What is an AI executive assistant?
An AI executive assistant is software that takes over the repeatable parts of managing a person's time and messages: finding meeting times, protecting focus time, triaging and drafting email, preparing for meetings and sending a daily summary. It works with access to your calendar and inbox, and the good ones ask before they do anything that other people will see.
The products sold under this name do different jobs. A calendar planner rearranges your schedule around tasks and meetings. An AI email client helps you get through your inbox faster. An AI agent takes a standing job, such as a morning briefing or scheduling requests that come in through Slack, and does it on its own. Decide which of these you need before you compare prices.
What a Reason executive assistant does
- Briefs you each morning: today's meetings, who they are with, what needs preparing and what conflicts.
- Schedules, moves and declines Calendar events when you ask in Slack or the app.
- Drafts replies and scheduling emails, shows you each one, and sends it through Gmail once you approve.
- Remembers your rules: meeting hours, who gets priority, how you like replies worded.
How we compared them
- Sources: each product's facts come only from its own website, read on November 1, 2026. We used no third-party reviews, and every source is linked at the end of this page.
- Price: the plans listed on each company's own pricing page as of November 1, 2026, per month in US dollars. Where a company publishes no price, we say "Contact sales" instead of guessing.
- Inbox and calendar: what the company's own site says its product does with email and calendars. We add nothing its site does not claim.
- Best for: the person or team each product's site is built around, including where it fits better than Reason.
- Disclosure: we make Reason, so read its row with that in mind.
Eight AI executive assistants compared
Prices are as of November 1, 2026, in US dollars, from each company's own pricing page. They change often; check the linked source before you buy.
| Price (as of November 1, 2026) | Where it works | Inbox and calendar | Best for | |
|---|---|---|---|---|
| Reason | Pro $50 a month per person (3-day free trial for eligible new customers); Max $200 | Web app, Mac app and Slack; runs on its own cloud computer | Reads and changes Google Calendar; sends Gmail after you approve each message; reading Gmail waits on Google's review for new connections | People who want an assistant on a schedule that can also do other work through Slack and connectors such as Stripe, PostHog and GitHub |
| Lindy | Free: $50 in credits for 7 days; Team from $49.99 a month per active user for 5,000 credits; Enterprise: contact sales | Slack, iMessage and a Chrome extension; connects 2 to 5 inboxes depending on plan | Inbox management, drafts in your voice, meeting scheduling, prep and follow-up, daily briefs; approvals built in | Slack-first teams that want one assistant for inbox, meetings and briefs |
| Motion | Individuals: Pro AI $29 a month billed yearly ($49 monthly), Business AI $39 ($69); Teams: $19 and $29 per seat billed yearly ($29 and $49 monthly); free trial | Web, desktop, iOS and Android apps | AI Calendar plans your day around tasks; meeting booking links; meeting notetaker | People whose problem is fitting tasks and projects into the calendar |
| Reclaim | Lite free; Starter $10 per seat a month billed yearly ($12 monthly); Business $15 ($18); Enterprise $22 per seat | Web app and a Google Calendar add-on; Slack, Asana, Jira, Linear, Zoom and other integrations | Focus Time, Habits, Buffer Time, Smart Meetings, Scheduling Links and an AI Assistant chat | Teams that want to protect focus time and find meeting times automatically |
| Clockwise | Discontinued: no longer available from March 27, 2026 | No longer offered | Its focus time and flexible meetings were removed when the service ended | Former users looking for a replacement; Clockwise's notice points to Reclaim for scheduling links |
| Superhuman | Starter $25 per member a month billed yearly ($30 monthly); Business $33 ($40); Enterprise: contact sales | Superhuman Mail, its email app | Email productivity, Superhuman AI, calendar and scheduling; Business adds auto drafts, Ask AI and Superhuman Mail MCP | People who live in email and want a faster inbox with AI drafts |
| Google Gemini | Included in Google Workspace: Business Starter $7 per user a month with a 1-year commitment ($8.40 monthly), Standard $14 ($16.80), Plus $22 ($26.40); Enterprise: contact sales | Gmail, Docs, Meet and other Workspace apps; the Gemini app on web and mobile | Gemini in Gmail finds, summarizes and writes emails (all plans); Standard and up add Gemini in Docs, Meet and more | Teams already on Google Workspace that want AI inside Gmail without another tool to buy |
| Microsoft Copilot | Microsoft 365 Copilot Business add-on $18 per user a month paid yearly (promotional, regularly $21); Microsoft 365 Business Standard with Copilot $23.50; Business Premium with Copilot $32 | Outlook, Teams, Word, Excel and PowerPoint | Copilot in Outlook catches up on email, drafts responses and manages your calendar | Teams that work in Outlook and Microsoft 365 |
The eight, one by one
- Reason: an agent that works on its own cloud computer. Each assistant is a Reason with its own instructions, memory and Loops (a schedule, a webhook, a GitHub event or Slack messages), using connectors such as Google Workspace and Slack. Choose something else if you need it to read your inbox on a new Google connection today, answer phone calls or work in Outlook.
- Lindy: sells itself as a Slack-native teammate with meeting recording and notes, scheduling, daily briefs, inbox management and iMessage access. Every active user is billed, and unused monthly credits do not roll over.
- Motion: an AI calendar and project manager. It plans your tasks into your calendar and includes booking links, docs and a notetaker, metered with monthly AI credits.
