Simply put, BlackBerry missed the consumerization of IT trend and now IT heads are straying from their hardware and their services. In addition, the company didn't help itself out by rebranding itself as a company named after its smartphone.
This makes it even more difficult for enterprise companies to just think about BlackBerry as a software and service provider, said Stephen Beck, a partner at cg42, a management consulting firm specializing in technology and telecommunications.
"BlackBerry, in retrospect, made a very poor decision to rebrand the company around the device brand," Beck said. "Given their failure in the device market, changing their name is going to have to be something that is on the table at some point."
Climbing back from that move isn't going to be easy, Milanesi said.
"It's sort of like the last nail in the coffin, it's so identified with the devices now, that it's going to be really, really hard to change that," Milanesi said. "It's like they are reminding everybody everyday they are a hardware company when they don't want to be that anymore."
However, even though Blackberry's enterprise bets look somewhat bleak, it's really the only card the company has left to play, experts said, and Chen seems to realize that.
"What kind of reputation does BlackBerry have out in the market? We are viewed as secure, we are viewed as having very high-quality devices and we are being used by mostly enterprises and so when I look at the situation I think we are going to offer end-to-end security solution in communication productivity that is mobile based ... at least for next couple years," Chen said.
Blackberry lost the consumer market, so it is doing what it can with what it has left, it just should have done it a few years ago, McGrath said.
"The company is looking at the space where it is most credible and to do that it's going to have to become a more niche company. But they need to be looking at new fresh segments of the market and unfortunately, these new segments tend to be small when they start. They don't look too attractive to a company that was once so big and successful," McGrath said. "And to be honest, I'm not sure if they can pull that off. I'm not very optimistic."
—By CNBC's Cadie Thompson. Follow her on Twitter