Best AI Tools for Executive Assistants in 2026
You are not looking for a robot to take your job. You are looking for something that can hold two executives’ inboxes, three calendars and your own day in its head at the same time.
This is a list of AI tools for the human EA or chief of staff. If you came looking for software that replaces the role, that is a different list: AI executive assistants.
Short answer: Carly is the pick, because it connects every mailbox and calendar you manage at once, replies from the executive’s own address, and keeps a separate set of rules for each executive you support. Microsoft 365 Copilot and Gemini in Workspace are strong inside one person’s own account. ChatGPT is the free general-purpose drafter. Superhuman and Fyxer work your inbox. Calendly and Reclaim handle booking. Fireflies takes the meeting notes.
1. Carly
Carly is an AI agent with its own real email address. You email it, forward to it, CC it on a thread, or text it. Each mailbox and calendar you manage is connected as its own authorized connection: Outlook, Gmail, Google Calendar and Outlook calendar, plus thousands of other apps your executives live in. The executive authorizes their own connection, or you do it with the delegated access you already hold.
Claire is EA to two executives at Meridian Logistics: Tomas, the CEO, and Emily, the CFO. Both run on Outlook. Claire keeps her own work Outlook and a personal Gmail. Monday at 7am, five things are waiting: a board member wants 30 minutes with Tomas this week, an auditor wants a document from Emily, a conference organizer confirms Tomas’s speaking slot and asks for a headshot and bio, a candidate wants to move a CFO interview, and Claire’s own dentist wants to reschedule a cleaning.
By the time Claire opens her laptop, Carly has checked all four calendars and:
- Replied to the board member from Tomas’s address with three slots that respect his rules (nothing before 9, never over Thursday board prep), then booked the one the board member confirmed
- Found the audit document in Emily’s OneDrive and drafted the reply for Claire to approve before it goes out
- Answered the conference organizer with Tomas’s bio and headshot pulled from Google Drive
- Moved the candidate interview to a slot free for Emily and both panel members, and sent the updated invite
- Booked Claire’s dentist around all of it, in her personal Gmail
At 8:30 Claire types one line: “Check all the mailboxes I manage for anything waiting on a reply longer than a day and tell me which exec each one is for.” She gets a list back grouped by executive, with the oldest first.
What makes it different: one request covers every mailbox and calendar you manage at once, and the reply goes out from the address that received the thread, in that executive’s voice rather than a generic assistant voice. You can give each executive their own agent holding their preferences: no meetings before 9, always CC the EA, protect Friday afternoons. You stay in control, because every agent can be set to draft for your review or to send, rule by rule. Carly starts on its own when something happens, so the board member gets three times at 7:04am instead of at 10. Steps you repeat, like “anything from the board chair goes on the CEO’s calendar and on my Monday list,” become free Zapier-style workflows. For scheduling, Carly offers times that are free across every calendar it holds, and you can give each executive a booking page instead of a back and forth. Carly connects to thousands of apps, so the same agent reaches Slack, Microsoft Teams, your CRM and your files.
Best for: EAs and chiefs of staff supporting one to three executives across separate mailboxes and calendars.
Pricing: Free Zapier-style workflows; AI agents from $35/month.
Connect your mailboxes at carlyassistant.com/integrations, or book a walkthrough if you want the delegated access set up with you on the call.
2. Microsoft 365 Copilot
If both of your executives run on Outlook, Copilot summarizes long threads, drafts replies, writes a meeting recap and pulls figures out of a deck without leaving the app. It respects shared mailbox and delegate permissions, so it can work inside a mailbox you already have access to.
What makes it different from Carly: Copilot answers inside the single account you are signed into, and it waits to be asked. Carly holds every mailbox you manage in one place and acts on new mail without you opening anything. See AI assistants for Outlook.
Best for: Microsoft-first teams where the EA already has delegate access.
Pricing: $21.00 per user/month billed yearly ($18 on the current promotion) or $25.20 monthly, in September 2026.
3. Gemini in Google Workspace
The Google-side equivalent. It drafts in Gmail, summarizes threads, builds slide decks from a brief and answers questions about files in Drive. For an EA writing board packs and travel briefs, the Docs and Slides work is the strong part.
What makes it different from Carly: one Google identity per connection, so the EA’s view stops at their own account. Carly connects all of the mailboxes and calendars you manage and shows which account each item came from. Compare AI assistants for multiple calendars.
Best for: EAs at Workspace companies who mostly need drafting and document work.
Pricing: included with Business Starter at $7, Standard at $14 and Plus at $22 per user/month, in September 2026.
4. ChatGPT
The free general-purpose tool most EAs already keep open: rewrite a difficult email, compress a 40 page report into a one page brief, build a travel itinerary, prep questions for a board meeting. Free accounts can schedule tasks, and paid plans can run a prompt when something happens in Gmail, Slack or GitHub.
What makes it different from Carly: it is a chat window you drive. Nothing arrives in your executives’ inboxes because of it unless you go and ask. Carly is reachable inside ChatGPT as the Carly plugin, which is how people get one chat to reach every mailbox they manage.
Best for: Drafting, research and briefing prep.
Pricing: free plan; paid plans from $20/month, in September 2026.
5. Superhuman
A fast email client built around keyboard shortcuts, with AI drafting in your own writing style, split inboxes and send later. One seat holds several Gmail and Outlook addresses, so you are not billed per inbox, but you switch between them rather than seeing one combined list.
What makes it different from Carly: it makes you faster at working the inbox. Carly works it while you are in a meeting. See Superhuman alternatives.
Best for: EAs who live in the inbox all day and want speed.
Pricing: Starter $25 and Business $33 per member/month billed annually ($30 and $40 monthly), in September 2026.
