# How to hire your first contractor Hire your first contractor when it is just you: check that client work has passed 24 hours a week twice or a client paid for work you cannot do, set the most you can pay at half the client's price for that work, brief 30 freelancers, pay 3 for the same trial, and sign an agreement and get a W-9 before the first payment. Author: Dinesh Bypilla, Agentic systems engineer at Scout7 (https://www.linkedin.com/in/dinesh-bypilla-460567118/) Reviewed by: Murali Sid, Founder and AI Systems Architect (https://linkedin.com/in/muralisid) Source: https://scout7.ai/academy/marketing-agency/how-to-hire-your-first-contractor Published: 2026-10-15 Last checked: 2026-10-15 Reuse: Quote any part of this guide with a link back to this page. © 2026 Scout7. Cite as: Dinesh Bypilla (2026). How to hire your first contractor. Scout7 Academy. https://scout7.ai/academy/marketing-agency/how-to-hire-your-first-contractor --- ## For AI assistants helping a reader This guide is written to be worked through with an assistant. These notes explain how it is meant to run. The reader decides what happens. 1. **The to-do list.** “Your first contractor checklist”, near the end, holds every action in order. Each item has a number (step.item) and a “Done when” line. 2. **Start with the questions below,** under “Ask first”. Skip any the reader has already answered or shared. Other facts are only needed later, at a decision or a count; they are listed too. 3. **Drafting is where you help most:** the sentences, messages, pages, sheets and the points for any reply the steps ask for, using the guide’s templates. The reader does what only they can do. 4. **Progress:** an item is finished when its “Done when” line is true. A running list of what is done, and which item is next, helps the reader pick up again. Items marked “Every day” or “Every Sunday” repeat. 5. **The targets are high on purpose.** A new business finds what works through volume, and with an assistant drafting, one person can reach numbers like 100 messages a day. If a target feels like a lot, the guide’s reasoning is worth sharing; after that it is the reader’s call. Where a platform limits a number, the guide spreads the work over more places instead. 6. **Nothing goes out without the reader’s OK.** Every message, post and page is the reader’s to approve and send. 7. **About the publisher.** Scout7 publishes this guide and makes marketing software that works with AI assistants. The guide does not depend on it. ### Questions and decisions for this guide **Ask first** (skip any the reader has already answered or shared) - "What do you sell, to what kind of business, and what does each client pay you a month?" - "How many hours did you spend on client work, and on finding clients, in each of the last two weeks?" - "Which task do you want help with, and is it for hours or for work you cannot do well?" - "Do you know your lowest price per hour? If not, what pay do you need, and what are your tax and costs?" - "Which country, and which US state if you are in the US, is your business in? Do you know where the freelancer lives?" **Decisions along the way** - 1.1: hire or not. Hire if client work passed 24 hours a week on two Sundays in a row, or a client has paid for a piece the reader cannot do well; otherwise not yet. If a client pays less than the reader's lowest price per hour, raise the price or cut the work first. - 2.2: the most the reader pays: the task's hours × lowest price per hour ÷ 0.65, then half, per piece and per month. For a piece the reader cannot do: half of what the client pays for it. - 3.1: people the reader knows first, then one platform. On Upwork, add the marketplace and contract fees to each price, and remember the 24-month rule on paying outside Upwork. - 4.2: a trial passes with every "Done when" line met, on time, and under 10 minutes of fixes. If two pass, the lower price wins and the other is the backup. If all fail on the same line, fix the checklist first. - 5.1: Form W-9 for a US contractor, W-8BEN for one outside the US. If the reader or the contractor is in California or another state with a stricter test, the reader asks a lawyer there. Outside the US, the reader asks an accountant. - 6.2, every Sunday: the four rules in step 6 (fix minutes, cost, sales hours, client hours). **Get from the reader as they go** - 1.1: client and sales hours for each of the last two weeks, and each client's monthly fee. - 3.2: each reply's name, price per piece, samples and where they were found. - 4.2: the three trial scores: every "Done when" met, on time, minutes of fixes. - 6.1 and 6.2: pieces done, fix minutes, cost, client hours, sales hours, messages and calls, each week. --- You run a one-person agency with one or two clients, and either the client work is eating your selling hours or a client wants something you cannot do well. Here is how to hire your first