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Somebody has to nag.It doesn’t have to be you.

Pesterly asks your clients for exactly what you need, then follows up on day 3, day 7 and day 10 until every last item is in — from your own Gmail, in the thread they already reply to. Your client gets one link. No login, no account, nothing to download.

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Mercer & Co · Hannah Mercer

2024 tax return

sending as hannah@mercerbooks.com

4 punched

3 still owed

  • W-2 from each employerw2-acme-2024.pdf
  • 1099-NEC1099-nec.pdf
  • 1099-INT1099-int.pdf
  • Prior-year return2023-return.pdf
  • 1098 mortgage interestStill owed
  • Property tax billStill owed
  • Charitable receiptsStill owed
One client’s request, mid-chase. Four punched, three to go — and three is the only reason Pesterly is still sending. Illustrative data; Pesterly hasn’t launched yet.

Clients ignore software. They answer people.

Not because they’re rude. A branded template from noreply@ is indistinguishable from the forty other automated emails that arrived that morning — and half the time it looks like phishing, which is precisely what their IT department trained them to delete.

What every other tool sends

from noreply@securedocs-portal.io

Action required

Your document request is awaiting completion in the client portal.

Access secure portal

You are receiving this because an account was created for you. Unsubscribe · Manage preferences · Please do not reply.

  • Reads as automated
  • Sender they don’t know
  • Reply goes nowhere

What Pesterly sends

from hannah@mercerbooks.com

Re: 2024 tax return — what I need from you

Hi Priya,

Thanks for sending what you have so far. Still waiting on:

- 1098 mortgage interest statement - Property tax bill - Charitable donation receipts

Same link as before:
pesterly.com/r/k4m9tq

Thanks, Hannah

  • Lands in an existing thread
  • From a person they know
  • Replies come to you

Same request, same day, same client. One of the two gets opened, and it isn’t the one with the logo on it.

Three things, and then you stop thinking about it.

  1. 1Make the list

    Name actual documents, not categories. “The 1098 from your lender” gets answered; “mortgage information” does not. Start from a template — 1040 return, monthly close, new client onboarding, matter intake — or write your own in a minute.

  2. 2Connect your inbox

    Sign in with Google. Pesterly gets permission to send as you, and nothing else. Gmail and Google Workspace, no DNS records, nothing to install, and no unfamiliar new address for your clients to squint at.

  3. 3Forget about it

    Day 0, day 3, day 7, day 10. Every message is shorter than the last and lists only what’s still missing. When the final file lands, the chasing stops by itself — including the nudge that was queued for tomorrow.

Four messages, each one shorter than the last.

Every follow-up replies into the same thread and lists only what is still outstanding, so the ask visibly shrinks instead of repeating. Below is one sequence end to end. The day 10 message does not appear, because by then there was nothing left to ask for.

  1. Day 0 · sent from hannah@mercerbooks.com

    to priya@

    2024 tax return — what I need from you

    Hi Priya, when you have a few minutes, could you send these over?

    • W-2 from each employer
    • 1099s (NEC, MISC, INT, DIV, B)
    • 1098 mortgage interest statement
    • Property tax bill
    • Charitable donation receipts

    Easiest way is this link — no login, works on your phone:

    Day 2 · punchedPriya uploaded the W-2 and the 1099s

  2. Day 3 · sent from hannah@mercerbooks.com

    to priya@

    Re: 2024 tax return — what I need from you

    Thanks for sending what you have so far. Still waiting on:

    • 1098 mortgage interest statement
    • Property tax bill
    • Charitable donation receipts

    Same link as before:

    Day 6 · punchedThe 1098 and the property tax bill landed

  3. Day 7 · sent from hannah@mercerbooks.com

    to priya@

    Re: 2024 tax return — what I need from you

    Down to one last thing: charitable donation receipts.

    If it's easier to send them another way, just reply and tell me.

    Day 8 · punchedThe last receipt. Day 10 was never sent.

pesterly.com/r/k4m9tq

Mercer & Co · Hannah Mercer

2024 tax return

4 of 7 in. Three left.

  • W-2 from each employerw2-acme-2024.pdf
  • 1099s (NEC, MISC, INT, DIV, B)1099-nec.pdf, 1099-int.pdf
  • Property tax billA photo of the mailed bill is fineAdd
  • Charitable donation receiptsAdd

Nothing to sign up for. Come back to this link any time.

One link. No password. Works on the phone they’re already holding.

