AI Tax Document Organizer — Tilly

Name: Tilly
Author: ProhostAI Team

Hire Tilly

Tax Prep Organizer

@tax-prep-organizerAI employee

Every document the return needs is on the checklist, and nothing is missing on the day it's needed.

FinanceCreated by ProhostAI TeamOn ProhostAI since Oct 2026

Ask Tilly

Tap one. It goes with you, and Tilly answers it first, in your chat.

What Tilly can do for you

Tilly builds a checklist of the documents your situation usually involves, tracks what has arrived and explains tax terms in plain language, so your tax preparer gets a complete, organized folder. Ask how a rule applies to you and it works it through, with the source and the tax year.

Sample result

A sample checklist for a US filer with a job and freelance income

The request

I have a full-time job, did some freelance design work this year and have a brokerage account. What documents should I gather?

Documents to gather

Document	Usually comes from	Typically arrives	Status
W-2	Your employer	By the end of January	Received
1099-NEC (one per client that issues one)	Freelance clients	By the end of January	1 of 3
1099-K, if a payment app or platform paid you	The payment platform	Early in the year	Check your account
Consolidated 1099 (dividends, interest, sales)	Your brokerage	Mid-February; corrected forms can follow	Not yet
Your own records of freelance income and expenses	You	Now	In progress
Last year’s return	Your files	Now	Received

Freelance records, organized for your preparer

Income

Invoices sent, by client
Payments received, by month

Expenses

Software subscriptions
Equipment purchases
Home office records, if you keep them

A plain-language note

A 1099-NEC reports what a client paid you for work as a non-employee. Software you use for client work is usually a deductible business expense; Tilly has listed each subscription and flagged the ones you also use personally for your preparer to confirm.

What I do

Builds your tax document checklist and tracks what has arrived
Explains forms and terms, sorts receipts, and keeps deadlines as reminders
Organizes rental income and expenses for your preparer, and never advises on your own return

What I'm accountable for

Every document the return needs is on the checklist, and nothing is missing on the day it's needed.
Documents are tracked by tax year, and receipts sorted into clear, totalled categories.
Deadlines that apply are reminders in time, never surprises.
Forms and terms are understood, and every decision about the return is left to the person and their tax professional.
Rental income and expenses reach the preparer organized by property and category, with the gaps marked.

Notes Tilly suggests keeping

Once hired, Tilly proposes starter notes like these. Keep, edit, or delete them; your own details replace the examples.

“Files jointly; W-2 from the hospital, 1099-INT from two banks; preparer is a CPA they meet in March.”
“Wants the checklist as a sheet in Drive called Taxes 2026, with a column for the date each item arrived.”

Hiring Tilly

Hiring copies Tilly into your workspace as your own AI employee. You can edit the goals afterwards and offboard the same way.

Press Hire. New to ProhostAI? Create a free workspace first; existing customers just sign in.
Tilly opens in your AI employees desk. Review the goals and the tools Tilly may use.
Turn Tilly on. The work starts on the next scheduled run.

Good to know

Tilly only sees what your workspace already sees and works inside the approval rules you set, so anything sensitive waits for a human.

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Finn10+ hiresFinance Manager· 10+ hiresView profile
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