Ask three things before committing to anything. Can I export my data, in a standard format, without asking anybody for help? Does it connect to the things I already use, through a real integration rather than a promise on a roadmap? And does the price still make sense at three times my current size, checked against the next tier rather than assumed? The first question is the one nobody asks and everybody regrets, because a customer list, an invoice history, or a body of content that cannot leave in a usable format means you are renting your own records.
Growth breaks tools in predictable ways, and knowing the pattern helps. Per user pricing that is trivial at one person becomes the largest line in your budget at ten. Tools designed for a single operator often have no concept of permissions, so your first employee gets access to everything or nothing. Anything requiring manual steps works at ten transactions a week and fails at a hundred. And a tool with no audit trail becomes a problem the moment more than one person can change things.
The counterweight is not to over build for a scale you have not reached. A first year business choosing enterprise software because it might grow into it pays for complexity it cannot use and slows itself down. The correct posture is to choose the simple thing, confirm you could leave it, and let the pain of outgrowing it be the signal to move. Migrations are unpleasant and they are cheaper than years of paying for capacity you never used.
The one place to be conservative is the foundation. Your domain, your email, your accounting, and your customer records should be boring, widely used, and easy to move. Everything above that layer can be replaced in a weekend if it turns out to be wrong.
Test the export before you depend on the tool rather than when you want to leave, because a documented export feature and a usable export file are different things. Run it once in the first month, open what comes out, and confirm it contains what you would need. Businesses discover during a migration that the export omits attachments, history, or the field they cared about, and by then you have no position from which to complain.