The Upward Bound director is a director at Upward Bound.
After Bart destroyed Springfield Elementary School, Homer had to take him to Upward Bound. The director there was mistaken for a colonel by Homer, but he isn't. The director then told Bart to kiss his childhood goodbye. Homer left, but after feeling bad for Bart, he came back to take him to Las Vegas. The director told Homer that his credit card was rejected, so he threw another credit card at the director as he left with Bart.