Hiring an AI-Native, Client-First Bookkeeper

What this role actually is

You will not spend your day manually keying transactions. Our platform (Digits) does the heavy lifting — categorization, reconciliation, daily updates. Your job is the part software can't do:

Reviewing what the AI did and catching the things that are wrong or don't make sense
Talking to clients: asking smart, specific questions when a transaction is unclear, explaining things in plain English
Spotting things worth flagging to a founder before they ask (a spike in spend, a margin that slipped, a bill that looks off)
Owning the client relationship so they feel looked after, not ignored

If you do this well, you make 5–10 clients feel like they each have a dedicated person — because the AI handles the volume and you handle the judgment.

This role is NOT for you if:

You believe "real" bookkeeping means manually entering and checking every line yourself
You're uncomfortable trusting software to do the first pass
You go quiet when something is unclear instead of asking the client
You prefer to work heads-down and avoid client contact

We've worked with people who do it the old-school way. It's not what we want. We want someone who reaches for the tool first and reserves their brain for the hard 10%.

You'll be great here if you:

Are genuinely comfortable with software and learn new tools fast
Write clear, warm, professional English (most of the job is communication)
Have a bias toward asking good questions instead of guessing
Take ownership — you notice problems and raise them without being told
Have bookkeeping/accounting fundamentals (you understand a P&L, debits/credits, reconciliation) even if you've never run them this way

Logistics: Remote · Overlap with US business hours · Month-to-month to start, with a path to a long-term role for the right person.

How to apply (read carefully):

Start your application with the word "BACKGROUND" in all caps as the first word. (We read every application; this tells us you read ours.)
In 3–4 sentences, tell us about a time you used a tool, app, or automation to avoid doing something manually — what was the manual way, and what did you do instead?
Tell us, honestly: how do you feel about software doing the first pass of bookkeeping and you reviewing it, versus doing it all yourself?

Applications that skip step 1 won't be read.