For accounting and bookkeeping firms · Washington DC metro

Tax season shouldn't be
a document hunt.

Every January the same thing: you send the portal link, they ignore it for three weeks, you remind them twice, they upload the wrong thing. I build automated document-collection systems that chase clients without your staff having to — personalized reminders, smart escalation, instant categorization when stuff arrives. So April is for returns, not for PDFs.

Book a 15-minute call or email matt@gardnertechgroup.com

a document chase, running

Hi Priya — Harbor Bookkeeping. To finish your return we still need your 1099 and mortgage interest form.

No reply · 4 days

Quick nudge on those two — you can upload them straight from this link.

Just uploaded both.

Both received — checklist updated, your preparer notified.

Example sequence, not a customer transcript.

The annual ritual

Send the portal link. Wait. Send a reminder. Wait. Get the wrong file. Resend.

The intake portal works fine when clients use it. They mostly don't. So your staff spends January, February, and half of March chasing — emails, phone calls, "did you get my voicemail," "I sent it last week." The clients who finally upload tend to upload the wrong year, the wrong form, or a photo of a document that needs OCR.

By the time everything's collected, your team is exhausted, and the actual work of preparing returns gets compressed into the last three weeks of the season. The bottleneck isn't the returns. It's the document hunt.

What I build

A system that chases clients so your staff doesn't have to.

Personalized reminders: Each client gets a reminder that names what's missing, in the channel they actually read — email, SMS, or both. Tone matches the relationship. Escalation cadence is configurable.
Smart categorization: When a document arrives, the system identifies what it is — W-2, 1099-MISC, brokerage statement, K-1 — and files it under the right client and the right category. Mis-uploads get flagged before your staff sees them.
Missing-doc detection: Compares what came in against last year's return. If a client had a 1099-INT from Schwab last year and there's nothing from Schwab this year, the system asks before April 14th — not after.
Status dashboard: One screen shows every client, what's collected, what's outstanding, and where the system is in the chase sequence. No more spreadsheet of who's behind.
Stops at the right moment: When a client's intake is complete, the reminders stop. When a client replies to a human, the automation steps back. Nobody gets a "you forgot your W-2" text the day after they sent it.

Works with what you have

No portal change required.

The system sits on top of whatever you already use — SmartVault, Liscio, Canopy, ShareFile, Drake portal, or plain email. It reads what's come in, sends the chase, and writes status back. You don't switch vendors and your clients don't relearn anything.

If you don't have a portal at all and have been collecting documents over email, even better — the system works directly from a shared inbox.

Timing

Build it in the off-season. Run it in the on-season.

The right time to scope this is May through November. Build and pilot in the summer — usually a one-to-two week engagement — so the system is battle-tested by the time the first 1099s start arriving in late January.

Pricing fits the homepage's $500–$1,500 automation range for a single-firm rollout. Multi-office or multi-entity scopes get quoted before we start. Either way, it's fixed-price, and you own everything afterward.

Want this in place before next January?

Fifteen minutes is enough to figure out if your current portal is the bottleneck or if it's the workflow around it. Either way, I'll tell you what I'd build.