If you want to get a handle on Heidegger, I recommend working through Being and Time while listening to Prof Hubert Dreyfus's UC Berkeley lecture series, 'Philosophy 185 - Heidegger'. I heard them on ITunes U long ago, but they are also available on archive.org [0].

Dreyfus wrote a critique of AI, "What Computers Can't Do" in the 70s, and talks a bit about a Heideggerian approach to AI in his lectures which may be of interest to a few people here.

[0] https://archive.org/details/Philosophy_185_Fall_2007_UC_Berk...