After selling Amuso to the BBC, he moved on to Outside.In, a local news aggregator, where he served as chief operating officer. Outside.In was sold to AOL (AOL - Get Report) in March, where it was folded into Patch, a group of hyperlocal news sites.
Bitten by the start-up bug, Deeming was encouraged to join Gilt in 2009 by then COO Jennifer Carr-Smith, a business school mentor.
"I was drawn to Gilt because I liked the model and had worked in e-commerce before," he said. "It looked like a company that was going to be on a path of growth."
Deeming thought right.Co-founded in 2007 by former DoubleClick exec Kevin Ryan, the company in May raised a whopping $138 million from investors including Japan's SoftBank and Goldman Sachs (GS) at a $1 billion valuation -- more than double the company's value a year prior. The company also posted $423 million in revenue last year, up from $170 million in 2009. Much of Gilt's growth comes not only from its core discount business, but new full-priced verticals such as its luxury travel site Jetsetter, its gourmet food site Gilt Taste and its men's fashion site Park & Bond, which combined are expected to generate $100 million within the next fiscal year. 100 Ideas a Week
Deeming first served as the so-called chief-of-staff to then CEO Susan Lyne where he helped improve communication and efficiencies within the company while coming up with ideas for new businesses. "At the time, Gilt was a lot smaller and a new project was a big deal because we didn't have so many verticals," he said. "Now we plow through 100 ideas a week." In mid-2010, Deeming began working for Ryan, who replaced Lyne as CEO. "At any one time I'm trying to manage a list of 10 to 15 businesses we're thinking about going into and then I'll put together two or three that might be the most interesting," he said. "I'll take that to the board, review them and then we'll decide what to move forward with so we can put together a team." One of the first new verticals Deeming was tasked with building out was Gilt City, the company's answer to Groupon, catering to a high end, urban audience. With Deeming's help, Gilt City has expanded into 10 metropolitan areas including New York, Atlanta, San Francisco and Los Angeles. And just a little more than a year after launching, the business will account for around 10% of Gilt's overall revenue next fiscal year.