I run a software engineering firm in NYC, and I'm looking to buy a business to bolt onto our operations, likely something in the lower-middle market that runs on spreadsheets and one or two people's institutional knowledge. So I've got an obvious bias toward "the tech matters," and I'd rather hear from people who've owned the outcome than trust my own bias. If you bought a company and then put real money into its systems, replacing spreadsheets, connecting tools that don't talk, or rebuilding an aging stack, I'm curious about two things. First, how did you get the work done, an in-house hire, an outside firm, or the people already there, and how did you get comfortable that whoever did it understood the business, not just the code? Second, was the payoff growth, or was it really about reducing key-person risk and keeping the process knowledge that would've walked out with the seller? My assumption is that the biggest return is usually operational. Getting the business out of one owner's head and a pile of spreadsheets, into systems that survive the transition. Tell me where that's naive, and where the tech just turned into an expensive distraction instead. Happy to discuss with anyone who's done it or is going through it right now. War stories welcome, especially the ones that didn't work.