The answer is absolutely yes.

You don't need to do any serious math to figure it out either, or the exact height of the Sears Tower. All you need to know is that the Sears Tower is a little over 100 stories high (I think it's something like 112, but I'm not even sure). You also need to know that the interview room you are in is about 1 story high. So all you need to do is fit just over 100 stacks of pennies in the room, an array of 10 by 15 stacks would do the trick easily.

Actually, I prefer the answer 'yes, in fact they could all fit on this desk' - considering that the desk can easily accomodate more than twice as many stacks, and it only loses a few feet of space to the ground.