Tag, segment, and update groups of contacts with the AI assistant

Some audience jobs are really “pick a few hundred people, mark them, and make a list of them.” Warming up a new sending domain is the usual one: you send to a small group on day one, a slightly bigger group on day two, and so on, and no one should land on two days. Instead of building that by hand, ask Penpal in plain words. It works on your whole company audience, and it sends nothing.

Look up one contact

Ask about a person by email address or name — “What do we have on [email protected]?” — and Penpal reads back what the Contacts screen shows: their name, tags, fields, which newsletters they’re on and each subscription status, anything stopping them being mailed, when they were last active, how they engage, and their most recent activity. It changes nothing, so there is nothing to confirm. If several contacts match, Penpal tells you who and asks which one you mean; if none match, it says so. It’s a handy check before or after changing a contact.

Narrow a group the way the Contacts screen does

When you tag a group or remove a tag or change a field, you can narrow it by the same things the Contacts screen filters on: a name or email search, tags a contact carries, which newsletters they’re on and their subscription status, and the values of your contact fields. Subscription changes and deletes take the same filters, and need at least one.

• “Tag everyone named Georgina as awesome.”
• “Tag contacts subscribed to the Daily newsletter who are tagged west-test as spring-push.”

A filter Penpal doesn’t understand is refused rather than ignored, so a group never grows beyond what you described. The preview and confirmation apply to exactly the group you narrowed to.

Tag a set number of contacts

Ask for a group by size and, if you want, by where the email address lives:

• “Tag 100 Gmail contacts as warmup-day-1.”
• “Tag 250 contacts who aren’t already tagged warmup-day-1 as warmup-day-2.”

Penpal creates the tag if it’s new, leaves out anyone who already carries a tag you name, and picks at most the number you asked for, up to 5,000 at a time. Before it writes anything it tells you how many contacts it would tag. Say yes and it tags that many — never more than it showed you. For the next hour, asking for the same thing again after you’ve confirmed gives you the recorded result instead of tagging more people; after that, the same request picks a new group of contacts who don’t have the tag yet.

It can’t pick contacts by how recently they opened, so a request like “100 Gmail contacts who opened in the last 30 days” is declined rather than quietly widened to everyone.

Create a segment

Ask for a segment built from tags, tags to leave out, and/or an email provider, and give it a name:

• “Make a segment called Warm-up day 1 of everyone tagged warmup-day-1.”

Every condition you give has to be true for a contact to be in the segment. Segment names have to be new. Penpal agrees the name with you, then creates the segment straight away, with no separate confirmation step and tells you how many contacts are in it right now. A segment is a live filter rather than a copy, so its size follows the tag: if it says zero, the tag probably hasn’t been applied to anyone yet.

Set up a whole warm-up schedule

Describe the schedule once — the provider, how many days, and how big each day is:

• “Plan a Gmail warm-up over five days: 100, 150, 250, 400, then 600.”

Penpal lays out the plan day by day: how many contacts each day would get, the tag, and the segment. If you don’t have enough contacts for the ramp, it says so and later days get fewer. You confirm the whole plan once, and it then creates a tag and a segment for every day, with no contact on two days. A plan can run up to 30 days, with at most 5,000 contacts on any one day and 25,000 in total. Tags are named like “warmup-day-3” and segments like “Warm-up day 3”. The name stem is yours to choose (“warmup” is just an example). Use a fresh one for each schedule, because a segment follows its tag; if a tag or segment name is already taken, Penpal asks for a different one.

If a day can’t be finished, Penpal stops there and tells you which days are in place; the later days weren’t started. If a day’s contacts are tagged but its segment couldn’t be created, Penpal says so.

Remove a tag or change a field for a group

Ask to take a tag off a group, or to set or clear one of your own contact fields across a group:

• “Remove the warmup-day-1 tag from the 200 contacts that have it.”
• “Set the Region field to West for 300 Outlook contacts.”
• “Clear the Region field for everyone tagged west-test.”

You can narrow the group by email provider and by a tag the contacts carry, and the group is capped at 5,000 a time. Penpal always shows you how many contacts the change applies to first. For setting or clearing a field it also says how many of them already have a value that would be replaced or erased. Field changes can’t be undone, so read that number before you confirm.

Penpal only changes fields your company has defined, refuses values that look sensitive, and keeps text values to 1,000 characters.

Subscribe, unsubscribe, or mark contacts not subscribed

Ask Penpal to change the subscription status of a group for one newsletter — the same change the Contacts screen offers:

• “Unsubscribe everyone tagged bounced-test from the Daily newsletter.”

Describe the group with at least one filter; Penpal won’t change the whole audience at once, and a group is capped at 5,000. It shows how many contacts would change and waits for your confirmation. This sends nothing. Changing status can’t be undone as a step: the opposite change sets every matching contact to that status and does not restore what each had before. When you subscribe contacts, only do it for people who have agreed to receive the newsletter. A few contacts may be skipped if they have opted out of everything.

Delete contacts

Ask Penpal to delete a group of contacts — the same delete the Contacts screen offers. Deleted contacts can’t be restored, so Penpal asks for more than a yes: it tells you how many contacts it would delete, and you type that number back to confirm. It refuses a request that doesn’t match the count it showed you, one that names no filter, and one over 5,000 contacts. The deletion is recorded once in your company’s activity log, with how many contacts were removed and who removed them, the same as a delete from the Contacts screen.

Using these from another AI tool

If you’ve connected an AI tool to Letterhead, tagging, segments, warm-up plans and bulk updates are available there, with the same preview-then-confirm step and the same narrowing filters for tagging and updating. Looking up a contact, changing subscriptions, and deleting contacts are Penpal only. They need you to be signed in as yourself, so a connection that uses only an API key can’t use them. A connection made before this was available needs you to sign in again.

Good to know

• Tagging, updating, subscription changes, deletes and warm-up plans start with a preview; nothing is written until you confirm it. In Penpal, confirm in the same chat conversation where you asked: a preview from one chat can’t be confirmed from another, so if you start a new chat, ask again and confirm there.
• Subscription changes and deletes are also available only where the Contacts screen’s own bulk actions are turned on for you.
• Only company administrators can use these; team members limited to certain channels can’t.
• Tags and segments you create show up with the rest of your audience tags and segments — see Using tags and segments.
• Contacts with no email address are never included, and contacts you added by phone number (SMS only) who gained an email address later may not be matched by an email-provider filter.