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Roland Gossage is the current CEO of GroupBy and has held various positions at different companies throughout their career. Roland started out as an Account Manager at Hummingbird Technologies in 1998 and then moved to Cognos in 2000 where they became a Sr. Account Manager. In 2006, Roland transferred to Endeca where they became the VP of North America - East. After Endeca was bought out by Oracle, Roland took some time off to pursue their own ventures. In 2012, they became the President of Xperscore (formerly Akatoo Inc.), and then in 2013 they rejoined GroupBy Inc. as the CEO.

Some direct reports include Jason Chidester - Senior Director of Client Services, Steve Cerovcec - President, and Arv Natarajan - Director of Product.