[rahimnathwani]

When you selected accountants #2 and #3, did you specify your requirements (paperless workflow, data exchange in the cloud, importing existing data)?

If so, did they say they could satisfy those requirements, and then later fail to do so? If so, did they give any reason why they misled you?

[rhythmvs]

Yes we did, and they promised a completely paperless workflow, relying on Dropbox for upload of raw documents (invoices, bank and credit card statements), and proprietary accounting software which would ‘automagically’ fetch, parse (including OCR), categorize, and eventually book those.

They did not maliciously mislead us, but failed on their promise because apparently the ‘automagical’ part does not seem to work out so well. Yet, that, imho, is more the fault of the implementation and of its users (the accountants), than it is because such things are too hard to accomplish with the state of current software development (and ‘AI’).

For one, I found it beyond comprehension that any such software would blindly rasterize well-structured PDFs, as does the software used by our accountant, to then OCR the resulting low-res jpg, while wastefully of resources throwing away most of the relevant information, with obviously bad ‘detection’ results. Worse, duplicate uploads would differ, resulting in double bookings requiring the accountant’s assistant using the software to manually fix those errors produced by the software. In the end we end up with a much more expensive accounting bill than we would have had when we sticked to a paper-based flow.

But is doable, and I truly hope some startup grabs the opportunity to implement it well.

[rahimnathwani]

So they didn't mislead you, but it sounds like the service they sold you was something they had never delivered before. So perhaps they were optimistic, hopeful, or just thought "what's the worst that can happen if we can't deliver?"