Portal is a series with a surprising depth of lore for only having two relatively short games. The developers love to add little clues, hints, and mysteries for the players to discover - so much so that it's hard to tell what's just an easter egg and what's important to the canon.
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If you were confused about Caroline, the woman who became GLaDOS - or just had some questions about her - have no fear! Everything we know about Caroline's story is detailed in this easily digested article.
Very little is known about Caroline except that she was the personal assistant to Cave Johnson, the CEO of Aperture Science. It is clear that Johnson regarded Caroline highly, calling her the "backbone" of the Aperture Science testing facility.
In 1982, before Cave Johnson died, he was attempting to extend his life by putting his mind into a computer through innovative brain mapping technology.
At this time, Aperture Science had an Enrichment Center where they were performing research, but it was not run by computers. Rather, it was run just like any office of the time. At some point, a precursor to the program that would end up becoming GLaDOS was added to help them operate the Enrichment Center.
In 1986, word reached Aperture Science that their competitor, Black Mesa, was also working on Portal technology. In response, they began work on GLaDOS to oversee testing more efficiently and beat Black Mesa in the race to create working Portals that could be sold commercially. It's assumed that Cave Johnson lived up to this point and directed that his mind should be put into GLaDOS so that he could continue to run the facility.
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Unfortunately, Johnson
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