Connor Gillivan – Inception of FreeeUp

Ep 210 Connor Gillivan


Today we are joined by Connor Gillivan, the Chief Marketing Officer and co-founder of FreeeUp, a staff resourcing platform. Connor started his eCommerce business in 2009 helping suppliers sell through Amazon that eventually ventured into outsourcing.

This is more of the kind of the freelance area as opposed to far more structured outsourcing but it’s really good to have a chat with Connor about the inception of I supposed his career but also his journey to outsourcing as well.

Connor Gillivan

Connor serves as the CMO of FreeeUp handling all marketing, advertising, content, partnerships, and website/software design. In the 3 short years that he’s been working on FreeeUp, they have grown their user base rapidly to over 15,000 clients from all over the world. FreeeUp also received over 150,000 applications from freelancers wanting to join the platform.



[email protected]


Full Transcript
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Derek: Welcome to the Outsource Accelerator podcast. This is a short format podcast where we explore business and outsourcing mastery. My name is Derek Gallimore and I’m really excited to bring you the leading podcast in outsourcing.

Hi, and welcome to another episode of the outsource accelerator podcast. My name is Derek Gallimore and this is Episode No. 210.

So today, I am joined by Connor Gillivan of FreeeUp. That’s Freee with   three e’s. We’ll put all of the contact details in the show notes of course, but this is one of those outsourcing platforms, but it’s an outsourcing platform with a difference. They’re really, you know, their angle is that they offer a far better more controlled supply of outsourcing contractors. This is more of the kind of the freelance area as opposed to far more structured outsourcing but it’s really good to have a chat with Connor about the inception of I supposed his career but also his journey to outsourcing as well. And as with many things, as with many I supposed foreign BPO or freelancer operated companies, he started this by scratching his own edge, in terms of his business and leading freelance stuff and better freelance stuff. So, it’s an interesting story and I certainly enjoyed having chat to Connor. So, without further ado we’ll get into this podcast.

If you want to get any of the show notes or know more about Connor or FreeeUp, then go the show notes which is at

Hi, and welcome back everybody. Today we are joined by Connor Gillivan. Hi, Connor, how are you?

Connor: Hey, how is it going? Thanks for hearing me out today.

Derek; Absolute pleasure. Connor is joining us from FreeeUp. Now, you might have seen FreeeUp around the Internet web. It’s a staff resourcing platform such as similar to some of the other platforms you’ve seen out there now but FreeeUp is a platform with a difference because it’s a workforce and gives a higher quality which I think a lot of people out there are looking for platforms, looking for resources whatever they need. So were going to talk to Connor about his journey in outsourcing and I think that’s relevant to our audience because a lot of people here are looking into the concept of outsourcing, or already outsourcing and I think that this is the very natural progression that lot of people go on. So, really excited to have you here Connor and to hear your story. Thanks for joining us. So, I supposed initially, do you want to just introduce yourself slightly better than I can, and tell everyone how you got in?

Connor: Yeah, of course. I’m going to give a little intro then we can kind of dive into more details as well.

Derek: Yes.

Connor: So, I live in the United States. I’m currently in Denver, Colorado. Originally from just north of New York City. I started my first eCommerce business in about 2009 with my current business partner. And we worked on that business for about five years and we are helping suppliers sell through the Amazon marketplace and kind of along the way, as I’m sure people who are listening have experienced or are experiencing, we had to start hiring people and figure out how to take things off our plate and move it on to others and build processes and systems to run that company. And it led us down this route of outsourcing and trying to find people in the United States, but also in the Philippines and other areas of the world. And it eventually led us to build our own freelance marketplace, like you mentioned. And today I served as the Chief Marketing Officer of the company.

Derek: Right. Fantastic. Thank you so much. And so, back in the day, back in 2009, because one of the things I say is ‘outsourcing is really only being available to small and medium size businesses really for about the last 10 years’. And one of the big aspects of popularizing the smaller utilization of outsourcing was Tim Ferriss’s 4-Hour Workweek, which really popularized this automation of processes and utilization outsourcing and just sort of getting the best out of everything you really can. And was that an influence on you by any chance back in 2009?

Connor: So it absolutely was. I read the 4-Hour Workweek, maybe in 2010 and it kind of shift in my mindset and had me starting to look for those types of options. But it wasn’t really until, I think it was 2011 or 2012 that we were starting to hire people in the United States and we had an office that we’re building and we are introduced to the idea of what used to be from another entrepreneur in the area that we’re living. He said he had found someone from the Philippines for a good price and it was using them to run his business and that we should check it out. So that was really when I, we kind of first jumped into it and saw this whole marketplace and saw this opportunity to hire people from outside of our direct area.

Derek: Right. And so you were in the sort of Amazon, is it Amazon that you deal with and drop shipping and things like that? What do you do?

Connor: Yes. That was the first business. We were working with manufacturers and brands around the United States that maybe have their own website or they were selling to big box retailers, but they weren’t yet selling too much on Amazon. And we partnered up with them to become almost their Amazon channel manager to help them sell more there.

Derek: Right, right. So because often, I find that the smaller end of businesses, they really are quite embracing and advance in terms of outsourcing, in terms of optimization of processes. And you might’ve seen them going to all kinds of clients that you were looking to get the products of. We’re they really quite sort of ignorant in terms of online commerce, the whole Amazon thing, outsourcing.? You, guys really were the sort of the switched-on crowd, yeah!

