We recently sat down with Maria, Senior Operations Associate at Jumpstart, and Sam Skerratt, Adfin's Head of Finance, with our Chief of Staff Lucy Grant hosting, to talk about getting paid reliably before you have a finance team. All three have owned billing at a growing business. Here are the key insights from the conversation.
In short
- A first billing process can be scrappy, as long as it's systematic and everything lives in one place.
- Every reminder should include a way to pay, and customers who don't respond need a human follow-up.
- It's much easier to agree how a customer pays when they sign up than to change it later.
- An invoice isn't cash. It's worth tracking what's been collected, not just what's been billed.
Start simple, but keep it in one system
Most early billing processes are improvised, and that's fine. At Jumpstart, the founder originally sent invoices to the team first and emailed them on by hand, with every chase done manually. Adfin's first version was a Google Sheet of customer usage and a script that generated PDF invoices, which were uploaded into Adfin and sent from there.
What made Adfin's version work was that the answers lived in one system. Has this customer been invoiced? Have they signed their mandate? Have they paid? All of it was visible in one place and synced to the accounting software, which kept month end simple. Most customers also signed a direct debit mandate up front, so once they'd signed, there was nothing to chase.
What is reconciliation?
It's matching the payments that arrive in your bank account to the invoices they're paying, so your accounts show what's been settled and what's still owed.
Make paying as easy as possible
Automating invoices and reminders early saves time on the customers who'd pay anyway. But as Jumpstart grew, two gaps showed up. The reminders didn't include a payment link, because the tools in use couldn't add one without engineering help. And nobody was talking to the customers who weren't paying.
When overdue debt built up, Maria and the founder spent two weeks calling customers, and after each call Maria emailed a payment link with a full explanation of what the invoice was for. Most paid quickly once they had everything in front of them.
"Make it as easy as possible for the customer to pay and the customer will pay you much quicker."
Maria, Jumpstart
People still reply to people
Customers often ignore several automated reminders and then reply straight away to an email from a named person. Lucy found this at Adfin when invoices started going overdue and she was copying details from Adfin into an email template by hand.
That manual process became the first version of Adfin's personalised reminders. You connect your own email, Adfin reads the invoice, and it drafts a reminder with the customer's name, the invoice number, the amount and a link to pay, sent as if it came from you.
Agree the payment method at onboarding
If customers have paid by bank transfer for years, asking them to move to direct debit or card on file can feel like a renegotiation, and it may prompt them to reassess the whole service. It's far easier to build the payment method into onboarding from day one.
What is card on file?
It's a customer's card details saved securely, with their permission, so you can take payment automatically when an invoice is due.
If you do need to move existing customers, it helps to explain what's in it for them. A reliable collection cycle keeps your costs down, which helps keep prices stable and pays for improvements to the service.
The pattern shows up in Adfin's data too. Customers with the lowest outstanding receivables tend to be the ones with a clear process from the start. For accountancy firms, that usually means a direct debit mandate signed with the letter of engagement.
An invoice isn't cash
It's easy, especially in a subscription business, to treat a sent invoice as money in. The system records revenue, everyone moves on, and nobody's watching when the cash arrives. Board and investor reporting then overstates what's actually been collected, and by the time someone notices, there can be months of history to unpick.
Tech businesses aren't exempt from credit control either. The question is how much of it software handles and where people step in.
Let software carry the volume as you grow
For a long time, more invoices meant more people to chase them. Software has broken that link. Before hiring someone to chase by hand, it's worth putting the right software in place, so the people you do hire spend their time on the conversations that need judgement.
Prevention helps as well. At Freetrade, Sam's team could see the habits of late payers in the data, and instead of chasing harder, they changed the onboarding and invoicing flow so fewer payments went late in the first place.
Jumpstart shows what this looks like in practice. Since moving to Adfin, its invoice volume has roughly quadrupled and Maria still runs invoicing on her own. In the first quarter, outstanding debt fell by 75%.
What a first finance hire wants to inherit
A first finance hire wants two things on day one. Clean customer data, so they can say who the customers are, when they pay and how. And a reconciliation that already works, so invoices match cash and month end closes without drama.
Without those, their first months go on clean-up. With them, they can get on with the forward-looking work they were hired for.
"Invoice to cash, if it's boring in a finance function, that's always a good thing."
Sam Skerratt, Adfin
A few things you could try
- Check that every invoice and reminder you send includes a payment link.
- Call the customers who've ignored more than two reminders, then follow up with the link.
- Add a payment step to onboarding, so new customers set up direct debit or card on file before their first invoice.
- Compare last month's billed revenue with the cash you actually received.
- List everywhere your billing data lives, and bring it into one system.
Common questions
When should a startup automate invoicing?
Once sending and chasing invoices starts taking time away from the work itself. Jumpstart automated sending first, then added payment links and smarter reminders once overdue debt started building.
Do startups need credit control?
Yes. Every business that invoices needs some form of credit control. The decision is how much of it software handles and where people step in.
How do you move customers from bank transfer to direct debit?
It's easiest at onboarding. For existing customers, explain the benefit to them, such as fewer reminders and more stable pricing, and expect it to take a conversation.
What should a first billing process include?
One place where customer, invoice and payment status live, a payment link on every invoice, automatic reminders, and a sync to your accounting software so month end is simple.