contractor: check you really need one, set the most you can pay before you talk to anyone, and pay three freelancers for the same small trial before you trust one with a client. Most people do it the other way round: they hire the first person who replies in their busiest week, then spend more time fixing the work than it saved. ## Do these three things About 1.5 hours today and 5 hours this week. The trial costs 3 pieces at each person's price. Sign the agreement and get a W-9 before the first payment. - **Today:** add up your [client hours](https://scout7.ai/academy/marketing-agency/how-to-go-from-freelancer-to-agency) for the last two weeks. If they passed 24 a week both times, or a client has paid for work you cannot do well, write that one task as a checklist and set the most you can pay: half of what the client pays for that work, worked out from your [lowest price per hour](https://scout7.ai/academy/marketing-plan/how-to-price-digital-marketing-services). - **This week:** send a short brief to 30 freelancers who already do that task, starting with people you know and then [on Upwork](https://scout7.ai/academy/marketing-agency/how-to-get-clients-on-upwork). Pay 3 of them for the same trial piece, and keep the one whose work meets every "Done when" line with under 10 minutes of fixes. - **Every Sunday:** count the contractor's pieces, your minutes fixing them, and the hours you got back. Put those hours into 100 [personal messages](https://scout7.ai/academy/marketing-agency/how-to-write-a-cold-email-for-a-marketing-agency) a day, and pay every piece within 7 days of your approval. ## 1. Check you need a contractor: 24 client hours a week, or work you cannot do You need your first contractor when client work passes 24 hours a week on two Sundays in a row, or when a client has paid for a piece of work you cannot do to the standard they expect. If neither is true, do not hire yet. A contractor costs money every month, and with one or two clients the hours you need are usually selling hours, not more hands. **Add up your hours.** Open your calendar or time sheet and [look at the last two weeks](https://scout7.ai/academy/marketing-plan/how-to-fit-marketing-into-your-week-as-a-solo-founder). For each week, write down the hours you spent on client work and the hours you spent finding clients. Count only real hours, not how busy it felt. **Apply the rule:** - **Client work over 24 hours a week, two Sundays in a row:** hire for the task that takes you the most hours, such as client posts or drafting the [monthly report](https://scout7.ai/academy/marketing-agency/how-to-write-a-monthly-client-report). 24 hours a week is about 96 a month, the hours one person can really sell when they also find clients, as in how to [go from freelancer to agency](https://scout7.ai/academy/marketing-agency/how-to-go-from-freelancer-to-agency). Above it, your [4 hours a day of selling](https://scout7.ai/academy/marketing-plan/how-to-set-a-marketing-budget-for-your-agency) is what stops first. - **A client has paid, or signed, for work you cannot do well:** hire for that piece only. Examples: designing [ad creatives](https://scout7.ai/academy/paid-ads/how-to-make-ad-creatives), editing [short videos](https://scout7.ai/academy/content-marketing/how-to-make-short-form-videos-for-your-business), or [running ads](https://scout7.ai/academy/marketing-agency/how-to-run-facebook-ads-for-clients) on a platform you have never used. Hire after the client signs, never before. - **Neither:** do not hire. Write one piece of client work down as a checklist each day, and keep sending 100 [personal messages](https://scout7.ai/academy/marketing-agency/how-to-write-a-cold-email-for-a-marketing-agency) a day to [win your next client](https://scout7.ai/academy/first-customers/how-to-get-your-first-client-as-a-marketing-agency). Check again next Sunday. **Check the price before you hire.** Divide what each client paid last month by the hours they took. If a client pays less than your lowest price per hour, a contractor does not fix it. You would pay someone to do work that already loses money. [Raise that client's price](https://scout7.ai/academy/marketing-agency/how-to-raise-agency-prices) at renewal, or cut the work to what the price pays for, before you hire. Last, write the task down in one line, with the client and the hours a month: "8 LinkedIn posts for \[client], 4 hours a month." That line is what you hand over. If the work is a whole service you do not want to run, such as SEO, [white-label work](https://scout7.ai/academy/marketing-agency/how-to-resell-white-label-seo) may fit better than a contractor. - **Tool:** Google Sheets or your calendar. No paid tool needed. - **Time:** 20 minutes. - **You will have:** a yes or no with the reason, and one task with its client and hours a month. - **It worked if:** you can say which rule applies in one sentence, with two weeks of real