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Get paid without chasing: invoices, portals, and follow-up

Brian Guy, founder of Stairkey
Brian Guy
Founder — working contractor & realtor · June 10, 2026 · 5 min read

Most unpaid invoices aren't disputes — they're drift. The job wrapped, the invoice went out late, the follow-up never happened, and now it's awkward.

The fix is less about persistence and more about plumbing: make the invoice fall out of the work, keep its status somewhere you actually look, and let follow-up run on rails.

1. Make the invoice fall out of the job

In Stairkey, finished work becomes the invoice — one-off jobs, recurring services, or completed scheduled visits. The line items come from the work that was actually done and approved, so there's nothing to retype and no reason to put it off until Sunday night.

For retainers and repeat arrangements, recurring invoices go out on schedule without you touching them.

2. Keep payment status where you can see it

Draft, sent, and paid live beside the job, with outstanding totals at a glance. "Who owes me what" is a screen, not a reconciliation project — which is what makes consistent follow-up possible at all.

3. Close the approval gap before it becomes a payment gap

Late payments often start as fuzzy approvals. When estimates and change orders are approved in the client portal, the sign-off sits on the same record as the invoice — the client is paying for something they can see they agreed to.

Tip: Invoice the day the work wraps. The same bill reads as housekeeping on Friday and as a demand letter three weeks later.

4. Put follow-up on rails

Stairkey's email tools send from your own business address, with personal templates for the messages you write over and over. Multi-step sequences can handle the polite-reminder cadence — and they pause when the contact replies, so nobody gets a robotic nudge mid-conversation.

5. Let the books catch up by themselves

With the optional accounting add-on, invoices, expenses, and change orders post into double-entry books from the records they came from. Getting paid and recording that you got paid stop being two separate chores.

Every step. Handled.

Try this workflow on your own jobs — every feature unlocked, first month free, no card required.