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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 😊
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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:
- 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.
- We will go to the locations tab and add a new location.
- We fill in all of the necessary information.
- We duplicate the menu from one of our existing locations.
- Device Management: We will go to device management and add all of our devices, including POS and KIOSK.
- 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.
- We set up Google My Business and
- We configure Google My Business under location management.
- We add delivery settings and store information for Square online under Fulfillment.
- We test to ensure that the location is online.
App Integration:
The last part of the process is App integrations. This includes:
- Shogo.IO for accounting and Quickbooks integration.
- Doordash integration linking Doordash to Square.
- Cuboh integration for Uber and Grub Hub.
- Homebase integration for HR management, scheduling, and labor management.
- Zapier integration for Square POS printing, Google Ads, Social Media, and CRM.

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We had an easy transition, it was stressful because our previous processor rapidly stopped processing but this was our first whole POS system (initially with iPad then later with Register and terminal). I can't think of any difficulties in the initial set up. We had some early register hiccups but got a replacement. We found the in-app messaging helped but also were relieved for the treasure trove of online help tutorials and articles.

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It's honestly been so long since I originally started with Square with just a reader (2014) that I don't really remember the original processes. Back then we just used it at festivals, but since then we have opened a brick & mortar shop and now use the Retail POS, payroll, loyalty, marketing, online, etc. I feel like each time we added a service there was adequate onboarding info to get up and running. I don't feel that I really am taking advantage of all the features of each service, but I also haven't spent (had) the time to deep dive into the info for each one either. I'm sure the info is here if I need it, I just haven't had time to sit and sift through it. I do wish Square would do a podcast that talked about the different systems and how different people use them, that would be something I can listen to and learn during my commute.

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It’s been a long time since I onboarded. Pretty sure it was mid 2009 for my first business. That one was pretty basic and a lot of trial and error to figure things out without support. 2013 for my next business and that was a lot easier due to the short videos and having already experienced how it worked. Probably took me a couple of days to get the POS all setup with my items. Last time I onboarded was for my 3rd business in 2019. That one went very quickly. The in app messaging definitely helped. Not sure if Square still sends out the emails with the links to short tutorials but those helped me to get inventory and categories setup correctly to make things very quick and simple
Mountain Vapors
www.mountainvapors.com

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It was 2013 when we onboarded with Square and we started with the POS iPad stand and then migrated quickly into a lot of other services such as Customers Directory, then Loyalty, Payroll and Teams, transitioned into square for retail and square for restaurant, heavily utilizing the inventory system, And now we use almost every feature that Square has to offer.
I don't recall there being any difficulty at all. It seemed very seamless every step of the way.
I don't recall seeing any onboarding documents. I'd love to see what those look like for the newcomers. Maybe back in 2013 those hadn't been developed yet.
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Burst Of Butterflies Create & Paint Studio
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lol. Yeah back then there really wasn’t much available in the way of documentation or how to set things up. Onboarding has really come a long way
Mountain Vapors
www.mountainvapors.com

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For us, getting our inventory from Quickbooks POS to Square for Retail was the biggest concern.
At the time, the fields you could import into Square were limited (no vendor code). I believe this has been mostly resolved.
I suppose you still can't import a secondary vendor (correct me if I'm wrong). That would be nice.
Other than that, we were up an running in a day. Obviously there's some settings tweaking as you actually run the business and realize what you need. But overall, it was an easy transition.

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It's been over 10 years, it seemed simple enough for me, but I like a good challenge anyway. Getting email with links to documentations, in-app messages are helpful. Also I have NEVER had one problem with receiving deposits.

