I’m not sure it’d work for your price point, but I’m running Meta ads, and then having leads schedule a call with me (no public pricing). I close them on the call (they give me their CC to start a trial). That’s worked well, though I do want to move towards a self-serve model over time.

I think you should avoid casting a wide net, i.e untargeted ads. Post or contribute to niche communities, reach out 1:1, ask friends for leads. If none of this works, you could try highly targeted ads.

POS first because everyone has to record money. The value proposition is theft prevention, bookkeeping & taxes, etc. Inventory next because supply chains are too complex for most generic systems. Then some kind of customer retention/acquisition thing so they don't feel like it's a cost center.

The market is too red ocean for VCs to enter. Sales doesn't scale exponentially. That's your moat. I would say just tackle one American sized state, not even the big ones.

Users won't come to you. They'd go to whatever well known system is in your area. You have to go to them. Skip the online ads, TikTok, etc.

Instead of 200, focus on 5 potential customers only.

I'm always surprised by things like the fact there are several software solutions for managing gyms, but there are also specific solutions for rock climbing gyms, yoga studios, etc. I know a guy who builds rock climbing gym software and he's got a team of 20+ employees.

Be helpful. Share an easy and free way to do it without using your tool/service. Then introduce your tool/service. Share its advantages and some proof that it works. Be genuine and honest, don't oversell it. Acknowledge alternative tools/solutions. Distribute it on reddit, twitter, etc.

If your blog is extremely good, Google Search will pick it up in a couple of weeks.