Working with Penpal, Letterhead's AI assistant

Penpal is Letterhead’s assistant — a panel that sits beside whatever you’re working on, in every account. This article covers how Penpal works in general (opening it, starting over, chat history, handing off to a person), everything it can do with a newsletter draft in conversation, and how to leave it a standing instruction it carries out later or on a repeat. For what Penpal can do in other parts of Letterhead — promotions, transactional email performance, or (from a connected AI client like Claude Desktop) goals, reports, and automations — see Related below.

You tell Penpal what you want in plain language — “shorten the subject line”, “make this intro punchier”, “swap in this story” — and it changes the newsletter for you. When it touches a draft, a preview of the finished email opens next to the conversation and re-renders as the work happens, so you can see the result without leaving the chat or reloading anything.

Open the assistant

Select the speech-bubble button in the top bar. The assistant slides out on the right; the page you were on stays visible beside it, so you can keep working while the conversation is open. On a narrow screen it opens as a full-width panel instead.

The button is in the top bar on every page, so you can reach the assistant from your newsletter list, the composer, your reports, or your settings — wherever the question comes up. Select it again to close the panel; your conversation is still there when you come back.

On a wide screen, Penpal may already be open when you arrive — it’s meant to be noticed rather than hunted for. If you’d rather it stayed out of the way, close it once and it won’t open itself again, on this visit or any later one. The speech-bubble button still opens it whenever you want it, and closing it never loses your conversation.

That choice is remembered across sessions, so closing the panel keeps it closed when you return to Letterhead later.

Ask for a change

Type what you want in the message box and send it. The assistant works with your real newsletters, so you can refer to them the way you’d say it out loud, and it knows which page you’re on — “this draft” is enough when you’re looking at one.

Things it can do with a newsletter:

• Read a draft back to you — its title, subject line, preview text, status (draft, scheduled, published), creation and last-modified times, and what’s in it.
• Change the subject line or preview text — including asking for a few options to choose from. This works on any newsletter.
• Rewrite the words of a draft it wrote — tighten the introduction, change the tone of a section, cut a paragraph down. See the note below on which drafts this covers.
• Pull in content — add a story you point it at, or something from your Curations library.
• Answer questions about how a send performed — opens, clicks, and the numbers behind your last newsletter.

Which drafts the assistant can rewrite

If you asked the assistant to draft a newsletter, it owns that draft’s wording and can keep editing it for you. A newsletter you built yourself in the composer is made of blocks, and its body is edited there — so if you ask the assistant to rewrite a section of one, it will tell you that and leave the body alone. Its subject line and preview text are still yours to change by asking.

Some example asks:

• “Make the opening two sentences punchier.”
• “Give me three subject lines for this issue.”
• “Shorten the second section — it’s twice as long as the others.”
• “Add the piece about the new library branch after the events roundup.”
• “How did last Thursday’s newsletter do?”

The assistant only changes something when you ask it to. It won’t edit or send a newsletter on its own.

Ask it to draft a whole newsletter

You can also start from nothing: describe the newsletter you want in conversational terms — “Draft a newsletter about this week’s tech policy updates” or “Create an issue with our top curated stories about sustainable design.” This works from the in-app panel and from a connected AI client such as Claude Desktop.

To build the draft, the assistant will:

• Pull relevant content from your curations
• Source fresh articles from the web when needed
• Write the newsletter body in your channel’s established voice, derived from your top-performing letters
• Render it into email-safe HTML with proper formatting
• Append a compliance footer with the correct unsubscribe link and mailing address
• Save it as a draft in your Letterhead account

Drafts arrive in your channel’s visual identity

A drafted newsletter is rendered in your channel’s brand colors, fonts, and logo, sourced from your channel’s settings — so it looks like your actual newsletter from the moment it’s created. The response also includes a direct editor link that opens the draft straight in the composer for review.

If a draft isn’t what you wanted, ask the assistant to delete it — “Delete that draft” — and request a new one, without manually removing the previous one first.

The assistant never schedules or sends anything: every draft waits for you to review it. When you’re happy with one, open it in the composer to make final edits, select your audience, choose a publication date, and send.

Ask it to take you somewhere

As well as answering, the assistant can move you around the app. Ask for a screen and it opens it, instead of telling you which menu to look under — “take me to my drafts”, “open the audience page”, “show me the analytics for the morning briefing”. It tells you where it’s taking you, then takes you there, and the panel stays open beside the new screen so you can keep talking.

It can reach the screens you’d normally click to: your newsletters, templates, automations, and curations; your audience; your analytics, reports, and goals; your promotions; your brand kits and image gallery; your settings, integrations, and team; your notifications and your own account. Name a newsletter and it opens that newsletter’s own editions, automations, audience, analytics, reports, or settings.

If you work in more than one Letterhead workspace, you can ask to move between them — “switch me over to Riverside” — using whatever you normally call it. A workspace is a separate place to work, so this one reloads the page, and you’ll start a fresh conversation on the other side.

It can only take you where you can already go. Ask for a newsletter or a workspace you don’t have access to and it says so instead of moving you — the same permissions apply as when you navigate yourself. If it can’t find what you named, it’ll ask you to name it the way it appears in your menus.

