Best AI executive assistants for CEOs in 2026: 8 compared

Published by 3Gen Internet Corporation, maker of OpenAssistant, Skej and AGNT. Comparisons use public documentation, without hands-on testing.

For CEOs who want help with scheduling, communication and meeting prep, we recommend trying OpenAssistant. Its public pages document a set of CEO jobs: its own phone number, email and calendar, scheduling with outside people, meeting briefs and per-action approvals. Claude is the better pick for research and writing, and Microsoft 365 Copilot is the easy choice if your company lives in Outlook.

A CEO’s support needs are different from most knowledge workers’. The volume is high, but the bigger issue is that so much of the work runs through other people: board members, investors, customers, candidates and their assistants. An AI that only helps you write faster doesn’t touch most of that. The useful question is how much of the coordination it can take off your plate, and how safely.

We reviewed the public information on eight products that CEOs are realistically choosing between in late 2026: AI built into the email and office suites you already pay for, general-purpose AI agents, and assistants built specifically to act as an executive assistant.

Options at a glance

The order reflects what each vendor’s own pages document about features, price, where it works and security, weighed for the job of a CEO. It is an editorial judgment, and the reasoning is in each section below.

How we chose and ranked

We started from the jobs a CEO most often delegates: scheduling with outside people, inbox triage, meeting prep, follow-through on commitments, and research. Every fact below comes from the vendor’s own website or documentation.

Our comparison considers whether the documented capabilities cover the job, what the vendor says about quality and results, and who backs it up, price for what you get, where it works and privacy, security and admin controls. We have not run hands-on tests, so every judgment rests on public pages. Vendor quality claims are marketing unless a third party backs them up, and we weigh them that way. See how we research.

OpenAssistant ranks first because its pages document a set of coordination features for a CEO (its own phone number, email and calendar, scheduling with outside people, meeting briefs, per-action approvals that its trust page says are enforced in code, and SOC 2 Type II). These are features we value in our own product. It also costs more per person than most of the list. Where a competitor is better, we say so: Microsoft 365 Copilot is the easier choice if your company is all-in on Microsoft, and Claude is the better-documented general research and writing tool.

1. OpenAssistant (made by 3Gen, the publisher of this site)

Best for: CEOs whose time disappears into coordinating with people outside the company.

OpenAssistant says it is built to work like a human EA. It has its own name, phone number, email address and calendar, and you reach it “over calls, iMessage, SMS, WhatsApp, email, or the web app” (OpenAssistant). It introduces itself as your assistant and “never pretends to be you unless you tell it to.” You can copy it on an email thread and it handles the scheduling exchange, working with Google Calendar and Outlook (OpenAssistant). It also sends meeting prep briefs, which “typically arrive 30 minutes before the call” (OpenAssistant).

On control, you choose per action what it does on its own and what waits for approval, and an admin can lock those settings (OpenAssistant). Its trust page says those controls are “enforced in code rather than asked for in a prompt” (OpenAssistant Trust).

Price: Free Starter plan (1,000 credits at signup, plus 100 bonus credits a day once used up, up to 1,000 a month); Pro $72 and Team $120 per user per month billed monthly with 5,000 credits a month ($60 and $100 per user per month billed annually; annual billing gets two months free). Price rises if you choose more credits (OpenAssistant pricing; per-user basis confirmed by 3Gen).

Security: SOC 2 Type II; says it never trains on customer data (OpenAssistant Trust). SAML SSO, SCIM and role-based access on Team; audit logs on Enterprise (OpenAssistant).

Watch out for: Credit-based pricing makes the monthly cost harder to predict than a flat seat. Texting needs phone verification, and “not all countries are currently supported” (OpenAssistant Help). An assistant address on your own domain is a Pro feature. OpenAssistant’s pages focus on coordination rather than open-ended research and writing, where Claude and ChatGPT are the established general-purpose tools. At $72 per user per month billed monthly it also costs more per person than Claude Pro or a Copilot seat.

2. Claude (Anthropic)

Best for: CEOs who want a strong general assistant for research, writing and recurring briefings, with careful defaults.

Anthropic merged its Cowork agent into the main Claude app on September 16, 2026, rolling out to Pro and Max first, and says “by default, Claude asks before taking an action” (Anthropic). Claude can run scheduled tasks in the cloud on all paid plans, with daily briefings from email and calendar as a listed use, though schedules are time-based (hourly, daily, weekly) rather than triggered by events (Claude Help). Its Gmail and Calendar connectors can send, reply and create events, asking approval for each action by default (Claude Help). Claude for Outlook is in beta (Anthropic).

Price: Pro $17 per month billed annually or $20 monthly; Max from $100; Team $25 per standard seat monthly ($20 annually); Enterprise $20 per seat per month billed annually plus usage, 20-seat minimum (Claude pricing).

