Alina and I started Chili Piper in 2016. We did not stumble upon a brilliant idea or fall in love with calendars.
Alina was building cool consumer apps at a Fortune 500 company, I was running Sales for a $2B telecom startup, but we both had the same complaint: the Enterprise Software apps we were required to use were dinosaurs, stuck in old ways of thinking.
We had a thesis: a tidal wave was about to happen, the Digitalization of Sales — what is called “Revenue Acceleration Software” today. We wanted to lead that movement.
But where could we get started?
As we were talking to potential customers about pain points, Stephanie Ouadah at Fivestars asked for help with her round robin distribution of meetings:
Alina rolled her eyes, “I didn’t leave a job designing systems for the school district of Los Angeles to spend my time on this little problem.” We almost declined.
Just like the dozens of investors who turned down Calendly in the early days, we initially underestimated the importance of MEETINGS in the revenue process.
Luckily, we agreed to help Stephanie, and the hundreds of revenue teams that followed, solve their ever growing challenges around meetings. The rest is history.