Off-the-shelf software isn't wrong, and custom software isn't always right. Here's the actual decision framework.
The "build vs. buy" question gets treated as a philosophical debate, but it's really a practical one: how much is your business bending to fit software that wasn't built for it, and what is that costing you?
For well-understood, standardized problems — accounting, generic project management, email — mature off-the-shelf tools are usually the right call. The problem is common enough that a general-purpose tool fits most businesses reasonably well, and building a custom version would mostly be reinventing a wheel that already works.
The tell isn't "we don't like our current tool" — it's "our team has built a set of workarounds, spreadsheets, and manual steps around the tool's limitations." That workaround layer is a strong signal that the off-the-shelf tool's model doesn't match how the business actually operates, and the cost of that mismatch (time, errors, inconsistency) is often larger than it looks day-to-day.
Custom doesn't have to mean "build everything from scratch." A common, pragmatic path is keeping the off-the-shelf tools that genuinely fit (accounting, email) and building custom software only for the specific workflow that's actually unique to your business — with real integrations connecting the two, instead of manual data entry between them.