Best Email Delegation Tools for Executive Assistants (2026)

The best email delegation tools for executive assistants depend on who does the work. For one executive and one EA, use Gmail or Outlook delegate access. For several people on one inbox, use Missive, Front or Hiver. When an AI agent drafts and a person approves every send, use AI Emaily, which we build.

This guide compares all of them on the things that decide the purchase: approval before send, who shows on the outgoing message, what the audit log really records, and how the calendar is handled. Packaging changes often, so check each vendor's pricing page before you commit. For the day-to-day EA workflow rather than the tools, see email management for executive assistants.

Comparison table#

Based on each vendor's own help and pricing pages as of November 2026. Where a vendor does not document something, the cell says so.

The short answer: who each pick is for#

"Delegation" hides several different jobs, so pick by the job you are actually doing.

If the executive lives in Gmail and one assistant handles the mail, set up Gmail delegate access. It has no third party to trust. If the executive lives in Outlook, use Outlook delegate access with a Reviewer, Author or Editor level. Our guide to delegate vs shared mailbox vs Send As in Outlook explains which one you need.

If two or more people handle the same address, such as an EA covering three executives, go to Missive, Front or Hiver so assignments and visibility are first-class. If the work goes to an agent as well as a person, AI Emaily is the pick. It drafts each reply, stages follow-ups, moves cold outreach to a Cold Email folder and keeps a per-action log. We build it, and where that is not your problem, one of the others is the better fit.

How we compared them#

We compared documented capabilities, not hands-on test scores. Four dimensions decided the order:

• Password never shared. Access runs on a native permission model or a seat, not on a copied login.
• Attribution on outbound mail. The recipient can tell a delegate sent the message, or cannot, by policy. Both are legitimate; the tool should make the behaviour clear.
• Per-action audit. A log that names the actor for sends, deletes and rule changes. Regulated teams need this by policy. Everyone else needs it the first time something goes wrong.
• Approval before send. Especially when the delegate is an AI, the manager sees a queued draft and approves it, rather than finding out after it went.

Which tools let executives approve replies before an assistant sends them?#

Few tools enforce this. Native Gmail and Outlook delegates can send straight away, and the shared-inbox tools offer draft collaboration rather than a formal gate. AI Emaily enforces it for agent drafts: in Copilot, nothing leaves until a person clicks Send.

If you use a remote EA or virtual assistant service, the same rule applies. The service runs on whichever tool you give it, so the approval step comes from your setup, not the provider. Ask for a draft-only agreement, give the assistant their own access rather than your password, and pick a tool from the table that fits how strict the gate has to be.

Delegation and permission controls for calendars#

For executive assistants managing several high-stakes calendars, the strongest permission controls sit in Google Calendar and Outlook themselves, not in an inbox tool. Gmail delegation and calendar access are separate settings, so grant both.

The tools, ranked#

The order reflects the executive-assistant angle above: approval, audit and permission control, not raw feature count. A tool lower on the list is often right for a different pattern, and each entry says which.

1. AI Emaily: approval-first delegation to a person or an agent#

We build AI Emaily. It is the pick when the executive wants an agent that drafts, files and stages follow-ups, and wants a person to approve every outbound send with an audit trail a compliance officer can read.

Three modes set the contract. Manual is AI on demand. Copilot drafts and queues, and nothing sends until a person clicks Send. Autopilot handles routine mail within your rules, for allow-listed senders, with a 5-minute countdown you can cancel. Autopilot is on the Autopilot and Team plans, and follow-up handling comes with it.

Drafts come from the Personal Context you set, plus per-client profiles. On a shared mailbox the agent drafts as the owner, whichever member asked, so the executive's tone holds when the EA is at the keyboard.

Here is how an EA actually gets access. It needs the Team plan, because Pro and Autopilot have no seat for a second person, and the only other way in would be sharing the executive's login. Don't do that.

• Best for: an executive who wants an agent plus a human approver in one queue.
• Limits: no on-behalf marker, so recipients see the mailbox or a verified Gmail alias, and no Outlook Send As or Send on Behalf. Outlook connects the signed-in mailbox only, so Microsoft 365 shared mailboxes and Outlook delegate access don't carry over. It is not a helpdesk: no SLAs or CSAT. On Android it is the installable web app; a native app is coming.
• Packaging: no free plan. Team is $14.92 per seat a month billed annually or $19.99 monthly, minimum 3 seats, no trial, so an executive-EA pair still pays for three. 7-day free trial on Pro or Autopilot for the solo executive.
• Audit: every agent action is logged with reasoning and undo, and team actions stay attributed to the member.

