While presenting at her last conference on behalf of Bazaarvoice, an investor approached her, asking if she would be interested in a position on a four-person team to build out the idea of City Deal. She put her master’s on hold, and within a week, she met the others on the team. In 18-months, Groupon started the process to acquire the company. She then became CEO of Russia Groupon.
“I arrived there at twenty-seven,” Skaya explains. “There was a 200 person team, and the mandate was to get to 600 by the end of the year. We were halfway through the year. I’m the CEO, and I’m totally freaked out. I go from running a part of City Deal in the U.K. to running the whole thing in Russia. ... My experience with that company really toughened me up. I got there and lots of big burly men were raising their eyebrows. I had a lot to prove. I exited when the company went public.
Skaya then went on to launch two more companies, VisualDNA and breakupbuddy. “My claim to fame is that I can sell things online,” she smiles. “I can get people to look at ads. ... By the time I was done with breakupbuddy, I was done with advertising. I was tired of chasing you around the web trying to sell you things. You could say that I had a little bit of an identity crisis of whether or not it was all worth it. I wanted to do something that was meaningful.
She was accepted into Silicon Valley’s Singularity University, now Singularity Group. At that time, the program was backed by Google and based at NASA’s Research facility in Mountain View. It focused on the challenges and opportunities presented by exponential technologies like robotics, artificial intelligence and genetic sequencing. During the year-long program, she built out
Without having any revenue, Skaya was able to raise $300,000 in pre-seed funding. She’s been on Shark Tank and has even faced investors telling her they didn’t want to invest because they were dog people. She and her team are now about to close out a Series A round in the upcoming months. “Had this been a dog company, anything dog, I think it would have been much easier,” she comments.