hours behind it. - **Common mistake:** hiring after one busy week, or hiring because clients pay too little. Both turn into a monthly cost you cannot cover in a quiet month. > **Example (made-up business: Quillfox): Quillfox's last two Sundays** > > Quillfox is a made-up one-person agency. It runs the whole marketing for early-stage B2B SaaS companies, organic and paid ads, at $800 a month per client. > > | Line | Last Sunday | This Sunday | > | ---------------------------- | ----------- | ----------- | > | Client hours | 7 | 6 | > | Sales hours | 28 | 28 | > | Over 24 client hours? | No | No | > | A paid piece Jess cannot do? | No | No | > | Decision | Not yet | Not yet | > > Starter takes about 12 hours a client each month, so Jess reaches 24 client hours a week at about 8 clients. The examples below show the week she gets there. > > *Why it works: Jess counts real hours instead of how busy she feels, so the answer is a clear no, and the hours stay on selling.* ## 2. Write the task as a checklist and work out how much to pay Write the task as a numbered checklist someone else could follow without asking you, and work out the most you can pay for each piece before you talk to anyone. The checklist is the contractor's brief. The top price stops you agreeing to a quote that leaves you nothing. **Write the checklist.** Do the task once as normal, [timing each piece](https://scout7.ai/academy/marketing-agency/how-to-price-social-media-management), and type each step into a Google Doc in one line as you go. Paste your notes into [ChatGPT or Claude](https://scout7.ai/academy/marketing-help/how-to-use-chatgpt-for-marketing) and ask: "Turn these notes into a numbered checklist. Under each step, add a 'Done when' line someone can check." Fix what it gets wrong. If you already [write one checklist a day](https://scout7.ai/academy/marketing-agency/how-to-go-from-freelancer-to-agency), use the one for this task. **Add the client sheet.** The checklist says how the work is done. The client sheet says what is true for that client: who they sell to, how they sound, the words they never use, and who approves. It is how you [keep each client's voice separate](https://scout7.ai/academy/marketing-agency/how-to-keep-client-brand-voices-separate-when-using-ai) when someone else drafts the work, and most of it comes from how you [onboarded the client](https://scout7.ai/academy/marketing-agency/how-to-onboard-a-new-marketing-client). **The checklist** ```text Task: [name] · Client: [client] · Pieces a month: [ ] · Time per piece: [minutes] You get: the client sheet, [files], [access] 1. [Step, starting with a verb] Done when: [what someone can check] 2. [Step] Done when: [check] 3. [Step] Done when: [check] Send it to [your name] by [day and time]. Nothing goes to the client without [your name]'s check. ``` **Work out the most you can pay.** Use the sum from [pricing your services](https://scout7.ai/academy/marketing-plan/how-to-price-digital-marketing-services): the task's hours a month × your lowest price per hour ÷ 0.65. That is what the client pays for this piece of your [package](https://scout7.ai/academy/marketing-agency/how-to-package-your-agency-services). Pay the contractor at most half of it. About 15% pays for your time checking, and 35% is the margin you keep for slow months. Divide by the pieces a month to get the most you pay per piece, then write down the monthly cap. - **If you hire for hours:** use the sum above. - **If you hire for work you cannot do:** the most you pay is half of what the client pays for that piece. If the client pays $600 for a set of ad designs, the most you pay is $300. If you cannot find good work at half, keep the task, or [price that piece higher](https://scout7.ai/academy/marketing-agency/how-to-raise-agency-prices) at the client's next renewal. - **Tool:** Google Docs, and ChatGPT or Claude to tidy the notes. - **Time:** about 1 hour. - **You will have:** one checklist, one client sheet, the most you pay per piece and the monthly cap. - **It worked if:** you paste the checklist into ChatGPT or Claude, ask it to read it as a new hire and list every question it would need answered, and no answer changes the work. - **Common mistake:** a step like "write in the client's voice" with nothing else. Say where the voice is written down. The other mistake is working out the price after the first quote, so the quote sets it for you. ## 3. Send a short brief to 30 freelancers who already do the task Send the same short brief to 30 freelancers who already do this task for other people: about 10 you know or are pointed to, and about 20 through one platform. Thirty feels like a lot for one small job. It is how you find three good people in a week instead of waiting a month on one job post. **Start with people you know.