<!-- canonical: https://deftridge.com/job/contractor-payment-and-1099-preparation-chicago-dt-2971390/ -->
Source: https://deftridge.com/job/contractor-payment-and-1099-preparation-chicago-dt-2971390/
Title: Contractor Payment, CL-63861, $58-70/h | Deftridge
Summary: Contractor Payment and 1099 Preparation for a senior Payroll Specialist, on site in Chicago. $58-$70 an hour, about 4 hours in total. Starts within 7 days.

One-off Posted Oct 30 · DT-2971390

# Contractor Payment and 1099 Preparation

Senior · Payroll Specialist · On-site · Chicago

**$58–$70** / hour About $190–$380 in total. Set by the company within a range checked against market pay for the role; your recruiter agrees your exact rate with you before anything is sent. Deftridge adds 15% on top and bills it to the company, so **nothing comes out of your rate**.

- **Company** Vertical software provider for law firms · 5,000+ employeesCL-63861 · based in Valencia

- **Where** On-site · Chicago

- **Format** One-off task

- **Time needed** about 4 h in total

- **Start** Starts within 7 days

- **Level** Senior · 5-10 years

- **When you work** Flexible hours, async1 h a week overlap with CT

**4** professionals have asked about this task **175** tasks of this type completed on Deftridge

## About this task

This vertical software provider for law firms (5,000+ employees) is looking for a senior Payroll Specialist for a single piece of work with a fixed scope and a fixed price. Collects forms, tests contractor status risks and prepares the year-end filings.

It is a self-contained job: scope, checklist and price are agreed before you start. The company sells subscription software, so deadlines follow release and billing cycles.

The company prefers a person who can come to Chicago for kickoff and the final review; the rest is remote. You choose your hours; nothing is scheduled except an occasional short call. About 1 hour a week should overlap with the team's day (CT).

## What you deliver

- Check W-9 completeness for 60 contractors and prepare the 1099-NEC figures for filing.

- A final note stating what was checked and what was left out of scope

- A 20-minute walkthrough call, or a recorded screen share if you prefer

- The finished deliverable in the agreed file format, with sources and assumptions listed

## How the work runs

- Day 1: kickoff call and access to the files

- Days 2 to 4: the work, with questions answered the same day

- Last day: delivery and a short walkthrough

**Duration:** 1 to 2 weeks. Accepted when the company contact confirms the deliverable against the written checklist. One round of edits is included.

## Tools

Gusto Bill.com Excel

## Who fits

- 5-10 years of hands-on work as a Payroll Specialist, or the equivalent mix of roles

- Comfortable working in Gusto, Bill.com and Excel

- Your own work history stays private; the company sees a first name, your field and a rate

### Nice to have

- Used to short written handovers

- A habit of asking one clarifying question early rather than five late

## Not included

- Anything that needs a signature in your own name unless the brief says so

- Work outside the scope written in the brief; extra items are quoted separately

- Managing other contractors or employees

## How you get paid

- The company prepays Deftridge before your first hour, so payment does not depend on a late invoice.

- Deftridge pays you in USD after the company confirms the hours or the deliverable. The payment date is written in your task agreement.

- You work as an independent contractor: you report your own income, and your recruiter sends the statements your accountant needs.

- You never chase the company. Questions about money go to Deftridge.

## What happens after you say you're interested

1. **Within one working day** A recruiter writes to you to confirm your hours and the rate you want.

1. **You agree the rate** You and the recruiter fix an exact rate inside the company's range. You decide whether to go ahead.

1. **With your written OK** The company sees the anonymous profile below. Most companies answer within three working days.

1. **Start** You sign the task agreement and the company's confidentiality terms through Deftridge, and begin on the date above.

## What the company sees about you

First name, field, experience, tools and the hours you offer. Not your surname, your employer or your contact details.

Your profile
**Alex** Senior Payroll Specialist

- **Experience** 5-10 years in finance & accounting

- **Tools** Gusto, Bill.com, Excel

- **Offers** 4 hours in total, weekday evenings

- **Rate** $64 an hour, agreed with the recruiter

## How this rate compares

The midpoint of this range, $64 an hour, is **above** the median senior Payroll Specialist rate in Illinois ($60). The shaded band is the 25th to 75th percentile of the market.

Median $60

This task $64

$41 $80

[All Payroll Specialist jobs in United States](https://deftridge.com/jobs/payroll-specialist/united-states/) · [Payroll Specialist rates in Illinois](https://deftridge.com/rates/payroll-specialist/illinois/) · [Finance & Accounting jobs](https://deftridge.com/jobs/finance-and-accounting/)

## Questions about pay and privacy

The rules are the same for every task. [Pricing](https://deftridge.com/pricing/) explains the 15% fee, prepayment and when you are paid; [How it works](https://deftridge.com/how-it-works/) covers matching, what the company sees and side work next to a job.

CL-63861 is the Deftridge code for this company. Its name is shared only after you agree to an introduction, and you decide whether to go ahead.

## Interested in this task?

Leave your first name and e-mail. You hear back from a recruiter inside one working day, and nothing reaches the company without your written OK.

- You see and agree the rate before the company hears about you

- Your employer and surname stay private

- E-mail only, no phone calls

Thank you, Contractor Payment and 1099 Preparation is noted. A recruiter writes to you from a @deftridge.com address within one working day; the next steps are listed on this page.

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**$58–$70 / hr** I'm interested
