How To Hire UpWork Freelancers: Writers, VAs, Developers and More

Please note that affiliate links may be included in some posts.

Below I outline my UpWork hiring strategy.

If you need to hire a freelancer- this post will walk you through my hiring strategy.

I've hired writers, virtual assistants, WordPress developers, specifically targeting high-quality/low-cost freelancers. 

This post focuses on how I've hired writers- but the techniques can be applied more broadly to recruit any type of freelancer you need. 

What Is UpWork?

If you're unfamiliar, UpWork is an awesome place to engage with writers, virtual assistants, developers, designers, all manner of creative and technical professionals from across the world.

It was launched after Elance & oDesk merged and has become a go-to resource for me whenever I need bloggers or administrative help. 

It's a global hiring platform that offers some advanced filtering features that enable niche site publishers the ability to recruit specialized talent for reasonable prices. 

This is my own process and it has been honed ​over several years as I built and scaled an affiliate site to six figure yearly profit.

Basically the way it works is that you can post Jobs that Freelancers can view and apply to. You can also search for and invite Freelancers to Jobs, hire them for work, and pay them using UpWork's escrow service. 

Now, on to my hiring strategy...

My UpWork Writer Hiring Strategy

When it comes to hiring writers on UpWork, my general formula has been to:

  1. Write up a short job description and post it to UpWork.
  2. Produce a screenshare video describing what the job is.
  3. Write up the requirements in a training document and include the video in the document. I save this document in DropBox so it's always accessible, wherever I am. And I make updates to it whenever something occurs to me. This way if I need to rehire for the position it's always available.
  4. Next, I IGNORE applicants. In my experience the applicants are not the best fit for the job. Oftentimes, they're automated responses. Though, to be fair, I'll skim through to see if any strike my interest.
  5. I use UpWork's Advanced Search Filters to recruit writers to the job.
  6. If they accept the invitation to the job then I send them the Training Document and if they are interested in the work I begin negotiating with them.
  7. Then I hire based on the time it takes to write 1,000 words, for example, rather than an arbitrary cost for 1,000 words. I dive into this negotiation strategy a little bit further down. 

Explained Further

The Job Description

To go into a bit more detail- I keep the Job Description brief because all of the useful information is contained in the Training Document.

Here's an example of a job I posted: 

UpWork Job post

When you go to recruit writers, UpWork requires that you use their 'Invite To Job' function initiate a conversation. 

If the writer agrees to interview for the job, then you can enter into a conversation in the Messages section of UpWork. 

Recruiting UpWork Writers

The Training Document

I only send the Training Document to the writers once they've accepted an offer to interview for the Job.

This is because the document is somewhat sensitive and contains URLs of some of my sites that I use to demonstrate how some of the finished writing looks.

Below is a sample training document- you can download it by clicking here or using the menu option at the bottom of the embedded document. 

This comprehensive document is specifically tailored for one of my sites and walks the writer through how to format the content, how to conduct basic keyword research, how to conduct & source internet research, and a variety of other intricate details that I've operationalized to get the best bang for dollar I spend on content.

The Screenshare Video Training

The screenshare video is an opportunity to cover the nuances of the writing requirements. It gives your writer a feel for who you are, what your site is about, and it can provide context to the step-by-step instructions included in the training document.

For example, one recent training video I shot, I explained the SEO strategy behind one of my sites. Because she's doing a lot of the content, it helps that she understands some of the higher-level ambitions- the 'why' behind the content she's creating. 

Rather than writing in a vacuum, my requirements now have greater context. Plus, it's easier to demonstrate the nuances.

For instance, I require my writers use tools like and Grammarly- my videos demonstrate how to use these online services- which is a lot easier to show in a video than typing out in a long training document. 

I've been using a premium version of Screencastify for unlimited-length video recordings. You can use it for free for 10 minutes at a time. It can record your desktop or just a tab on your browser. 

Using ScreenCastify

What I like about it is that you can synchronize it with your Google Drive and quickly generate a shareable link to the video you shot. I then include this link inside of the Training Document.

Recruiting Writers

Once you've posted your job, it's time to use UpWork's Advanced Filters and recruit some writers.

The search criteria you select will depend on the job you're hiring for. 

UpWork Advanced Filters Example

For example, when I first started publishing niche sites, the startup that had been employing me as a Digital Marketing Product Manager had failed, so I was basically jobless.

This meant I needed cheap, but good, writers.

So, I searched for writers with a rate of $10 and below, who had earned at least $1, with either Fluent or Native English skills. Sometimes I would throw in a keyword to screen further.

For example, sometimes if I was searching for a writer in Europe, I would add the keyword "ESL" to find "English as a Second Language" teachers. 

