Automated Bench Bookkeeper Question Chasing
Every morning, WebRun opens Bench, reads the in-app messages from your bookkeeping team, finds the questions still waiting on an answer, matches each one to the transaction or document it concerns, drafts a Gmail reply for your approval, and cards the open items in Trello.
How do I keep on top of my bookkeeper's open questions?
Every morning, WebRun opens Bench, reads the in-app messages from your bookkeeping team, and pulls out the questions nobody has answered yet, with the transaction or document each one concerns. It cards them in Trello and drafts a Gmail reply for you to approve, so the month closes on time.
- The month closes on time instead of stalling on one message
- Every question arrives with the transaction it concerns attached
- Close blockers sit at the top of the board every morning
Built for small business owners · founders · freelancers · office managers
What does WebRun do on every run?
The exact actions WebRun takes, in order - in plain language, so you can adjust anything.
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WebRun signs in and gets to work
Opens
bench.co/loginin a real browser with your saved login - no setup, no API keys. -
1
Bench - find unanswered questions
bench.co
WebRun opens Bench to find unanswered questions. - Open Bench and go to your messages with the bookkeeping team
- Read every thread and pick out the questions that have no reply from your side
- For each question, find the transaction, receipt, or document it refers to
- Note how many days each question has been waiting
- Check which of them block the current month close
- Record what is needed to answer: a receipt, a category, or a short explanation
Done when Every unanswered bookkeeper question is listed with its transaction and its age.
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2
Gmail - draft your reply for approval
gmail.com
WebRun opens Gmail to draft your reply for approval. - Draft an email summarising the open questions and the answers you have on file
- Attach nothing and assert nothing you cannot see: leave the unknowns marked as unknown
- Leave every email in Drafts. WebRun never replies to your bookkeeper and never posts an answer inside Bench
Done when A reply summarising the open questions sits in Drafts, unsent.
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3
Trello - card what is still open
trello.com
WebRun opens Trello to card what is still open. - Open a Trello card for each unanswered question
- Put the question, the transaction it concerns, and the days waiting in the card
- Mark the cards that block the current month close so they are cleared first
- Move cards that were answered overnight to Done
Done when The board shows only questions still waiting on you, close blockers first.
How is each run configured?
Secure by default
Connect once, stays signed in
WebRun signs in once and keeps each session in a persistent environment, so every run picks up right where it left off.
Every action is checked against this policy before it runs.
Questions, answered
Will it answer my bookkeeper for me?
No. WebRun never replies inside Bench and never sends the email. It drafts a reply in Gmail from what it can see and leaves it for you to check, because only you know what a payment was really for.
How does it know which transaction a question is about?
It reads the message thread and matches the amount, date, or merchant named in the question to the transaction in your Bench account, then puts both on the same Trello card.
What if a question blocks the month close?
Those are marked separately and moved to the top of the Trello board, so the one unanswered message holding up the close is the first thing you see.
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Put this on autopilot.
Turn it on in minutes - or have our team set it up for you.