thread Re: Need help with advanced services in Payments Troubleshooting

Need help with advanced services

hikeikimuseum — Sat, 20 Sep 2025 06:53:43 GMT

I'm sure this has been asked and answered loads of times but I can't find anything on this impossible to use community bulletin board. Sorry about that.

I use Square for a lot of stuff including: payroll, website, email marketing, and more. I need someone to help me go over it all and make sure I've configured everything correctly. I don't like the workflow for annual subscriptions - is it just me or is this feature poorly implemented by square? I might be interested in setting up appointments but I just don't know, I need and expert to help me.

I've also looked on fiverr but can't find anyone there who is good at the square system (the search results are all square space web designers). Where can I find a square concierge to help walk me through my system and make it more clean and efficient for all my staff and work?

Thanks for reading this!

Re: Need help with advanced services

JTPets — Sun, 09 Mar 2025 13:53:14 GMT

I am happy to charge you $100/hr to set up all Square functions however you like as far as they can be configured, if you decide to take a stab at it and get stuck most of us are also here to help you with specific issues free of charge 🙂

Re: Need help with advanced services

hikeikimuseum — Sun, 09 Mar 2025 19:29:11 GMT

Aloha JT Pets, thanks for replying! I have so many little issues that I'm looking for something like an audit of my square system. I'm sure there are ways that I can use it better, but I've developed workarounds that are probably making things harder, not easier. For example:

- I have two locations and the plans on my dashboard for the subscription annual membership that I sell isn't in sync with what's on the POS iPads

- Right now when the system sends an invoice for a subscription it automatically registers that person as paid up (for the year) instead of, you know, waiting for that person to actually pay, which is making my book keeping a nightmare.

- I run free events and listing these on my homepage as a "featured event" is awkward because it's free, is there a better way? Should I setup free events as a "service" instead?

- Is there an easy way to identify someone as a member/subscription holder at the POS terminal? I saw an article about making QR codes but it required me to issue a pass that they have to bring with them, is there any other way to do this? Lookup by phone number or last name?

- I use quickbooks and square payroll and I would like to configure the square app that transfers the data between them to categorize the state and workers comp withdrawal transactions separately from gross pay

- I'm interesting in understanding if appointments will work for me. I book parties and field trips and I need a demo, or a way to try it out and see if the calendar that Square creates and maintains will sync with what my staff are using.

See what I mean? It's a lot of questions, and a lot of stumbling around. I saw you were tagged as a "Champion", what does that mean exactly? Can I hire champions to work through issues with me directly? Or are there account specialists that Square offers to help with things like this?

Re: Need help with advanced services

JTPets — Mon, 10 Mar 2025 14:52:20 GMT

Square champions are active members of the square community who are recognized a product experts who help bridge the gaps between company and community. We advocate for ourselves and other sellers and help people along the way - Learn more about the program here:
https://community.squareup.com/t5/Square-Champions-Program/ct-p/SquareChampionsProgram

Re: Need help with advanced services

JTPets — Mon, 10 Mar 2025 15:06:34 GMT

You’ve got quite a few moving parts here—I'll tackle what I can based on my overall strong understanding of Square’s services and capabilities. While I’m not familiar with every specific aspect of these questions, I can offer general guidance:

1️⃣ Subscriptions Not Syncing Across Locations

Square subscriptions are often tied to specific locations. Check if your plan is enabled for both locations under Subscriptions → Plans → Manage Locations in the Square Dashboard. If it's assigned to only one location, it won’t appear properly on the other POS devices.

2️⃣ Invoices Auto-Marking Subscriptions as Paid

Square’s subscription invoices currently assume payment upon sending. If that’s causing bookkeeping issues, one workaround is manually invoicing customers separately and using automated reminders.

3️⃣ Listing Free Events on the Homepage

Free events don’t always fit neatly into Square’s online store. You might have better luck using Square Appointments as a free service or utilizing the Event Listings feature. An embedded Google Calendar or a blog section could also help.