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It has been about 18 months since we did our onboarding, and in general, our experience was positive. I think that it was helpful that;
- We could schedule our sessions based on our needs/schedule.
- There were multiple videos on Youtube that we could look at as well.
- The support community had plenty of information as well.
- Our onboarding specialist did a bunch of our data entry by me sending an Excel file of our inventory.
We don't really remember anything negative per se about the experience at all really. What was different to us is that we had always had an on-site trainer before. Doing it remotely and on our own was a different experience. Different. Not bad.
Sun Valley Lanes & Games
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It's been almost 13 years since we onboarded and I have no memory of the process. 😆

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for me it was an easy onboarding. I got into restaurant business for the first time and my partner was taking care of main onboarding processes and for EPOS system etc. Soon during setup process itself we could see a lot of hidden charges started appearing.
I used one of the old ipad, and trialed the setup with Square and demo to my two partners and they liked the setup and ease of use.
Square's loan for hardware was also useful and motivator for this. We got onboarded in Dec-2019/Jan-2020.

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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:
- 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.
- We will go to the locations tab and add a new location.
- We fill in all of the necessary information.
- We duplicate the menu from one of our existing locations.
- Device Management: We will go to device management and add all of our devices, including POS and KIOSK.
- 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.
- We set up Google My Business and
- We configure Google My Business under location management.
- We add delivery settings and store information for Square online under Fulfillment.
- We test to ensure that the location is online.
App Integration:
The last part of the process is App integrations. This includes:
- Shogo.IO for accounting and Quickbooks integration.
- Doordash integration linking Doordash to Square.
- Cuboh integration for Uber and Grub Hub.
- Homebase integration for HR management, scheduling, and labor management.
- Zapier integration for Square POS printing, Google Ads, Social Media, and CRM.

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Oh, Zapier, what integration did you build, I am currently using it to transfer some sales data to another ecosystem with our vending products.?
Multi-Unit Manager
Order Up Cafe/Tombras Cafe/Riverview Cafe/City County Cafe
Roddy Vending Company, Inc.
www.OrderUpCafe.com
Using Square since July, 2017
Square Champion
Breaker of Things
"Good judgment comes from experience, and experience comes from bad judgment."
"You can have everything in life you want, if you will just help other people get what they want." Z.Z.
Do you want to have great restaurant menus that are easy to edit and don't cost a fortune? I use MustHaveMenus and you can too!
MustHaveMenus

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With Zapier we have almost 50 automation. Below are a few:
- Google Reviews, Square POS, and Open AI: When a review is left for a GMB location, Zapier will categorize the review rating and write an appropriate response to the customer. Automation as follows:
- Categories Review
- Generates suggested response based on 1-5 rating.
- Send review message to POS printer via Square POS.
- Sends Text Messages to managers and executive team using Twilio API
- Schedules response to be sent within 24 hours of review. This allows us time to edit if needed.
- Team Messages to Square POS Printer: Sends messages to POS printer based for execution, operational tasks, and daily tasks.
- Uses Gmail Account.
- Each store is assigned a filter Code.
- Google sheets are created: Morning, Mid shift, and Evening.
- Daily tasks are put into Google Sheets to be sent daily (reoccurring tasks).
- The calendar is scheduled to send daily tasks and messages.
- At scheduled intervals throughout the day, tasks are sent.
- We can also email the printer directly as needed using the Gmail filter code.
- Google Ads / Square POS
- When a new customer registers or orders online, that data is sent to Google Ads for Display advertising.
- Instagram, Google My Business.
- When a message is posted on our Instagram account, it automatically posts to Google My Business.
- Adverse Weather Conditions:
- Sends message to POS printer, and text messages to management in order to manage labor during Snow days.

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SNAP! This is a beautiful example of setting up a system and utilizing it so that each step is followed for each set up. Very impressive.

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Wow...Very impressive!!!!
Owner of Jackie's Uniquely U Boutique
Owner of Uniquely U Anime

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Hi @Hailey
Onboarding for our company was a long time ago in a galaxy far, far away!
But of what I do remember it was very easy, if it wasn't easy we wouldn't be here now enjoying the benefits of a great system for our business. Lots of Square help articles, forum help and experience to draw on made the process easy peasey, frictionless onboarding. Technically we are probably not the sharpest tools in the box so this is testimony to a good system and onboarding process that really works well.
Many years on the support available has just grown and grown, at lot more knowledge on the forum and apps that pretty much take the worry out of the unknown. We added an additional location to the business about 4 years ago and it really was seamless.
Sorry Square team if you were probably after some helpful feedback for your continual improvement process.

