Yes its easy, but ... in my experience, very early customers usually get special pricing, terms, and support. IMO its not worth the time to configure plans, pricing pages, and glue code that you'll probably change later. An invoice tool/service that uses Stripe or PayPal would be fine.
Also, if people can sign-up with stripe online they're also going to expect to be able to cancel, view billing history, and print invoices online. That stuff takes a little more work.
Some of this is dependent on OP's actual product, target market, and pricing. I think its better to start with a high-touch approach. Act as their account manager, hand-hold them through the onboarding process, let them know they can contact you for anything from billing to tech support.
Very interesting. I think you've made some great points there.
I like the high touch approach: it keeps you personally connected to the customer until such a time as you wish to automate away that interaction and just chase sales (but obviously still providing a great service.)
Also, if people can sign-up with stripe online they're also going to expect to be able to cancel, view billing history, and print invoices online. That stuff takes a little more work.
Some of this is dependent on OP's actual product, target market, and pricing. I think its better to start with a high-touch approach. Act as their account manager, hand-hold them through the onboarding process, let them know they can contact you for anything from billing to tech support.