· AI Operating System

Turn ChatGPT into a real employee.

We build an AI operations manager that runs your busywork and plugs into the tools you already use. It knows your business and gets sharper every week.

Book your strategy callFor owners of trades and service businesses.

$397 setup, free if it does not work that day. Then from $327/mo, cancel anytime and keep everything.

AIOSYOUR COREGmailCalendarQuickBooksPhoneNotesFollow-up sentInvoice remindedMeeting bookedTime back

You believe in AI. You still cannot make it work.

Buried in your own business.

The real work waits until after dinner.

Tried doing it alone.

ChatGPT forgets you by morning.

Scared to hand it the real stuff.

One wrong move and something breaks.

· How it works

See the whole thing. Click through it.

A two minute walk through how scattered AI becomes one system around your business.

Click through itSlide 1 of 9
The problem

Right now, you are the wire.

ChatGPT, your inbox, your calendar, your CRM all sit apart. You hold them together by hand, all day.

ChatGPTInboxCalendarCRMYOU
ShadowDeskShadowDesk

Slide 1 of 9: Right now, you are the wire.. ChatGPT, your inbox, your calendar, your CRM all sit apart. You hold them together by hand, all day.

· Step one

First, the foundation.

The Setup Session$397one-time · 2 hours

One done-with-you session, two hours. We audit what you run, build your AI operations manager, and have it doing one real job in your own tools before you hang up. If it is not working by the end, the setup is free.

  • 01A full audit of what you already use and what you actually need
  • 02We build your personal operations manager: an AI that learns your business and does the busywork the same day
  • 03We connect Gmail, Outlook, QuickBooks, Calendar, Slack, Notion, and Zoom
  • 04You walk out with it already handling busywork like chasing unpaid invoices, sending quotes, and booking jobs, and your evenings back

You also get

  • The First-Week Playbook. the three jobs we hand your AI first, so it is earning its keep from day one.
  • Access to our skill library. the same skills we build to run our own business, ready for you to use.
  • A 30-day tune-up call. we come back in a month and sharpen what we built around how you actually used it.
· Then, pick your pace

Same system. You choose how involved we are.

Cruise and Accelerate are the same system at your pace, you just pick how involved we are. When one setup is too small for the whole company, the Director of AI runs it across your team.

Founding rate, locked for life if you start before October 1st.

Cruise

Keep it sharp. Run it yourself.

$327/mo$497/mo

billed monthly

  • included: 2 hours a month of 1:1 coaching with our team
  • included: Weekly members call, one hour every week
  • included: Email and text support, replies within 72 hours
  • included: The full ShadowDesk skill marketplace, newsletter, and more

Perfect for

Technically capable owners who want it to run.

  • Comfortable running the system on your own
  • Want it kept sharp, not managed for you
  • Here for the new builds we surface each month

30-day guarantee. If your first month does not hand you back real hours, we refund the month. Cancel anytime and keep everything we built.

Most pick this

Accelerate

Build faster, with us in the loop.

$697/mo$997/mo

billed monthly

Requires a Claude Max subscription.

  • included: 8 hours a month of 1:1 coaching with our team
  • included: Weekly members call, one hour every week
  • included: Email and text support, replies within 24 hours
  • included: The full ShadowDesk skill marketplace, newsletter, and more

Perfect for

The curious builder with several projects who wants us more involved.

  • Several projects you want built, and built fast
  • Want more of our time in the loop each month
  • Self-sufficient between our sessions

30-day guarantee. If your first month does not hand you back real hours, we refund the month. Cancel anytime and keep everything we built.

By application

Director of AI

We run AI across your whole company.

$997+/mo

custom scope, billed monthly

Price may vary depending on the complexity of the tasks or custom build.

  • included: A dedicated Director of AI embedded with your team
  • included: Company-wide rollout, not one setup in the corner
  • included: Strategy, build, and training scoped to your playbook
  • included: Priority support and a standing weekly working session

Perfect for

Medium and large teams putting AI to work company-wide.

