Generalists or Specialists for your Workplace
For new startups, it's often important to hire generalists, because the business can pivot easily, will doubtless change direction, and it's important to keep the OODA loop quick and tight.
However, as a company starts to fit into its shape, then specialists need to be added to the mix. Bring them in too soon, however, and you risk creating a rut in your business process that will cause resistance when you change direction again.
The Digital Workplace environment is still at its early stages, and while vendors may have specialists to hawk their wares, and their specific perspectives, most commercial companies are still trying to figure out what the shape of the digital workplace will be for their culture, and where it will be the most streamlined.
Bringing a company to new levels of cloud productivity is a generalist task for the time being, as what the practitioner may uncover within existing business processes may require a quick pivot and a change in more than one direction.
A great discussion about one aspect of this thought - the change in a company direction and the need to bring in specialists, can be found in Reid Hoffman's Masters of Scale podcast, episode 5. MP3 Audio for Episode 5: http://rss.art19.com/episodes/49165a83-d45d-4fc3-b97b-2f99ecbb1a47.mp3
If you aren't already listening to the Masters of Scale podcast, I recommend it. (https://mastersofscale.com)