AI Chief of Staff

A dedicated AI assistant that actually runs things.

Email, calendar, projects, and operational follow-ups, all handled by a private AI assistant connected to your tools. For founders who want personal leverage in 48 hours, not a six-month strategy engagement.

Get Started → See how it works
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YouMove my 2pm to Thursday and prep me for the Ortiz call.
CDone. 2pm is now Thursday 10am. I dropped a one-pager on Ortiz in your inbox: last thread, open items, and their renewal date.
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Capabilities

What it actually does

Everything a great chief of staff would do, except it never sleeps, never forgets, and costs a fraction of a salary.

Chief of your inbox

Reads, prioritizes, and drafts replies in your voice. Surfaces what matters. Buries what doesn't. You review and send.

Chief of your calendar

Prepares a brief before every meeting: who you're meeting, what was discussed last time, what to bring up. No more walking in cold.

Chief of your projects

Connected to ClickUp, Asana, Notion, or Linear. Creates tasks, tracks deadlines, follows up with your team.

Chief of your files

Knows where everything lives: Drive, Dropbox, Notion. Ask it to find a document and it pulls it up.

Chief of your communication

Lives in your messaging app: Telegram, WhatsApp, or Slack. Talk to it like a colleague.

Chief of your knowledge

Remembers your preferences, clients, team, workflows. Gets smarter every week.

How it works

Live in
48 hours

From sign-up to a working chief of staff, no technical skills required.

Step 01

Sign Up

Pick your plan. We immediately start building your dedicated, private server.

Step 02

Onboarding Call

One hour on Zoom. We connect all your tools live: email, calendar, files, everything.

Step 03

Go

Within 48 hours of your onboarding call, your Chief is live and working.

Pricing

Straightforward pricing

No setup fee. Your monthly subscription starts today. Cancel anytime.

Operational tier

AI Chief of Staff

$2,500/ month
No setup fee · month-to-month, cancel anytime
  • Dedicated private server: your data, your instance
  • Connect your tools: email, calendar, files, projects
  • Messaging integration: Telegram, WhatsApp, or Slack
  • Custom personality & knowledge base
  • 1-hour guided onboarding call
  • Daily briefings & proactive monitoring
  • Request new tools connected anytime
  • Monthly optimization call
  • Enterprise-grade credential security
Get Started →
Need company-wide AI strategy?

Consider a Fractional Chief AI Officer

The AI Chief of Staff gives you personal leverage. If you're looking to roll AI out across a 50–500 person company, covering strategy, custom agents, board reporting, and compliance, our Fractional CAIO engagement is the right tier.

See Fractional CAIO →

Questions

How is this different from ChatGPT or Claude?

Those are general-purpose AI you talk to. Your Chief is a dedicated assistant that's connected to your actual tools and takes action on your behalf. It remembers everything about you and gets smarter over time.

Is my data safe?

Your Chief runs on a dedicated server. Your data never touches another customer's instance. All credentials are stored in enterprise-grade vaults. Encrypted connections, key-only access.

What tools can it connect to?

Gmail, Google Calendar, Google Drive, Slack, ClickUp, Asana, Trello, Notion, and many more. If it has an API, we can likely connect it.

How is this different from the Fractional CAIO offering?

The AI Chief of Staff is for personal leverage, serving one founder or executive. The Fractional CAIO is for company-wide AI strategy, providing a senior executive who designs your roadmap, builds custom agents across the org, and reports to your board. Different tier, different price, different problem.

How fast can I be up and running?

Within 48 hours of your onboarding call, your Chief is live and working.

What if I want to cancel?

Month-to-month, no contracts. If you cancel, we help you export your data and shut everything down cleanly.

Ready for your AI Chief of Staff?

Setup takes minutes. Your Chief is live within 48 hours.

Get Started →