There are a number of ways to do this, but most involve multiple pieces of geometry and usually 3 toolpaths, which need to be coordinated in terms of ordering.
Wrote this up a while back:
which seems to work well, at least conceptually — so the basic form would be:
given an approximate design which one wishes to cut thus, select it:
No argument at all, I use a bowl bit from WP’s to finish the pocket and counter cut. Hog out the pocket leaving 0.075” from full cut depth and offset from design by 0.01”. Swap to the bowl bit and run pocket tool path at full depth and same offset , then (inside) contour tool path to full dimension and depth. So, 3 cuts with two bits. I got the set of three of these and they cut exceptionally well, the limit is the 0.5” D. WP also has smaller bits with cut radius on them as well that could be used in your scenario.