1. 1

   The executive connects their mailbox

   Gmail and Microsoft 365 use OAuth. iCloud, Yahoo, Fastmail and other IMAP providers use an app password you can revoke.

2. 2

   The EA joins with their own login

   Invite the EA by email. They accept and take a seat.

3. 3

   An owner or admin shares the mailbox

   Settings, Mailboxes, Share with team. The EA can read and reply on its threads but never sees the owner's OAuth tokens or private context.

4. 4

   The EA works the queue

   The EA assigns threads to a person or the agent, comments internally and approves Copilot drafts. Mail leaves from the connected mailbox.

5. 5

   The executive keeps a check

   An EA can move a thread to needs_review so the executive checks the reply first. That is a workflow step, not a lock. If someone must never send, give them the Viewer role, which can read and comment only.

2. Gmail delegate access: the native answer, and often the correct one#

The executive opens Settings, See all settings, Accounts and Import, then Grant access to your account, and adds the delegate. The delegate has a week to accept, and access can take up to 24 hours to start. A delegate can read, send and delete mail, but can't chat, change the password or open Google Account settings.

• Best for: one executive and one EA on Google, with no agent involved.
• Limits: personal Gmail allows up to 10 delegates; Workspace allows up to 1,000, with about 40 using the account at once in typical use. The Gmail API caps delegates at 25 per user and needs a service account with domain-wide authority. On the delegated account there is no Gemini, Smart Compose, Smart Reply, spell check, or Drive and Photos attachments.
• Packaging: included with Google accounts.
• Audit: on Workspace Enterprise and Education Standard/Plus, Gmail log events show delegate activity, including opens and replies. Other editions don't get those delegate columns, per Google's announcement.

3. Outlook / Microsoft 365 delegate access: permission levels and a real audit trail#

Outlook delegation is more granular than Gmail's. The executive assigns Reviewer (read only), Author (read and create, and change their own items) or Editor (read, create and modify, including the owner's items). Levels apply per folder, so an EA can have Editor on the calendar and Reviewer on the inbox. For setup, see how to give someone access to your Outlook inbox.

Send on Behalf shows "Delegate on behalf of Manager" in the From line. Send As is granted by an Exchange admin and shows no sign of the delegate. Which one the executive picks is a policy call worth writing down. Note that Microsoft says assigning mail-folder delegates is only partly available in new Outlook, so you may need classic Outlook to set them up.

• Best for: Microsoft 365 pairs who need clear accountability, and calendar work.
• Limits: no approval step before send.
• Packaging: included with Outlook on Microsoft 365 or Exchange accounts.
• Audit: mailbox auditing is on by default. For delegates, Microsoft's default set logs Send As, Send on Behalf, deletes, item updates, mail access, and inbox rule and folder permission changes. Moves are not in the delegate default set, so add them if you need them, and confirm your retention period in Purview.

4. Missive: role-based shared inbox with per-user attribution#

Missive shares the executive's account with a team, and each teammate signs in as themselves. Team members are Active (notified, and see conversations in Team Inboxes) or Observers (no notifications, for oversight). An EA covering three executives can be Active on one team and an Observer on another. Live collaborative drafting lets an EA prepare a reply the executive edits before it sends.

• Best for: one EA across several executives who want a lighter tool than Front.
• Limits: no approval workflow on the pricing page. Collaborative drafts don't sync back to Gmail's drafts folder.
• Packaging: per seat with Starter, Productive and Business plans. No free plan; new teams get a 30-day trial.
• Audit: "Audit trail" is listed as a collaboration feature, without saying which plans include it.

5. Front: inbox delegation with a catch#

Front has a real delegation feature. The executive goes to Inboxes, then Delegations, and shares all sections or specific inboxes. The delegate can archive, snooze, assign and reply, but replies come from the delegate's own address. They cannot send as the executive, and they cannot see the executive's Drafts or Sent sections. If the EA must reply as the executive, Front's delegation won't do it.

