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Tell us about your Square onboarding experience to help us improve

Hi Square Community! I'm Hailey from the Community team, and I’m working with the Square Onboarding team to improve the onboarding experience for our sellers.

 

Thinking back to when you first started using Square, how was your onboarding experience? Did the emails, in-app messages, or other communications guide you smoothly, or were there moments where you felt lost or needed more information?

 

 

Our teams are working hard to make onboarding as seamless as possible, so we’d love to hear what worked well and what could be better. Thanks in advance 😊

️ Hailey
Seller Community Marketing Manager
Square Community
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We have 19 locations.  The onboarding experience has gotten better throughout the years.  For our locations we do the following:

 

New Store:

  1. The first thing we do is establish a location profile.  This includes the store's email address, physical location, phone number, and other necessary information.
  2. We will go to the locations tab and add a new location.
    1. We fill in all of the necessary information.
  3. We duplicate the menu from one of our existing locations.
  4. Device Management: We will go to device management and add all of our devices, including POS and KIOSK.
  5. We will turn on the POS and begin the configuration using the Device ID code.  This process takes between 30-60 minutes depending on updates.

Online Settings:

Once the store is set, we go to Square Online / Menu Management and add any necessary items or changes.

  1. We set up Google My Business and  
  2. We configure Google My Business under location management.
  3. We add delivery settings and store information for Square online under Fulfillment.
  4. We test to ensure that the location is online.

App Integration:

The last part of the process is App integrations.  This includes:

  1. Shogo.IO for accounting and Quickbooks integration.
  2. Doordash integration linking Doordash to Square.
  3. Cuboh integration for Uber and Grub Hub.
  4. Homebase integration for HR management, scheduling, and labor management.
  5. Zapier integration for Square POS printing, Google Ads, Social Media, and CRM.

Screenshot 2025-02-12 at 3.09.18 PM.png

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In a nutshell: a little bit of everything. 

Onboarding as a hairstylist was challenging as well as a breeze, depending on what part of the business I was implementing; some things were a piece of cake, other things made me want to gouge my eyes out. 

Easy-peasy
1. Setting up my "employees" in Appointments so that I could easily get started with online booking. 
2. Inputting inventory so I had actual items to sell
3. Built-in automated communication with clients that took care of confirming appointments easily 

4. Fairly straightforward user interface.

 

Where the gouging started:

1. Setting up Payroll for a solo-provider business (LLC) ended up confusing the Support Representative I was talking to and instead of seeking outside guidance, I was told everything was good only to find that not to be true on my first year of taxes

2. Finding out I couldn't do basic things in my booking/POS system that I could do when I had a 'pen and paper business'; reaching out to Support to figure it out, only to be directed to Seller Community to submit a ticket, and I am (with loads of other Sellers) still waiting on those updates

3. Getting lost in how to set up "Modifiers" and "Variations" when creating inventory because what I sell doesn't fit the "standard retail model"; again trying to talk to Support only to get nowhere. 

TLDR

For basic business operations, onboarding was simple. 

For businesses that are complex, dynamic offerings to serve the needs of the community we cater to: painful beyond reason

 

I wish there could have been someone in my industry (a Mentor/Champion/Expert if you will) that could have helped me go through screen by screen, step by step, going through how to a) set things up and b) explain why a tool/feature might be necessary in my business. Overall the onboarding felt very "ope...guess you're gonna have to figure that out on your own or find a workaround."

Jess
Hair Designer | Certified Trichologist


Visit My Website - Scalp Haven Hair Studio
Check out the magic on Instagram - @JESS.POYNTER
Make an impact on Facebook - @SCALPHAVENHAIRSTUDIO
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Man, this feels forever ago but it was only 5 years ago. Also it was 2020 so systems were so much different for companies. 

Overall we enjoyed it but did feel at first we were kinda playing guessing games but as we engaged and weren't afraid to ask questions and really dive into the square community discussions and found a lot of help that way. Probably from "super sellers" back then and now we are one of those people! 

