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Cart Features at Checkout - Drive Sales and Customer Engagement
I was just wondering what other users experiences are of the Square Cart on checkout and could this be improved, streamlined or is it doing a great job as it is?
For me it feels a missed opportunity to drive sales and connect with the customer on checkout. So looking at the checkout for other systems, things like the spend bar, which shows the progression of our spend to unlock free shipping, is great it encourages more buying (even with the concession of free shipping), then there is gift wrapping at checkout and add a note (not at the item level but at checkout), nice personal touch. Then there is the upsell, the 'you may also like' in the cart. These are all super ways to engage and drive sales. See image below.
What features like this have you comer across which would enhance the checkout experience and help drive your sales.
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We carry many products that have accessories available as an upgrade (high margin). For scooters and wheelchairs we have cup holders, cell phone holders, etc. and for lift chairs we have fabric upgrades like leather and cross-over fabrics. We utilize Square's modifiers functions to present these options at checkout. This helps are team be consistent in offering and, in most cases, a client will opt for additional accessories (we also have these accessories outfitted on your showroom stock, so customers can't miss it). It also provides us an easy way to provide overall price to a customer without having to lookup prices elsewhere.
I like the "free shipping" based on spend idea. We manage this on transaction by transaction, but having an automated capability would provide consistency. Its similar to how we present our service plan (2nd picture below). We offer the plan on specific categories and mark the selection at transaction.

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@CSprink I like the modifiers route, makes for a good method to upsell.
I like the spend to free shipping idea, its a nice visual progress bar, draws one in to spend a little more to hit the free shipping trigger.
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yes i feel there is room for a lot of improvements for the stores side of square site and i am working on a start up with a ship station and having major issues with shipping costs between online and in person sales
[1] if you want to make the shipping free base off price you can use rewards just an idea just need to do some magic math like 1 star is 0.01 or they just see it as spending making items cheaper .. but there be a bump every now and then
say the goal is 35.00 in spend usually people buy like 20 things/$value at 1.00 the 1 star needs to be 1.75 in spending/earnings to get free shipping or items /reduced costs can cut it many ways
[2] the problem i see is its easy to manage the in person stations over the online
- so the online i want to add the card fees and shipping packages in there own lines not baked in for transparency/accounting to customers
-so online only shows on check out is the area taxes and shipping cost not able to adjust theses so i cant apply the card fee
-then in person station i am able to have those lines and manage all the costs and add the card fees but not its own line
so as a start up i find it a huge pain i cant display these and or make it work cross platforms
[3] more features behind the pay wall slowing growth and profits for both square and me because some marketer big wig figured its a good idea to sell more subscriptions but if the product is not fully fictional to joe average no tech guy .. it just makes things harder for all
- so the "item cost" just got put behind the pay wall and making accounting more a huge pain on reports so unless you keep records in other spits then you cant tell your cap gains for taxes or extra
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Agree on the basket for online - I feel it could definitely be doing a bit more. Love the idea of the free shipping!

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Great post @doc_choc , there is a free shipping progress bar option, I've been using for a while, and I think it's motivational for customers to keep adding to their cart until they get free shipping. I have my shipping profiles set by cart dollar amount, so my shipping costs progressively increase as their cart gets more full, but at a certain point the Shipping becomes Free. I think this makes ordering more seem more cost effective. You can see the setting here:
https://www.weebly.com/app/store/users/126405578/sites/122496413704188776/#/store/checkout
You have to enable "Fulfillment progress meter in cart "
Note: you'll have to set a free shipping option first so you'll be able to enable the progress meter.
Homestyle Charlie
Handmade Heirloom Ornaments & Charms
Check our links for retail Etsy orders and Wholesale Ordering Info

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@HC_Charlie thanks for the information on this, thought it would be a feature that made sense for Square to have on their system. Just checked and its not available outside the US just yet. 😭
- You must have a US-based Square account.
- You can only have one default shipping profile with free shipping.
- The shipping profile must offer free shipping throughout the lower 48 US states (the continental United States).
Hopefully it will arrive this side of the pond soon 😊🙏

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@Marco How can we get this fullfillment meter in Canada?