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@Hailey Back in the day, it was pretty easy from what I remember. Nowadays, it is something else since I just add locations and roll out. The ability to copy items/catalogs/set ups isn't bad at all.
Now, as an observer in the community, it seems like the initial account set up is the biggest hiccup. The verification process is where when people have issues they hit a big roadblock. I am sure 95+% have no problem at all or are rejected appropriately. But it is a big big negative as it is a first impression. The explanation of business types could be better and give people a little more of a nudge to have all their info up front.
There is just so much info now, that is probably the biggest hurdle..what all you can do, versus, what you need to do business right now. The hardware team on the setup in the boxes instructions is great.
The youtube videos are also a big help, it's just almost common place to not see written guides but youtube videos. I am surprised you all haven't packaged them in the install of the software to pop up and play as you are setting up.
Multi-Unit Manager
Order Up Cafe/Tombras Cafe/Riverview Cafe/City County Cafe
Roddy Vending Company, Inc.
www.OrderUpCafe.com
Using Square since July, 2017
Square Champion
Breaker of Things
"Good judgment comes from experience, and experience comes from bad judgment."
"You can have everything in life you want, if you will just help other people get what they want." Z.Z.
Do you want to have great restaurant menus that are easy to edit and don't cost a fortune? I use MustHaveMenus and you can too!
MustHaveMenus

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@Hailey You're asking me to remember something from 2011 when I can't even remember what I did last week?!?🙃
When I started with Square, it was simply the dongle onto a phone and the app was the keypad. The tablet version had just launched. So documentation was pretty much "plug this in, open the app, make a sale." Verification was relatively painless otherwise from what I remember. The one thing I do remember was when I called into support. I was curious if the iPad mini was going to have the same UI as the tablet or the phone. The tablet version was so new that none of the CS reps had the answer to that question! I ended up borrowing a mini and loaded Square onto it just to answer my own question.
Otherwise, I agree with @Donnie-M about how relatively smooth the onboarding process is currently. Yes, there are times where people get tripped up, that's to be expected. Having the online help files and YouTube tutorials definitely makes things easier.
Golden Pine Coffee Roasters
Colorado Springs, CO, USA
Square Champion: I know stuff.
Beta Tester: I break stuff.
he/him/hey you/coffee guy/whatever.
Happy Selling!

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It's been awhile for me as well, but I do remember the in-app messages being really helpful to guide me through how the setup process worked. I also remember getting phone calls from support or sales that helped me with certain features.
Probably like most entrepreneurs/business owners, I am quite a self-starter so I personally have no issue reading articles or support docs if I get stuck. I know some others would rather a more guided process, but with software I've always been one to "play around" until I'm familiar with everything.

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Wowza, I had to look it up but started using Square back in 2014 for our retail store and then carried it over to our little breakfast cafe that did a very small business but it was perfect for that operation. We used the little side swiper that Square offered for free and thought we were on the cutting edge of technology. 🙂 Now we have grown up and are using Square for Restaurants for our food service operation. We started with the Square Stands/iPads and were using up to eight on a busy evening. Currently, we have rotated a few Square Stands out as they seem to die quickly and have added two Square Registers. I have done all of the onboarding and all of it was done with trial and error and asking lots of questions.
We added the pre-authorization function last year and it was a game changer for our operation. It took a great deal of patience and a huge learning curve but LOVE IT more and more every day.
I never want to have a POS system where I have to rely on a company to make my updates/changes. I like to figure it out on my own, test it on my personal iPad and then implement in the system. There were times when the onboarding was a challenge but it is all intuitive as you continue to look at it. Sometimes you have to think outside the box to make something work correctly and then you realize that the answer was plain and simple and right in front of your eyes the whole time. And then there are those times that nothing is working correctly and you realize that you need to update your app, restart and keep moving forward. I also appreciate that Square is constantly working to make a better product.