Category reporting for businesses with large catalogues is very limited currently. The system of having to choose a single 'reporting category' means that we have to choose only one hierarchy level on which to report.
We have a catalogue with around 10 top-level broad categories e.g. 'Pets', 'Gardening', 'Home' and it is useful to have a broad overview of the sales breakdown between these top-level categories in reports. However, it's also essential that we're able to look at e.g. our 'Gardening' category and see the performance of the subcategories ('Compost', 'Seeds', 'Furniture' etc.). At the moment, we have to choose one or the other. We either have just the broad reporting and can't do any drilling down, or we choose the second tier as the reporting category, but get a fairly messy list of subcategories (that display only the subcategory name, not it's parent ... which would be useful context), and we can't even group that by parent category.
There is a workaround; Category Rollups, but again, this is pretty limited because a) it has to be manually maintained (add a new category, you have to go and edit the category rollups), b) you can't roll up a rollup (so necessarily only two tiers of report) and c) these rollups aren't available in the APIs (and therefore not in third party integrations either).
I think it would be a big improvement if this 'category rollup'/drill down approach could be automatic, and in reports you could simply start at the top level categories, and drill down for deeper comparisons.
I think this would require two changes:
A) Basically, this request. Parent categories become automatically inherited. It has always seemed strange that Square allows you to put an item in its subcategory, then still have to choose whether it is also in its parent category, or just in the subcat.
B) You then choose a 'primary category' (or 'reporting category') that applies to the whole category path. E.g. an item could be in Gardening > Garden Clothing > Garden Shoes, as well as in Clothing > Footwear > Clogs ... only one can be the 'primary', and that product will report in that category all the way 'up the tree' - i.e. if the primary category was 'Garden Shoes', then when looking at the 'rolled up' report, that product would report in Gardening, not Clothing.
As well as helping with the reporting, I think A & B would also result in a simpler overall approach to categories. You simply choose one category, the first one you choose inherits its parents and by default becomes your primary category. Further categories just become secondary categories (and in the UI you can later switch which one you want to be the primary).
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