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Ep. 62 Hiring a Freelancer with Connor Gillivan of FreeeUp

Freee Up Hiring a Freelancer

Brad Post, Create the Movement, host

Connor Gillivan, FreeeUp, guest

Connor Gillivan is currently a Founder and Owner of He was an Owner of, which he helped scale and was acquired in 2019 by The HOTH. Connor is an expert in hiring and scaling with virtual assistants and shares his business insights on his own blog, He currently lives in Denver, Colorado. 

Connor Gillivan FreeeUp




Personal blog:


Connor calendar:

Connor email:

Coupon Code “CreateTheMovement25”

Brad Post, Create the Movement, host: Welcome back to Create the Movement Podcast. I’m excited today to be speaking with a new friend of mine, Connor Gilligan. He is the Chief Marketing Officer of a company called FreeeUp. They help companies hire top freelancers to grow their business.

Connor, how are you doing today?

Connor Gillivan of FreeeUp: A Freelancing Company

Connor Gillivan, FreeeUp, guest: Hey, how’s it going? I’m doing well. A little bit of a busy day, but nothing out of the norm.

BP: Awesome. You guys have an interesting story, a really exciting thing to share with small business and companies, so I’m excited to hear your story.

CG: Yeah, it should be a great conversation.

BP: Yeah, so you want to start at the beginning? I think the last time we talked we talked about when you graduated school and whatnot. Go ahead and start.

CG: Yeah, of course. So, I ran into my business partner that I continue to work with today while I was still in college. This was about nine years ago. We were in the same business law class. He was just starting to experiment selling books on Around this time Amazon was really blowing up and expanding and selling a lot of different products and starting their whole Amazon Prime program.

So, it was a really interesting time to get into the space. He was looking for someone to help him run the business and take it to the next level and start to sell different products. I was someone that was always interested in entrepreneurship and business from a young age. I took him up on the opportunity not sure what would come of it.

But it ended up turning into about four or five years of working together, graduating from school, building a team, moving down to Orlando, Florida from where we were in Connecticut. And then starting to hire a lot of independent contractors both from the US and from outside of the US as well. We really spent those years becoming experts at selling products through Amazon and working with suppliers and brands around the United States. It was just a great experience that opened our eyes to a lot of parts of running a business and building out a team.

Towards the end of that five years we had been using websites like Upwork and Fiverr and Freelancer and a number of other ones where you kind of have a similar experience – you can go and post the job, you’ll get 10-20 applicants, you can look through their profiles. But then it’s your job to actually interview them and try to figure out who’s the best for you.

We found that we were just spending a lot of time doing that, and then we were also running into turnover. So, we were just frustrated by this process and that was really the reason that we decided to create FreeeUp – to make a slightly different marketplace that was trying to make hiring simpler for business owners. And, so, that’s what I do today. We have a marketplace that’s been around for three years. We actually interview and vet hundreds of freelancers every week and then only allow the top 1% of applicants into our network.

And, so, for business owners they can find curated, pre-vetted freelancers from $5 all the way up to $75 per hour ranging from a variety of skill sets.

So, that’s pretty much my story here in the past nine years, or so.

BP: That’s exciting. So, one thing, too, is you have people in the United States and you have people outside the United States that are within your network, correct?

CG: Yeah, exactly. Right now we have about a 1000 freelancers in the network and 40% are US and 40% are Philippines, and then the remaining 20% are scattered across about 30 other countries.

BP: Oh wow, okay. That’s exciting. So, one process we’ve run into in the past that’s been frustrating is with Upwork, or Fiver, or really Upwork, is you look to hire someone and you don’t even know if they’re active. So, all of your applicants are actually active, correct, and willing to take the jobs?

CG: Yeah, definitely. So, most of them, and this is something we look for in our vetting process, most of them run their freelance business full-time. They’re always doing this. They’re working with handfuls of clients and they’re always looking to take on more clients if they’re capacity allows for it.

The FreeeUp Process

BP: Well, tell us a little bit about the process. You can sign up for a free account. Right?

CG: Yes.

BP: So, tell us, if you could, about both sides. If you want to be a freelancer what that looks like. And then, if you want to, sign up as someone you want to outsource to.

CG: Of course. So, if you want to apply to be a freelancer there is, like I said, an application and interview process. Right on the site you can click ‘Apply to be a Freelancer.’ You’ll submit some basic information about yourself and answer some questions as to why you’re interested in joining the marketplace. If you make it through that portion of the process you’ll be invited to a one-on-one interview with someone from our team where you get asked a lot more questions about your skills, how you communicate with clients, and then really just your attitude around being a freelancer, as well.

