Seems like an interesting idea... the question would be, what are the design forces that you're going for here? Will it be a smooth approach into the shop, or will you be having a lip at the door to keep water out? I ask, because any obstruction to the rolling of the tires will add additional resistance that the winch will have to overcome. Will you be dragging things off of a trailer that cannot easily be rolled off? If so, that's going to require more force.
Couch67 is correct about the height... the taller the post, the more force that is going to be transferred into the base. As an example, if the post was 1 foot tall off the floor, and you had a pulling force of 200 lbs, that's 200 ft lbs applied at the base. If the post is 2 ft, that's now 400 ft lbs. 3 ft, is 600 ft lbs. All of that torque would be applied at the base of the post where it penetrates the concrete, so you need to know the forces to design it correctly. The deeper the post, the more force than can be counteracted and spread across the post.
As WSSLX99 mentioned, unless you design the floor for that type of stress, it could cause your slab to crack. Isolation with the top slab to prevent cracks is a good idea in that regard, and if you are still in the planning stages then I'd be talking to an engineer about adding some additional concrete in that area to really beef it up.
All things considered, raw concrete is cheap compared to the labor for forming it up, screeding it, and finishing it. I haven't priced a yard of concrete in a while, but last time I checked it was less than $150/yard. A yard is basically a 3' x 3' x 3' cube. (27 cu ft) The deeper and wider you go, the more the Earth and the weight of the concrete will help in counteracting the force put on the post. So why not plan on just setting the post in place during the pour, with that section of the slab being deeper and longer in the direction of the pull? Use rebar reinforcement, and I'd even weld the rebar to the post in each direction to hold it in place during the pour, and spread out the forces across a greater area.
If you are going to be pouring a footing, then the slab, then you could account for an additional form for the footing for the post mounting. Pour the footing with the post and rebar solid, with no gaps. Then when you pour the slab, use a piece of PVC pipe around the receiver to give it some space around it relative to the slab. Then come back and fill that gap with something soft/pliable. (Foam, sand, caulk, etc...)
All of that being said, you mentioned removing the winch to use on your trailer... so would you want this receiver flush with the floor? My first thought was to have your typical receiver hitch style post in the ground that sticks up a few inches or so, making the inner post capable of sliding into the receiver in the floor when in use, and easily removed when not. A simple receiver hitch cover would keep it protected from debris when not in use. But that might be a trip hazard unless you cover it with a cone, or stick something in there to keep you aware of it.
But what if you wanted to use it for more than one purpose? Why not make a post and pad to mount a bench grinder on it? Drill two holes, then weld a nut on two sides of the receiver 90 degrees from each other, so that when you slide the post in you can use two bolts screwed into the nuts to cinch the post down so that it doesn't wobble on you. When you need to use the winch, simply loosen the bolts, slide the post and grinder out and set it aside. When you're done, put it back in place.
Just throwing ideas out there... I hope that they are useful. To me, a few hundred in extra concrete up front to make a solid base for the post is a good investment.
Mark