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When you send a letter on behalf of someone else, the letter stays theirs. Their name is on the letterhead, in the signature block and in the return address on the envelope, and the file copy goes into their records, not your inbox. On the page, your part shows in one small place at most: lowercase typist initials under the signature, if your office uses them.

That rule settles most of what comes up when an executive forwards a PDF with "can you get this in the mail?"

First, decide whose letter it is#

A letter from your executive is in their voice and signed by them, or by you with their permission. You don't appear in it. Client letters and engagement letters are usually this kind. Chron's guide to writing for a boss says to mention that you're writing on their behalf only where it's appropriate, such as a letter to a court.

A letter from you, on their behalf is in your voice, signed by you with your own title. It suits scheduling, logistics and replies your executive asked you to handle. Say so in the first line: "I'm writing on behalf of Ms. Rivera, who has asked me to confirm…"

Detail
A letter from your executive
A letter from you, on their behalf
Top of the page
Their letterhead, or their name, title and address
Their letterhead
First line
Their voice; no mention of you
"I'm writing on behalf of [name]…"
Signature block
Their name and title
Your name, then "Executive Assistant to [name]"
Who signs
They do, or you with their permission
You do
Typist initials
Yours, lowercase, below the block
Leave them off; you wrote it
Envelope return address
The address that handles their mail
The same, unless replies should come to you
File copy
Their file
Their file

How the letter reads: letterhead, signature block, initials#

Letterhead. Purdue OWL's business-letter guide puts the sender's address in the letterhead, or at the top, one line above the date, when there's no letterhead. Virtual assistants: ask each client for a letterhead file once and keep it. One list of virtual-assistant tasks describes the job exactly: the VA "prints letters on your stationery and mails them the following day."

Signature block. Purdue leaves four lines between the closing and the typed name for the signature; the title goes under the name. If your executive signs the PDF, the signature lands in that gap. If you sign for them, the notation (p.p., "for", initials) is its own question; our guide to signing for your boss covers it.

Typist initials. Purdue says they "indicate the person who typed the letter," and you leave them off a letter you typed yourself. McGraw-Hill's business-format guide sets them in lowercase with no punctuation.

Copies and enclosures. A copy line ("c Dana Ortiz") names everyone else who gets the letter, and "Enclosures (2)" tells the reader what should be in the envelope. Each person on the copy line needs their own copy, which means a second letter to a second address.

Whose return address goes on the envelope#

Where it goes on the envelope is the easy part. Whose address it is takes a decision: use the one where someone will open a returned letter and act on it, usually your executive's office or the company's mailing address, with their name or the company on the first line. Matching the letterhead sends replies and returns to the same place.

Some principals make this harder. One assistant described an executive with "mail going across 6 states." Pick the one address someone checks every week and use it every time.

Can you mail a letter with a different return address, such as your own? Some virtual assistants do, so replies come straight to them. Do it only when the client agrees and you'll handle whatever comes back; otherwise use the client's business address.

Two to avoid:

Sending it from your desk with Postmarkr#

Remote assistants don't have the office printer and stamp drawer; as one put it on r/ExecutiveAssistants, they would "rather just find a site that does it all." When you upload the signed PDF for your executive, three things differ from mailing your own:

  • Their return address, saved once. Keep each executive's address in your address book and set the one you use most as the default.
  • Check it on the preview. The address page shows that return address before you pay.
  • Batch the evening's letters. Five signed letters to five people are one Cart checkout: up to 10 PDFs, each to its own recipient.

The upload itself is walked through in mailing a letter without a printer. The rest of the routine is on Postmarkr for executive assistants.

Where Postmarkr fits

Good for: letters your executive signed or approved as a PDF, mailed First-Class to U.S. addresses, with the return address you choose and the production PDF once it is available.

Not for: Certified Mail, a Certificate of Mailing or a USPS-confirmed mailing date (use a post office counter); handwritten notes or cards; custom envelopes, so no logo or "Personal and Confidential" line; signing, so sign the PDF before you upload; addresses outside the U.S.

Who keeps the copy, and where#

The copy belongs in your executive's records. Chron's advice is to "keep a copy of every letter you sign for the boss in addition to other outgoing letters, in case problems arise in the future," and, from Heather Beckell, to staple the copy to the incoming letter when yours is a reply. Digitally, save it next to the letter it answers.

Keep the approved source and the available status-page PDF. Save the PDF available from the letter's status page alongside the source document your executive approved. Keep the status record with them so you can refer back to the file and the processing history.

File it where your executive, or your successor, would look: the shared folder for that client, matter or household. Name files the same way every time: date, recipient, subject.

Save the approval with it. If your executive said "send it" by email or text, file that too, especially when you signed.

Keep a one-line log: date, recipient, return address, who approved, status. When someone asks in March about a January letter, the log answers.

How your executive sees it went out#

Don't make them ask. The day it goes to print, send one short note: what went, to whom, and where the copy is filed. What you can show:

  • Two emails to you. Postmarkr emails the account holder a "Payment received" receipt, then a note that the letter "has been submitted for printing and mailing." Forward the second.
  • A status page with processing milestones and USPS scan updates when available, plus the recipient and return address the letter carried.
  • The production PDF, once available.
  • A delivery estimate. USPS estimates 1–5 days for First-Class delivery; pass it on as an estimate.

Postmarkr doesn't send an email that says "mailed," and it doesn't give a USPS-confirmed mailing date. If your executive must prove when a letter was mailed, for a contract notice or a filing deadline, get a postmark or Certificate of Mailing at a post office counter (how to postmark a letter; Certified Mail alternatives; mailing a signed contract).

If USPS confirms a letter was lost, Postmarkr resends it for free. A letter returned for a wrong or incomplete address isn't eligible for a refund or a free resend.

When your executive is travelling#

It's 6 pm and five signed client letters land in your inbox from a plane. Each goes to a different address, and one is a condolence letter your principal wants out first thing.

  • Signing. They sign the PDF on a phone or tablet (the steps for iPhone and Android). If you sign for them, follow the signing guide and get the go-ahead in writing.
  • Return address. Keep the office, or the home address someone checks. A trip changes where your executive sleeps, not where their mail comes back to.
  • Batch it. All five go in one Cart checkout tonight and are printed the next business day. Your executive gets one note when they land, not five.
  • No printer on the road. One assistant whose boss was looking into portable printers said "it can be hard to find one on site due to extensive travel." With the PDF route, no printer has to travel.
  • The condolence letter. Emily Post's advice is that email "shouldn't replace a handwritten condolence note." If your principal would normally write this one by hand, keep it for their pen. A typed condolence letter on letterhead, signed by them, can go with the others.

Questions assistants ask about mailing for an executive#

I support three executives. Can I mail for all of them from one account?#

One account works. Save each executive's return address in your address book and pick the right one on every letter; the preview shows it on the address page before you pay.

My executive is abroad. Can I still mail their letters?#

Yes, to U.S. addresses, with a U.S. return address such as the office. Postmarkr doesn't mail to addresses outside the U.S.

What happens if a letter comes back?#

USPS returns it to the return address, and the status page shows "Returned to Sender" once USPS reports it. Fix the address and send it again.

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