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Square Online/Weebly needs so much help...I feel like they're just not trying to improve it much.
These are my thoughts:
- I checked out your website and I love the font choice for your products!
- I've never actually been able to get free shipping progress bar to work on my store.
- I would love to see an upsell option. I sell candles, and in the summer, it would be so helpful to be able to have an icepack recommendation in the cart.
@isabelle I know you probably have 150+ tags to review...but are any of the Square Online product managers in the community to chime in?
Square Champion | Innovator
Wood Candle Co | Verona, WI | USA
Socials: Instagram | Facebook | LinkedIn
Online: woodcandleco.com
LGBTQ+ owned business.

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We too have a temp sensitive product, so I like the idea of the icepack recommendation upsell.
Perhaps its a little bug stopping it from working?? Do you have more than one default shipping profile with free shipping? The link from @HC_Charlie below gives instruction on how to add the progress bar. I see you are US based so this should be active in your region.
Manage online checkout options | Square Support Center - US

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I love the idea of suggested products.. also- no idea about free shipping progress meter- does anyone know how to turn it on?
Co-Owner Amityville Apothecary
www.shopamityvilleapothecary.com
Instagram | TikTok @AmityvilleApothecary
Podcast: Apothecary After Dark (YouTube & Spotify)

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Hi @DinaLRosenberg, instructions link for turning on the 'free shipping progress meter' supplied by @HC_Charlie see below.
Looks pretty straightforward to do. 😊

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I can't access via weebly- wondering if there was a way to access via square online
Co-Owner Amityville Apothecary
www.shopamityvilleapothecary.com
Instagram | TikTok @AmityvilleApothecary
Podcast: Apothecary After Dark (YouTube & Spotify)

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@DinaLRosenberglook at this are on your Square Dashboard...
Online > Settings (or Shared Settings) > Checkout
Hope you can find the setting...its in the last Section called Checkout experience
Homestyle Charlie
Handmade Heirloom Ornaments & Charms
Check our links for retail Etsy orders and Wholesale Ordering Info

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Thanks!! apparently we already had this turned on!
Co-Owner Amityville Apothecary
www.shopamityvilleapothecary.com
Instagram | TikTok @AmityvilleApothecary
Podcast: Apothecary After Dark (YouTube & Spotify)

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Great thread with some excellent points already shared! Here are a few ideas I believe would significantly enhance our checkout and drive customer engagement even further:
Item Subscription for Local Delivery: Allow customers to easily subscribe to items they frequently purchase, especially beneficial for local delivery services. This convenience boosts repeat sales and customer satisfaction.
Smart Upsell Recommendations: Implement upselling by suggesting frequently purchased items that customers haven't added to their current cart. This can increase average order values effectively.
Encourage Reward Redemption at Checkout: Before finalizing payments—whether in-store via POS after confirming loyalty members or during online checkout—prompt customers to redeem available rewards. This emphasizes value, reduces outstanding reward liabilities, and promotes loyalty program engagement.
Allow Unverified Address Orders with Flags: To reduce abandoned carts, let orders with unverified or partially verified addresses proceed through checkout while clearly flagged for manual review. This ensures fewer missed sales opportunities.
Re-engage Customers Opted Out of Marketing: Offer gentle opt-in prompts during checkout to customers who've previously opted out of marketing communications, highlighting benefits or incentives to encourage reconnection.
Curious to hear your thoughts and see what other suggestions might be out there!

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@JTPets really liking some of your ideas such as gently re-engaging with customer who have opted out, if they like your product to keep returning they may be encouraged back, I have signed in and out of the same newsletters many times and keep coming back especially if they are a more seasonal company. Also the encouraging of reward redemption at checkout, not everyone is tech savvy so on the Register we end up walking them through their available rewards so if this could be improved.
I just think there are some great ideas where technology can help us drive the sales, capture and engage customers at checkout. If done well it should require minimal input from the from the business owner and the customer, keeping it simple. The first sale is great, the repeat purchase is the big win!
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I love these ideas too. I think we would use all of them.