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Lessons from spending $300k hiring content talent on UpWork

Helloooo content connoisseurs.

It’s Perrin from Content Bites.

I’ve hired a lot of content talent on UpWork. When I need to hire new content talent, I still use UpWork, even if I need someone full-time.

If you get it right, UpWork can be the absolute most efficient way to build a content team. But most people get it wrong. So today, I want to share 7 lessons I’ve learned in the last decade of building content teams on UpWork.

  • Appetizers: Links from Glenn Gabe, Demand Curve, and more…

  • Main Course: Lessons Learned from Spending $300k Hiring Content Talent on UpWork.

Let’s dig in.

Appetizers: Content about content 🤯

  • Highly Visible and Low Quality (or Unhelpful) – A Most Dangerous SEO Combination (link)

  • Influencers vs. Creators: What's the Difference & Which Should Marketers Invest In? (link)

  • New Data: Here’s What Kind of Content Will Perform The Best on Social Media in 2024 (link)

  • How to Maximize Brand Visibility With Employee-Generated Content (link)

  • The ‘Ship It’ Manifesto: How to get your content assets out of Marketing Purgatory (link)

Main Course: Lessons from spending $300k hiring content talent on UpWork

I’ve spent $300k hiring content talent on UpWork. $300k that I can track, anyway. 

Honestly, across all the businesses and websites I’ve built, I wouldn’t at all be surprised If I’d spent half a million dollars on UpWork. 

And it’s been awesome. 

Truly, I love UpWork. 

I’ve used UpWork a lot as both a freelancer representing the agency I owned; it was how I used to find clients before I learned actual sales. 

And I’ve used it even more as a client; it’s how I’ve built basically every time I’ve ever assembled. 

So I really do love the platform. I think it’s one of the single best resources available to any business – but especially for businesses just starting out who can’t afford to hire talent full-time. 

That said, I see lots and lots of people f*ck it up. 

I think there are lots of misconceptions about (1) the platform and (2) the best way to approach freelancers (especially when building teams of freelancers). 

So here are some lessons I’ve heard running the UpWork hiring gauntlet over the past 8 years.

Lesson #1: Pay people fairly. 

For whatever reason, this is the mistake people make most often. 

I think a lot of people (mistakenly) view UpWork as a source to get cheap labor. 

That’s not what UpWork is. 

Can you find less expensive talent on UpWork than other places? 

Yea, of course.

That’s the nature of a platform with global talent. It’s also the nature of hiring freelancers. 

But I’ve seen folks posting jobs for $4/hr. 

That’s not going to help you build a business. And it’s sure as hell not going to help you get real work done. 

And I’m not saying that folks working at that rate aren’t good enough workers. 

I’m saying that $4/hr isn’t a competitive rate to be offering as an employer. It’s also WAY too low if you’re trying to assemble a team of content professionals. 

Yes, labor basically everywhere outside of the US is going to be less expensive than US talent. 

And that’s certainly a reason to even use UpWork in the first place. 

But the goal should never be to pay the least possible amount. 

Instead, it should be to:

  • Find amazing talent

  • Pay them really well relative to their cost of living

  • Build relationships

My rule of thumb is: if I hire someone long term, I want them to be able to live very comfortably, not have to work any other jobs, and be able to save money. 

If you’re hiring global talent, you can hire consultants to help you understand costs of living and pay brackets. 

Shoot to make people happy, comfortable and prosperous. They’re on your team. Be on their team. 

Paying people fairly should be an end in itself. 

But as a bonus, you’ll get better results this way, too. Happy, comfortable, secure teams that don’t have to split their attention between several jobs always produce better results than fractured, insecure teams. 

Lesson #2: Freelancers value stability over almost everything else.

Before running an agency, I was a freelancer.

I made a living as a freelancer for a long time. Hell, I even made a living as a freelancer during a recession

So please believe me when I tell you that by far the most difficult part of being a freelancer is not knowing where the next dollar is coming from. 

You’ll get gigs that seem great, and they’ll end abruptly. 

You’ll be hurting for cash, so you’ll be forced to take short-term gigs. 

You’ll take gigs that look good, but you won’t get paid. 

A lot of the time, the best way to make the most money as a freelancer is to accumulate stable gigs

Stable gigs are super, super hard to find

And they’re the most difficult to find when you’re just starting out. 

…which is why the very, very best team members I’ve ever hired as freelancers were people who were NEW to the freelancer game and to whom I offered long-term work. 

