The AI assistant that asks before it sends.
Ask AI AutoPilot about clients, invoices, projects and your calendar. It answers from your workspace, drafts and updates the records, and waits for your approval before anything goes to a client.
14-day free trial. Card required. After the trial: from $29/month. Renews automatically every month until you cancel. Cancel anytime in Settings → Billing.
Request a demo- 01
- Ask in plain language and get answers from your own records.
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- It drafts and updates records; sends to clients always wait for you.
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- Compose, rewrite, translate and summarize, with AI usage on every plan.
What is an AI workspace assistant?
An AI workspace assistant helps people find, summarize, write, and change information inside the system where the work happens. In Workspace369 it is called AI AutoPilot: a chat that answers from your clients, invoices, projects, calendar and messages, drafts and updates those records in visible steps, and asks for your approval before anything is sent to a client.
Reviewed August 30, 2026 by the Workspace369 Product Team. Availability can vary by plan, region, and workspace configuration.
Read the AI and communication documentationWatch · 1:22
Ask Workspace AI about your business in Workspace369
Ask Workspace AI about your business in Workspace369: it plans your day, answers from your own numbers, and never sends anything without your approval.
Read the transcript and chapter guide →Recorded in a demonstration workspace. Check current plans and settings for availability.
From a question to finished work, in one chat.
AI AutoPilot is the assistant inside Workspace369. It reads the same records your team works from, does the busywork in steps you can follow, and stops for you before anything reaches a client. It also keeps a Today list of what needs you, without being asked.
See AI AutoPilot Today- 01
Ask in your own words
Type a request or start from a shortcut like Plan my day, Draft an invoice or Review my workspace. Mention a client, an invoice or a team member with @ so it starts from the right record.
- Add a photo or a file to the question
- Speak instead of typing with voice input
- Pick short or detailed answers
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Watch it work through the steps
Each lookup and draft shows up as a step while it runs, with what it found. You can see what it read and what it is about to change before anything is saved.
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Approve anything that leaves the workspace
Before it sends an invoice, a proposal, an email or a text, AI AutoPilot shows you exactly what will go out and to whom, and waits. Nothing reaches a client until you confirm.
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Open the result
Answers come back as a short summary or a table whose rows open the records. Every change is a real record in your workspace, and a table can be exported as CSV.
Answers from your records, not from guesswork.
AI AutoPilot works with the same clients, money, projects, calendar and messages your team already keeps in Workspace369, so a question about a client is answered from that client's real history.
- ClientsLook up and update client records
- RequestsRead new requests and leads
- ProposalsDraft proposals and edit their sections
- InvoicesFind balances and draft invoices
- Projects and tasksCreate tasks, add notes, log time
- CalendarCheck availability and add events
- InboxSearch messages and draft replies
- Knowledge baseAnswer from your team's saved notes
Write the reply, then make it sound like you.
Draft a reply from the thread, then rewrite it shorter or warmer, or translate it before you send. Long threads can be summarized into the next step.
- Compose and rewrite messages and documents
- Translate messages and summarize long threads, on every plan
- You review every draft; nothing is sent for you
From the client
Maya Ortiz Hi! Can we move the shoot to next Thursday? And is the second invoice due before or after delivery?
Hi Maya, Thursday works. I can move the shoot to October 30 at 10:00. The second invoice (INV-1051) is due on delivery, so nothing changes before the shoot. Let me know if that time suits you. Best, Sam
Sample text. Try the buttons to see the same reply rewritten.
It does the work. You keep the final say.
An assistant that can change records needs clear limits. These are built into AI AutoPilot, not left to a prompt.
- Sends always ask
- Emailing an invoice or a proposal, texts and bulk sends wait for your confirmation every time, in every mode.
- Auto mode is an admin call
- Only a workspace admin can let AI AutoPilot create and update records without asking. It can be turned off at any time.
- Your chats are yours
- Only the person who started a chat can change it. You can pin, rename or delete your own chats.
- Every step is visible
- Each answer shows the steps it ran, so you can check what it read and what it changed.
AI usage that grows with your plan.
Every plan includes AI AutoPilot, writing tools and AI Import. Each plan adds a monthly AI usage allowance, shared by every AI feature, and higher plans include more of it.
Compare plans- Cadet$29/moNot included
- Voyager$74/moIncluded
- Specialist$149/moIncluded
- Commander$299/moIncluded
- Enterprise$699/moIncluded
Allowances are shown as multiples of the Cadet allowance (Standard). One monthly allowance shared by every AI feature — Ask AI, compose, rewrite, translate, summarize. Your plan adds it each billing period, and unused usage carries over while your account is active. Add more any time.
Use the same tools from Claude or ChatGPT.
Prefer to work in another AI app? The Workspace369 MCP server gives Claude, ChatGPT and other MCP apps the same tools AI AutoPilot uses, with the same rule: sends wait for your approval.
See how the MCP connection worksAI apps that connect over MCP, on every plan once an admin turns on AI connections
ClaudeConnector, over OAuth
ChatGPTConnector, over OAuth
GrokConnector, over OAuth
CursorConnector, over OAuth
WindsurfConnector, over OAuth- +Other MCP appsAny app with MCP over OAuth
Automation tools that use webhooks and the Builder API on every plan
AI AutoPilot questions
What can Workspace AI help with?
Workspace AI supports chat, semantic knowledge search, drafting, rewriting, translation, summaries, communication assistance, and automation-related workflows within Workspace369.
Does Workspace AI replace human review?
No. AI output should be reviewed by the user responsible for the work, especially before client communication, financial decisions, or workflow actions are finalized.
Can AI AutoPilot send emails or invoices on its own?
No. Sending to a client, such as emailing an invoice or a proposal, a text or a bulk send, always waits for your confirmation, in every mode. A workspace admin can let it create and update records without asking, but sends still ask.
Who can change my AI AutoPilot chats?
Only the person who started a chat can change it. You can pin, rename or delete your own chats, and start a new chat at any time.
Is AI usage included in every Workspace369 plan?
Yes. Every plan includes AI AutoPilot and a monthly AI usage allowance that higher plans increase. AI tools are Starter on Cadet, fully included on Voyager and Specialist, and Advanced on Commander and Enterprise. The daily briefing starts on Voyager. The pricing page has the full comparison.
Recent updates
All release notes- New workspaces get a Set up my pipeline starter in AI chatIn a new workspace, AutoPilot chat offers Set up my pipeline in place of Review my workspace. Its request asks the AI to change nothing until you say yes.
- Reports now opens with your key figuresThe Reports page now starts with an At a glance strip of net income, cash, owed to you and to pay on Commander and up, then lists every report in a quiet two-column index.
- Add emails to your CRM with AI, and import proposals and client listsAI turns an email from someone new into a client, a note and a follow-up you review first. Rebuild an old proposal from a PDF, or import clients from a screenshot.
Ask it something real about your workspace.
Start free and bring this workflow into the rest of your workspace.
14-day free trial. Card required. After the trial: from $29/month. Renews automatically every month until you cancel. Cancel anytime in Settings → Billing.
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