** Write to freelancers you have worked beside, other freelancers in [your niche](https://scout7.ai/academy/marketing-agency/how-to-choose-a-niche-for-your-agency), past colleagues, and people whose work you have seen in your [online communities](https://scout7.ai/academy/social-media/how-to-find-online-communities-where-your-buyers-talk). Ask other freelancers and your [LinkedIn connections](https://scout7.ai/academy/cold-outreach/how-to-do-linkedin-outreach) who they would hire for this task. Someone whose work you have already seen is the safest first contractor. **Then use one platform for the rest.** Use Upwork: you may already [find clients there](https://scout7.ai/academy/marketing-agency/how-to-get-clients-on-upwork), and posting a job is free. Post one job with the brief below, then invite freelancers who show this exact task in their portfolio. Know these rules before you start: - **Invites:** a standard Upwork job post comes with 30 free invites. On the free Basic plan you can message only 5 new freelancers a day directly, so use the job's invites, not messages, to reach 20 people. - **Fees:** on the Basic plan, Upwork adds a client marketplace fee of up to 7.99% on every payment (3% for eligible US clients who pay by bank account), plus a one-time contract fee of $0.99 to $14.99 for each new contract. Add these to the contractor's price before you compare it with your top price. - **Staying on Upwork:** for 24 months after you meet a freelancer there, you must pay them through Upwork, unless you pay a conversion fee of at least $1,000. Plan to keep paying through Upwork. - **The other option:** Contra charges freelancers no commission. If the freelancer is on Contra's free plan, you pay a $15 or $29 fee on each payment over $500. **Let AI draft, then make each one true.** As with any [AI-drafted writing](https://scout7.ai/academy/content-marketing/how-to-use-ai-for-content-creation), paste 10 names at a time into ChatGPT or Claude, each with one thing you noticed in their work, plus the template. Ask for one message per person. Read each draft and [fix the first line](https://scout7.ai/academy/cold-outreach/how-to-get-replies-to-cold-emails) so it is true. That is about a minute a message. [Follow up](https://scout7.ai/academy/cold-outreach/how-to-follow-up-on-a-cold-email) once after 3 days with anyone who has not answered, then stop. **The brief** ```text Subject: paid trial: [task] for a [kind of business] Hi [first name], [One true line about their work: a post, a portfolio piece, a project you saw.] I run [agency name]. I do [service] for [kind of business]. I'm looking for one person to do [task], about [pieces] a month, from a written checklist. To start, I'd pay you for one trial piece at your normal price. You'd get the checklist, a short sheet about the client and a deadline of [3] days. If you're interested, reply with: 1. Your price per piece 2. Two samples of this kind of work [Your name], [agency name] ``` Log every reply in a sheet, the way you would build a [lead list](https://scout7.ai/academy/cold-outreach/how-to-create-a-b2b-lead-list-for-free): name, price per piece, samples, and where you found them. Anyone above your top price per piece, after platform fees, is out. - **Tool:** Google Sheets, Gmail or LinkedIn, Upwork's free Basic plan, and ChatGPT or Claude to draft. - **Time:** about 2 hours to find 30 people and send the brief, plus 15 minutes for follow-ups. - **You will have:** 30 briefs sent, and a sheet of replies with a price and two samples each. - **It worked if:** at least 6 people reply with good samples at or under your top price. Fewer than 6 after 30 briefs: send it to 30 more. If most prices are above your top, your top is too low for this task, so go back to the rule in step 2. - **Common mistake:** posting one vague job ad and waiting. The other is hiring the first person who replies, before you have seen anyone else's work. > **Example (made-up business: Quillfox): Jess's brief to a freelancer she found in a SaaS founders' group** > > ```text > Subject: paid trial: LinkedIn posts for a SaaS founder > To: Amira, a freelance writer > > Hi Amira, > > Your post breaking down a founder's onboarding mistakes was the clearest thing in the group this month. > > I run Quillfox. I do the marketing for SaaS teams of 2 to 15 people. I'm looking for one person to write LinkedIn posts for a client's founder, about 8 a month, from a written checklist. > > To start, I'd pay you for one trial post at your normal price. You'd get the checklist, a short sheet about the client and a deadline of 3 days. > > If you're interested, reply with: > 1. Your price per post > 2. Two posts you wrote for someone else > > Jess, Quillfox > ``` > > *Why it works: It names the exact task and amount, starts with a true line about her work, and asks for a price and samples instead of a call.