Most of the time, if you’re offering someone long-term work, you can negotiate a bit on their rate. 

Still, please, pay people fairly.

But offering a good freelancer stable work typically saves them so much money in opportunity cost, (unpaid) time spent looking for work, and stress, that it’s pretty easy to find a win-win.

Most of the time, I’m only hire from UpWork for: super, super short-term problems I need solved urgently, or long-term, stable contracts. 

Lesson #3: Do (paid) test gigs.

K. This is the #1 hack. 

This is the process:

  • Post a gig for long-term work

  • When you get applicants, shortlist 3 of them

  • Ask them if they’d be willing to do a paid test gig at their regular rate

  • If they say yes, hire them hourly (you can just do it under the same job posting); keep the job open after hiring, so you don’t have to create more jobs

  • Test three people, hire the best one

Give anyone who completes the test a 5-star review as a thank you. 

Create tests that are super similar to the job you’d like done. 

If you’re hiring for a design role, ask your top three candidates to design something similar. If you’re hiring writers, ask them to write something.

Don’t go more than 5 hours. 

Give people clear instructions.

Be quick to pay. 

Bonus tip: while you’re doing these tests, keep an eye out for communication style, professionalism, etc. 

Test gigs are slightly more work up front but save a LOT of work down the line. 

Here’s a paid writing test template I made (and use) if you just want to copy mine. 

Lesson #4: You can find exceptional talent anywhere. 

I’m not sure where this misconception comes from. 

But a lot of people I’ve worked with operate under the assumption that the US has the best talent. 

It doesn’t.

There’s great talent everywhere. And it’s certainly not true that western countries have a monopoly on smart people. 

At my agency’s peak, we had team members in: the US, the Philippines, the UK, Sri Lanka, Canada, Nigeria, India, and Argentina. 

It doesn’t matter. 

Smart, professional people live everywhere. Just budget the role and find the right person for the job. 

UpWork makes it REALLY easy to hire globally, but you can also use stuff like Deel if you want to take people off of UpWork. 

Which brings me to my next point…

Lesson #5: When you find someone good, offer to move off of UpWork. 

First, to clarify, this is not against UpWork’s terms of service.

Here’s what would be: 

  • Posting a job on UpWork

  • Using the job to get in contact with people

  • Hiring them outside the platform without using the platform

Don’t do that. 

Here’s what I’m suggesting. 

Work with someone on UpWork for a few months. 

If they’re good, offer to move them off UpWork using your established email/Slack/whatever channels. 

This way, everything stays kosher with UpWork, the platform gets a fee, and if a relationship is working out, you can optimize it.

By (eventually) eliminating UpWork’s fees, you can save a bit of money, and your team members can make a bit more money (just meet in the middle). 

Super easy win-win. 

Lesson #6: Chill, friendly, respectful vibes go a long way.

It breaks my heart a little bit, having to say this.

But freelancers, by and large, aren’t treated as well as full-time employees. They also don’t have the same protections. 

This is especially true for freelancers overseas. 

We’re running marketing teams here. We’re trying to get stuff done.

And the best way to do that is to build teams of smart people who like each other and treat each other well. 

Be professional. Set goals. Hold people to high standards. 

But at the same time, shoot for chill, friendly, respectful vibes. 

It’s rare enough that I even make this promise in my job postings, and I think it helps drive a disproportionate number of applicants. 

Plus, it’ll make work a lot more fun. 

If you want to see how I do this in job postings, here’s the template I use

Lesson #7: Clear instructions go a really long way. 

Lastly, in general, for most of us, we’re hiring on UpWork to fill roles that we already know how to do but don’t have time for. We need extra manpower. 

For these kinds of roles, it’s critically important to tee people up for success. 

That means, when you hire a freelancer, they should walk in to find:

  • A clear definition of the job

  • Clear expectations and KPIs

  • Clear, detailed SOPs

  • Clear workflows & team structures

  • Clear deadlines

Doesn't matter how you do those things. Everyone one of them could just be a Notion doc. Whatever.

What you shouldn’t do is hire people to do things you don’t want to figure out

Actually, let me amend that. 

You CAN hire people to figure stuff out for you. 

But you should expect these people to be WAY more expensive and come with preloaded expertise. 

But most of the time, if you’re hiring extra muscle, make sure you’ve teed people up for success by documenting exactly what the job is and exactly what you expect them to do. 

Not to be dramatic, but confusion is DEATH.

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