 

Square payroll and banking are great but felt it was hard to reach an actual human when we needed help. Mind you it all worked out but it felt like the gap between us and someone who could help was a large one. 

Lovewell Tea & Coffee//
Ventura, Ca


https://www.lovewellteaandcoffee.com/
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From my memory, we had a good experience.

I'm fairly certain we had a dedicated onboarding person for a while (who I think later became our account manager). It was a little overwhelming, but only as much as adopting any new technology or changing systems can be. I think we also paid for some extra service to help us bring across all our information from previous POS, and/or maybe help set up our square online store.

I think having something like a clear action plan over a 2-4 week period for onboarding is helpful, with regular check-in's from an onboarding team member (can't remember if that was something that already happened).


Daniel Neuhaus

Trader & Co.

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Its been 5 years, I have had a lot of opportunities to complain and celebrate both my business and Sqaure over that time. I can't recall my onboarding being memorable at all either positive or negative which mean it was pretty easy I suppose. 

Happy to chat with anyone as desired about anything with Square as always 🙂

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Back in 2011 or 2012, we were at the Florida state fair, using ShopKeep for our POS. This is how our onboarding with Square went. A guy approached our booth, carrying a messenger bag. He asked if we’d heard of Square and if we’d be interested in using it. He pulled out a small dongle and explained that Square POS was free (compared to ShopKeep’s $49.99 monthly fee). He also said that after we set up Square, we wouldn’t need the handheld credit card machine anymore. He gave us his card and we signed up. We’ve been with Square ever since! 

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We moved over from Shopkeep as well....I'll just say we are very happy we did.

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Shopkeep was ok at the time, but 49.99 per iPad per month was murder. We just had one iPad active. We were happy to get rid of ShopKeep when Square came along.

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The Square onboarding process was fairly easy to start back in 2019. However, as I delved deeper into my business and needed to transition it online during the covid era, I found it more challenging to navigate the platform and tailor it to my needs. During that time, the available features felt quite limited.

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I joined Square back in 2015 and the onboarding was fairly easy.  I loved that the system basically walked me through each step making it seamless.  The same for the online store.  I so love all updates Sqaure has implemented since then.

Jacqueline Mull
Owner of Jackie's Uniquely U Boutique
Owner of Uniquely U Anime

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I set everything up a couple years ago and I never really felt like I did it right or that it went well. Even to this day when I go to set something up it's confusing and frustrating. It's been almost a year now of me trying to get my products set up to be able to ship out, and for monthly subscriptions. It still doesn't work. When I try to work my way through a screen it basically tells me Oh wait, can't do that yet, go change this other feature, or this other option first. You need to turn this other thing on. So I go to that screen then it says Well, you can't do that yet because you don't have this available to you. You have to go over here and do another thing first. It not just item set ups, it's with every part of Square that I have like employees, permissions, and scheduling, timecards. It's with the online site stuff. Nothing seems intuitive. I've learned that I basically just need to start with the bottom of the screen and work my way up. Global settings first, left side of the menus bottom, and go up one by one. Everything seems to be backwards. And it's so easy to lose my place, once I'm directed to three different screens to set up one thing I don't know how to get back to what I was doing. It's hard to know what the consequences are of turning off or on things. 

Briana Schrodt - Square Champion

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I have a small update, I've been trying to get things set up to ship out coffee. So I thought I finally had it all figured out and texted my Uncle whose been bugging me about it since he lives States away. Well, come to find out whatever I did wasn't good enough because my Uncle's order didn't have shipping or taxes on it! I poked around enough to figure out that I didn't have the polymailer "assigned" to the items, so that *might* fix the shipping going forward, but I was still expecting the "Fall Back Rate" to kick in but it didn't. And I have no idea how come taxes weren't on there. 