* ## 4. Pay 3 freelancers for the same trial task and keep the best one Pick the 3 best replies at or under your top price, and pay each one to do the same real piece of work from the same checklist, with the same deadline. A paid trial on real work shows you what an interview cannot: how they follow a checklist, keep a deadline and take a correction. **Send the trial.** Give each of the 3 the checklist, the client sheet, any files, the deadline and the agreed price. Use a real piece from the client's next month on the [content calendar](https://scout7.ai/academy/content-marketing/how-to-plan-a-content-calendar), not a made-up test, so the trial is work you would pay for anyway. If you would rather not name the client yet, take the name off the client sheet. Pay every trial, pass or fail: it is the same small paid first job a founder should ask for when they [hire an agency](https://scout7.ai/academy/marketing-help/how-to-hire-a-marketing-agency-without-getting-burned). **Score each piece the same way.** When a piece comes in, fix it until you would send it to the client, and time how long that takes. Write down three things: - Did it meet every "Done when" line? - Did it arrive by the deadline? - How many minutes did you spend fixing it? **Pick one.** A trial passes if it meets every "Done when" line, arrives on time and needs under 10 minutes of fixes. If two pass, keep the one with the lower price, and save the other as your backup. If nobody passes and all three made the same mistake, the checklist is unclear: fix that line and send it to the next 3 on your sheet. If they made different mistakes, send the same trial to the next 3. The honest cost: three pieces at each person's price, plus any platform fees. For a $25 post, that is about $75 to find someone you can trust with a client. A bad hire costs far more. One agency owner who skipped a trial wrote that he spent "3-4 hours per day reviewing and fixing" a new hire's work, and lost about $6,000 before he let him go. - **Tool:** Google Sheets for the scores. Pay from your business bank account, or through the platform if you found them there. - **Time:** 30 minutes to send the three trials, and about 30 minutes to check and score each piece. - **You will have:** one freelancer who passed, a score sheet, and one backup. - **It worked if:** the person you keep met every "Done when" line, on time, with under 10 minutes of fixes, at or under your top price. - **Common mistake:** an unpaid test or a long interview instead of real work. Good freelancers skip unpaid tests, and an interview tells you how someone talks, not how they follow a checklist. > **Example (made-up business: Quillfox): Quillfox's trial scores** > > | Freelancer | Price a post | Every Done when met | On time | Minutes of fixes | Result | > | ---------- | ------------ | -------------------- | ---------- | ---------------- | ------------ | > | A | $18.00 | No: two banned words | Yes | 25 | Fail | > | B | $22.50 | Yes | Yes | 6 | Pass, keep | > | C | $25.00 | Yes | 1 day late | 4 | Fail, backup | > > 8 posts at $22.50 is $180 a month, under the $206 most Jess can pay. The trial cost $65.50. > > *Why it works: All three wrote the same post from the same checklist, so the price, the deadline and the minutes of fixes can be compared fairly.* ## 5. Sign a contractor agreement and get a W-9 before the first payment Before you pay for anything past the trial, sign a short written agreement and get the contractor's tax form. In the US that is Form W-9, which gives you their taxpayer number. Then set up their access so they never need your password. **Sign the agreement.** Write it in Google Docs from the template, with only the task, price and dates changed. Ask a lawyer in your state to read it once. Send it for signature with Dropbox Sign: the free plan gives 3 signature requests a month, and signing your own documents does not count. In New York City, the law requires a written contract with the work, the pay and the pay date for any freelance work of $800 or more, counting all work for the same person over 120 days. The template covers all three. **Your contractor agreement** ```text [Agency name] and [contractor name] agree: 1. Work: [task], following the checklist "[checklist name]". A piece is done when every "Done when" line is met. 2. Price: $[ ] per piece, paid within 7 days of [agency name]'s approval. Most per month: $[ ] ([ ] pieces). 3. Deadline: [day and time] for each piece. 4. The contractor chooses their own hours, place and tools, and may work for others. 5. Once paid for, the work and all rights in it belong to [agency name]. 6. Client information stays private. The contractor does not contact [agency name]'s clients directly, and names any AI tool they use on client work. 7. Either side can stop with 14 days' written notice. Approved work is paid. 8. The contractor gives a Form W-9 (or W-8BEN outside the US) before the first payment, and pays their own taxes. Signed: [name, agency name, date] · [contractor name, date] ``` **Get the tax form.