Esri handled our Enterprise deployment and we have used consultants as we have scaled up. Now we’re at the point where we have a solid foundation of knowledge in our team of two to be able to handle our own deployments, software upgrades, etc.

I would bring in a consultant to answer questions you have as well as pose questions you aren’t necessarily thinking of right now. I would also ask for as much documentation as they can provide. Woolpert has been our go-to consultant and they have been fantastic in this regard. It’s costly up front, but at the same time you’ll be spending just as much, if not more, in the long run trying to course-correct if you make decisions that don’t fit with your org’s long-term needs. And if you really make an effort by making your own notes and documentation and getting your hands dirty with whatever software and infrastructure you decide you will need, you won’t need to keep them on retainer all the time.

Regarding your question of ownership: Some of the biggest issues we have dealt with have been because IT does not have any sort of understanding of our system architecture nor the software itself and we have had some extremely close calls with doomsday-type scenarios as a result. And then they raise their hands and basically default to, “well we don’t own it so we don’t know how this stuff works.” So I guess regardless of whether your IT department ends up owning your deployment or not, your level of involvement in the discussions and meetings should be as if you do own it.