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Founder's Therapy

Founder’s Therapy with Tope Awotona

Calendly CEO Tope Awotona shares how his journey in developing a successful tech company.


I grew up in an African country. Everybody there is black, but even there discrimination exists between people of different tribes. If you were poor you were discriminated against. If you were from the North you were discriminated against, or maybe because you were from the South…The lesson I learned from my mom is to never let someone else’s discrimination determine your success.

I skipped two grades as a kid and have always been an ambitious person, seriously ambitious in a sense. I was born in Lagos, Nigeria, came to the States in ’96 to attend high school for two years, then went to University of Georgia. Primary and secondary education is great in Nigeria, but University level education isn’t so good. In the 90s schools were on strike often–what should’ve been a four year degree took eight for many. I came from a family that could afford to send me to the States for school. My dad was a microbiologist, and my mom worked for the Central Bank, one of the largest employers in Lagos. It had its own massive clinic system of which my mom was chief pharmacist. Even so, they were both entrepreneurs and still managed to dabble in other business ventures.

Like my parents, I’ve always explored entrepreneurship while being comfortably employed. Up until I started Calendly I spent all of my professional career in sales. I worked at EMC (which was acquired by Dell in the largest tech acquisition of all time) as an Enterprise Software Sales Rep, selling Enterprise software systems to large companies like Coke and Aflac and Equifax and Blue Cross and Shield. I had about 20 or so similar billion dollar accounts.

In my sales role, I was a victim of the email song and dance every single day, where it took multiple email exchanges to schedule mutually accommodating meeting times. Few scheduling tools I researched were built for professional salespeople and the existing legacy tools looked like they were built in 1989: clunky, and difficult to use. I had a hard time getting people to adopt them because they were so terrible to use. The more I looked around, the more I saw an obvious gap in terms of usability for business professionals. Even before and after scheduling, there are CRMs or marketing allocation systems that need to be updated, and with the explosion of different applications and SAAS, people clamored for point tools that would integrate into the entire ecosystem of tasks they were using. That’s what we wanted to address.

Calendly allows users to create rules around their availability. You can set rules, and as requests for meetings arise, share the Calendly link to communicate available time slots. We make it super simple for people in customization roles: entrepreneurs, inside sales reps, recruiters, financial survey advisors, and sole premium freelancers. People who spend the majority of their work interacting with people outside of their organization.

I initially had the idea for Calendly in 2012, but took a cautionary approach, spending a lot of time researching the market. I went into customer discovery without attachment to a specific outcome and let the process guide me in determining if there was an opening in the market. I probably spent about two to six months on customer discovery, validation, and determining opportunity. I wasn’t naive about what I would need to take this idea and and turn it into a real product: develop a working product, acquire users, monetize those users, and employ a team of engineers, marketers, and customer success agents. Initially I hired a company based out of Europe called RailsWare to build the MVP, they’re known for excellent work and are very well respected in the community of Rails engineers. I kept them on board as I raised money for an in house CTO. In terms of the quality, it’s built on Rails, as well as Backbone, hosted on Amazon web services. I hired a Marketer, Engineers, Designers and Customer Success agents, with about half of the team focusing on the product and the other half on marketing and customer success.

I’d previously worked for IBM in Atlanta and did well there before leaving for a fast growing startup in Kansas City. It was my first experience with a startup and I learned a lot about what it takes to take a product from idea to market and create an ecosystem around it. People who start a company and grow them to hundred million dollar businesses are definitely smart and bold, but what they all have in common is that they take action. They’re special in many ways and ordinary in many other ways, and I believed I could do it too.

I didn’t initially seek to raise money. I’d done very well in sales and had enough to build the MVP product and brand. I was hoping I would never have to raise money, thinking it might be an opportunity to simply scale the business indefinitely. I ended up accepting funding after leaving my job at EMC, though I took over a month to sign the loan terms. Although the fundraising journey wasn’t difficult, I had to spend a couple hundred thousand dollars of my own money to bring it to a viable point with a developed product, users, verticals, and product adoption.

We’re always experimenting and have grown pretty fast. Just about every single month since we launched two years ago, we’ve grown double digits, anywhere from 15-20% a month compounded. By far the best user acquisition channel are users who experience the product. 70% of people who sign up do so because someone invited them to schedule a meeting. On top of that, we’re really responsive and helpful with customer service. Our customer happiness teams are super are part of user acquisition strategy in fact. If users need assistance we’re there to help whether they’re free or premium customers.

It was difficult and interesting to go back to people who signed up for a free product and change the pricing policy to monetize it. We read what felt like 100 emails calling us ‘bait and switchers’ and nasty names. But for every email we got to complain about it, there were 10 or 20 more who were happy to not only upgrade, but to pay for the product and ensure it would stay on the market. We lost a few but acquired many more and users took us more seriously once we had a premium product. We tested the pricing and found it was inelastic, at multiple price points the propensity to upgrade did not change. Charging users added a lot of clarity to the most important elements. It helped us grow by focusing not on incremental changes but on changes which dramatically increase product value and practical utility for our users.

I’m not a big activist, but what I can do I really want to do: make Calendly successful. If I make Calendly successful then my nephew and niece (my biggest motivations), have people in tech that look just like them. Bringing awareness to the underrepresentation of minorities in technology fields is an important way to attack it, but we also need existing minorities in the field to be successful. I want to let young black males and girls know that while it may take a while, being a minority doesn’t have to be an obstacle to getting into the tech industry.

You may not have the same access to capital that somebody of similar qualifications has, so you have to work harder to make sure your business model is solid and you can access resources to hire the right people. When you are forced to work harder, your chances of being successful dramatically increase. I’m an example of that. A lot of companies have raised a ton more money than we have and don’t have the same success to show for it. While you’re hoping and working towards things changing, use it as an asset for motivation. You’ll chart a different course, and become more prosperous in the process.