterprise software sales. His roles across various technology companies were not just jobs; they were integral in developing his sales acumen, understanding of the tech industry, and the crucial realization that successful businesses often sprout from addressing common problems.

The road to Calendly: Learning from failures

Early ventures: A path of discovery

Prior to Calendly, Tope embarked on several business ventures, each teaching vital lessons. From a dating website to e-commerce platforms, these early failures were instrumental in shaping his understanding of market needs, the importance of product passion, and the value of targeted solutions.

Calendly: Turning frustration into innovation

The eureka moment

The concept for Calendly originated from Tope's own frustration as a sales professional - the inefficient and time-consuming process of scheduling meetings. Recognizing this as a widespread issue, he saw an opportunity to streamline this universal challenge.

Risk and reward: Investing in the vision

Embodying true entrepreneurial spirit, Tope poured his life savings into Calendly. It was a bold, all-in move, reflecting his conviction in the idea. This risk was a pivotal moment, setting Calendly on its path to success.

Skyrocketing to success: Calendly's growth story

Confronting and overcoming funding challenges

In the early stages, securing venture capital for Calendly proved challenging, especially in a landscape rife with biases. Nevertheless, Tope's unwavering determination led to a pivotal $550K seed funding from Atlanta Ventures, a critical juncture in Calendly's journey.

Capturing the market: Rapid adoption and expansion

Calendly's user-friendly interface and practical functionality resonated quickly with its audience. Its growth was exponential, attracting millions of users and major corporate clients, effectively doubling its revenue year over year and leading to a staggering $3 billion valuation in 2021.

Visionary Leadership: Beyond mere scheduling

Reinventing the wheel in tech

Under Tope's guidance, Calendly has transcended its initial purpose, evolving into a vital tool in corporate communication and productivity. His strategic expansion of the platform's capabilities continues to position Calendly as a leader in the tech industry.

Envisioning the Future: Calendly's continued evolution

Scaling New Heights

Looking forward, Tope remains focused on enhancing and broadening Calendly's impact. His commitment to refining corporate communication and meeting efficiency underscores his broader vision of streamlined and productive business operations.

A legacy of inspiration and impact

Tope Awotona's story transcends the typical narrative of business success. It is a profound account of transformation from adversity to influence, from Lagos to leading a revolutionary tech platform. His journey is a testament to resilience, the power of a visionary idea, and the impact one individual can have on the global business landscape.

Share this story
Back to playbooks