As well, you'll find that U.S. content writers will be more expensive, on average, than international writers. But you can still find fluent English writers in non-U.S. countries. I've often targeted that demographic to get quality English writing at non-U.S. prices.​

So, try toggling the U.S. only switch on and off- see what you can find exploring the U.S. and non-U.S. localities for blogging talent. 

In terms of how much you should be paying, it will really depend on the quality of the work.

*UpWork recently instituted some new platform changes that restrict the number of job application invitations you can send to freelancers. You can read about these changes on TimeDoctor- they have an in-depth summary of these new policies.

How Much Should You Pay For Writing?

SEO Content

There's a class of writing that I call "SEO content"- it's decent and readable, but not the first thing you'd want your site visitor to pay attention to. If a review post  has 2,000 words, this is the 1,500 word 'gristle'. The filler that bulks up the burger, not the sirloin. I would try to get this style of writing for $8-$11 for 1,000 words.

Premium Content

The other class of writing I loosely refer to as premium content- this is writing that is the first thing a visitor sees when they land on a particular post on your site. It's generally clean, Native-English prose, designed for user experience instead of search engines. I would try to get this style of writing for $20-30 for 1,000 words. 

Find Good Writers With No UpWork Experience

Another strategy I employ is targeting and recruiting new UpWork Freelancers.

You can find them by targeting the Earned Amount- find people who haven't earned anything yet, for example. These are writers who don't have any work experience on UpWork, but they could still be decent.

Imagine a current college student who needs some spare cash- these can be a real bargain.

They will often work for a discounted rate, relative to the quality of their writing, until they have enough work experience to justify charging higher amounts. The upside here is that you get discounted writing, but there's higher 'churn' as they graduate to higher compensation requirements.

But some writers will work for you for years without ever asking for a raise. Even though they probably should.

Fun fact: I have some writers that I would happily pay more money if they would only ask- but they haven't yet. 

First Contact

Before you contact writers, make sure you've thoroughly read through their profiles and any work samples to spot sloppy grammatical issues or poor phrasing.

If they make sloppy errors on their UpWork profile, it's an immediate red flag for me. 

I would message the ones who seemed like they were quality writers and either request more work samples if they didn't have any, or if they had decent work samples, I'd send them the Training Document to see what they thought of the project.

Negotiating A Price

Then, depending on their hourly rate, and how much I wanted to pay, I would either suggest a rate for the word count ($1 for 100 words, for example), or I would say something like "This 1,000 word writing task takes me an hour and a half to do, so how about we try [their hourly rate x 1.5] for 1,000 words".

Affiliate Monetization

This would be a sample writing task.

Once they've finished the sample and it looks good I ask them "What are your thoughts about doing more".

One caveat- don't write up a critique of their writing until they've agreed to do more. I made the mistake a couple times of writing up a full critique of the writing and then ultimately not working with them- a bunch of wasted effort. Get to know their thoughts.

Often times they'll be down to do more at the original price, which is good. Sometimes they want more.

I've found it's useful to tie them to their hourly rate.

So if their rate is $6 an hour and I believe that the writing task takes an hour to do, I try to hire them for $6. 

This is helpful because if you just asked for a price quote for 1,000 words, they might ask for $30, which would logically mean it takes them 5 hours ($6 x 5 hours = $30).

Always bring it back to their hourly rate rather than the word count itself. In this example, if they balk at $6 for 1,000 words, you can up it to $9 for 1,000 words, which means you're buying 1.5 hours of their time.

This creates a logical framework for pricing and has helped me simplify the negotiation process.

Once you begin negotiating with writers, you'll get into a rhythm doing this and it becomes somewhat intuitive. 

Batch The Writing In Bulk

Then I try to 'batch' the writing as much as I can- so if one article is 1,000 words, I try to send 5 over at a time, sometimes even trying to get a discount.

So if the rate is $10 for 1,000 words, I might try to hire them at $45 for 5,000 words, for example. You'll want to keep them busy. 

Once you find a good writer who's willing to work at an acceptable price, keep ordering content from them. Otherwise you risk losing them.

Remember to spot-check the work. Writers will oftentimes get lazy and take you for granted if you don't provide feedback every so often.

Final Thoughts

So, the general idea is to create super-specific requirements that exist inside of a 'living' Training Document, to actively search and recruit writers, and then negotiate on price smartly by holding them to their hourly rate, rather than an arbitrary number for a word count.

My process has been informed by my experience using UpWork, but I also worked as a Digital Marketing Product Manager for several years at a startup.

In this capacity I was in direct communication with overseas developers and designers. I was responsible for defining requirements and overseeing the work they produced​. So, to me, I take a perverse joy in writing up Training Documents, operationalizing processes, and automating workflows. 

I hope this guide helps inform your own hiring process. ​I've heavily depended on Gael and Mark over at Authority Hacker- they have some amazing resources on content creation that I heavily advise reading. 

Last Updated on November 15, 2023 by Ryan Nelson


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