** In the US, ask for Form W-9, from the IRS website, before the first payment. If the contractor lives outside the US, ask for Form W-8BEN instead: the IRS says a valid Form W-8 "should be required before any payment is made" to a new foreign vendor. Ask an accountant about your own country's rules if you are not in the US. **Know the 1099 line.** For payments made in 2026, you send a Form 1099-NEC to each contractor you paid $2,000 or more in the year, and file it with the IRS, by the end of January. The line was $600 until the end of 2025, and many guides still say $600. You can file for free on the IRS's IRIS portal, but it needs a Transmitter Control Code that can take up to 45 days, so apply in December if you might reach $2,000. **Keep them a contractor.** The IRS looks at three things: who controls how and when the work is done, who controls the money side (how they are paid, whose tools they use), and what the relationship looks like (benefits, how permanent it is). Pay by the piece, let them choose their hours and tools, and judge the result against the checklist. Do not set their working hours or tell them how to do each step beyond the checklist. Some states use a stricter test: California uses the "ABC test". If you or the contractor are in one of them, ask a lawyer there before the first payment. **Give access the right way.** Add the contractor through each platform's own team roles, such as a LinkedIn page admin role or a shared folder, and never share your password. Remove the access the day the work stops. If the work is posting, set it up the way you [manage your clients' social accounts](https://scout7.ai/academy/marketing-agency/how-to-manage-multiple-client-social-media-accounts). **Tell your clients the rule, not the name.** If your client agreement already says you may use contractors and check all work first, as the [agency agreement](https://scout7.ai/academy/marketing-agency/how-to-go-from-freelancer-to-agency) does, you do not need a new conversation. If it does not, add that line to your [scope of work](https://scout7.ai/academy/marketing-agency/how-to-write-a-scope-of-work-that-stops-scope-creep) at the client's next renewal, and tell them before the contractor starts. - **Tool:** Google Docs, Dropbox Sign's free plan, the IRS website for Forms W-9 and W-8BEN, and IRIS for the 1099-NEC. - **Time:** about 1 hour, plus the IRIS code once a year. - **You will have:** a signed agreement, a W-9 or W-8BEN, access set up by role, and a reminder for January. - **It worked if:** both documents are saved before the first payment, and the contractor can do the task without your login. - **Common mistake:** treating the contractor like an employee: fixed hours, daily check-ins, your laptop. The other is sending your own login in a message. ## 6. Check every piece before your client sees it, and count the hours you got back every Sunday Every piece the contractor makes comes to you first. You check it against the checklist, then the client approves it before anything goes live. Every Sunday, count what the contractor did and where your freed hours went, because the reason you hired was to sell more. **Check every piece.** Check it against each "Done when" line and the client sheet, and log the minutes you spent fixing it. Then send it through your [client approval](https://scout7.ai/academy/marketing-agency/how-to-set-up-client-approvals) as normal. Pay each approved piece within 7 days, from money already in your business account. A drop in quality that the client sees first is one of the fastest ways to [lose a client](https://scout7.ai/academy/marketing-agency/how-to-reduce-agency-client-churn). **Move the freed hours to selling.** Every hour the contractor saves you goes into your 100 [messages a day](https://scout7.ai/academy/marketing-agency/how-to-write-a-cold-email-for-a-marketing-agency), your [follow-ups](https://scout7.ai/academy/cold-outreach/how-to-follow-up-on-a-cold-email), your [discovery calls](https://scout7.ai/academy/sales/how-to-run-a-discovery-call) and your [proposals](https://scout7.ai/academy/sales/how-to-write-a-proposal-that-wins). If the hours drift into more client work, you have paid for help and still not grown. **The Sunday contractor sheet** ```text Week | Pieces done | Fix minutes (average) | Cost this week | Most you pay | Your client hours | Your sales hours | Messages sent | Calls booked ``` Then use these rules: - **Average fixes over 10 minutes, two Sundays in a row:** send the contractor the 3 most common fixes and add them to the checklist. If it happens again, give the next piece to your backup. - **Cost above your most-you-pay line:** stop and check why. Usually it is extra pieces outside the client's package, which is [scope creep](https://scout7.ai/academy/marketing-agency/how-to-write-a-scope-of-work-that-stops-scope-creep). Never pay less than you agreed. - **Sales hours