No account, ever
They click, they see the list, they upload. Nothing to sign up for, no password to reset, no invitation to accept before they can help you.
The same link the whole way through
Day 0 and day 10 point at the same page. Nothing expires mid-chase, and forwarding it to their spouse or their bookkeeper simply works.
Made for the phone in their hand
Most of what you’re waiting on is a piece of paper on somebody’s kitchen table. They photograph it and they’re done, standing up.
They can watch it shrink
Received items go quiet; outstanding ones stay loud. A list that visibly gets shorter is a list people actually finish.

Can Pesterly read my email?

No. Not the inbox, not your replies, not one word of it.

Connecting a mailbox grants exactly one permission: permission to send. That boundary is enforced by Google, not by our privacy policy. Below is the whole list, straight off the consent screen.

  • gmail.sendSend email on your behalfGranted
  • drive.fileSave uploads to your Drive — only files we createGranted
  • gmail.readonlyRead all your emailNot requested
  • driveSee and manage everything in your DriveNot requested
  • gmail.modifyRead, change and delete messagesNot requested
  • mail.google.comFull mailbox accessNot requested

Your documents, your Drive

Mailbox tokens are sealed with AES-256-GCM before they ever reach our database. The documents themselves never touch it — uploads go straight into a folder in your own Google Drive, so they are yours the moment they arrive.

Revoked in one click

Google Account → Data & privacy → Third-party access. Remove Pesterly and the sending stops that second. You don’t have to ask us, or wait for us.

The tradeoff, said out loud

Because Pesterly can’t see replies, a sequence stops when a file is uploaded or when you pause it — not when a client emails you back. If they write “sending this Friday”, hit pause. We think that’s a fair price for never holding a key to your mail, and we’d rather tell you now than have you discover it in week three.

Monthly, yearly, or once. Never by request.

Rival tools cap how many requests you may have open at once, which is a strange thing to ration when chasing people is the entire job. Pesterly never does. Tiers differ by how many mailboxes you send from, and whether the page your client lands on carries your name or ours.

  • Solo

    $9/month

    $90/year if you pay annually

    1 connected mailbox

    One person doing all the chasing.

    • Unlimited clients, requests and files
    • White-label — your name, not ours — not on this tier
    • Custom chase cadence and wording — not on this tier
    Start free
  • Most firms

    Practice

    $19/month

    $190/year if you pay annually

    3 connected mailboxes

    Anyone whose clients should see their name on it, not ours.

    • Unlimited clients, requests and files
    • White-label — your name, not ours
    • Custom chase cadence and wording
    Start free

  • Firm

    $39/month

    $390/year if you pay annually

    10 connected mailboxes

    Multi-partner firms, or running this on behalf of your own clients.

    • Unlimited clients, requests and files
    • White-label — your name, not ours
    • Custom chase cadence and wording
    Start free

On every tier — including the cheapest

  • Unlimited clients
  • Unlimited open requests
  • Unlimited items and files
  • The full day 0 / 3 / 7 / 10 sequence
  • Every template in the library
  • Your own saved templates

No tier caps how many clients you chase, how many requests you keep open, or how many files come back. Those are the numbers competitors ration, and rationing them is the opposite of what this product is for.

The questions you were about to ask.

Do my clients need an account?
No, and there is no version of this where they do. They get a link, they see their list, they upload. No password, no app, no “accept this invitation” step standing between you and the document you need. The same link keeps working until the request is finished.
Will these end up in spam?
Nobody can promise inbox placement and we won’t start. What we can say is that everything working against you elsewhere is absent here: the mail leaves your own Gmail on your own domain’s reputation, it’s plain text with no tracking pixel and no link shortener, the wording changes on every touch instead of repeating itself, and follow-ups reply into a thread your client has already engaged with.
Can I use it for things that aren’t documents?
Yes. Underneath, it’s a checklist plus a nudge. Firms use it for approvals, answers, analytics access, a signed agreement, a billing contact, “three sites you like and why”. If you can put it on a list, Pesterly will keep asking for it.
Do I have to leave the tools I already use?
No. Pesterly doesn’t replace your portal, your practice management software or your Drive — it’s the thing that gets clients to actually use them. What your client uploads lands straight in a folder in your own Google Drive, so the files are already where you work and already yours.
How new is this?
New, and we’d rather say so than fake it. Pesterly started as a done-for-you service — chasing documents by hand, on behalf of firms — and this is that job turned into software. It costs $9 a month. There are no customer logos on this page because there aren’t any yet. When there are, they’ll be real ones.

Let it be the bad guy.

Write the list once, connect one inbox, and go back to work you can actually bill for. Pesterly does the part nobody wants to do — and it never gets embarrassed on the fourth reminder.

Start free

No card to start. $9/month after that, and you can cancel whenever you like.