Has this shift made the executive branch LESS democratic?To what extent has the rise in the influence of the members of the executive office...

I would argue that yes, it has made the Executive Branch
less democratic in that it has more power, less oversight, and is less transparent
(records and actions more hidden from public view) than in most previous
Administrations, and certainly less democratic than many of the Founding Fathers were
arguing for at the time.

I argue this because the Executive
Branch in recent times, even when issued a legal summons by Congress to testify, had
often ignored the orders, or deleted and destroyed files, and taken covert actions using
the military and the CIA with very little or no oversight or control by elected
representatives.  In the name of national security, the Executive Branch has been able
to operate, often times, out of the public view, and out of view of the court system. 
This is an expansion of their power and, I would argue, it has made us less
democratic.