Today’s plays › All plays › Collections & quote-to-cash
Put an agent on invoicing and collections the minute a contract is signed
Picked and checked by Olga Pearson, SalesUpLevel
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Reported by SaaStr's CEO after about a quarter of the agent running quote-to-cash: invoices paid late fell from 56% to 8%, average days overdue fell from 17 to 6, and the longest overdue invoice fell from 51 days to 12.
Jason Lemkin's team found that 56% of SaaStr invoices were paid late while part-time contractors billed deals by hand. They gave their AI VP of Revenue agent the whole quote-to-cash job: read the signed contract, close the deal in Salesforce, create the invoice from the real terms, send it within minutes, check open invoices daily and pull in a human at 7 days past due. It ran on 3 supervised deals before going on its own.
By Jason Lemkin, Founder and CEO of SaaStr · LinkedIn post ↗ · Oct 14, 2026
If you sell: check your own closed deals got invoiced
- When a contract is signed, have the agent read the whole contract, not just the order form, so split payments and odd terms are caught.
- Have it move the deal to Closed Won in your CRM and add any missing contacts.
- Have it create the invoice in your billing tool from the actual contract terms.
- Send the invoice within minutes to the signer, your deal contact, the business owner and a finance contact (found through enrichment if the contract names none).
- Have the agent check every open invoice daily and follow up weekly.
- Pull a human in at 7 days past due.
- Run the first 3 deals supervised, checking every invoice, before you let it run on its own.
You are our collections agent. Here is a signed contract: [paste full contract]. Here is the CRM record: [paste]. 1) List every billing term in the contract: amounts, payment schedule, split payments, due dates, billing contacts and anything unusual. Quote the clause for each. 2) Draft the invoice line by line from those terms only. If a term is unclear, flag it for a human and do not guess. 3) List who should receive the invoice: signer, deal contact, business owner, finance contact. Mark any you could not find. 4) Write a short, friendly cover email. Then, for open invoices I paste each day: [paste list], tell me which need a reminder today and which are 7+ days past due and need a human.
If you lead a team: roll it out
- Start with invoices only, supervised, for your next 3 signed deals.
- Measure % of invoices paid late and average days overdue before and after.
Watch out for
- SaaStr built its own agent; Lemkin is describing his company's internal tool, not selling one.
- It ran 3 supervised deals before going autonomous and has sent one wrong invoice since. Keep a human checking early on and cap how much it can send unreviewed.
- Sending invoices to a finance contact found through enrichment may raise privacy questions in some regions (a commenter flagged GDPR).
Source: Jason Lemkin, LinkedIn post, Oct 14, 2026. Results are as reported by the source; we did not measure them.
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