Pignataro spent his early career as a bond trader before he founded ION Trading, a global provider of multi-asset class trading software, in 1999. He sold 30 percent of the company to TA Associates in 2004.
In 2016, he came under some scrutiny for his involvement in closing off land access to L'anse Guyac, a beach on Canouan island in St. Vincent and the Grenadines. Local residents claimed that the beach was public property, and that the road to the beach should be open. Pignataro was one of a number of developers on the island who had restricted access.
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