Yeah, though he was in kind of a tough spot. When your team has Crosby and Malkin on it every year, you can conceivably think of every year as a "go for it" year. The window's always open, especially with a mostly strong supporting cast that he did have a hand in assembling.
But he didn't hedge enough, IMO. He completely sold out the future for chances at the cup, and the fact that his idea of "going for it" was trading for Brenden Morrow and Doug Murray is probably one of the biggest and most worrying knocks against him.
It's kind of interesting because the end of his tenure mirrors recent Devils' history in an uncanny way. It wasn't that Shero was terrible at drafting. But he did trade away lots of picks, and the picks he DID have were used on promising defensemen. But when lots of his D picks hit, and none of his forwards did, it left the franchise in a weird limbo where they were a contender, but had to make trades just to keep the forward depth in respectable condition.
So even though they have all of Maatta, Pouliot, Dumoulin, Harrington to look forward to, their depth at F is so bad that Shero had to leverage the future just to keep an average bottom-6 together.