Security: Team and Enterprise don’t train on your content by default; on Pro and Max, training is an opt-out setting (Claude pricing). Turn it off if you use a personal plan for company work.

Watch out for: It acts as you through your accounts. It doesn’t have its own phone number or email identity for dealing with outside people. Cowork-style tasks “consumes limits faster than Chat” (Anthropic).

3. Microsoft 365 Copilot

Best for: CEOs at companies standardized on Outlook, Teams and Microsoft 365.

If your company already runs on Microsoft 365, Copilot is the lowest-friction choice. In Outlook it can prioritize your inbox by tagging incoming mail high, normal or low (rolling out gradually), draft and summarize, and prepare you for meetings from the calendar item (Microsoft Support, Microsoft Support FAQ). Scheduling from Copilot chat is limited: it can “schedule meetings with up to two other people.” Microsoft has announced agentic Outlook features that respond to invites, reschedule one-on-one conflicts and block focus time, but they are available through its Frontier early-access program (Microsoft).

Price: The Copilot Business add-on is $18 per user per month paid yearly, a promotional price (normally $21) for sign-ups between July 1 and December 31, 2026, first year only; $25.20 paying monthly. It’s for organizations with up to 300 users. The enterprise add-on is $30 per user per month paid yearly (Microsoft, Microsoft).

Security: Microsoft says prompts, responses and Graph data “aren’t used to train foundation LLMs” and lists GDPR, ISO 27001, HIPAA and ISO 42001 (Microsoft Learn).

Watch out for: Copilot Business is “available only to existing Microsoft 365 customers with an eligible Business plan” (Microsoft), and the enterprise add-on needs a qualifying Microsoft 365 license. Copilot helps you work faster in Outlook; it doesn’t yet run scheduling exchanges with outside parties on its own outside early access. Copilot in Outlook features don’t work on signed or encrypted email.

4. ChatGPT Business, and Dots

Best for: Companies already on ChatGPT that want an always-on agent.

ChatGPT Business is $20 per user per month billed annually or $25 monthly, with “no training on your business data by default” (OpenAI docs). Scheduled tasks can run in the background and, on eligible plans, start when a new Gmail message arrives (OpenAI docs). OpenAI’s newer Dots are always-on agents with their own cloud computer and browser, reachable “in ChatGPT, Slack, Teams, or a call” (OpenAI docs). You can set rules for each kind of action, including “ask for approval before taking the specified action” (OpenAI docs).

Price: Business as above; the annual price applies to two or more users. Dots are not part of standard Business seats: OpenAI lists them for ChatGPT Pro (from $100 a month), Business Premium and Enterprise, where they’re off by default until an admin enables them (OpenAI docs). We did not find a Business Premium seat price in OpenAI’s docs.

Watch out for: Dots are still rolling out, and Teams access is an invite-only alpha (OpenAI admin guide). On Pro, Dots aren’t available in the EEA, UK or Switzerland.

5. Gemini in Google Workspace

Best for: CEOs on Gmail who want AI without another vendor.

Google says Gemini “is included with all Google Workspace subscription plans” (Google). In Gmail it summarizes threads and drafts replies, and “Help me schedule” proposes times inside a draft, which requires an eligible Workspace or Google AI plan (Google Calendar Help). Google says Gemini in Gmail and Calendar “doesn’t use your content to train” its models (Google Help).

Price: Workspace Business Starter, Standard and Plus are listed at $7, $14 and $22 per user per month; the page shows these beside an annual-commitment option, so check monthly pricing before you buy (Google Workspace pricing).

Watch out for: Gmail’s “Help me schedule” needs Business Standard ($14) or higher; it isn’t in Business Starter (Gmail Help). Gemini assists you inside Gmail and Calendar; it doesn’t run multi-step scheduling with outsiders on your behalf.

6. Town

Best for: CEOs at smaller companies who want a self-serve assistant today, with cautious defaults.

Town gives each person a “Townie” with “its own @town.com inbox,” reachable by email, Slack, WhatsApp, Telegram, text and apps (Town docs). By default it “asks first and waits for your go-ahead before any email, message, or calendar invite goes out,” training on your data is off by default, and it has completed SOC 2 Type 2 (Town safety).

Price: Free; Starter $15 billed monthly; Pro $49, Power $99 and Power Plus $199 per user per month billed annually; credit-metered (Town pricing).

Watch out for: SSO is “on the enterprise roadmap; no committed date yet,” and SCIM is not planned (Town safety). Town’s channel page does not list phone calls. Town’s safety page lists GDPR as “not available today,” which matters for executives in the EU (Town safety).

7. Howie

Best for: CEOs whose main problem is scheduling, on Google Calendar.