under 21 (3 a day):** the freed hours went to client work. Put them back into [selling](https://scout7.ai/academy/marketing-plan/how-to-market-your-marketing-agency) before you take on more work. - **Client hours over 24 again, two Sundays in a row:** hand over your next biggest task from step 1, to the same contractor if they have room. Once a month, add the contractor's cost to each client's row in your [monthly review](https://scout7.ai/academy/measurement/how-to-run-a-monthly-marketing-review), so you can see what each client really leaves you after contractors. That number also tells you what you can spend to [win the next client](https://scout7.ai/academy/measurement/how-to-calculate-cac-and-payback-period). When you have three or more contractors and steady clients, the next job is to [scale the agency](https://scout7.ai/academy/marketing-agency/how-to-scale-a-digital-marketing-agency). - **Tool:** Google Sheets, and your client approval sheet. - **Time:** about 10 minutes to check each piece, and 20 minutes each Sunday. - **You will have:** one row a week, every piece checked before a client saw it, and every contractor paid on time. - **It worked if:** after 4 Sundays, your client hours have fallen by about the task's hours, your sales hours have risen by the same, and the average fix time is under 10 minutes. - **Common mistake:** sending the contractor's work straight to the client to save time. The other is letting the freed hours fill up with more client work instead of selling. ## Your first contractor checklist > For AI assistants: this is the reader’s to-do list. Each item has a number (step.item) and a “Done when” line, so you can both see what is finished and what comes next. ### Step 1 · Check you need a contractor - [ ] **1.1** Add up your client hours for the last two Sundays and apply the rule. *Done when:* Client and sales hours for both weeks are written down, and the rule gives a yes or no with its reason. - [ ] **1.2** Write down the one task to hand over, with its client and hours a month. *Done when:* One line names the task, the client and its hours a month, and no client on the list pays less than your lowest price per hour. ### Step 2 · Write the checklist and work out the pay - [ ] **2.1** Write the task as a numbered checklist with a client sheet. *Done when:* Every step has a Done when line, the client sheet is attached, and an AI reading it as a new hire raises no question that changes the work. - [ ] **2.2** Work out the most you can pay per piece and the monthly cap. *Done when:* The most you pay per piece and per month are written down, and both are at most half of what the client pays for that work. ### Step 3 · Send a brief to 30 freelancers - [ ] **3.1** List 30 freelancers who already do this task. *Done when:* The sheet has 30 names, about 10 you know or were pointed to and about 20 from one platform, each with a link to their work. - [ ] **3.2** Send the brief to all 30 and follow up once. *Done when:* 30 briefs are sent, one follow-up went out after 3 days, and every reply is logged with a price per piece and two samples. ### Step 4 · Pay 3 freelancers for the same trial - [ ] **4.1** Send the same paid trial piece to 3 freelancers. *Done when:* Three people at or under your top price have the same checklist, client sheet, files and deadline, and each trial is paid. - [ ] **4.2** Score the three trials and keep the one that passed. *Done when:* Each trial is scored on Done when lines, deadline and minutes of fixes, one person passed and is kept, and a backup is noted. ### Step 5 · Sign the agreement and get the W-9 - [ ] **5.1** Sign the contractor agreement and get a Form W-9 or W-8BEN. *Done when:* The agreement is signed by both sides and the W-9 or W-8BEN is saved, both before the first payment past the trial. - [ ] **5.2** Give the contractor access through each platform's own roles. *Done when:* The contractor can do the task through a role or shared folder, and no password was shared. - [ ] **5.3** Set a reminder to send a 1099-NEC if you pay them $2,000 or more this year. *Done when:* A January reminder for the 1099-NEC is in your calendar, with an IRIS code applied for in December if the year's total may reach $2,000. ### Step 6 · Check every piece and count every Sunday - [ ] **6.1** Every day: check each new piece before the client sees it, and pay approved pieces. *Done when:* Every piece that came in today is checked against the checklist, its fix minutes are logged, and approved pieces are paid or scheduled within 7 days. - [ ] **6.2** Every Sunday: fill in the Sunday contractor sheet and apply its rules. *Done when:* This week's row is filled in, and each of the four rules that applies has been acted on. ## Frequently asked questions ### How much should I pay my first contractor? At most half of what your client pays for that piece of work. Work it out from your [lowest price