The image shows while editing an area of expertise, but once I am back at my expertise page, it only shows the grey template photo image.
I've had similar issues.
I think there's a bug with the Clarity system and saving cover images.
The way I got around it was:
1. Log out, clear cookies.
2. Log in, upload image, hit save.
3. After saving, notice if the browser is still connecting (see the bottom left of your browser). It probably is.
4. Just leave it for 5 minutes.
5. Log out, clear cookies.
6. Log back in and check again.
May take a couple of tries, but I managed to get all my cover images up over a couple of days.
Worst case I know Clarity support is more than happy to change them for you - just email them and attach the images and tell them where to put them!