thread Re: 40% Layoffs: Is anyone else worried about the human side of Square? in Community Corner

40% Layoffs: Is anyone else worried about the human side of Square?

mitin — Fri, 27 Feb 2026 23:53:20 GMT

Hi everyone,

I’m posting this because I’ve been using Square for a little while, and like many of you, I’ve seen this platform evolve but with lots of challenges. But after yesterday’s news that they are cutting 40% of their team (over 4,000 people), I’m feeling pretty uneasy.

I know the corporate line is about becoming "leaner" and moving toward an "AI-first" model. I’m all for innovation, but as someone who has already struggled with Square support in the past, I’m worried that we’re losing the human safety net that small businesses actually need.

A few things I can't stop thinking about:

When things go wrong, will anyone answer? We’ve all had those moments where we’re stuck on hold or waiting days for a ticket. If 4,000 people are gone, is "support" just going to be an AI bot that quotes the Terms of Service at us? When it’s 11:00 AM on a Saturday and my hardware isn’t working, a "smart bot" isn't a replacement for a person who can actually fix it.
The "Account Frozen" fear: This is the big one. We know the automated risk flags can be aggressive. My concern is that with fewer human reviewers, those account freezes will happen more often and stay locked for longer. Can your business really survive a two-week funds-hold while waiting for an algorithm to "review" your appeal?
What happens to the tools we use? There are so many small bugs and feature requests we’ve been waiting on. When a company pivots this hard to AI, does the "boring" stuff like fixing inventory glitches or improving the dashboard just get abandoned?

I truly want Square to be successful because I don’t want to have to move my entire business to another platform. But 40% is a massive cut, and it feels like the sellers are the ones who might pay the price for this "efficiency."

I’d love to hear from anyone else—are you sticking it out, or are you starting to look at other options? And if anyone from the Square team is reading this, can you give us some real reassurance that we aren't about to be left on an island with just an AI bot for company?

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

mitin — Sat, 28 Feb 2026 00:54:31 GMT

I am obviously late to the events that transpired with our Square moderators, just now catching up on it, but I am so sorry to hear about how this has affected the people at @Square .
I wish everyone the best in their future endeavor and hope for nothing but the best for them.
I know at times I have been little harsh on Square but I do want to say the moderators have been the rock in these forums, keeping everything going, and while some of them have gone and might not be able to read this message, I do want to tell you all THANK YOU from the bottom of my heart
I am tagging people from Square, some might still be here some probably gone, but this is just to express my gratitude, Please tag your Square moderators and team members in this please
@isabel @Summer2024 @LeahK @nika @kristen @katie

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

JUYBoutique20 — Tue, 03 Mar 2026 19:59:19 GMT

@isabelle and @nika are no longer with Square. I don't know about the others you tagged. It's definitely concerning. @isabelle was great in our communities and really worked hard for all of us.

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

Missy22cc — Tue, 03 Mar 2026 20:03:01 GMT

Ahhh, that may explain why the sales team never gets back to me. I've had questions about my plan and hardware that keep hitting dead ends. Now hearing about mass layoffs has me thinking of jumping ship instead of bringing in payroll, online, and expanded retail.

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

forwardfoods — Wed, 04 Mar 2026 20:00:00 GMT

Will all the layoffs mean rate and fee reductions for users? It better, right? Mr. JD (net worth 5.9B) better not be using any savings for his own pockets.

I dread trying to fix glitches with AI bots. It's already such a struggle through a labyrinthe system to find specific answer to a unique problem.

So yes, @mitin, I'm very worried.

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

TheRealChipA — Wed, 04 Mar 2026 20:17:53 GMT

Only Leah and Katie are still around, You can find out about anyone by looking up their profile. If it says they are in the "Alumni" group, that is this Community software's way of saying they no longer are here.

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

lennys26 — Sat, 07 Mar 2026 10:01:22 GMT

I didn't know about the layoffs, however, hearing about it now, I have huge concerns going forward.

My experience with the product, including interactions with Support, making feature requests, bug reports, and the overall software reliability, has been far less than stellar, and the loss of so many employees can only be negatively impacting.

I think this is a real concern.

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

Missy22cc — Fri, 13 Mar 2026 17:30:51 GMT

SAME! I need to integrate my online, customer email collection, pos, and payroll. It would have been easiest to just go with Square, but customer service is almost none existent and that was before the layoffs. They literally had me on the hook for more monthly fees and seriously dropped the ball. I even waited 15 minutes at a trade show to speak with them in-person and gave up.

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

CareyJo — Fri, 03 Apr 2026 16:06:18 GMT

I felt the exact same way when I learned of the layoffs. My first thought was, I don't want computers taking over the world. My second thought was, how horrible to hurt all of those people and their families. How incredibly insensitive is this guy for what he's doing?!? And my last thought was, I truly don't know if I'm going to stick around to support a company that can be so mindful of the "owner's" pocket and no one else's. I truly don't know if I will stay or not....

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

mitin — Mon, 06 Apr 2026 12:49:19 GMT

I feel like the biggest hit would be on Square support. My personal experience with Square support has been horrible. My background is IT and technical so I am very well involved with the AI battles within companies, and I have a feeling square might be trying to use that for support as well, but I don't think out of the 5-6 times that I have called or engaged square support in over 18 months that they were able to resolve any issues for me.
While I appreciate and love the feedback and engagement I see in the community forum, i don't think it should be a replacement for square support.
I am trying to stay positive but also watching the change carefully.
At least on the square appointments side, which is what i use, Square is definitely way behind, and I did consider switching to different platforms, but I realized that customers love it, so decided to stay with it and figure out alternatives for the roadblocks I run into.

Mitin

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

CareyJo — Tue, 07 Apr 2026 16:40:37 GMT

This is really important feedback for Square to see. Thanks for sharing. If an IT person can't get support, how are the rest of us supposed to? That's a big deal. Hopefully Square will take note of this and seriously consider this in reworking the new structure of the company and using AI. I also appreciate hearing you acknowledge that your customers love the service you can provide through Square and that you want to keep it.

Re: 40% Layoffs: Is anyone else worried about the human side of Square?

MagicToybox — Tue, 07 Apr 2026 20:03:20 GMT

Well, This explains a lot. @Square you need real people working for you, and you NEED a customer support team. No, it's not something that generates revenue, but it maintains your current clients, and keeps them happy. Right now, I'm not happy. I've been trying to get a response from Square for the better part of a month, and no contact. You are really telling me that my business is not worth your time. And I am telling you, that Square is not worth the money I am spending on you. I'm looking into other providers.