 

So for onboarding it's things like this, where I have to go back and forth, back and forth. There was no tutorial, direction, pop-up, flag, arrow, nothing to sign post what I'm supposed to do next. I saw no alerts telling me that after I click on that items fulfillment methods for shipping that I would then have to 'assign' the box. I'm pretty sure that option wasn't even there until I saved and went back into the item so it was literally impossible for me to see or know. 

 

And where was the 'fall back rate'? Why didn't that kick in if there wasn't a box assigned. 

 

And what about taxes? I don't even know where to start to research that one. I've never seen taxes not show on an order before. 

 

A suggestion that might help is if I had a way to test what I'm doing before sending it out to my customers. I would love to be able to see how the shipping process works for them, what they have to click on, what the customer's process is like. So that way I can ensure it's how I want it to look, how I expect it to go, that it's providing my customer's with a great experience, and so that if a customer has any issues or questions for me I can actually answer them instead of shrugging and saying I don't know.

 

This is my first and only POS experience so I'm very green to it, but I feel like I'm walking around with lead boots and a blinder on. I am experienced with videogames. Right now my kids are playing a lot of Donkey Kong Country Returns HD and the 'signposting' for all the hidden locations are there. A lone banana on the edge of the screen so you know to roll jump into the no where to grab the platform you can't see. The coin glittering obscured by a bush telling you that there's something behind it. 

 

It's hints like that that really help an onboarding process, imo.

Briana Schrodt - Square Champion

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Sign in and click Mark as Best Answer if my reply answers your question.
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I have been using Square for 8 years, so its a bit fuzzy haha. I found it easy, but I have done a lot of POS over the years. The only thing I find a touch annoying, is I don't seem to get updates on new products and features.

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Make it a habit to pop into your app store and check for updates! 

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My on boarding experience was a few years ago, and at the time, I had no prior experience building websites or selling products. I come from a healthcare background and was looking for a side project when COVID hit. Despite my lack of technical expertise, I successfully navigated the process of creating a website with minimal challenges. It was an eye-opening experience, and I have highly encourage others who are unsure about diving into something new to give Square a try. They might be surprised by how capable they are in learning and succeeding, even without prior experience.

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Hailey I'm going to be honest with you...it was so long ago I really can't remember lol.  I feel as if it was smooth and if I did run into any problem or had a question I was happy that they had a dedicated customer service team that I could call instead of having to use twitter.  Through the years I feel like it's getting easier with more features that I'm loving.  I love having everything in one place!

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Onboarding was pretty good, but i have since been appointed an account manager and I am disappointed with the efficiency of how matters are being dealt with.  I really feel that they have taken on too much.  It's getting frustrating. 

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Getting additional training for square online set up and QR code ordering. They're trying to tell me I got all the training but I didn't and it's taken them over 2 weeks to give me an answer as to whether I can have more training. Things just aren't been dealt with promptly. Another issue regarding the search function under transactions, it's not working either. 

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My experience was horrendous. I couldn't even get to the point where I could launch the POS. I spent hours getting my online store and POS system set up. My account then suffered multiple strange issues - all modifiers disappeared from my website and items would randomly disappear from the library and website. I spent hours with chat and phone support, each time thinking we got somewhere. I quickly learned that the support agents just lie to you if it is not a simple issue. It got to a point where my case would "randomly" get dropped in the middle of our chat. The support agent was super quick to help me cancel my account though lol

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Wow. It's been a long time. In 2014 we were doing transactions by hand with a pen and paper. Every transaction/item/date/and total... Obviously, it was arduous and time consuming. It only made sense to use something like Square to keep track of everything. Onboarding was easy and intuitive back then. I have to imagine that onboarding is a bit more complicated today (depending on your individual business and needs). As a business owner that is constantly innovating, and growing in a similar fashion, I do not envy Square developers who must be working around the clock to make sure that everything is still approachable, easy to use, and intuitive. I am constantly impressed by updates, and rollouts by Square devs.

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Hi Hailey! Onboarding was smooth overall. The emails and in-app tips helped, but a short step-by-step checklist would’ve made it even easier. Thanks for improving the process!

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