At some point, we’ve all been sucked into what feels like an endless loop of phone tag, texts and back and forth emails just trying to meet up with someone.
Between unpredictable schedules, priority shifts and notification fatigue, simply booking a meeting can turn into a time and energy vortex.
Over a decade ago, an ambitious businessman named Tope Awotona saw a gaping hole in workflow efficiency due to this clunky communication flaw.
As a software salesman, he recognized it as a serious problem and he was summoned by an inner call to action to fix it.
He wanted to streamline communication system not only for his own purposes, but also for business professionals across the board.
This frustration is what inspired Tope to create Calendly — an online tool that schedules, prepares and delivers follow-ups for external meetings.
Calendly transformed Tope’s life from chasing dreams of grandeur to finding success and personal fulfilment. Presently, Calendly has over 20 million users.
Resilience through turbulence
Tope’s story began in Lagos, Nigeria, a sprawling city known for its beach resorts, energetic nightlife, and art scene.
His mother came from a wealthy family and was the Chief Pharmacist for the Central Bank of Nigeria, whereas his Dad, came from an impoverished background.
His father worked extremely hard to become a microbiologist. He secured a position with Unilever and experimented with start-ups on the side, indulging in his own entrepreneurial spirit.
The imbalance of wealth in Nigeria was exemplified by Tope’s parent’s experiences. Within Tope, it instilled a strong desire to achieve personal financial security in his own life.
In tandem with that, his parents imprinted the importance of gratitude onto their four sons, a message that stayed with Tope life-long.
A tragic turning point
Tragically, when Tope was 12, he witnessed the murder of his father during a carjacking in Lagos. The trauma from the incident triggered 6 months of insomnia that, to this day, Tope battles with.
In many interviews, Tope has expressed that he has always wanted to redeem his father’s tumultuous path to becoming a successful business owner.
To build upon his father’s legacy, education was key. Tope was a part of a program for gifted children and graduated high school two years in advance.
At only 15 years old, he was granted a scholarship to a College in the US.
Moving to America
While Tope was clearly ahead of the game, his mother decided against him to jumping straight into college in a foreign country.
Instead, she gathered up their family and they moved to Marietta, Georgia in 1996, where Tope attended an American High School for two years.
Tope was not required by the education system to re-do these high school years. However it was invaluable in helping him familiarize with American culture.
Indecision & vision
From there, Tope studied Computer Science at The University of Georgia. He struggled with the anti-social, monotony of coding and soon transferred into business and management information.
Upon graduating from University, Tope didn’t waste any time launching into the tech industry. He started out selling software for large companies, like IMB and Vertafore.
Very quickly, he realized that it would take too long for his liking to climb the corporate ladder and wanted to accelerate sooner.
And this did not come from a place of self-doubt, but rather his observations of the workplace trajectory.
Start-up life
Ever an opportunity-seeker, Tope discovered a start up called Perceptive Software.
They are an enterprise content management company based out of Kansas City that specializes in the effective capture and transfer of information.
He joined their team as an account executive, selling services to over 50 colleges and universities across the US.
Tope credits his time at Perceptive Software to building the framework for his personal business goals.
He explained: “It was the best thing that ever happened to me! I had to learn how to make customers happy, sell the product, and work with legal, all while maintaining a $2M quota.”
Perceptive Software’s adaptability and vibrant culture showed Tope the raw, real and unpredictable nature of being an entrepreneur. He thrived on it!
Finding the broken link
As a motivated and goal-oriented person, Tope was frustrated with the game of tag that ensued when trying to schedule meetings.
When researching existing scheduling tools, he was disappointed with how clunky and cumbersome they were.
He just could not find something that met his expectations.
Scheduling was, in his words, broken, and needed to be fixed. On a gut-level, he knew he was the person to do it.
Between his failed attempts at launching a dating site and trying to sell projectors, then later gardening tools, he realized that he was trying to chase money. And not meaningful change.
But this was it. This was the missing link, quite literally.
Tope invested every last cent of what he owned into building Calendly. His entire life savings.
He told Forbes that he raided his 401(k) and maxed out his credit cards, knowing that things could be disastrous his plan didn’t work out.
Risk & Reward
For programming support, he contracted with a Ukrainian firm called Railsware. This business relationship took Tope to Kyiv ten years ago, where he witnessed the early protests of the Russo-Ukrainian War, which left a powerful impact on him.
By late 2013, Tope had bootstrapped Calendly as fiercely as possible. Around this time, his mother was sadly diagnosed with cancer, causing him to move to Atlanta to be closer to her.
Atlanta then became the launch pad for Calendly’s ascension.
Soon after publicly releasing the platform, Tope became a member of the Atlanta Tech Village, which is a start up hub and co-working space for entrepreneurs.
His gratitude to be a part of such a forward-thinking community was widely felt, fostering powerful connections and a gravitational pull towards his energy.
Tope’s fellow members used Calendly and posted about it on their social channels. This attracted the attention of the founder of Atlanta Tech Village, David Cummings.
Seeing great potential, Cummings invested half a million dollars into Calendly, pushing the company to a bigger and better stage.
A solid business strategy
Calendly caught on and became increasingly popular. It stands out for it’s simple, intuitive design and accessibility.
They offer an ‘Always Free’ account that allows integration with one calendar platform, like Google Calendar, the customization of your booking page, website embedding, automated meeting notifications and unlimited bookings.
Paid accounts that offer greater features are priced affordably between $10 to $16 per month.
Calendly’s Standard and Teams memberships allow enhanced customization, more meeting types and integrations with financial services technology, like PayPal and Stripe.
Users with Enterprise memberships are granted high levels of security, extensive integrations, administrative control and immediate support services.
The power Calendly has to streamline communication has proven to nurture the growth and workflow efficiency of participating businesses.
CarGurus is a publicly traded car shopping site that sings the praises of Calendly. Their senior digital strategist, Michael Riley, claims that they scheduled approximately 2,000 sales meetings with dealers through Calendly in less than one year of signing up.
This saved 500 hours of employees’ time, enabling them to focus on other valuable tasks.
People matter
Tope built Calendly with the goal of improving professional communication through keeping people connected in a purposeful, organized and intentional format.
He has been able to truly help other companies actualize their potential further by preventing unnecessary delays and encouraging accountability.
His human-centered approach is also reflected in the relationships he has garnered over the years.
In light of the intensification of the Russo-Ukranian war, Calendly has relocated 10 of their Ukraine-based contractors at Railsware — while also providing them and their families with financial support (Forbes).
Evolving, adapting & elevating
As the tech world continues to advance and Calendly’s influence spreads world-wide, Tope remains humble while being excited about the direction his company is heading.
He plans to enhance Calendly with features that help members accomplish even more before and after their meetings.
For example, enabling resumes to be attached to a recruiter calendar invitations and provide them with key analytics upon the end of an interview with a candidate.
At Eau Claire Partners, we recognize Tope’s commitment and actualization of Calendly as a portrait of his drive to serve others. And to do so exceptionally.
His competency in computer science, combined with his social flair, fueled the confident risk he took in investing everything he had.
On top of that, the elegant design of the platform allows ease of use to members of varying technical knowledge and skill.
Life-long learning & legacy
While neither of Tope’s parents lived to see the impact he has created, he has extended and embellished their legacies, showing the world the strength of both his Mother’s resilience and his Father’s entrepreneurial drive .
Now every time you open Calendly, or go to book a meeting, you can think of the insightful young boy who took a painfully tragic moment, and translated it into an unstoppable source of light, creativity and purpose that he will carry life-long.
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