Road Map

The only real indication I'd look into for a Road Map would be under the Feature Requests tab here on JAMF Nation. Since you can see clearly what is planning to be added into the software but with the range you're looking at, it's hard to know where Casper will be in 5 years time, let alone iOS and OS X.

When you say road map are you talking about the product itself or about how you plan to use it in your environment to manage devices? If it's the latter then I would start by thinking of certain things that you would like to accomplish (or in reverse, look at all the problems in your environment that you wish you could change). It would essentially be a little bit of project planning.

I'll be the bad guy..

Getting a road map from a Jamf with it's sole purpose is to support Apple products and Apple it's self doesn't provided a road map is crazy...

And you providing a road map on how you are going to use Casper is just as nuts..as there is no visibility to what Apple is going to do..

Let not even talk about 3 to 5 years, let talk about tomorrow ... what happens if Apple locks down Mac OS X this June at WWDC? There is no amount of road map/planning that Jamf/you/Apple could do that is going to help anybody solve all the issues that this would cause..

C

PS You are going to wrong no matter what you do, just make stuff up... or try and teach your manager that he can't move it his speed or at a road map speed ... we all have to move at Apple speed, there is no other choice!

What dpertschi said, plus perhaps removing admin rights from users.

Stay on top of the release notes so you understand and are aware of new features as they are added. Both major and point releases can have a lot of little and big changes.

There are some good outlines presented above by others, regarding how you can make good use of Casper over the next few to 5 years. So I won't repeat anything already said.
Hopefully this is what you meant when you mentioned a roadmap. If you meant what JAMF/Casper Suite will look like in the next 5 years, that's pretty difficult to say. Honestly, I'm not sure JAMF has a clear picture where it will be since much of what they can do in their software is dependent on what Apple's adds to their respective OSes.
I think what we can say is that things like:

• A full patch management framework will definitely be in the product by then
• 'Sites' functionality will be greatly improved
• Integration into 3rd party 2FA authentication will probably be there
• I'm also guessing some more robust reporting will be there (I can only hope!)

Other than that, not really sure. The suggestion to peruse the Feature Request section for clues is a good one, so I'd head there and take a look at ones in the Planned stage, as well as the really popular ones in the Under Review stage for some ideas.

Wow thanks for all the suggestions. I didn't even know you could look at Feature Requests. That is a great place to start for sure. Luckily, he is a Apple user at home so he knows how much we're at the mercy of them. @gachowski so your not the bad guy.

@dpertschi This is exactly what he is looking for. How we plan to utilize the software he invested in to help the business in the next 3-5 years. Thanks for the ideas everyone.

For the sake of it, you can also review the 2014 and 2015 JNUC keynotes with him, they are available online.