You've found a contractor who can take overflow work. They have the skills and a truck, and they say they can start Monday. The temptation is to send them a job Monday morning and sort the paperwork out later. That is how you end up with a sub on a customer's roof whose insurance lapsed last month, or a pay dispute over a job neither side priced.
Week one is for setting up the relationship so the first job goes right and the twentieth job doesn't need a phone call. This guide covers the scheduling side: credentials, pay terms, availability and the first jobs. It is not tax or legal advice.
First, the classification question
Whether someone is an independent contractor or an employee is not your choice to make by calling them one. As of October 2026, the IRS page on independent contractor or employee looks at three kinds of evidence: behavioral control, financial control and the type of relationship. It says there is no "magic" or set number of factors that decides it, and that either party can ask the IRS for a determination with Form SS-8. States have their own tests too, and some are stricter.
This affects how you onboard. If you set a sub's hours, tell them how to do the work and supply their tools, you may be building an employee relationship whatever the paperwork says. Talk to a CPA or employment lawyer before you start, and read subcontract vs hire for the operational trade-offs.
Day 1: paperwork and credentials
Collect everything before you send a job. Nothing goes on the schedule until this list is done.
- [ ] Form W-9. The IRS Form W-9 page (as of October 2026) describes it as the form a payee uses to provide their correct taxpayer identification number to the person who has to file an information return. You'll need it for year-end reporting on Form 1099-NEC, which the IRS uses to report nonemployee compensation. Check the current filing rules with your CPA.
- [ ] Certificate of insurance. General liability at the limits your customers and contracts require, and workers' comp or a valid exemption as your state requires. Ask for the certificate from their insurance agent, not a photo of a policy page. Note the expiration date.
- [ ] Trade license. For licensed trades, the license number, the state or local board that issued it, and the expiration. Look it up on the board's website yourself.
- [ ] Certifications. Anything your work requires: refrigerant handling, manufacturer install certifications, safety training.
- [ ] Background check, if your customers or contracts call for one.
- [ ] A written agreement. Scope, pay, insurance, who owns the customer, and how disputes get resolved. Have a lawyer review the template once.
Put every expiration date in one place. A credential that lapses in March is a problem you can see coming in January.
Day 2: agree pay terms in writing
Pay disagreements usually start with terms that were never stated. Before the first job, agree:
- How each job is priced. A flat amount per job type, or a percentage of the job price.
- When it's due. A set number of days after the job is marked done, for example net 15.
- What counts as done. Photos, a signed completion, a passed inspection.
- Callbacks. Who pays for a return visit on the sub's work.
Write it as a table both sides sign off on. Here is the arithmetic for comparing a percent deal with a flat one, with illustrative numbers.
Sub pay on a percent deal = P × Job price
Your margin = Job price − Sub pay − Your costs on the job (booking, materials you supply)
If job sizes vary widely, a percentage tracks the work better. If every job is about the same, flat is simpler for both sides.
Day 3: set up their availability
A sub is not your employee and doesn't owe you a schedule. What you need is a reliable picture of when they can take your work. Ask for:
- Their working area, so you don't send them jobs two counties away.
- Which days and hours they're open for your work.
- How much notice they need. Next-day, same-week, or longer.
- How they want jobs sent. Text, a shared calendar, or a scheduling system they can see.
The common failure is offering a customer a time based on what the sub said last month. Their own customers fill their week too. The workable approach is to see their open times when you book, not their whole calendar. The subcontractor scheduling page explains how CrewLink's CrewConnect does this in early access: you see a partner's open times at the job's address and nothing else, and you can require license, insurance, certification or background check so a contractor whose credential has lapsed isn't offered.
Days 4 and 5: the first job, sized small
Make the first job one you could do yourself if it went wrong. A short repair, not a three-day install. Then:
- Send the full job details the night before: address, customer notes, equipment, photos, and what the customer was promised.
- Decide whose name the customer sees on texts and on the truck, and tell the customer in advance who is coming.
- Ask for completion photos and a short note.
- Call the customer afterward. Not to check up on the sub, but to hear how it went.
Then talk to the sub. What was unclear? What did they need that they didn't have? Fix the job template before job two.
What to check at the end of week one
| Check | Done when |
|---|---|
| W-9, COI, license, certifications on file | Every item has a document and an expiration date |
| Pay terms | Written, agreed, with a due date rule |
| Availability | You know their area, days and notice period |
| First job | Completed, photos in, customer called |
| Job template | Updated with what the first job taught you |
For a reference on what the term covers, see 1099 subcontractor. For the scheduling side once you have several subs, read scheduling subcontractors and 1099 crews.
What to take away
- Classification is decided by the relationship, not the label. Check with a CPA or employment lawyer.
- Collect W-9, insurance certificate, license and certifications before the first job, with expiration dates.
- Write the pay terms down: price, due date, what counts as done, and who pays for callbacks.
- Book subs into their open times, not into what they told you last month.
- Make the first job small and learn from it before sending big work.
Common questions
What documents do I need from a 1099 subcontractor?
At minimum, a Form W-9, a certificate of insurance from their agent, and their trade license if the work is licensed. Add certifications and a background check if your work or customers require them, plus a written agreement reviewed by a lawyer.
How do I verify a subcontractor's insurance?
Ask for a certificate of insurance issued by their agent, check the limits and the expiration date, and call the agent to confirm if anything looks off. Put the expiration date somewhere you'll see it before it passes.
Can I set a 1099 contractor's schedule?
Controlling when and how someone works is one of the factors the IRS looks at for classification. Ask for their open times rather than assigning hours, and get advice from a CPA or employment lawyer on your setup.
How should I pay a subcontractor, percent or flat rate?
Percent tracks varied job sizes better; flat is simpler when jobs are uniform. Either way, agree the due date and what counts as done before the first job.