• Best for: several people on one address with SLA discipline. That is the support-ops shape, not the exec-EA one.
• Limits: no send-as for delegates, and drafts are shared rather than approved.
• Packaging: per seat with Starter, Professional and Enterprise plans. No free plan listed; 14-day free trial. Check front.com/pricing.
• Audit: the audit log is on all plans and tracks changes to inboxes, rules, teammates and templates. Message sends are not listed, so don't assume it answers "who sent this".

6. Hiver: Gmail extension or standalone Omni#

Hiver comes in two forms. Hiver in Gmail is a Chrome extension that adds assignment, notes and shared drafts inside Gmail. Hiver Omni is a standalone platform that also connects Outlook shared mailboxes. Older comparisons call Hiver Google-only, which no longer holds.

• Best for: a team that wants to stay inside Gmail.
• Limits: each user holds one role across all shared inboxes, and custom roles are on the Elite plan. On Omni with Outlook, syncing stops if the person who authorized the mailbox loses access. Shared drafts are documented for the Gmail extension.
• Packaging: per user. Pricing pages list Growth, Pro and Elite with a free trial, and no free plan that we could find. Check hiverhq.com.
• Audit: Hiver's marketing mentions audit trails, but we found no detailed spec. Ask for one if it decides the purchase.

Hiver vs Front for executive assistants#

Which is better, Hiver or Front? For an EA who wants to stay in Gmail, Hiver is the smaller step. For multi-channel teams with heavy automation, Front is the stronger platform. Neither is built around one executive and one EA, and Front's delegation stops short of sending as the executive.

7. Superhuman Mail: for the executive, while the EA stays in Gmail#

Superhuman Mail is built hard around keyboard speed, and it beats us on that axis. If the executive is a solo power user with no EA, it's worth a trial. Its help center describes a working EA pattern: the assistant uses Gmail delegation, drafts in Gmail, and the executive reviews and sends in Superhuman because drafts sync both ways.

• Best for: an executive who wants Superhuman's speed and already has Gmail delegation.
• Limits: its help center says you can't sign in to a delegated mailbox in Superhuman Mail, and describes Outlook support as coming soon. Check for current status.
• Packaging: check superhuman.com/plans for current plans.
• Audit: nothing delegate-specific documented.

8. Fyxer: overlay drafting, not delegation#

Fyxer works inside Gmail and Outlook, puts drafts in your inbox and says it never sends without your permission. That is a light "AI prepared it, human approves" pattern for one person.

• Best for: a single executive who wants drafting help without changing clients.
• Limits: its public pages describe no delegate role, so don't count on clear roles for Fyxer and a human EA on one account.
• Packaging: check fyxer.com for current plans.
• Audit: no per-actor audit documented.

The audit picture: can you name who sent it?#

Compliance officers and boards ask the same question after something goes wrong: who sent this. Outlook with Purview answers it for Send As and Send on Behalf. Gmail answers it through log events on Enterprise and Education editions, and less well on the others. Front answers it on the message itself, because a delegate's reply comes from their own address.

AI Emaily answers it in our own log, not in the mail: recipients see the mailbox, and the audit trail shows the agent action or team member. If the executive is in a regulated seat, such as legal, finance, healthcare or investor relations, treat this axis as the tiebreaker and ask each vendor for a sample log.

How to choose for your situation#

Match the pick to the shape of the pair, not to the loudest marketing.

1. 1

   One executive, one EA, Google Workspace

   Use Gmail delegate access and share the calendar separately. Check whether your edition includes delegate log events if audit matters.

2. 2

   One executive, one EA, Microsoft 365

   Use Outlook delegate access at Author or Editor, and Delegate on the calendar. Ask an Exchange admin for Send As only if the executive wants the delegation hidden.

3. 3

   One EA covering several executives

   Missive or Front. Missive is the lighter lift; Front is stronger when SLAs and automation matter.

4. 4

   Executive who wants an agent as well as an EA

   AI Emaily on the Team plan, so the EA has a seat and approves the agent's Copilot queue. If the executive will approve alone, Pro is enough. We build it.

5. 5

   Executive in a regulated seat

   Outlook plus Purview, or Workspace Enterprise with Gmail log events. Add a tool like AI Emaily only if its log meets your policy, and confirm retention first.

Security: what to insist on before you delegate#

The other two non-negotiables are minimum access scopes and an audit surface you can read. If a tool cannot show who sent a specific message on a specific date, it is a shared login with better branding.