4️⃣ Identifying Members at POS Without QR Codes

Customers can be looked up by phone number, email, or last name at the POS. You can also use customer tags (e.g., "Member") to make searches faster.

5️⃣ QuickBooks & Payroll Categorization

Square Payroll syncs with QuickBooks but categorizes transactions in broad wage-based groups by default. You may need to manually adjust categories in QuickBooks or set up automated rules to separate taxes and workers' comp.

6️⃣ Trying Out Square Appointments for Field Trips & Parties

Square Appointments offers scheduling and Google Calendar sync, which might work for your needs. Since most of Square’s services offer trial periods or one-month subscriptions, you can test it out before committing.

Let me know if you’d like more details or need help troubleshooting specific issues!

John

Re: Need help with advanced services

Summer2024 — Tue, 18 Mar 2025 14:36:51 GMT

Hi there, @hikeikimuseum ! Thank you for such a detailed breakdown of your needs. I can see you're managing a complex business with multiple locations and various services. Let me address each point and suggest some optimizations: (I also see @JTPets provided his insights as well)

1. Location Plan Sync Issues

This sounds like a configuration issue that needs attention
To sync plans across locations:
- Review Settings → Locations → Item Sync settings
- Ensure both locations have the same subscription settings
- Check that item libraries are properly synced

2. Subscription Invoice Payment Status

This definitely shouldn't auto-mark as paid! Let's fix that:

Check your Invoice settings
Review Subscription configuration
Consider using Square's newer Recurring Billing feature instead
- Better payment tracking
- More accurate status updates
- Improved bookkeeping integration

3. QuickBooks Integration

For better categorization:

Review Square → QuickBooks mapping settings
Set up custom categories for:
- State withdrawals
- Workers comp
- Gross pay
Consider using Square's advanced payroll reports

4. Appointments Evaluation

To test Appointments for parties and field trips:

Trial Setup
- Start with free trial
- Set up test services
- Create sample bookings
Calendar Integration
- Supports Google Calendar sync
- Can sync with staff calendars
- Manages multiple staff schedules

I hope this helps!

Re: Need help with advanced services

hikeikimuseum — Tue, 10 Jun 2025 23:26:40 GMT

Thanks guys! I am running what I think is a simple business. However, I had a second location and then had to shut it, so maybe that's what makes it complex? In any event I appreciate the help trying to unravel these mysteries of the Square features!

1️⃣ Subscriptions Not Syncing Across Locations

- Subscriptions → Plans → Manage Locations in the Square Dashboard doesn't exist. There is no option to manage locations within subscriptions 😞

- Account & Settings → My Business -> Locations → Item Sync settings doesn't exist 😞 I remember seeing this when I first setup my second location, but I can't find this menu anymore. Also, I don't want all my inventory to be synced, just the Subscriptions.

- Again my issue is that the Subscription plans listed in my Square Dashboard are different from what is shown as available on the POS devices. I'm sure this is a bug.

2️⃣ Invoices Auto-Marking Subscriptions as Paid

- Invoices -> Settings -> Invoices there's nothing in there about Subscription Confirmation 😞

- Consider the Recurring Billing feature - I would, but change is scary.

3️⃣ Listing Free Events on the Homepage

- I've got this working using the Event Listings feature.
- Consider using Square Appointments - I want to, but again, I'm afraid to turn on all this new functionality.

4️⃣ Identifying Members at POS Without issuing them membership cards with QR Codes

- Use customer tags (e.g., "Member") to make searches faster. Where are customer tags? I can find groups, but the workflow of putting every subscription member into a group manually is onerous. And it's not available in the "smart group" functionality. 😞

5️⃣ QuickBooks Payroll Categorization

- Staff-> Payroll -> Integration → Edit QuickBooks mapping settings THIS WORKED! THANK YOU!

- Consider using Square's advanced payroll reports. Where? How?

6️⃣ Trying Out Square Appointments

- I know this feature is available but it's a heavy lift to implement it all and I don't know how to integrate it into my workload. This is why I need some sort of "personal Champion assistant" to help me get setup and sort this out. Maybe I should just hire you for $100/hour?