My perception is over the years, it has seemed to be fairly small to maybe medium but every once in awhile they come off as having a large staff. How big is the SKP side in reality?
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Thats an interesting question. I don’t think it can be many people because the rate of development is so slow. Maybe it’s less than we imagine with most of Thimbles new talent being deployed on newer products. My guess would be 1 or 2 people on the desktop version who know the code inside out although obviously it could be quite a few more.
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There are 151 users registers in this forum as SketchUp Team member.
In Linkedin, the size of the company ranges from 51 to 200 people.
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spot on, one is named brian, the other mike, and they maintain the illusion by having several linkedin and forum accounts 
the bigger the company, the more people they have, the slower the development, because of layers of teams and hierarchy.
look at extensions, if the dev is alone, they can decide to fix / upgrade whatever they want on a given day and push it.
in a big company, there will be plannings, objectives, stuff will be pushed on a calendar so the right hand doesn’t push and break stuff the left hand was working on.
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I do not know off the top of my head how many employees work exclusively on SketchUp and I’m certainly not authorized to publish any company information (I am just a developer) but I think I am safe to say the following.
I sometimes see this idea that SketchUp development is slow because Trimble leadership has made a conscious decision not to invest in it. From my perspective that simply is not true. As @ateliernab says, the coordination of a large number of people is challenging, as is the nature of maintaining a large application with a long history, a broad user base, a powerful extension API, and multiple platforms.
Could we do better? Sure. Any software development team that thinks it cannot improve is in trouble. However, this conspiracy theory that Trimble does not care to invest in SketchUp for the long term is just silly.
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One of the adages in Fred Brooks classic “The Mythical Man-month” is (something like) “when a project is behind schedule, adding more developers will put it farther behind”. The message being that the amount of coordination and communication required is combinatoric.
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It seems like there have been some posts complaining about an annual update being late. I dont remember there ever being a promise of such updates. I can see where from a marketing point of view rolling out new features could be necessary to attract new users. We have seen energy put into cleaning up buggy features. This gets few cheers from the “gallery” and I prefer smooth operation to new stuff! The iPad development seems like a way to attract new users. However I cannot see a person generating construction documents with it but Architects arent the only market. That said we are using it in our day to day professional lives, so lets hope development continues and prices are able to be maintained.
I didn’t intend this thread to be an attack thread. I certainly don’t believe Trimble has ignored SKP as an overall product and certainly a lot of energy has been spent building out all IOS and apple side and cloud and web portions of the product. Personally, I wish more energy was spent on the desktop side which hasn’t had much love lately but I get the business case of the rest of it. I was simply curious if it was a stretched too thin kind of thing of just not a major priority or… in reality… just curios what the actual reality actually is. Personally, I would hope SKP would be successful far into the future and maybe that means it is that way on a larger or smaller scale but I’m just curious what that scale actually is.
It’s more than 1 or 2 people. 
Seriously, though, there is more love and much more blood, sweat, and tears than meet the eye.
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I’m guessing that many are in fact silhouettes that orient themselves according to the trajectory of the view
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in case there are only two of you, for safety reasons, you cannot eat the same thing!
Edit : it was humor…