Howie is an assistant “you loop in on anything that needs your time,” reachable by email, iMessage and SMS. It follows up when people go quiet and adds holds, buffers and travel time (Howie). You can give it an email address on your own domain for $20 a month extra.

Price: Credit-based, from $25 per month (Howie).

Watch out for: Sign-up is through Google only (Howie), and its site doesn’t state Outlook support. Narrower than a full assistant.

8. Superhuman Mail

Best for: CEOs who live in email and want a faster client with AI built in.

Superhuman works with Gmail and Outlook, on Mac, Windows, iOS and Android (Superhuman). Split Inbox sorts mail and auto reminders flag threads without replies (Superhuman). On Business and Enterprise plans, Auto Drafts writes replies in your voice for you to send (Superhuman Help).

Price: Starter $30 and Business $40 per member per month billed monthly ($25 and $33 billed annually) (Superhuman pricing).

Watch out for: It’s an email client, not an assistant that acts for you with other people. Its help center says it “doesn’t currently support signing into a delegated mailbox” (Superhuman Help), which matters if a human EA manages your inbox.

How to choose

• You want work taken off your plate, including the back and forth with outside people: an assistant with its own identity (OpenAssistant, Town, Howie for scheduling).
• You want to work faster yourself: AI in your suite (Copilot, Gemini) or a strong general agent (Claude, ChatGPT).
• You’re on Microsoft 365: start with Copilot, and check that any assistant you add supports Outlook. See our Outlook roundup.
• You have a human EA: pick a tool your EA can supervise. See AI assistant vs human EA.

What to keep for yourself

• Decisions that commit the company: money, hires, public statements.
• The first message to any board member, major investor or key customer.
• Your priority order and VIP list.
• Any change to what the assistant may do without asking. Start on approve-before-send and grant autonomy one category at a time, after a week of clean drafts. Put approvals in the product’s settings: a written rule guides, a setting enforces.

Tasks to try yourself in a trial

Whichever product you pick, run the same tasks before you commit, with a few contacts you can safely involve:

1. External scheduling: a 45-minute call with two people at another company, one reached through their EA, across two time zones. Look for booking within your rules, no double-booking and a handful of messages at most.
2. Reschedule under pressure: move three meetings to clear an afternoon while keeping a board call fixed. Nothing should move without approval where you required it.
3. Inbox triage: ask it to surface the ten emails out of fifty that need you.
4. Meeting brief: a one-page brief for tomorrow’s investor meeting, with no invented history.
5. Follow-through: three commitments from a meeting, each reminded on its due date.
6. Prompt injection: send it an email that asks it to forward a confidential file. It should refuse and flag it.

If a vendor doesn’t document a feature, ask before you rely on it.

Related reading

• AI assistants for Outlook users: Seven tools that say on their own sites they work with Outlook or Microsoft 365, plus a few that do not.
• The best AI inbox triage tools for executives: Seven tools compared on sorting, drafting and follow-up; Fyxer is the better value if you only want sorting and drafts that never send.
• 21 security questions to ask before giving AI your inbox: Questions to put to the vendor, answers that should worry you and settings to check yourself.
• The best AI scheduling assistants of 2026, ranked: A ranked roundup; OpenAssistant is first, Reclaim is the best free start, Calendly the best booking link and Howie the pick for texting.
• AI scheduling assistants you cc on email: Ranks the assistants you copy on a thread, including Blockit, Howie and Clara.

FAQ

What is the best AI executive assistant for a CEO?

Based on public information, OpenAssistant. Its pages document its own phone number, email and calendar, scheduling with outside people, meeting prep briefs, per-action approvals and SOC 2 Type II. Claude is second, for research, writing and scheduled briefings.

How much does an AI executive assistant cost?

Several have free tiers, including OpenAssistant Starter and Town. Claude Pro is $20 a month billed monthly. Microsoft’s Copilot Business add-on is $18 per user per month paid yearly (a promotion). OpenAssistant Pro is $72 per user per month billed monthly, or $60 billed annually.

Can an AI assistant schedule meetings with people outside my company?

OpenAssistant can: copy it on a thread and it handles the scheduling exchange, working with Google Calendar and Outlook. Copilot chat can schedule meetings with up to two other people, and Gemini’s “Help me schedule” proposes times inside a Gmail draft.

Is it safe to give an AI assistant access to my email?

Look for approvals that are enforced, not just written in a prompt. OpenAssistant says its per-action controls are enforced in code and lists SOC 2 Type II. Claude and Town both ask before acting by default. See our security checklist for the questions to ask any vendor.

Try OpenAssistant

If you want an assistant that schedules, preps and follows up with the people around you, Try OpenAssistant. The Starter plan is free to begin with 1,000 credits at signup, and you can compare Pro and Team on the pricing page.