You sold mostly within your network and it was a fully high-touch, founder-led effort, so there hasn’t ever been any need for automation or formality. Invoices are a manual yet necessary evil, where you have to go back to the original contract (sort through five or six pdfs to figure out which was the one they actually agreed to) and then make sure you’re charging them with their custom discount, and calculate the correct number of seats/usage to bill them for, and then send either a Stripe payment link or email them an invoice for them to pay via ACH.

This was never really an issue up till this point: It was a couple hours of your time once a week on Friday nights and you’re working late anyways. (And maybe you secretly don’t mind it? In a way, it’s sort of calming and therapeutic, like raking leaves or scrubbing the tile…) But that number has been creeping up – every time you onboard a new customer, you’re adding 15-20 minutes between the invoicing and the follow-up. And obviously if you hit your sales targets, that’s going to balloon.

You could hire a finance team to manually handle all this, but that would be very non-Scrappy Startup Founder of you. And eventually you’ll need to add some CS roles to handle the questions, because finance will have too many invoices to send out.

That’s actually not even the big problem though. The real issue is your pestering revenue loss from customers who are frankly underpaying and getting access to things they’re not supposed to have access to. The entitlements (if you can call them that) is on the honor system. The access data is stored in a spreadsheet that someone updates manually when they can, if they remember, but honestly nobody is checking.

When you ship new features, your grandfathered customers are keeping the same early-adopter prices but getting access to these new features. Other customers are going way over their usage – valuable revenue you could be generating.. This is really dragging down your growth, traction and revenue numbers. Investors aren’t going to want to see that come next fundraise (or board meeting).