How to Pay After-School Instructors: W-2 or 1099 (Ep. 25)

Episode 25 · June 29, 2026 · Solo episode

Pay after-school instructors from the schedule as it happened, on one fixed payday. Decide employee or contractor first, using the IRS factors and your state labor agency, because the rules differ by state. Keep every sub, late pickup and weather day in one record. Then spend your retention money on belonging. Bonuses did nothing for us.

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This is my written companion to How to Pay Enrichment Instructors Without Payroll Chaos: every way I have paid instructors at Journey to STEAM, what each one cost, and the bonus experiment I was sure would work. It is for operators about to hire a first instructor, and anyone whose payroll eats the weekend.

Why does instructor payroll get harder as you grow?

Because pay is built from exceptions, and exceptions multiply with every instructor you add. A parent picks up ten minutes late. Someone subs a class and nobody writes it down. Snow closes three schools, so the printed schedule is wrong for the week.

I started with bank transfers, a spreadsheet of what each person had earned that year, and pay stubs my husband built by hand. I did the math myself and still got it wrong sometimes.

I can mess up my own money. I refuse to mess up somebody else's.

Should instructors log their own hours?

Only if you can compare what they log against what the schedule says happened. I moved to a payroll service where each instructor entered their own time, sure that a person watching their own paycheck would be accurate. That was not the case.

People forgot. Payroll ran Monday, so my weekends went to reminders and cleanup. The numbers never matched the schedule, because nothing connected the hours reported to the classes taught.

One rule I hold is that people get paid on time. I kept that rule by hand for two years, on weekends and on holidays. Something had to give.

Is an after-school instructor a W-2 employee or a 1099 contractor?

It depends on the facts of the job, and the answer changes by state. I made my call in Oregon with an employment attorney. The label you put on the role does not decide it.

Start with the IRS. It looks at three things: behavioral control, financial control and the type of relationship. If you treat someone as a contractor with no reasonable basis, the IRS says you may be held liable for employment taxes for that worker. When the status is unclear, either side can file Form SS-8, and a determination can take at least six months (irs.gov/businesses/small-businesses-self-employed).

Then read your state. Oregon's Bureau of Labor and Industries says status is determined by the reality of the work relationship, and that other state agencies make their own determination with their own tests (oregon.gov/boli/employers). The U.S. Department of Labor lists every state labor office (dol.gov/agencies/whd/state/contacts).

That is the operator's view. Read those pages, then sit down with an employment attorney in your state before you post the role.

What does manual payroll really cost?

You pay twice: the fee for the tool, then a time tax for everything the tool does not do. The most accurate manual system I ever ran took three people. A part-time assistant built a sheet of scheduled hours each term and reconciled it weekly against what happened. We forwarded her every late text and sub swap. Then my program manager entered the corrected time.

It was accurate. It was expensive.

Here is the time tax with example numbers. Say 12 instructors teach 4 sessions a week. That is 48 sessions to confirm. At 3 minutes each, that is 144 minutes. Add 5 exceptions at 15 minutes each, 75 more. You are at 219 minutes, about 3.7 hours a week. Over a 10-week term that is 36.5 hours, close to a full work week spent checking math.

What should a weekly instructor pay process look like?

One source of truth, one payday, and exceptions captured the day they happen.

1. Settle classification first. IRS page, state labor agency, attorney.
2. Pick one payday and protect it. Ours ran Mondays.
3. Pay from the schedule as it happened. The planned schedule is only the starting point.
4. Record every sub the moment it is assigned, with who taught.
5. Log late pickups and weather days the same day. Memory fails by Friday.
6. Compare reported time to the schedule before money moves.
7. Keep a running total per instructor for the year. You will need it at tax time.

This is the job we built enrops to do for us. At Journey to STEAM, sub assignments happen in the platform, so who taught what is already known when pay runs. Contractor instructor pay through Stripe is set up with our team today. See how it works, or read how Journey to STEAM cut $83K in annual admin costs running on enrops. Related: how to schedule instructors across multiple schools.

Do bonuses and higher pay keep instructors longer?

They did not for us. We already paid at the higher end for our area. Then I added a full menu on top: travel pay for long drives, a bump for teaching five days a week, raises at three, six and twelve months, instructor of the month, and extra for piloting a new program.

Retention went down, and reported satisfaction did not move. My program manager saw why. When a list of bonuses leads the first conversation with a candidate, the role starts to feel like a tally sheet, and that is a different relationship than the one we wanted. It was also very expensive. We right-sized it.

What helped instructors stay?

Time together. Instructors in a mobile business teach alone. They never pass each other in a hallway. Karaoke nights and trivia nights gave them a team to belong to, and other operators have told me informal gatherings did the same for their morale and loyalty. Pay well, pay right, pay on time. Then put the next dollar into connection. For the days someone still calls out, here is how to build a sub plan that holds.

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Frequently asked questions

How often should I switch payroll tools?

As rarely as you can. Every switch lands on your instructors: new logins, new forms, paperwork they already did once. Many of them already complete a separate background check for each district they teach in. Be considerate with their time.

What do I do when I overpay or underpay someone?

Tell the instructor plainly and correct it on the next run. Then find the step where the record broke and fix that step.

Can I pay instructors through enrops?

Contractor instructor pay through Stripe is set up with our team today. See what's on each plan.

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Arielle Hammond, Ed.D. is the founder of enrops and host of The Youth Enrichment Leader, presented by enrops.