And then, the final step to make it into the marketplace is a test on communication with clients. It really dives into different scenarios and situations as to how you would handle working with a client. And that’s for us to make sure that clients are getting the best experience possible, and they’re getting people that know how to communicate at a high level.

So, that’s how you get in as a freelancer.

And, then if you’re looking to become a client, someone who’s going to hire freelancers, you can create an account for free right through the website. It takes a couple of minutes, and then you gain access to the FreeeUp software. Within there you can click a very simple button that allows you to request a freelancer. You give details about the person that you’re interested in hiring, you give your budget, some other information that will help us find the right person, and within one business day we find you someone that matches up with all of your needs and we introduce them to you. You can speak with them, ask them questions, see if they’re the right fit. You can hire them through the platform, or if you don’t like them you can give us feedback and we’ll introduce you to someone else.

We really try to keep both processes very simple for the freelancers and clients.

BP: So, literally within a day you’ll have somebody ready for the project.

CG: Yeah, sometimes it’s within hours, too. Sometimes it can be quicker. But, yeah, you can hire someone very quickly through the platform. That’s the reason why a lot of businesses really enjoy working with us, too.

How FreeeUp Differs from Competitors

BP: That’s exciting. I kind of want to go back to the freelancer part because we’ve had experience using Upwork and other companies. We literally would just pay $25 or $50 just to test some to see if they could follow the instructions that we gave them. Simple instructions. Yeah, we probably ran 20 tests in the past few years just to try to find someone. And, so, you guys actually take them through the test process somewhat.

CG: Exactly. Yeah. We put them through a lot of questions that, doing this for six, seven years, we’ve found very useful in finding reliable freelancers. And, so, that is our hope: remove those instances where you as a business owner have to do those test runs and invest in that before you find the right person.

BP: The other thing that I wanted to mention, too, to you, and if you could just talk through this process was when you sign up you literally get, not a lot, you don’t get spam emails, but you get emails. And I think it’s actually from Nathan, right? He’s the guy that you’ve been working with, correct?

CG: Yeah.

BP: If you could talk through that process. I think I even got a text message from him, “Hey, if you want to talk to me here’s my Calendly calendar. Talk us through that process.

CG: Yeah, so that was another part of the other marketplaces we were frustrated by. We didn’t always have someone that we could turn to when we were having issues or we ran into problems with just getting started. And, so, a main focus of ours is to try to be as hands-on as possible. And Nate does that by being the face for all clients. We send out an email. We send out a text. We try to reach people and then figure what is the best way that they enjoy communicating. We can always be there as a resource for them as they’re getting started hiring with us. He’s very hands on. Every client also gets a client-success assistant – another person in our internal team that’s solely there to help clients hire freelancers, answer questions, deal with billing issues, and make sure that their experience is really smooth and positive.

BP: That’s exciting. Yeah, try to get a hold of someone that actually works at Upwork. Good luck doing that, right?

CG: Right.

What’s New at FreeeUp

BP: Tell us about future plans, what you guys are looking at doing in the future.

CG: Yeah, sure. When we started this marketplace we were very focused on the Amazon seller and the Amazon Marketplace. That was very much our core niche when we started because of our past experiences with selling there. But in the second year, we quickly expanded into selling and working with a lot of people that use other e-commerce platforms to sell their products online.

So, we were able to see some great expansion there, and start to bring in some more digital marketers and advertisers into the marketplace who were able to offer their services. As we’ve been growing over the past nine months, or so, and as we move through this year our goal is to become another household name as a marketplace where any business owner could come to find reliable freelance help.

We’ve really built out our skill sets that we offer. I’m going to be launching a new re-design of our website in the next month and you’ll be able to see the 85+ different skill sets that the freelancers are offering.

We’re really excited to take the company brand to that next level and become a solution for really anyone that’s running a business out there.

BP: That’s great. That’s one thing I was going to mention, too, on the existing site on the ‘Pricing’ tab it literally gives you all of the different skill sets, what non-US would cost, what US would cost, what people can do. It’s pretty thorough. So, that’s exciting.

You guys are doing quite a bit and getting quite a bit of people working for you.

Simplifying the Hiring of Freelancers for Business Owners

CG: It’s just a common question that we’ve found. A lot of business owners that haven’t hired freelance talent before, they don’t necessarily know what they should pay for a specific skill set or someone for someone. So it can be hard to even get over that hump as a business owner sometimes. So, we provide those ranges to try to give people a general idea of what would be realistic to pay at an hourly rate.

