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1) I gained insight __ working practices of such companies

2) I gained insight __ how a software project is done from scratch

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    I think this is General Reference. Although to gain insight isn't a phrasal verb for which you can look up usage in a dictionary, I think it's significant that when I type I gained insight in the Google search box with "Instant" turned on, the first "autocomplete" offered to me is into.
    – FumbleFingers
    Commented Jan 9, 2014 at 17:19

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"Into" would be used in both of those examples.

I'm not certain of the grammatical rules that govern it but the use of on rather than into would indicate a less detailed view. For example "I gained insight on the working practices of such companies" would be more taken to mean that you knew what the working practices were, whereas "I gained insight into the working practices of such companies" would indicate that you'd had a more detailed understanding, learning more both about what the practices were and also -why- they were in place

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