Work sample 07 / 17Clean-up & reconciliation
Recurring billing and contract tracker, from signed contract to paid invoice
How I set up a contract register that drives retainer and milestone invoices in Xero, with renewals and overdue accounts in view.
- Area
- Clean-up & reconciliation
- Tools
- Xero · ClickUp · Make
- Typical scope
- US$1,500–3,000
- Timeline
- About 4 weeks · 4 fixed milestones
Work sample: realistic data, built to show how I approach this kind of project. Not a past client job.
01The problem
Agencies and consultancies with retainers and milestone contracts often raise invoices from memory and a calendar. Retainers get missed, milestones are billed before the work is done, expired contracts keep billing and renewals are noticed late.
A contract register that drives the invoice schedule, with checks on every row, makes billing predictable and leaves approval with a person.
Owners usually notice it as
- Invoices raised from a calendar reminder
- Contracts in several currencies
- Renewal dates kept in email
- No single view of what is overdue
02Scope
A fixed scope agreed in writing before anything is built. The table shows what a project like this usually covers and what it leaves out.
| Area | Included |
|---|---|
| Contract register | Type, currency, term, billing day, renewal notice and status by formula |
| Invoice schedule | Retainers on their day, milestones on a 'task done' flag, duplicate key on every row |
| Xero | Repeating invoices for retainers, drafts for milestones |
| AR tracker | Reminder stage set from days overdue |
| Automation | ClickUp and Make steps from won deal to paid invoice |
| Not included | Collections calls and legal follow-up |
Typical volumes for a business of this size. The sample files are sized as described in section 05.
| Milestone | Deliverable | Timing | Share | Weeks 1–4 |
|---|---|---|---|---|
| M1 Map and design | Current process, register design, automation map | Week 1 | 25% | |
| M2 Register and schedule | Register, schedule and checks built and loaded | Week 2 | 30% | |
| M3 Xero and ClickUp | Repeating invoices, milestone drafts, Make scenario | Week 3 | 30% | |
| M4 Handover | Month-end checks, SOP, walkthrough | Week 4 | 15% |
Typical scope for this kind of project: US$1,500–3,000
About 4 weeks across 4 fixed milestones. The fixed quote follows a US$300 Systems Health Check, which confirms the volumes and the scope first. Your software subscriptions are billed to you by the vendors.
03What I fixed, and why
Construction drawing. Each stage has its own check before the next one starts.
- 01
Start from the contracts
Every invoice should trace back to a contract row with its terms.
- 02
Schedule, then automate
The schedule is built and checked before any automation is switched on.
- 03
Hold, don't bill, when unsure
An expired contract or missing task flag holds the invoice for review.
- 04
Keep a person in the loop
Drafts are approved in Xero before they are sent.
- 05
Check monthly
A Checks tab confirms no duplicates and no billing outside a contract window.
04Checks
Nothing goes live on trust. These checks run before sign-off and stay in the files, so they can be re-run after every change.
- No duplicate invoice keys
- No invoice scheduled outside its contract window
- Milestones only billed when the task is done
- Overdue stages match days overdue
- Renewals inside the notice window flagged
| Check | What it catches | Status |
|---|---|---|
| No duplicate invoice keys in the schedule | One contract, one period, one invoice. Stops double billing. | PASS |
| Milestone % adds to 100% (C-103) | Every dollar of the project is billed once. | PASS |
| Milestone % adds to 100% (C-104) | Same for the one-off project. | PASS |
| Every retainer live in Nov has a cleared Nov invoice | No retainer is missed in the month. | PASS |
| Schedule rows held outside a contract window | Expired or unrenewed contracts are held, not invoiced. | INFO |
| Month total = cleared + waiting rows for the month | The summary agrees with the schedule. | PASS |
Status read from the sample workbook. Each check is a formula, not a typed value.
05Handover
Everything is handed over in editable files you own, with the steps written down so your team is not dependent on me.
In this work sample
A contract register, a 12-row invoice schedule with checks, an AR tracker and an 11-step automation map, small enough to read end to end.
- Contract register and invoice schedule workbook
- Xero repeating invoices and draft rules
- Make scenario and ClickUp set-up
- Month-end checklist
- A recorded walkthrough
06Files in this work sample
Screens from the sample files. Select one to open it full size.
| File | What it is | Size |
|---|---|---|
| Recurring-Billing-and-Contract-Tracker.xlsx | Workbook: contracts, milestones, invoice schedule, AR tracker, automation map, month summary and checks | 24.3 KB |
Tell me what’s bugging you and I’ll tell you where I’d look first.
Send a short note on Upwork about what is slowing the business down. I’ll reply with where I’d start, and whether the US$300 Systems Health Check is the right first step.