Ask it to do something later, or keep doing it

Some things are worth more than one reply — going through a year of sends, watching what comes into your curations over a week, reading every newsletter you schedule with fresh eyes. Ask for work like that — “go through my last twenty sends and tell me which subject lines pulled best” — and Penpal can take it away, finish it after the conversation ends, and come back to you when it’s done. You can close the tab.

Early access

Standing instructions are being switched on gradually and aren’t available on every account yet. If you ask for one and Penpal doesn’t offer it, that’s why.

Name a time and it waits for then instead of starting now:

• “Tomorrow at 7am, look through what I’ve curated about school funding and show me what’s there.”
• “Friday afternoon, check whether the events roundup is still pulling its weight.”

Ask for it to come back and it becomes a standing instruction — something Penpal keeps doing until you stop it:

• “Every weekday morning at 7, give me the overnight numbers.”
• “Every Friday, pull the five best things from my curations this week.”
• “Monthly, tell me how my open rate is trending.”

A repeating instruction picks up its rhythm from the first time you give it: “every weekday at 7am” fixes the hour, “every Friday” fixes the day, and a monthly one has to start on the 28th of the month or earlier so it lands every month rather than skipping February.

Penpal reads the day and time back to you before it sets anything up, so a misunderstanding is caught in the conversation rather than at 7am tomorrow. If it isn’t sure which time zone you’re in, it asks — a task set in the wrong zone runs hours off and nothing about it looks wrong until you miss it.

Or when something happens, rather than at a time

Instead of a time, you can name a moment to wait for:

• “When a newsletter is scheduled, review it and tell me what you’d change.”

Right now there is one thing Penpal can watch for — a newsletter actually being scheduled to send. Ask it to watch for something else and it will tell you plainly that this is the only one it can watch today, rather than agreeing and quietly doing nothing.

What a standing instruction can and can’t do

A standing instruction reads, researches, and reports. It can look through your newsletters, your audience, your curations and your numbers, and write you an answer. It cannot create, change, send, or delete anything while you’re away — if you ask for something that would, Penpal says so at the time rather than accepting it and surprising you later.

Long jobs are fine. If the work needs more digging than one stretch allows, it carries on across several, and if it genuinely runs out of room it tells you it stopped partway instead of handing you half an answer dressed up as a whole one.

How the answer reaches you

The answer waits for you in the app as a notification. Ask for it by email — “email me the results” — and it arrives in your inbox as well. It goes to you and nobody else; if you ask for it to be sent to a colleague, Penpal will tell you it can only send it to you.

If a run can’t finish, you hear about that too, rather than being left waiting for something that isn’t coming.

A repeating instruction remembers what it told you last time and reports what’s changed rather than resending the same finds every morning — and if nothing has changed, it says so plainly, which is a useful answer rather than a failed one.

Ask what you’ve got running, or call one off

You don’t have to leave the conversation to keep track of them:

• “What have you got running for me?” lists your standing instructions, how often each one repeats, and when it last ran.
• “Stop the school funding one.” calls it off.

A run already under way finishes — stopping an instruction prevents the ones still to come, so if one is mid-flight when you call it off, Penpal says so rather than letting an answer arrive after you thought you’d stopped it.

See and manage your standing instructions

Everything you’ve asked Penpal to keep doing is listed under Standing instructions, alongside your other company pages. Each one shows what you asked for in your own words, how often it repeats, when it next runs, when it last ran, and what that run told you.

From here you can:

• Pause one — it stops running and keeps its place, so you can start it again later. A paused instruction won’t run until you turn it back on, and a repeating one picks up at its next proper occurrence rather than replaying the one it missed.
• Delete one — it stops for good. Anything it has already sent you stays where it is.

Times are shown in the time zone you set the instruction in, so “every weekday at 7am” reads as 7am even when you’re reading it from somewhere else.

Watch the draft update beside the conversation

As soon as the assistant works on a draft, a Live preview pane opens to the left of the conversation showing the newsletter as a reader would receive it, with the draft’s title above it. Each time the assistant makes another change, the preview re-renders — so you can ask for a rewrite, read it in place, and ask for another pass without opening the composer.

Close the preview with the × in its header when you want the room back. The draft itself keeps every change the assistant made; closing the preview only hides the view.

The preview appears on desktop-width screens, where there’s space for it beside the conversation.

If the newsletter is open in the composer

You can have a newsletter open in the composer and talk to the assistant at the same time. When you ask it to change the subject line or preview text, the new wording drops straight into the fields you’re looking at, and a short message tells you it’s arrived.

It isn’t saved yet. Save the newsletter the way you normally would to keep the new wording — or change it again yourself first, since it’s just sitting in the editor like anything else you typed.

Start over, or pick up an earlier conversation

The ⋯ menu in the panel header has two entries:

• New chat clears the conversation and starts fresh. Penpal greets you differently each time, so a new conversation doesn’t feel like a form.
• Chat history opens your past conversations with the assistant and with Letterhead’s support team, so you can re-read one or carry it on.

When you’d rather talk to a person

Ask for a human at any point — or select Talk to a human — and the assistant hands the conversation to Letterhead’s support team in the same panel. They can see the conversation so far, so you don’t have to explain it twice. If you go

Related

• AI Agents overview
• Manage your promotions with the AI assistant
• Set goals, schedule reports, and manage automations with the AI assistant
• Ask the assistant why a link looks different in the inbox
• View performance metrics for transactional emails