Hi everyone,
I’ve been quite vocal in this community lately—perhaps a tad too much at times! But my passion comes from a place of genuine investment. I’ve always viewed Square not just as another credit card processor, but as a tech-forward leader. That’s why it’s so "perplexing" when we encounter roadblocks on features that have been standard in retail for decades.
I truly appreciate the Square Champions and the moderators who keep this ship sailing. I’ve tagged a few moderators in the past, and I want to apologize if that came across as rude or as if I was pointing fingers at individuals to 'fix' things. My intent was simply to bring visibility to these critical issues, hoping that a tag might help these concerns reach the right eyes and get the momentum they deserve
However, as business owners, our time should be spent growing our brands, not engineering workarounds in the forums.
In the spirit of constructive growth, I’ve compiled 10 "Basic" gaps that feel less like "innovative feature requests" and more like essential tools for a modern business:
Staff Attribution: Mistakes happen. Not being able to edit the staff member assigned to a completed transaction results in hours of manual commission math. It’s a 101-level retail need.
Discount Logic: We have the ability to create discounts, yet applying and tracking them effectively remains surprisingly restrictive.
Appointment Source Tracking: In 2026, we shouldn’t need to build our own booking platforms just to see if a Google ad converted. A 10-year-old feature request shouldn't still be in a "black hole."
Custom Tender Types: Whether it’s Groupon or a local voucher, we need to name our payment types. Without this, reconciliation is a daily nightmare.
Tip-Only Transactions: For voucher-based services, customers still want to tip. We shouldn't be barred from processing a gratuity just because the "sale" happened elsewhere.
Manual Tip Adjustments: We know our teams best. We need the autonomy to split tips manually rather than being locked into a "one-size-fits-all" algorithm.
Post-Transaction Automation: We have pre-appointment messages; why not post-appointment? Sending a "Thank You" or a review link shouldn't require an expensive third-party subscription.
Multi-Guest Bookings: People get their nails done in pairs. Forcing separate bookings for a "+1" is a major friction point for the customer and the seller.
Professional Reporting: Square’s reports are functional, but they lack polish. No direct "Email as PDF" option and a lack of branding makes them look unprofessional when presenting to stakeholders.
Attribution Accuracy: Currently, one purchase can be attributed to multiple campaigns, leading to overstated data. We need transaction-level detail to spend our marketing dollars wisely.
I’ve spoken with sales reps and support, and while I respect the "product cycle," the lack of transparency makes it feel like these ideas go into a void. I truly believe Square has the potential to be the best in the world, but that requires listening to the people in the trenches.
To my fellow sellers: Which of these is your biggest bottleneck? Or am I missing something even more "basic" that has been on your wish-list for years?
Looking forward to hearing your thoughts.
