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Managing inventory between physical and online Square, using current Square system

My apologies for the long post! I’ve talked to maybe six support folks so far at Square and Weebly with conflicting and never-effective direction. Frustrating, always starting over. We have a clothing & accessories store. Maybe 3,500 SKUs in stock, and are now building an online store. Our current brick & mortar Square inventory has very limited categories (maybe two levels) and that version of Square does not permit more.  But, for the online store, we need five to six levels of categories. For example:

- Clothing

- - Beach 

- - - Girls

- - - - Cover-up

- - - - - Brand

- - - - - - Variation (size)

We've created the new categories in Square for Retail (SfR) and we'll have to hand-enter each item into SfR, argh! That's thousands of entries that we originally thought Square could do with a simple synch, but when we tried, it was an unusable, unfixable mess given the categories don't synch. But, we need to coordinate the two inventories so we don't sell the same item twice. 

Our need: I know we’ll need to re-enter each item into SfR, which is a major task given the # of SKUs. The two detailed issues are:

 

1) When we list something, say a girl’s t-shirt, it will come in generally five sizes. We want to show just one picture of that shirt online, and when the customer selects that shirt, they will then choose the size they need (which we can enter into SfR as a variation). Once sold in either the physical or online store, we need that product to then be deducted from the primary Square inventory so we don’t sell it twice. How can we do that? Please note that each variation/size has its own SKU. We only carry one of each size, being a boutique. 

 

2) Also, entering SKUs is a challenge. From what I’ve seen, when I create that item in the item library, I’ll upload the picture, click the various specifications such as shipping, then specify the sizes available in the “variation” section. But then I’ll also then have to enter the SKU in each variation line by hand, I don't see a way to import or click on the right SKU. This SKU hand-entry task SIGNIFICANTLY slows down the process and is the greatest source of error. Is there a way I can choose the SKUs from a drop down of some sort?

 

The online videos and support are too shallow to help (and talk too fast for beginners to follow). It seems that most Square support info is based for restaurants and businesses with less complicated categories than clothing stores have. We really don't want to shut the store to implement a new POS system and have to rescan everything, but maybe that's best. Any advice? Thank you!

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