After graduating from Stanford, Grenadier moved to Boston to play with vibraphonist Gary Burton. In 1991, he moved to New York. He continued to collaborate with some of the musicians he had met during his time in Boston, such as Kurt Rosenwinkel, Joshua Redman, Mark Turner, Jorge Rossy, and Chris Cheek. Others he met for the first time in New York include Bill Stewart, Kevin Hays, Renee Rosnes, Ralph Moore, Billy Drummond, Danilo Perez, David Sánchez, Tom Harrell and Billy Hart. Grenadier continued his association with Joe Henderson, touring with his band which at times included Al Foster, Renee Rosnes and Larry Willis. He also spent a few months during his earlier years in New York playing in Betty Carter's band.