Runs on your own Mac · Works inside your own AI app
An AI that finally knows your business.
Chief Staffer is a private AI chief of staff that lives on your own Mac. It builds a verified memory of your business from your own documents, so the work you ask for is grounded in your real facts: sources on demand, gaps named, nothing invented. And it gets smarter every day you use it.
Renewal Proposal: Hartman & Co.
Drafted from your own facts
Scope of engagement
Grounded · 9 sourcesContinuation of the quarterly advisory retainer, with the workshop series renewed through Q3…
Pricing & retainer
Sources shownMonthly retainer of $7,500, per the March agreement.
Where did that come from?
Email, J. Hartman, 14 Mar 2026: ”let's proceed at $7,500 monthly.” Corrected by you, 02 Apr 2026. Receipt kept.
Renewal terms
Gap namedMissing: 2025 renewal terms. Ask me, and I'll hold the space until you fill it.
The problem
You've tried AI. Three things keep getting in the way.
01
It doesn’t know your business.
You brief it from scratch, every single time.
Generic AI knows business in general. It doesn’t know your clients, your numbers, your history. So you re-paste the same context every session — and it still fills the gaps with things that aren’t true.
02
You fix more than you save.
The output is almost right, which is the expensive kind of wrong.
A polished draft that’s wrong in exactly the places your clients would notice. It never tells you which places. So you re-check everything, and the time you were going to save goes into fixing it.
03
Your work can’t go just anywhere.
Your knowledge is scattered, and some of it is confidential.
It lives in notes, documents, threads, and your head — so things slip. And much of it is client work that can’t be handed to some cloud. You’re one person carrying what a team would carry, and the tools don’t help you hold it.
The fix isn’t a smarter chatbot. It’s an AI that learns your business, answers from your real facts, and shows its sources. That’s what we built.
How it works
Four steps, and the memory compounds.
Step 1It learns your business.
Point it at your conversations and documents, and it builds a private, verified memory of how your business actually runs: clients, commitments, numbers, decisions, and how they connect. All of it stays on your Mac.
Step 2It answers from your facts, with sources.
Ask anything and the answer comes from your real record, not the internet’s averages. Every fact traces back to where it came from. Ask “where did that come from?” and you get a citation, not a shrug.
Step 3It produces grounded work.
Proposals, reviews, briefs, a second opinion — drafted from your verified facts, in your context. Each section carries its confidence. What’s missing is named so you can fill it, never invented to look complete.
Step 4It gets better with use.
Every correction sticks and carries a receipt. Every document you produce deepens the memory. A daily brief opens your morning with your commitments and what’s changed. You pick up where you left off, across sessions and across days.
The work
Work product, not chat transcripts.
Chief Staffer is tuned to the work you actually do. Pick a specialization for your profession and you get document blueprints and advisors built for it — each one drafted from your verified facts, section by section.
Client proposals & engagement letters
The client advisor
Quarterly business reviews
The strategy advisor
Pricing & packaging analyses
The pricing advisor
Marketing & positioning plans
The marketing advisor
Client & account briefs
The client advisor
Board & investor updates
The finance advisor
Operating plans & decision memos
The operations advisor
…and more, tuned to the work you do.
Behind the blueprints sits a bench of advisors — strategy, finance, marketing, operations and more — each one prepared with your context before it writes a word. You don't pick the advisor. The work finds the right one.
Every document, the same standard: confidence marked, sources available, gaps flagged for you to fill. Not filled in for you.
Why you can trust it
Built for people who can't afford to be casual about this.
Local-first, and private by architecture.
Chief Staffer runs entirely on your Mac. There is no Chief Staffer cloud. We never host your data, and we cannot see it — not during setup, not after. Your client work stays in your office.
Sources, on demand.
Every fact in every answer traces back to where it came from. Ask “where did that come from?” and you get a citation, not an apology.
Gaps named, never invented.
Each section carries its confidence. When something is missing, it’s named (“I don’t have your 2025 renewal terms”) so you can fill it — never papered over to look complete.
Your own AI app, your own tokens.
Chief Staffer runs inside the AI app you already use — Claude, ChatGPT, Cursor, VS Code, Windsurf, Goose — connected over MCP. You bring your own model tokens. We don’t resell AI, and we don’t sit between you and it.
Getting started
Two ways to start.
Priced against the work, not against software. One specialization at a serious firm runs a multiple of this a month — Chief Staffer is the leverage of that work without the headcount.
Ontology · $100/mo
The knowledge layer.
A structured, verified memory of your business — the model every business shares, built from your own facts. Knowledge, without the execution engine. The place to start if you want the memory first.
Chief Staffer · $300/mo
The full chief of staff.
The execution engine plus one specialization for the work you do. It produces grounded work, keeps the memory current, and gets sharper with use — all on your Mac.
Specializations · $50/mo each. Tune the whole thing to your profession. Chief Staffer includes one; add more for the kinds of work you take on.
Authoring · $200/mo (premium, Chief Staffer only). When no specialization fits, it authors a custom memory from your own corpus. Token-intensive — you bring your own.
Chief Staffer runs on your own AI app and your own model tokens. We don't resell AI, and we don't sit between you and it.
Where does my data live?
On your Mac, and only there. We never host it or see it.
What do I need to run it?
A Mac and an AI app you likely already use — Claude, ChatGPT, Cursor, and more — connected over MCP. You bring your own model tokens.
What happens if I cancel?
You keep your data and every document. It’s on your machine; it was never ours to keep.
Give your AI a memory of your business.
Grounded in your own facts, private to your Mac, and getting smarter every day you use it.