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Freelance Interview Series – Hiring Freelancers With Jimmy Daly

Jimmy Daly is the co-founder of Superpath, a digital community that helps over 5,000 content marketers and creators connect and grow their careers together. Before founding Superpath, Jimmy spent over five years managing content marketing programs at companies like Animalz, QuickBooks, and Vero. He has a wide range of experience working with freelancers—and a bit of experience as a freelancer himself.

We interviewed Jimmy to find out what the freelance hiring process is like on the other side. He gave us the scoop and shared his best tips on how to navigate it more smoothly and build trust with your clients as a freelancer.

Hiring Freelancers with Jimmy Daly

1. What criteria do you use to determine if you should hire a freelancer vs a full-time employee? 

What I’ve found in my work at Superpath—and before that at Animalz—is that this is not always the question that companies are trying to assess. Sometimes they’re trying to decide if they should hire a full-time content person or an agency. But the most common scenario I find is that companies bring on a content manager or a content lead and then let that person figure out how to actually execute the work.

The content leader then goes out and assesses: Should we bring on a content creator in-house? Should we bring on a freelancer or a couple of freelancers? Or should we hire an agency? And then usually they end up with a mix of those three things. So if you’re deciding between hiring a freelancer or a full-time employee, I would say don’t hire freelancers to write until you have someone that can manage those freelancers.

I’ve seen quite a few arrangements go badly when a marketing director hires freelance writers and just isn’t able to give them enough guidance for them to be successful. So let the in-house content person figure out how to run the process, how to create content briefs, who’s going to do the work, etc. Let someone who really has expertise in that area and time focus on it.

2. When you start looking for a new freelancer, where do you go to find them?

Personally, I go to our Slack community, because there are lots of freelancers participating and I’ve had quite a bit of success finding good folks there. If you work in content marketing or you’re a freelance writer, the community is a valuable place to hang out because it’s easy to make those connections.

Before I had that, I relied on LinkedIn and Twitter. Generally, networking with people is a good way to find freelancers. I have used job boards to hire freelancers as well, with mixed results. You just run into the same problem that you do when you’re hiring anyone: You’re likely to get a bunch of applications and then you have to sort through them and vet them. It’s a little cumbersome. The networking approach is nice because you can just rely on word of mouth. It’s a great way to validate whether or not a person has a track record of doing good work.

This is part of the reason we’re launching a marketplace at Superpath. We’re connecting companies to freelancers and we’re doing the vetting for you. We’re also running everything through a process that we’ve tested and know for a fact generates good content on a regular basis. So we can take some of that off your plate—finding the people, vetting them, and making sure the processes are sound.

3. Give us an example of a way you’ve improved your process of working with freelancers over time?

At one point I had a team of 15 freelancers, and I learned pretty quickly that if you don’t set very, very, very clear expectations and give the writer everything you could possibly give them, you will likely be frustrated with the end result. Without those clear expectations, and without a great deal of context, the freelancer is forced to go out and figure it all out on their own. It doesn’t mean they can’t create good work. It just means it may not meet your expectations.

So we started off with these very basic outlines that I would send freelancers, and over time those developed into very robust content briefs. As that process improved, it significantly reduced the number of revisions and back-and-forths. In the beginning, I would get a lot of articles back where I was like, Oh my gosh, I’m supposed to publish this in two days. It has to be totally ripped apart.

After a few months, that just wasn’t happening anymore. You get to know freelancers, you work better together, and you get through that learning curve. But a good process makes those relationships work so much more smoothly.

4. If you could give freelancers looking for a new gig advice, what would you tell them?

Tip #1: Pick relevant work samples and offer context.

I’m on the hunt for freelancers right now for our marketplace. I’m collecting writing samples, and so many people just send me a link to a portfolio with a dozen things. That’s not helpful to me at all. So I changed the copy in our intake form to say: Send me three links to published pieces but don’t send me a portfolio. Show me your best work. Show me where it’s been published.
Also, give me some context. Who else was involved in this? I find that some freelancers want their portfolios to speak for itself. I disagree because I don’t know who else was involved with the projects in your portfolio. I don’t know if you came up with this amazing idea on your own and did the heavy lifting, or if you were handed an awesome idea. Be honest with your context, it’ll make the relationship go a lot smoother.

Tip #2: Diversify your income.

This is actually coming from my own experience as a freelancer, which was a disaster. I left a job to pursue freelancing and realized quickly that it was not for me. The takeaway for me was that freelancers should aim to create a few different sources of income. I found myself just selling my time constantly. I was writing so much trying to earn the same amount of money that I was earning at the job I had just left.

Had I pursued freelancing for a longer period of time, I would have started by building out courses, eBooks, coaching… There are so many different ways that you can earn revenue beyond writing. I would encourage freelancers to think about building some of those out from the very beginning, especially as they develop expertise in certain areas. Be thinking early on about how you can diversify what you offer. That will create a buffer that makes it easier for you to be very picky about the projects you work on.

Check out the latest on Superpath’s new marketplace here or follow Jimmy on Twitter to follow along. 

About the AuthorSamantha is co-founder of Harlow. Previously she was a marketing and demand gen freelancer. She enjoys traveling, connecting with new people, spending time with her dog Karl, and throwing back an extra dirty martini every now and then.

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