McKittrick grew up in Bradenton, Florida and graduated from Bayshore High School in 1991. Following high school, he attended the State College of Florida, Manatee–Sarasota.
While working jobs in multiple restaurants in the 1990s, McKittrick conceived the original concept for Waiting... based on his experiences working at Bennigans in Bradenton, Fl. He credited the idea for the story to two fellow waiters , Ben Bakker and Jim Moses, who helped write the script.
In 2009, he worked on Universal and Jay Baruchel's project based on Baruchel's Johnny Klutz character. He co-wrote the 2018 comedy Tag for New Line Cinema.

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