  • Too big for a single local setup to cover everyone
  • Want one person accountable for AI across the company
  • Have your own guidelines we build the program around

90-day rollout guarantee. If the rollout misses the plan we scoped, we work free until it is delivered. Cancel anytime and keep everything.

Accelerate is the most we do for a single owner. When it is the whole company, that is Director of AI.

Or one at a time

$397/hr. Not ready to commit? Book a single session, one at a time, no commitment.

· Line them up

Every plan, side by side.

Cruise and Accelerate start from the same $397 setup. Director of AI is custom, scoped to your company.

Compare plans
Cruise
$327/mo$497/mo
Accelerate
$697/mo$997/mo
Director of AI
$997+/mo
1:1 coaching with our team2 hrs / mo8 hrs / moEmbedded, ongoing
Weekly members call
Support response72 hrs24 hrsPriority, same day
Skill marketplace + newsletter
RolloutYour setupYour setupCompany-wide
SeatsOpenOpenBy application
Best forTechnically capable owners who want it to run.The curious builder with several projects who wants us more involved.Medium and large teams putting AI to work company-wide.
· The promise

We carry the risk, not you.

If it does not work, the setup is free.

If your system is not doing real work by the end of your setup session, the $397 costs you nothing.

First automation live in 90 days, or your money back.

Show up and do the work. If your first automation is not live within 90 days, we refund every dollar you have paid us, setup and membership both.

Cancel any time, keep everything.

It all lives in your own accounts. Walk away whenever you want and take everything we built with you.

5+ hours a week handed back.
Matt CantonShadowDesk client
· Plugs into the tools you already use

We wire up your stack.

We connect what you already run, not make you buy more.

  • Gmail logoGmail
  • Outlook logoOutlook
  • Google Drive logoGoogle Drive
  • Google Calendar logoGoogle Calendar
  • Excel logoExcel
  • Notion logoNotion
  • Obsidian logoObsidian
  • Slack logoSlack
  • Telegram logoTelegram
  • WhatsApp logoWhatsApp
  • Stripe logoStripe
  • QuickBooks logoQuickBooks
  • HubSpot logoHubSpot
  • Zoom logoZoom
  • Google Meet logoGoogle Meet
  • Microsoft Teams logoMicrosoft Teams
  • Calendly logoCalendly
  • Google Sheets logoGoogle Sheets
  • Dropbox logoDropbox
  • Salesforce logoSalesforce
  • PayPal logoPayPal
  • Canva logoCanva
  • Perplexity logoPerplexity
  • Jobber logoJobber
  • ServiceTitan logoServiceTitan
  • and whatever else you run
Your customersYour jobsYour voiceAIOS
· FAQ

Questions, answered.

How is this different from ChatGPT?

ChatGPT is the engine. Your system is the vehicle we build around it. It lives inside your email, calendar, payments, and notes, knows your business by name, and gets sharper every week.

Do I need to know anything technical?

No. If you can talk, you can do this. You bring your logins, we do the connecting, and we drive the whole build on your screen.

What does it cost?

A $397 setup session to turn it on, then you pick your pace: Cruise or Accelerate, billed monthly. Bigger teams can bring us in as a Director of AI on a custom scope, from $997 a month. Prefer no commitment? Book single sessions a la carte at $397 an hour.

What if it does not work?

Then you do not pay. The setup is free if it does not do real work, and we refund you in full if your first automation is not live within 90 days.

How fast do I see something real?

Your first session. You leave your setup session with your system doing real work in your own tools.

Will it replace my team?

No. It takes the busywork that was never really theirs. Your team spends time on the work that needs them.

Is my business data safe?

It lives in your own accounts and you own all of it. Nothing is sold, nothing goes out without your yes.

Get your evenings back.

30 minutes, no pitch. Tell us what keeps you at the desk after dinner and we will show you the part that ends it, live.