How hard is filing your own global taxes?

Hey folks 👋🏻

Long time lurker, first time posting 😁

By far the topic I search for mostly on here is around taxes, and I’m sure you’ll all know with good reason given how complex it can become for SaaS businesses.

I’ve been building a premium newsletter solution on and off for a while now which I’ve currently based around Paddle in order to simplify my tax burden due to them being a Merchant of Record (MoR).

During the development though, because of the workflow I wish to follow (I want to setup a subscription but only activate it after the user confirms their email) I’ve had to do some weird setup subscribing people to a zero value plan and moving them to the true plan after confirmation and also having to request for specific emails to be disabled on my account because of this (I don’t want people receiving notifications about the zero value plan)

Needless to say this all feels a bit hacky but speaking with Padddle, this seems to be my only option with them. I can’t help but think though that this would all be so much easier with Stripe and their SetupIntents such that I can capture the customer’s details and create the subscription on email confirmation.

But, Stripe isn’t a MoR so switching to Stripe would result in me being liable to submit the relevant sales taxes myself.

I know Stripe have Stripe Taxes now for correctly calculating your global tax implications, but the one thing I can’t find info on is if you were to go this route, how hard is it to do all the filing yourself?

I’d love to hear the experience of anyone filing their taxes themselves and whether it’s a manageable and worthwhile route when you have tools that do all the calculations for you.

Are you actually filing them yourselves? Or do you have an accountant to do it for you? Are there any services out there that will file your taxes globally for you? (I know of TaxJar but this is only US specific as far as I know, so are there any services that handle filing globally?) If you are filing them yourself, how hard is it registering in all the countries you are selling into? Do you restrict signups in any areas you don’t want to have to deal with?

Any insight would be greatly appreciated 🙏