Honest question: what part of your business do you not let Square automate anymore?

[Vanilla]

I use Square every day and appreciate how much it can do. But over time, I’ve noticed I’m more selective about what I let run automatically vs what I handle manually.

Not because Square is bad, but because some parts of service-based businesses feel too nuanced to “set and forget.”

So I’m curious:

• What do you always keep manual?

• What did you try automating and then roll back?

• What works great in theory but not in real life?

Especially interested in answers from appointment-based and high-touch service businesses.

Would love to compare notes.

[Lovewell]

@Doran any insight on this? 

[mitin]

Hi @Vanilla 

I totally get the appeal of an "all-in-one" platform like Square for the convenience, but honestly, I prefer keeping the critical parts of my business under my own control.

I actually started on Square Online, but the limitations were a major bottleneck. Since switching to my own site, my traffic jumped 90% in a single month just because I could finally implement proper optimizations. As someone in tech, keeping my Domain separate is a non-negotiable—it’s about having total ownership and not being locked into one ecosystem.

The biggest thing I’ll never hand over to a platform to automate is money, and the same goes for data. I always keep an off-site copy of my customer data. It takes years to build that database, and I’m not willing to lose it all over a glitch or a policy change on Square’s end. I want complete control over my financial and customer logistics.

What do I always keep manual/separate? My Domain, my customer backups, and anything financial—payroll, bill payments, etc. I keep all of that strictly separate from the POS.

What did I try automating and then roll back? To be honest, you can automate almost anything these days, but Square is so far behind on basic automation that I’ve never even been in a position where I had to "roll back" to them. Their tools just aren't there yet.

What works great in theory, but not in real life? Square Marketing. I’m really not a fan. Between the poor design templates and the limited tracking for conversions, it just doesn't deliver the results a growing brand needs.

Hope this helps!

[Vanilla]

This is such a solid breakdown! Thank you for taking the time to articulate it so clearly.

I completely agree on ownership, especially when it comes to money and data. That “one glitch or policy change away” feeling is real, and I think a lot of service providers quietly feel the same way but haven’t put words to it yet.

What stood out to me most is how you framed automation as something that should support control, not replace it. Square is powerful, but the lack of flexibility in areas like optimization, reporting, and marketing makes it hard to trust certain tools at scale. This is exactly the kind of feedback that helps clarify where automation actually breaks down in real businesses.

[perkits]

We still keep DoorDash and Uber Eats separate. Also use homebase for scheduling and timecards which data migrates to Square. 

[Vanilla]

That makes a lot of sense, especially separating delivery platforms and scheduling from the POS itself.

I’m seeing a clear pattern in these replies: Square works best as a hub, but not as a single source of truth for everything. A lot of us still need parallel systems to maintain accuracy, flexibility, or reliability.

It’s helpful to hear how others are structuring their stack instead of forcing everything into one workflow that doesn’t quite fit.

[lilisalazar]

Hi @perkits!

Do you mean you keep them separate as in you don't offer delivery in your online ordering or separate as you don't sync items between the platforms and Square? 

I'm curious now that Square no longer charges the $1.50 dispatch fee, if that incentivizes food businesses to push people more to their own online ordering website.