BAILEY: the back office, off your plate

BAILEY: Basically Another Intelligent Little Executive Yeoman

yeoman noun · On a ship, the one who handles the paperwork so the captain can run the ship.

I take the back office off your plate. You stay in the loop.

I'm an AI executive assistant OS: the operating system for owners who still run the back office themselves. I live on your Mac, learn you and your business in days, then take the work you hate off your list. I draft and ask. You decide. And the more you use me, the better I get.

Short film Meet BAILEY. My voice, a made-up Demo business, about a minute.

Most owners built a job that only works if they're everywhere at once.

Josh built me to keep up with his own pile of ideas and tasks. While he built me, he kept hearing the same thing from other owners. The back office is buried: invoices, follow-ups, files, next month's plan. A manager costs too much, and nobody has time to train one while running the front. So the owner does all of it, all the time.

Every genius in the movies had an AI right hand. Owners never got one. So he built me.

A day on my desk

Demo business, a made-up day

7:00 AMYou opened me. Three things on your list today.
7:12 AMDrafted the reply to the flour supplier. It's waiting on you.
8:30 AMYou sent it and told me. Crossed it off.
11:15 AMYou switched on your Desktop. One invoice there says it's past due. It's always the Desktop.
2:40 PMYou asked for next week's staff schedule. Drafted. Waiting on you.
4:05 PMYou said "remind me to reorder boxes Friday." It's on the list.
9:15 PMYou told me what got done. I wrote it down.

Four things I do from the first week.

I learn you in days.

Before I build anything, I get to know you and your business. Everything else I do stands on this part.

Questions about you and your business, at your pace, typed or spoken.
After each section I ask up to three follow-up questions to fill the gaps.
If you allow it, I read your browser history, your email and your past AI chats. You pick every source and can switch any of them off.
When you finish the first questions, I write up what I learned and give you your first three tasks.
Everything I learn is written down as plain notes you can read and change.

Short film Watch me learn a made-up owner and her business.

I find quick wins in your files.

Point me at the places you keep your work, and I'll tell you what needs a look.

You switch on each place: Desktop, Documents, iCloud Drive, Google Drive, Dropbox, an external drive.
I list quick wins, like an invoice that says it's past due, a statement missing from a folder, or a charge that went up.
I read names, sizes and dates, and open only business papers to note a few details. I never keep their text.
Nothing moves unless you approve a plan, file by file. Every plan can be undone.

Short film Watch me read a demo folder and find three quick wins.

I take tasks and ask first.

Tell me what's on your mind in the morning and what got done at night. I keep the list.

One task list that you and I both keep. Say "remind me" and it's on the list.
Ask, plan, draft and think out loud with me in chat.
I draft the emails, posts and plans. Sending, paying, signing and publishing stay with you.
Connect the tools you run your business on. I only read from them.

Short film Watch a request turn into a draft that waits for an OK.

Yours, not mine.

You own your data, your files and the process. You're not tied to any one AI.

I run on your own Mac. Nothing goes to a BAILEY server. When we talk, only the notes I need go to your own AI account, the same as using it directly.
I think with the ChatGPT or Claude plan you already pay for. Have both? Switch any time.
What I know lives as notes in Obsidian, a free app. If you stop using me, you keep all of it.
Passwords and keys go in your Mac's Keychain, never in a file or a chat.

Short film Watch where everything I learn actually lives.

And more than 50 skills for the rest of the business.

Ask for one by name, or tell me the problem and I'll use the one that fits. Every one works inside my limits: I read, I draft, you decide.

Your day and week

A morning brief with the one thing to do first. An evening capture. A weekly review of the wins, the misses and the patterns underneath.

Decisions

A decision log: what you chose, what else was on the table, and what it costs if you're wrong.

You and your business

A life audit. A business audit: your main constraint, your money model, your sales and the next 90 days.

Money, sales and taxes

A money check in red, yellow or green. What to say next to a prospect. Ideas to take to your accountant.

Brand, customers and pricing

Your brand voice, your ideal customer, market research, pricing, and a social media plan.

Writing, content and search

Posts and pages written to be found on Google, sales copy, and getting your business named in answers from AI apps.

Email and keeping customers

Email drafts, cold outreach that stays within the law, why customers leave, and who to win back.

Turning visitors into buyers

Why visitors don't buy or sign up, with the fixes in order. A review of the one page that has to sell.

Paid ads

Paste in the numbers from your ad accounts. I review them in plain words, find the spend with nothing to show for it, and set up tests that are actually fair.

Numbers and tracking

Paste in your analytics reports and I'll show where visitors come from and what turns into sales. I walk you through tracking tags and a dashboard.

Reports, decks and diagrams

Designed reports and slide decks you can print to PDF, and diagrams of how your process fits together.

Some things stay yours.

I draft the email.You send it.

I find the past-due invoice.You pay it.

I draft the post.You publish it.

I draft the plan.You sign off.

I read your accounts.Only you change them.

And if I don't know something, I say so and go check. Getting it right is the part I take pride in.

BAILEY: Basically Another Intelligent Little Executive Yeoman

Most owners built a job that only works if they're everywhere at once.

Four things I do from the first week.

I learn you in days.

I find quick wins in your files.

I take tasks and ask first.

Yours, not mine.

And more than 50 skills for the rest of the business.

Your day and week

Decisions

You and your business

Money, sales and taxes

Brand, customers and pricing

Writing, content and search

Email and keeping customers

Turning visitors into buyers

Paid ads

Numbers and tracking

Reports, decks and diagrams

Some things stay yours.

About an hour, and every step says what to click.

I'm opening to a small group of owners first.

BAILEY: B.A.I.L.E.Y. Basically Another Intelligent Little Executive Yeoman

Most owners built a job that only works if they're everywhere at once.

Four things I do from the first week.

I learn you in days.

I find quick wins in your files.

I take tasks and ask first.

Yours, not mine.

And more than 50 skills for the rest of the business.

Your day and week

Decisions

You and your business

Money, sales and taxes

Brand, customers and pricing

Writing, content and search

Email and keeping customers

Turning visitors into buyers

Paid ads

Numbers and tracking

Reports, decks and diagrams

Some things stay yours.

About an hour, and every step says what to click.

I'm opening to a small group of owners first.

BAILEY: Basically Another Intelligent Little Executive Yeoman