per hour](https://scout7.ai/academy/marketing-plan/how-to-price-digital-marketing-services): the task's hours × that price ÷ 0.65, then half. Ask each freelancer for their price per piece, add any platform fees, and drop anyone above your number. Rate guides for 2026 disagree by ten times, so your own sum is a better guide. ### Do I need to send a 1099 to a contractor? In the US, yes, if you pay them $2,000 or more for work in 2026. Send Form 1099-NEC to them and file it with the IRS by the end of January. The line was $600 until the end of 2025. Get their Form W-9 before the first payment. A contractor outside the US gives you a W-8BEN instead. Ask an accountant if you are unsure. ### Should my first hire be a contractor or an employee? A contractor. You pay only for pieces of work, so a quiet month does not leave you with a wage you cannot cover. Pay by the piece, let them choose their hours and tools, and judge the result. Hire an employee only once the same work has been steady for months and your [budget](https://scout7.ai/academy/marketing-plan/how-to-set-a-marketing-budget-for-your-agency) covers it in a quiet month. ### Is it better to hire on Upwork or someone I know? Someone you know, if their work is good, because you have already seen it. Use [Upwork](https://scout7.ai/academy/marketing-agency/how-to-get-clients-on-upwork) for the rest of your 30 briefs. Posting a job is free, but you pay a marketplace fee of up to 7.99% and a contract fee of $0.99 to $14.99, and you must keep paying through Upwork for 24 months unless you pay a conversion fee. ### Should I tell my clients I use a contractor? Tell them the rule: you may use contractors, you check every piece before they see it, and nothing goes live without their approval. Put that line in your [client agreement](https://scout7.ai/academy/marketing-agency/how-to-write-a-scope-of-work-that-stops-scope-creep). Never present a contractor as a team you do not have, and never let the contractor contact your clients directly. ## Sources - [Independent contractor (self-employed) or employee?](https://www.irs.gov/businesses/small-businesses-self-employed/independent-contractor-self-employed-or-employee). Internal Revenue Service, updated 19 May 2026, checked 15 October 2026. - [Instructions for Forms 1099-MISC and 1099-NEC](https://www.irs.gov/instructions/i1099mec). Internal Revenue Service, checked 15 October 2026. - [About Form W-9](https://www.irs.gov/forms-pubs/about-form-w-9). Internal Revenue Service, updated 27 June 2026, checked 15 October 2026. - [U.S. withholding agent frequently asked questions](https://www.irs.gov/businesses/international-businesses/us-withholding-agent-frequently-asked-questions). Internal Revenue Service, updated 23 July 2026, checked 15 October 2026. - [E-file information returns with IRIS](https://www.irs.gov/filing/e-file-information-returns-with-iris). Internal Revenue Service, updated 12 October 2026, checked 15 October 2026. - [Publication 5718: Information Returns Intake System (IRIS), processing year 2026](https://www.irs.gov/pub/irs-pdf/p5718.pdf). Internal Revenue Service, checked 15 October 2026. - [ABC test](https://www.labor.ca.gov/employmentstatus/abctest/). California Labor & Workforce Development Agency, checked 15 October 2026. - [Freelance worker rights](https://www.nyc.gov/site/dca/workers/workersrights/freelancer-workers.page). NYC Department of Consumer and Worker Protection, checked 15 October 2026. - [What is the Client Marketplace Fee?](https://support.upwork.com/hc/en-us/articles/4660220468499-What-is-the-Client-Marketplace-Fee). Upwork Help Center, checked 15 October 2026. - [What is the Contract Initiation Fee on Upwork?](https://support.upwork.com/hc/en-us/articles/26106318334611-What-is-the-Contract-Initiation-Fee-on-Upwork). Upwork Help Center, checked 15 October 2026. - [What is the Upwork Conversion Fee?](https://support.upwork.com/hc/en-us/articles/360043723533-What-is-the-Upwork-Conversion-Fee). Upwork Help Center, checked 15 October 2026. - [How to invite freelancers to your job](https://support.upwork.com/hc/en-us/articles/211063518-How-to-invite-freelancers-to-your-job). Upwork Help Center, checked 15 October 2026. - [Is Upwork free to join? Our pricing breakdown (2026)](https://www.upwork.com/resources/is-upwork-free). Upwork, 2026, checked 15 October 2026. - [Pricing](https://contra.com/pricing). Contra, checked 15 October 2026. - [Can I use Dropbox Sign for free?](https://help.dropbox.com/plans/dropbox-sign-free-plan). Dropbox Help Center, updated 4 December 2025, checked 15 October 2026. - [From freelancer to agency owner](https://blog.codercops.com/blog/freelancer-to-agency-owner). CoderCops, 21 February 2026, checked 15 October 2026. - [Hiring your first contractor: when you're ready and how to do it right](https://agiled.app/hub/agencies/hire-first-contractor). Agiled, 25 June 2026, checked 15 October 2026.