Listing Light ·the hiring playbook
01 / 18

How to hire
virtual assistants.

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Where the talent is Upwork Fiverr OnlineJobs.ph
A Listing Light training
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First principle
02 / 18
The one thing that matters

The platform isn’t the lever.
The way you hire is.

Great people are on every site, and no platform consistently wins on price — it depends on the role. So we’ll spend almost no time on which site, and almost all of it on how to hire. That’s where the biggest returns are.

Where to hire
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Three good options

Great people are on all of them.

Upwork
Upwork
What I use for everything. The rest of this guide is Upwork-centric.
Fiverr
Fiverr
A solid alternative on the same general model.
OnlineJobs.ph
OnlineJobs.ph
Specifically for Philippine workers.
The website is not the lever. Your hiring process is.
Why Upwork
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Why it runs the whole thing

Everything through one platform.

01
Free to post
Put up as many jobs as you want. You pay nothing until you actually hire someone.
02
You set the pay
From the $5 minimum up to as high as you like.
03
Easy payments
Add a card or bank account — like checking out on Amazon.
04
Taxes handled
No chasing 1099s from overseas contractors — Upwork handles the paperwork.
~$100k
spent on the platform over about two years. The little “$5 here, $5 there” adds up — and I routinely pay ~$200 for a whole project.
Part 01 · The process
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How it actually works

The hiring process.

Know the job → write the post → build the trainings → batch-hire → keep the one who delivers.

Step 1
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Step 1

Know the job.

Have a clear idea of what you actually need done — before anything else. Everything downstream depends on it.

The whole flow
  • Define the job
  • Write a tight post
  • Build the trainings up front
  • Hire 3–5, keep the best
Step 2
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Step 2

Write a great job post.

As few words as possible, while detailing as much as possible. Applicants have a lot of posts to skim — make the role instantly clear and you attract better people (and can tell who actually read it).

Watch out
Applicants are getting smart.
Plenty use AI to mass-apply. You can usually tell — template answers that echo the last person. As you read replies, ask: does this feel like a real human, or a copy-paste?
My process
08 / 18
From brain-dump to post

How I actually write it.

1
Walk & rant.
Go for a walk and record ~20 minutes of specs — everything you want the role to be.
2
Condense with AI.
Hand the recording to Gemini (or any AI) to tighten it and organize the thoughts.
3
Review & post.
Read it once more, approve it, and put it up.
Tool I use Gemini  Gemini
Step 3
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Step 3

Build the trainings up front.

Before anyone asks a question, prepare everything in Notion: Loom walkthroughs, logins, passwords, and step-by-step guides. Then you don’t train live — you point people to the resource. This is also what lets you hire several people at once.

Notion  Notion Loom  Loom
What goes in the doc
  • Loom videos: how to log in & what to look for
  • Logins, passwords, emails
  • Step-by-step guides for the task
Part 02 · The best tip
10 / 18
The single best tip

Hire 3–5.
Keep one.

Step 4
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Step 4 · the #1 tip

Hire 3–5 people at once.

Test them in parallel on the same trainings. Keep the one who delivers; fire the rest and run another batch until you find your person.

Why it works
You’re not running charity.
If one slacks, another is locked in. You go with whoever actually gets it done — no single point of failure.
Reality check
Even millionaire agents struggle here.
Top producers doing many listings a year still get hiring wrong. Batching solves it. You don’t have to tell candidates it’s a batch — just let them work.
How to choose
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How to choose

Let them prove it.

People will brag about why they’re the best. Skip it — watch the work across your 3–5 and let it speak.

  • Initiative
  • Speed
  • Quality of work
  • Communication
  • The right number of questions
  • Takes up less of your time
  • Actually gets the job done
When it doesn't fit
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When it doesn’t fit

Fire kindly. Rehire.

Keep the one you vibe with and who delivers; let the rest go. Don’t be mean — they’re still human. Be honest and give feedback, then run another batch until you find your person.

Roughly how I word it

“You’re great, and I liked working with you. You were strong at X and Y, but slipping on Z — so I’m taking the work elsewhere. I hope it all goes well.”

Pricing
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Pricing reality check

No clear link between pay and quality.

The floor
$5

The minimum. People will apply — and some outwork anyone you’ve ever seen, for very little.

The catch
Paid a lot, got poor work too.

More money did not mean better work. Pick a number you’re comfortable with — then push it a little lower than feels natural.

Mechanics
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How you pay

Two ways to pay.

1
Hourly.
Pay per hour worked.
2
Milestones.
Pay per project or deliverable — e.g. one $200 budget for a whole job.
Built-in messaging makes coordinating either one easy.
Don't get banned
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The one rule to not break

Keep payments on-platform.

Upwork makes money on every payment — from both sides. Post a job, “hire” someone, then pay them off-platform and they can shut your account down. Keep it all on Upwork.

Also worth knowing
Boosting? Skip it.
You can pay to boost a post, but I’ve seen little to no difference — I still find great talent without it.
Taxes
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The quiet bonus

Let Upwork handle the paperwork.

You don’t collect 1099s (or the overseas-contractor equivalent) from everyone — Upwork handles that filing. They verify your ID at signup, which is part of how they manage it for you.

At tax time
Hand it to your CPA.
“I used these guys.” They reconcile the records and you’re done — nothing else to chase.
That’s the playbook
18 / 18
Over to you

Go hire.

Write a tight post, record-and-condense it, pre-build your Notion + Loom trainings, hire 3–5 at once, judge on proof, and keep the one who delivers. Keep payments on-platform; let Upwork handle the tax paperwork.

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