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"Showstopper!: The Breakneck Race to Create Windows NT and the Next Generation at Microsof" by G. Pascal Zachary is great, about an interesting period of Microsoft's life.

Not sure if it fits your bill, but I found "I Sing The Body Electronic" by Fred Moody a very interesting read.

Moody was able to get some pretty intimate insights into the development of a software product at Microsoft at the beginning of the 1990s (1992-1993, I think).

I was surprised to learn afterwards that Moody had (has?) a reputation for being very pro-Microsoft; this book does not embellish the problems the people on the project team face, nor their conflicts.

I liked "The Friendly Orange Glow: The Untold Story of the PLATO System and the Dawn of Cyberculture" which sounds related... I hadn't heard about PLATO before, and the book was strongly redolent of "online culture".

I will add as well:

"The Chip: How Two Americans Invented the Microchip and Launched a Revolution"

"We were burning: Japanese Entrepreneurs And The Forging Of The Electronic Age"