Feature Request: Let Square sellers choose how we use our own data — including with ChatGPT

[ZoeyAshwood]

I own and operate an independent craft cocktail bar and have used Square for years. I genuinely like Square and have chosen to stay with it rather than move to a restaurant POS that might be more naturally suited to the complexity of my business.

But making Square work for a serious craft cocktail program has taken an enormous amount of time and patience.

My inventory and pricing structure is complicated. I have hundreds of spirits, multiple pour sizes, modifiers, seasonal cocktails, house ingredients, changing liquor costs, and margins that need to be monitored constantly. I have essentially built a complex beverage-management system inside Square’s relatively basic structure.

As a business owner, I believe I should be able to decide how I use my own business data and which tools I authorize to help me manage it.

I already use ChatGPT as an operational tool for my business. With my permission, it can work with information from my bank accounts, email, documents, spreadsheets, and other sources. That allows it to understand more than sales in isolation. It can help me look at the larger financial picture of the business.

For example, I can provide state liquor price lists and have ChatGPT audit my cocktail and pour pricing against current bottle costs. I can track utilities, insurance, accounting expenses, labor, overhead, and other operating costs and evaluate those expenses alongside sales and margins.

Square is one of the most important missing pieces.

I want the ability to securely authorize ChatGPT to access the Square data that belongs to my business and, when I explicitly permit it, assist me in managing the POS itself.

That should include not only read access for analysis, but optional write access for things like pricing, inventory, items, modifiers, menu organization, and other administrative work — with appropriate permissions and confirmation before consequential changes are made.

If I choose to use AI to perform work that I would otherwise have to spend hours doing myself or pay an employee to perform, that should be my decision as the merchant.

I am not asking Square to replace business owners’ judgment. I am asking Square to give business owners more control over the tools we use to exercise that judgment.

Independent hospitality businesses are operating in an increasingly difficult economic environment. My time is limited, and I need to spend as much of it as possible doing the parts of running a bar that cannot be automated: developing the menu, training staff, taking care of guests, maintaining the space, building the brand, and growing the business.

Administrative work inside a POS is exactly the kind of work technology should be helping us reduce.

I love Square and would prefer to continue using it. But part of keeping Square competitive should be allowing merchants to securely connect the AI tools of their choice to their own data and workflows.

Square already has substantial API infrastructure and has begun building MCP support. Please give sellers an official, secure Square → ChatGPT integration with granular permissions for both analysis and merchant-approved management actions.

I want every reasonable tool at my disposal to make my business more efficient, financially sustainable, and capable of growing — and I believe that choice should belong to me.

[ChickenRacer]

Really well put @ZoeyAshwood. A pub has the same headache: hundreds of products, multiple pour sizes, spirits sold as a nip, a double, or a bottle to take away, and supplier prices changing all the time. I'm in the middle of a full supplier review across our two venues right now, and getting clean cost and sales data out of Square to line up against supplier price lists is half the battle.

It's our data. Being able to securely connect it to whatever tools we choose (with our permission, and with good controls) would make Square a lot more valuable, not less.

Business type: outback pub and tourism venue, two venues in regional Queensland.