Who to Hire First in a Kids Enrichment Business (Ep. 9)

Episode 9 · May 4, 2026 · Solo episode

Your first hire should be the lowest-cost help that takes real work off your plate, and that is rarely an instructor. Go in order: AI tools for admin, a virtual assistant for behind-the-scenes tasks, specialized contractors and free mentors, then a part-time local team member, then a full-time leader. Each level teaches you to delegate before the stakes rise.

Listen or watch: Spotify · YouTube · Apple Podcasts

This is my written companion to Episode 9 of The Youth Enrichment Leader, "How to Hire for an After-School Program Business." Owners with one or two sites tell me they do everything alone. Owners with 10 or 15 have at least one person helping. All of them say finding good help that stays is the hardest part. I come from a long line of "I'll just do it myself" women. I had to learn this on purpose.

Who should I hire first for my after-school program business?

Hire for the work that is easiest to hand off, which is usually admin. Most of us assume the first hire is an instructor. That is the riskiest handoff you can make, because it takes real preparation to train someone to teach at your level.

The book that changed my mind is Buy Back Your Time by Dan Martell. Before it, I believed my first hire had to be a leader I could not afford. After it, I started with the least expensive help and moved up. The starting question: what am I doing that someone else could do? Write down every task you touch in a week. That list is your hiring roadmap. Clockwork by Mike Michalowicz adds a test: plan a multi-week vacation and see what falls apart without you.

What can AI take off my plate before I hire anyone?

Run your task list through an AI assistant before you post a job. Ask which items need no person at all. Drafting family messages, sorting an inbox, research and formatting are all fair game. It costs the least, and it forces you to describe your tasks clearly, which every later level requires.

What should a virtual assistant do, and what does it cost?

Give a virtual assistant behind-the-scenes work: data entry, formatting, research, simple scheduling, editing, social post production. Rates vary widely, so price the help against the hours it gives you back. You can start at $20 a week. Over a 12 week term that is 12 x $20 = $240 to learn how to delegate.

That learning is the real value. You practice writing clear instructions and letting go. I found ongoing help on Upwork. Fiverr was better for one-time jobs.

The mistake I made was confusing the role. Do not hand a VA tasks that need a lot of context from you, or anything where an error lands on a family or a school partner. Keep them away from your reputation until they have earned more.

Where do I find expert help for free?

Start with SCORE. Level two on my ladder is specialized contractors: a CPA, an attorney you can call when you need one, an editor, part-time marketing help. Before you pay for any of it, get a mentor. SCORE is a nonprofit and a resource partner of the U.S. Small Business Administration, its mentors are volunteers, and mentoring is free (score.org/about-score).

A SCORE mentor helped me build my first budget and financial projections when I started Journey to STEAM. When she gave me a directive, I carried it out. You can search mentors by business function and by industry. Also look up small business support organizations in your state. Some cover the bill for a website or branding.

When should I bring on a part-time or full-time team member?

Bring on a part-time local person when the business needs to function while you are not in the room. Ten hours a week is a fine start. They might deliver materials, represent you at a community event, assist in a class and grow into teaching, or handle family questions.

Great part-timers often want part-time work. When the role grows into full time, you may need someone new. Handle departures with the same care as arrivals.

A full-time hire is your right hand: a program coordinator or manager who is you when you are not there. They cost more and they are putting all their eggs in your basket, so be ready for benefits like health insurance and retirement. Rules for classifying and paying workers differ by state. Start with the IRS guidance (irs.gov/independent-contractor-self-employed-or-employee) and your state labor agency. Go slow here. The right leader gives you back a day a week for strategy. The wrong one leaves you owning every outcome.

What does the team look like as I add sites?

I laid out four stages on the episode.

Journey to STEAM runs programs at 75+ school sites, so stage three is where I live. For what to build at each step, read how to grow an after-school program business in stages.

How do I lead the people I hire?

Hire for your weak spots and give grace while people learn. The first time something is done differently than you would do it, you will want to take it all back. Don't. If you hired well, that person is better than you at several things. I would rather someone act and check with me after than wait on me. Keep the work you are brilliant at and love. Hand off first what you are bad at and dislike.

Who should listen to this episode?

Owners who are maxed out and think they can't afford help. Pair it with Episode 7 on getting organized, because written processes make every level of this ladder work. If your next hire is an instructor, read when to stop teaching every class and how to pay after-school instructors.

Listen or watch: Spotify · YouTube · Apple Podcasts

Frequently asked questions

Do I need everything figured out before I bring someone in?

No. A process only gets better once a real person runs it and you see where it breaks. Prepare what you can, then start.

Is getting help a sign I can't handle my business?

It is a sign you are growing. Nothing great is built alone. The goal is a business that keeps serving kids when you are sick or away.

What should a virtual assistant never touch?

Early on, anything that speaks to families or school partners in your name, and anything that needs deep context to get right.

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