guide
Signs a project has outgrown off the shelf software
Off the shelf software is almost always the correct starting point. The interesting question is not whether to use it but how to recognise the moment it stops paying for itself.
These are the signals that tend to appear before a team admits the tool is the problem.
The workarounds have become the process
Somebody maintains a spreadsheet that reconciles two systems. A step exists only because the tool cannot express it. When the workaround is documented in onboarding, it is no longer a workaround, it is the software, and it is being maintained by people rather than code.
You are paying per seat for something most seats do not use
Per user pricing punishes growth in a way that is invisible until it is not. When the licence line is climbing faster than the value anybody gets from it, the arithmetic on building starts to change.
The thing that makes you distinctive is the thing the tool cannot do
Generic software is designed for the average of its market. If your advantage is a way of operating that nobody else has, generic software will flatten it toward the average, which is the opposite of what you want it doing.
Your data is somewhere you cannot get it out of
Export formats that lose relationships, APIs that are rate limited into uselessness, records only reachable through a UI. This is the cost that is never on the invoice, and it compounds quietly until a migration becomes a project of its own.
You have been waiting on a roadmap for over a year
A feature request that matters to you and to almost nobody else will not ship. Vendors are correct to prioritise the majority. That is precisely why depending on them for the thing that differentiates you is a bad structural bet.
An outage in someone else's product stops your work
Worth quantifying honestly rather than dramatically. If a third party being down costs a day, that is a business risk sitting entirely outside your control, and it should be priced as one.
In short
One of these alone is rarely enough to justify building. Several at once usually means the cost of staying has quietly overtaken the cost of leaving, and that the conversation worth having is about scope rather than whether.
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