Jason Richelson and his partner, Amy Bennett, lost thousands of dollars in sales after the server-based cash-register system crashed at Green Grape, their Fort Greene, Brooklyn-based business, in 2008. That disaster at the wine shop and gourmet food stores soon inspired Mr. Richelson to launch ShopKeep, a cloud-based point-of-sale system for high-volume retailers.
Fast-forward to today. The 180-employee firm has raised $37.2 million in venture capital from investors including Tom Glocer, a former CEO of Thomson Reuters. To max out the company’s valuation, it brought in Norm Merritt, former chief executive of iQor, a $550 million business-process outsourcing firm, as CEO and president eight months ago.