6. Fyxer
Sorts your inbox into categories and writes drafts in your voice overnight, so replies are waiting in the morning. Starter covers exactly one inbox and one calendar; managing a second person’s mail means Professional. It drafts only, and states plainly that it will not send on your behalf.
What makes it different from Carly: the price moves when you add the second inbox, and a human has to press send on everything. With Carly, each rule decides whether something is drafted for review or sent. See Fyxer alternatives.
Best for: A single inbox that needs triage and morning drafts.
Pricing: Starter $30 monthly ($22.50 annual, one inbox), Professional $50 monthly ($37.50 annual, multiple inboxes), in September 2026.
7. Calendly
The booking link most external parties already know how to use. Managed event types let you build and run booking pages on behalf of your executives, routing forms send the right people to the right page, and the Callie add-on answers questions about meetings.
What makes it different from Carly: it hands out a link and waits. Carly also reads the email asking for the meeting, offers times that work across every calendar it holds, and books the one that comes back. See AI scheduling assistants.
Best for: High volume external booking where a link beats a conversation.
Pricing: Standard $10 and Teams $16 per seat/month on yearly billing, in September 2026.
8. Reclaim
Defends focus time. It finds slots for recurring tasks and habits, auto-schedules them around meetings, and moves them when something more important lands. Useful when an executive keeps losing their prep blocks to meeting requests.
What makes it different from Carly: it optimizes one person’s calendar in the background. Carly negotiates the meeting itself, across the calendars of everyone you support.
Best for: Protecting an executive’s deep work and prep time.
Pricing: free Lite plan; Starter $10 per seat/month billed yearly or $12 monthly, in September 2026.
9. Fireflies
Joins Zoom, Google Meet and Teams calls, transcribes them and produces summaries and action items you can forward to your executive. For an EA covering meetings you were not in, this is the one tool on the list that fills that gap.
What makes it different from Carly: it produces the record of the meeting. Carly takes the follow-ups out of that record and chases them, books the next session and updates the calendars. They pair well.
Best for: EAs who have to brief an executive on a call they missed.
Pricing: free plan; Pro $10 and Business $19 per seat/month billed annually ($18 and $29 monthly), in September 2026.
Compared
| Tool | What an EA gets | Price (September 2026) |
|---|---|---|
| Carly | Acts across every mailbox and calendar you manage, replies from the executive’s address | From $35/month |
| Microsoft 365 Copilot | Drafting and summaries inside Outlook and Teams | $21.00/user/mo yearly |
| Gemini in Workspace | Drafting, Docs and Slides inside one Google account | From $7/user/mo |
| ChatGPT | Briefs, rewrites, itineraries on request | Free; paid from $20/mo |
| Superhuman | A faster inbox across several addresses | $25/member/mo annual |
| Fyxer | Overnight triage and drafts, no sending | $30/mo, 1 inbox |
| Calendly | Booking pages you manage for your execs | $10/seat/mo yearly |
| Reclaim | Auto-scheduled focus and prep blocks | Free; $10/seat/mo yearly |
| Fireflies | Meeting transcripts, summaries, action items | Free; $10/seat/mo annual |
How to pick
Ask what you want back: time at the keyboard, or time off the hook.
If your problem is typing speed, Superhuman or Copilot will help today, and Fyxer will have drafts waiting. If your problem is that meeting requests eat your morning, Calendly and Reclaim take the scheduling load off. If you were not in the room, Fireflies gives you the record.
If your problem is that you are the single point of failure for two or three people’s inboxes and calendars, go with Carly. It is the only one here that holds all of those accounts at once, acts the moment something arrives, and keeps a different set of rules for each executive you support.
FAQ
Can an AI assistant work inside my executive’s inbox, not just mine? Yes. With Carly, each mailbox is its own authorized connection. Your executive authorizes theirs, or you connect it using the delegated access you already have. A reply then goes out from the address that received the thread.
Will it send email as my executive without me seeing it? Only if you set it up that way. Every rule can be set to draft for your review or to send. Most EAs start with drafts for the executive’s outside mail and sending for the routine confirmations, then loosen it.
How does it keep two executives’ preferences straight? You give each one their own agent with their own instructions and memory: earliest meeting time, protected blocks, who gets a same-day reply, who always gets you CC’d.
Can I ask about all the inboxes at once? Yes, and that is the point. “Check all the mailboxes I manage for anything waiting on a reply longer than a day and tell me which exec each one is for” returns one list, labelled by account.
What about meeting recordings? Use a notetaker like Fireflies for the transcript itself, then let Carly work the follow-ups that come out of it: the recap email, the next booking, the tasks.
What does it cost to cover two executives and me? Carly is free Zapier-style workflows and AI agents from $35/month, and connecting another mailbox or calendar does not change the price. Connect them at carlyassistant.com/integrations.
More: AI executive assistants · AI agents for executive assistants · Executive assistant software · AI assistants for Outlook · AI email assistants · AI assistants for multiple Outlook accounts
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"Before Carly, I relied on a Calendly link, but the whole process felt impersonal and not very professional. Carly changed that by handling all the back-and-forth, so I'm no longer stuck in endless email threads trying to line up schedules.
Now Carly reaches out to candidates, shares my real-time availability, lets them pick a slot, then sends a Zoom link and drops it straight into my calendar. She sends reminders to both of us before each call, which has significantly reduced no-shows and last-minute confusion.
On top of scheduling, Carly acts like a full executive assistant, sending me my schedule the night before so I can prepare for each call. It reminds me of the old x.ai assistant, but Carly is noticeably smarter, faster, and better suited to my healthcare recruitment business."
