Seven years later, he was named senior vice president and managing director of Bloomingdales by mail. Senk took progressively challenging roles in retail, from the London retailer, Habitat, to Williams-Sonoma, where he set the strategy and groundwork for Pottery Barn's rapid expansion and sales growth.
As he was preparing to launch his own firm in 1993, he met the founder of Urban Outfitters. The chemistry was instant, and Senk agreed to table his own plans and instead lead the Anthropologie brand, turning the single-store prototype into a billion-dollar-plus retail operation with sales over $650 million by 2007. In May 2007, he was promoted to CEO of Urban Outfitters, Inc., which includes the brands Urban Outfitters, Anthropologie, and Free People. In 2008, the firm launched Leifsdottir and introduced Terrain. Despite the challenging economic environment, the firm saw total company sales for the first quarter of 2010 increase 25 percent over first quarter 2009.