On getting paid faster

By Garrett, 29 Sep 2025

These five cashflow levers are arguably the quickest, easiest wins when optimizing your service business.

Frequency of online payment deposits

Update your online payment system to deposit into your bank account daily instead of weekly. Or whatever the quickest interval available. Yes, this adds a bit more bookkeeping work, but you’ll no longer have a week’s worth of cash sitting unused in Stripe (or similar) when it could be in your bank account instead.

Reduce invoice payment terms

Change your invoice payment terms from 30 days to 20 days. This is a simple update that immediately accelerates (most) cash by 10 days. Most clients won’t push back and will be happy with the terms you set.

Automated payment reminders

Set up automated payment reminders if you haven’t already. For instance, Harvest’s default sends a reminder 3 days after an invoice is late, and every 7 days after that. You can customize the times and adjust the subject and body contents to lean more human than robotic to ensure your payment reminders are on brand.

Restructure payment milestones

Different services and project types warrant different payment terms. And especially for the larger projects, we need to make sure we never go too long without income. For instance, a typical multi-month project could be billed as 50% up front and 50% on completion. But, depending on timeline, that could leave a lot of empty room in the middle.

For example, if you’re doing work that requires a feedback phase, consider billing 50% up front, 30% at the feedback phase, and 20% on completion.

Bill more frequently

This one is for smaller, on-off projects: maintenance, support, etc. I used to bill monthly for this type of work and would sit down and send 50-100 invoices all in the same day. As we grew and were looking for ways to improve cashflow and get better real-time visibility, we adjusted our process for this to a Friday morning event. Grab a cup of coffee, chat through what was complete that week, and send 5-10 invoices. For smaller invoices (which is what most of these were) clients often paid on receipt, even when terms say net-20 or 30.

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Quick, fairly conservative math says that these levers can accelerate your cash collection by 20-45 days, freeing up $50K-$100K+ in cash for every $1M in annual revenue.

There are a thousand ways to set up this system, but my favorite is a mix of Stripe, Harvest and Quickbooks or Xero. There’s also the simpler Stripe + Freeagent option.