He guest edited an issue of Wired and has been talking about automation and job loss a fair bit lately. And managed (albeit not personally) to convince Matt Cutts to leave Google and word for the USDS
https://www.mattcutts.com/blog/join-the-us-digital-service/The colossal failure of Healthcare.gov and the effort to save it were a slap in the face and then a quick education for Obama and we had a president who really "got" tech for a few years... and I don't have high hopes for the one replacing him.