BP: Perfect. And then you pay literally through the portal itself, right? So, you guys have your own payment portal system set up on the back end?

CG: Yes. Our software tracks all hours that the freelancers bills to you as a client. And then on a weekly basis you’re billed for those freelancer’s hours and you pay through FreeeUp, and then we pay the remainder to the freelancer.

BP: That’s great the way you guys have it set up. The other thing I was going to ask is, not to pick on Fiverr, we’ve picked on Upworks so let’s pick on Fiverr for a bit. There’s just so many people out there and they’re like, “We’ll do this for $5, or do this for $10.”

You guys have to where if you have a specific project that you know what you want to do, you can pay that person to do that whether it’s SEO or Amazon. I even noticed some telemarketing sales positions in there. I thought that was great because sometimes you can overwhelmed with Fiverr-type stuff. You know?

CG: It makes sense. It’s totally different. So, with us the client, or the business owner, is very much in control where they are the one that’s creating the request, creating the post, and really telling us what they want. Whereas, on Fiver, it’s kind of the freelancer, the contractor, who’s in control. Posting their package or their service. And it’s up to the business owner to try to find someone who matches exactly what they’re looking for.

That’s the difference I see between us and Fiverr in terms of how the posts are being put out there and made public on the site.

BP: One thing I was going to ask, too, is if you don’t mind sharing. So, you’re getting a lot of people applying to be a freelancer right now. And you don’t have to go into full detail, but how are you guys marketing that right now to find freelancers?

CG: A couple ones that contribute the most. The first is our referral program. So, for the freelancers that are already in the network we pay them to refer people to us. And we pay them 25 cents for every hour billed any freelancer they refer.

BP: Really, okay.

CG: So, they can make a little bit of extra money every week on their weekly payments if they refer good people into the network and they get in and then start billing a lot of hours. That’s been a really great marketing tactic for us.

We also partner with a lot of freelance communities, or publications. So, people that have built a large Facebook group, or have a blog that’s dedicated to being a freelancer, or themselves are just an influencer within the freelancer community, we’ll partner up with them. We’ll, again, get them involved in the referral program and we’ll create content with them that’s geared toward freelancers. We’ve seen a lot of success with those partnerships as well.

BP: On the other end of things, I think you said you do a lot of podcasts, reach out to podcasts. Thanks for being on ours.

CG: Of course.

BP: But what are some things that you guys are doing to reach the business owner as well?

CG: Kind of same side, but we have the referral program. We do a lot of partnerships. Like you said, we do the podcasts. And then, we’ve just started to get into a little bit of advertising with very special niche publications, or sometimes podcasts or conferences. So, we’re trying to get our name out there in those types of relationships.

We also have found a lot of success working with coaches and consultants who have communities of entrepreneurs that they’re teaching how to build a specific business. For example, they’re coaching a community of people on how to build a Shopify store and how to sell products that way. We’ll team up with them and have a really great relationship where we’re trading content, we’re linking back and forth with each other. And then we’re able to gain a lot of clients from their community because they trust us, and then they recommend those people to us.

BP: That’s great. So, you said a new website’s coming out hopefully in the next month is what you’re planning?

CG: Yep, next month. So, the a new website will be coming out with a new look, some updates, a little bit of a redesign. Kind of bringing it up to the next level.

On the back end, our software just went through a redesign for clients just about a month ago. So, there was a bunch of new features added there. We just made it a little bit cleaner. And that’s going to be happening for the freelancers as well within the next month and a half. We’re excited to get those out there and just take everything up to the next level.

BP: Good. We’ll put a link in the transcription of the content, but it’s That’s with an extra ‘e.’ Connor, thank you for being on the podcast today. Is there anything else you’d want to add?

CG: Yeah, I’d like to give a special offer to anyone who’s listening today. I’ll give you a coupon code and we’ll give anyone that’s listening $25 off their account if they sign up to try our FreeeUp. I’ll send that coupon code over to you and when they sign up they can just add it into the coupon section of the sign-up process.

Coupon Code “CreateTheMovement25”

BP: That’s awesome. Yeah, you can definitely find somebody to do something for $25, right? Just for an hour, or a blog post or something like that. So, thank you for that. That’s exciting.

CG: Yeah, of course. Thank you for having me on the show.

BP: Absolutely, Connor.

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