I was actually the PM at Avalara for their flagship product. Now as a founder (of a tax software business, too), we're just at the point of needing to address transactional taxes, too. Unfortunately, there are no good options here that are better than #2. I actually built global tax registration products too, and those are painful.
My POV now is that the entire system needs to be disrupted to make this lower friction. By doing this, we can unlock huge amounts of macro economic potential by just eliminating friction.
Transactional tax is so broken that technology can't make it much easier than the solutions you pointed to above. I'm focused on more fundamental disruption to address this, but it's not going to solve your challenges in the near-term.
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I was actually the PM at Avalara for their flagship product. Now as a founder (of a tax software business, too), we're just at the point of needing to address transactional taxes, too. Unfortunately, there are no good options here that are better than #2. I actually built global tax registration products too, and those are painful.
My POV now is that the entire system needs to be disrupted to make this lower friction. By doing this, we can unlock huge amounts of macro economic potential by just eliminating friction.
Transactional tax is so broken that technology can't make it much easier than the solutions you pointed to above. I'm focused on more fundamental disruption to address this, but it's not going to solve your challenges in the near-term.
If you're open to it, I would love to chat for 20 minutes, compensated as you like ofc. DMs open @ https://twitter.com/cemerick, or chas@pdfdata.com