Yes, this was fun to play with.
We can trust Jibo not to cheat more than the human, so Jibo could wait to reveal his "hand" until the human announces theirs. So the sequence would be: Jibo and human pick -> human reveals -> Jibo reveals -> Jibo announces results.
[Alternate: Jibo could cheat, very rarely, just to spice things up. To keep this within Jibo's personality guidelines, he could sheepishly admit to cheating, then strike that game from the record.]
I was a bit confused about how to start (I had to peek at the code.) I was also surprised when it ended and just stopped. It might be good to start automatically and announce that we'll play five times, then announce that we're finished at the end. It would be nice to see the score at the end, too.
For a little more complex action, Jibo could play best three out of five, or five out of seven, or whatever, offering to extend if you get to the end and Jibo would be the winner. This scoring is a little tricker, because you have to drop the draws out of the scoring.