By OptiVal Editorial Desk
Three months ago you hired a remote bookkeeper. The first month was training: logins, the chart of accounts, where the receipts live. The second month was the first real close, probably a bit rough around the edges. Now the third month is done, and that means it is time for an honest remote bookkeeper review.
Day 90 is the moment of truth for any hire, and it matters more for a bookkeeper you never see in person. You cannot watch them work. You can only judge the output. So judge it properly: a short, evidence-based review that separates a keeper from a costly mistake.
Set the bar before you score anything
By day 90, a competent remote bookkeeper should have completed three month-end closes under their own steam, kept day-to-day entries current, and produced books you can trust without spot-checking every line. You should be able to open your accounting software and believe the balances. Monthly reports should land on a schedule. Payroll and filings should simply happen, on time, without reminders from you.
If training took 30 days and the first clean close took another 30, then the third close is the real test. That is what you are grading.
The 90-day remote bookkeeper review scorecard
Score each of these pass or fail. Evidence, not vibes. Pull the actual numbers before the conversation.
1. Close speed
The books should close within 10 business days of month-end. That is a generous bar. One widely cited APQC benchmark puts the median monthly close at 6.4 calendar days across more than 2,300 organisations, with the top quartile finishing in 4.8 days or less. Small teams with under 500 monthly transactions can reasonably target a five-business-day close when the data is clean. And the minimum standard for books you can actually operate from is a close within the first two weeks of the following month. Three months in, your bookkeeper should be at or under 10 business days. Missing that repeatedly is a fail.
2. Reconciliation completeness
Every bank account, credit card, and loan reconciled every month. Zero unreconciled items older than 90 days. No growing “ask my accountant” holding account full of mystery transactions. Finance teams that run a tight close target near-100% reconciliation completion on key accounts by the close cutoff. If your bookkeeper’s recs are current, the balance sheet is reliable. If they are not, nothing downstream is.
3. Monthly reporting
You should receive a profit and loss statement, a balance sheet, and a cash flow statement each month, plus a plain-English note on anything unusual: a big variance, a margin shift, a customer balance aging past 60 days. A report that arrives six weeks after month-end is a history lesson, not management information. The right monthly package should leave you better able to act, not just better informed.
4. Payroll and remittances
Every payroll run and every CRA remittance on time, no exceptions. The schedules are not negotiable: employers with average monthly withholding under $25,000 remit monthly by the 15th; $25,000 to $99,999 remit twice monthly; $100,000 or more remit within three business days. Late penalties escalate from 3% to 10% depending on how late, and a repeat failure can hit 20%, with interest compounding daily at the prescribed rate. One late remittance in 90 days is a serious mark. Two is a pattern.
5. GST/HST filings
Filed and paid by the deadline, every period. Businesses with $1.5 million or less in annual taxable supplies file annually; $1.5 million to $6 million file quarterly; over $6 million file monthly. Quarterly filers, the most common setup for growing small businesses, must file and remit within one month after quarter-end. If your bookkeeper has missed or scrambled a filing in the first 90 days, treat it as a red flag, not a growing pain.
6. Communication
A weekly check-in or written update. Questions batched and specific, not a daily drip of “what is this invoice for?” A reply within one business day. Remote only works with rhythm; without it, small gaps become month-end surprises. (We wrote a whole playbook on communication cadence for a remote finance team if yours needs structure.)
7. Proactivity
Does your bookkeeper flag a cash crunch before it lands? Chase an overdue invoice without being asked? Ask for missing receipts before month-end instead of after? This is the line between data entry and a real bookkeeper. At 90 days you should have at least two or three examples of them catching something you missed.
Five red flags at 90 days
If any of these sound familiar, the review conversation needs to be blunt:
- The books are still more than two weeks behind at month-end.
- Your tax bill would still be a surprise; nobody is tracking it during the year.
- The same miscodings keep repeating after you corrected them twice.
- You chase them for updates instead of the other way around.
- Everything is “fine,” but you still cannot answer “what is our cash position?” from the books.
Green flags worth keeping
On the other side, these are the signs you hired well:
- They found and fixed their own error, then told you before you noticed.
- Month-end close got faster each month, not slower.
- They built or improved a process doc without being asked.
- They ask questions about the business, not just the transactions.
How to run the review in 30 minutes
Keep it simple and keep it written. Send the seven scorecard items ahead of time and ask your bookkeeper to self-score each one from 1 to 5. Then:
- 10 minutes: their view. Let them talk first; you will learn how self-aware they are.
- 10 minutes: your scores, with evidence. Numbers and dates, not adjectives.
- 5 minutes: three things going well. Name them specifically.
- 5 minutes: three fixes, each with a date attached. Vague goals die; dated ones get done.
End by agreeing on the next-90-day targets in writing. Good examples: close by business day 7, zero unreconciled items over 60 days, the monthly report package in your inbox by the 10th.
If the scorecard says it is not working
Be fair but be decisive. A 30-day improvement plan with one or two measurable goals gives a struggling bookkeeper a real chance and gives you a clean, documented decision if it does not work. And if you do part ways, protect the handover: revoke and reissue system access, take a full export of the books and supporting documents, and settle final pay on schedule. Our secure offboarding checklist for a remote bookkeeper walks through the whole process.
If the review leaves you thinking the books deserve better, that is exactly what we do. OptiVal’s remote bookkeeping starts at $199/month, delivered by an offshore team led by qualified professionals with more than 75 years of combined experience. If the books are a mess, cleanup from $45/hr gets you current first. Book a free consultation and we will take a look at where things stand.
