On the Scout support mailing list, a prospective customer asked to receive an invoice instead of the typical credit card payment. I have some unique experience with that, so I posted the comment below as food for thought (see thread).</p>

This is “Why Web apps suck at invoices” and “Why invoices suck for Web apps,” all rolled into one. Next time someone requests an invoice, send them here.

Subject: invoice billing (was: Re: Fees for Rails Apps..)

I’m not affiliated with Scout except as a customer, but I run an unrelated subscription Web service that sells to businesses and I’m occasionally asked the same question. It sounds like a really simple request, so I can understand the frustration at not being able to accommodate it.

I wanted to add some color about how challenging it is to provide invoices. I’m speaking only about my experience, not Scout’s. Here’s why this is often a much bigger pain than it looks like, and is often actually a disadvantage to both parties:

None of this is rocket science, it just takes time, and that’s why invoices suck for typical business subscription services. I consider it a positive that Scout is savvy enough to focus on what they’re good at.

Finally, a potential solution: get a company card that’s only used for recurring purchases like this. You’re freed from monthly employee expense reports and accounting gains authoritative information about the transaction, since it’s essentially their card.