I'm, not really familiar with him or CNN.
I usually don't watch CNN except on weekends, in late afternoon when MSNBC is showing reruns. And I'd never been aware of Scott Jennings till this past weekend, though I think he's been with CNN for a while. Earlier in the week, I'd seen some articles by him that I didn't care for. On TV, he's very snarky. I didn't see his encounter with George Conway, but I can guess what ti was like.
He worked in Dubya's White House, and is from Kentucky.