- Reclaim: a scheduling layer on top of your calendar that defends focus time and habits, adds buffers and finds meeting times across attendees, with a free Lite plan.
- Clockwise: was a calendar optimizer for teams. Its own site says the team is joining Salesforce and the product is no longer available from March 27, 2026, with user data deleted shortly after.
- Superhuman: an AI email app. Its plans add AI drafting, calendar and scheduling and, on Business, auto drafts and Ask AI.
- Google Gemini: built into Google Workspace plans, so there is no separate tool to buy if you already pay for Workspace; every plan includes Gemini in Gmail.
- Microsoft Copilot: built into Microsoft 365 apps; in Outlook it catches you up on email, drafts responses and manages your calendar. Some advanced features bill by usage on top of the license.
How to choose an AI executive assistant
- Start where your work already lives. If your company runs on Google Workspace, try Gemini in Gmail first; if it runs on Outlook, try Copilot. Both come with plans you may already pay for.
- Name the bottleneck. A crowded calendar with no time to work points to Reclaim or Motion. An overflowing inbox points to Superhuman, Gemini or Copilot. Work that should happen without you asking, such as a morning briefing or replying to scheduling requests, points to an agent like Lindy or Reason.
- Check what it does without asking. Look for approval before anything is sent or accepted on your behalf, and for a way to make that rule stricter.
- Count the real price. Per-seat plans bill everyone who uses them, and credit-based plans (Lindy, Motion) cost more for heavier work. Compare yearly and monthly prices, since most discounts need a yearly commitment.
- Grant the least access that works. Connect only the calendar and mailbox the job needs, and prefer a dedicated account for an assistant a whole team shares.
- Run it on real work for a week. Read every briefing and draft in the first days, correct it, and only then let it act on its own.
How to set it up in Reason
Create a Reason named for the job in the web app or the Mac app, and give it instructions like these:
- Instructions sketch: "You manage my calendar and the email around it. Keep mornings before 10:00 free of meetings. Never accept on my behalf without asking. Draft replies in my voice, short and direct; show me every email before it is sent. Only email people I have already been in contact with."
- Connectors: Google Workspace (Gmail send and Calendar) and Slack, so you can ask it things from your phone.
- Example Loop: weekdays at 7:30 (cron 30 7 * * 1-5), post today's briefing to you in Slack; a second Loop on Fridays at 16:00 lists next week's open decisions.
- Optional: a workspace rule in Settings › Policies that makes it ask before sending any email.
What it won't do
- Send email without your approval: every Gmail send through the Google Workspace connector shows a preview, and only that exact message can be sent.
- Read your inbox on a new connection yet: reading Gmail is waiting for Google's review, so new connections can send and manage Calendar but not search mail.
- Answer phone calls or have an email address of its own.
Pricing sources
Prices and features were read from each company's own website on November 1, 2026. Lindy, Motion, Reclaim, Clockwise, Superhuman, Google Gemini, Google Workspace, Microsoft Copilot and Microsoft 365 are trademarks of their owners. Reason Machines is not affiliated with or endorsed by them.
Questions
What is an AI executive assistant?
An AI agent or tool that manages a person's calendar and the email around it: briefings, scheduling, focus time and replies the person approves before they go out.
What can an AI executive assistant do?
Depending on the product: plan tasks and meetings into your calendar, defend focus time, find meeting times, summarize and draft email, prepare you for meetings and send a daily briefing. Agents such as Reason and Lindy can also do this on a schedule and through Slack. None of them replaces judgment calls about people and priorities.
How much does an AI executive assistant cost?
As of November 1, 2026, from each company's own pricing page: Reclaim has a free plan and paid seats from $10 a month billed yearly, Gemini comes with Google Workspace from $7 a user a month on a yearly commitment, the Microsoft 365 Copilot Business add-on is $18 a user a month paid yearly (promotional), Superhuman starts at $25 per member billed yearly, Motion at $19 per team seat or $29 for individuals billed yearly, Lindy at $49.99 per active user, and Reason Pro at $50 a month per person (Max $200), with a 3-day free trial for eligible new customers. Every assistant you set up in Reason shares your plan's usage.
Is it safe to give an AI assistant access to my inbox and calendar?
It can be if you limit what it can reach and what it can do alone. Connect only the accounts the job needs, require approval before anything is sent or accepted, and read each vendor's own security page. In Reason, every Gmail send shows a preview and only that exact message can be sent, a workspace rule can make it ask before any email, and new Google connections cannot read the inbox until Google finishes reviewing that access.
Can it send email for me?
In Reason, yes, through the Google Workspace connector, and only with your approval: the first send returns a preview, and you approve that exact message in the chat or by clicking Send on the email card.
Can it read my Gmail inbox?
Not on a new Google connection in Reason yet. Reading Gmail is waiting for Google's review, so a new connection can send Gmail and read and change Calendar. Connections made earlier keep what they were granted.
Is an AI executive assistant as good as a human EA?
For repeatable, checkable work, such as scheduling, briefings and first drafts, an AI assistant is fast and always available. A human executive assistant is still better at judgment, relationships, phone calls and anything new or sensitive. Many people use both: the AI handles routine work, and a person approves what goes out.
Can a whole team share one assistant account?
In Reason, yes. Where a Reason can have its own connections, set its Google Workspace plugin to "Connect once and every member can use" with an account you made for it, such as agent@yourcompany.com.