They got Kent to go outside. The photographer realised the eye of the viewer needs distracting. The eye of the viewer needs to find something - ANYTHING - to focus on other than Kent's is it/isn't it hairline.
The grey stones of the wall may have helped Kent's hair flap blend in, but, sadly, the ivy only serves to emphasise the peculiarly arranged top third of Kent's skull by mirroring his arrangement. You can't blame the photographer for not taking the ivy into account. There's only so much they can do to make businessmen look like normal people.
The problem for Kent is he's too old and podgy to "just shave it off". A man with a head that size can't go for the full shave. There's no way the human brain would assume Kent had shaved all his hair off because it interferes with his extreme sports lifestyle.