Connor: Yeah, completely. I mean in 2009, 2010 even 2011, 2012 there, a lot of the people were working with were very, they didn’t have anyone on their team that knew the Internet that well. They didn’t really see Amazon as a big sales channel yet. And so we kind of had to educate that and on that a little bit and show them the opportunity. And I think it was in around 2013 that the market really started to shift. You started seeing brands understanding Amazon a bit more. They were starting to understand their intellectual property and copyrights on the Internet and how they want to manage those. And you saw a lot of these companies that didn’t know anything about the Internet prior to starting to hire people who had more knowledge about it. And I think that was a big shift in the whole eCommerce market.


Derek: And then in terms of you finding your resources and using ODesk as it was, and again, I think it’s quite a specialized area that you guys are in the sort of drop shipping area and because you’re dealing with a lot of really engaged, kind of younger people that are just kind of pushing the boundaries on everything. And I find it amazing that, that sort of sectors, the early adopters of outsourcing. And really there’s a lot that the SMEs and sort of bigger businesses can really learn from that. So you started outsourcing in some form or another, in about 2011, 2012, and how were your initial experiences with it?

Connor: Yeah, great question. So at first, I think we were just amazed by the ability to find and work with someone halfway across the world for a cheaper price than what we were able to hire someone for in the States. So I would say initially it was kind of like almost like a shock and just in awe of what was happening. But as we spent the next six months to a year really diving deeper into it and trying to build out a team of people that could help us grow our business. We ran into a lot of frustrations with these different marketplaces we were trying out. We found that a lot of the individuals offering their services through these marketplaces didn’t necessarily have the experience. Not all of them spoke great English, so it’s tougher to communicate for us. And then we also have friends who areeyeball as they proclaim themselves to be where we may have found someone, we’d hire them, they disappeared, and we were kind of back to stage one. So I would say in the first year we had a lot of ups and downs. We found some really amazing people, but we also spent a lot of time wasted just trying to find those good people at first.

Derek: Yeah, there really is a kind of baptismal fire [?] [00:09:54]. How much do you put that down to your own learning of the process? As you do within the business, you sort of maybe pay the taxes, tumble along until you develop new skills in certain new areas. This is the kind of unreliable nature of the broader freelance market kind of thing?

Connor: Yeah, fair question. I would say some of it definitely falls on us. We were brand new to it. We hadn’t managed people remotely before. We didn’t interview people remotely before. So we were slowly hashing out our own interview and hiring process as well as how do we manage these people we’ve hired remotely. And what do we use as communication? What do we use and how we get updates through email and things along these lines? So in that first year, a lot of it was probably our own mistakes we were making. And looking back on that, I think it was a combination of the both that led to some of those ups and downs.

Derek: Again, that’s the incredible journey of entrepreneurship, isn’t it? It’s kind of learning as you’re doing. And you build the aircraft as you jump off the cliff kind of thing. It’s sometimes good, and, so then, we’re going to move into FreeeUp obviously. Now, I want to get you back so that we can really deep dive into exactly what FreeeUp offers and its sort of unique position because my story to people is that every business out there really should outsource. At least, really properly consider outsourcing and I think FreeeUp and these platforms are fantastic opportunities of really people just quickly engaging and dipping their toe in. And just trying this outsourcing thing and seeing that it’s actually great value and it’s not quite as scary as you know from things. What do you see as the main kind of inhibitors of people giving this a go? Do you see especially State side, where do you see resistance or kind of apathy from potential clients?

Connor: Yeah, great question. There’s a few things. So the first is they may have tried it, let’s say five years ago or so and had a first poor experience and they just wrote it out. They kind of said, “Hey, I tried this, it didn’t work and I’m not going to try it again.” So I’ve had a lot of reluctance from people in that manner.

Derek: That’s a big one issue, isn’t it? I have come across that a lot. And also people say that, you know, they have had a bad experience talking to a customer service rep from a bank. So they of course, they’re not going to try it. It’s a tough one.

Connor: And then another one that’s very common as well is just, some people aren’t comfortable yet with working with someone or trusting someone to work for them that are on the other side of the world working remotely or even in a BPO office. They just, it’s hard for them to wrap their head around that at first. And so, that’s a big hurdle that a lot of entrepreneurs I’ve met have to get over at first. But from what I’ve seen in my history of working with clients that are starting outsourcing and then actually getting into it. The ones that are able to get over that first hump and kind of understand the process for how it can incorporate with their business, they ended up not turning back and they have a great time with it and build out large teams that continue to grow their business. So it’s kind of like an ON and OFF switch that people go through as they’re getting into it.

Derek: Yeah. That’s interesting. And what is that, I suppose typical journey of some of that fine success eventually. Is it sort of inevitable that there are frustrations? Can those frustrations be kind of sidetracked, or is it natural that there’s just going to be a few wins and losses along the way?

Connor: Yeah, I think I’ve run into some ups and downs, but for me what I’ve found to help people find success quickly and avoid some of the other more deeper downs is, the first thing is making sure you have a good interview process and you know what you’re actually looking for. So you kind of you have a role in mind. You know what type of experience you’re looking for. You know what skill sets you’re looking for and you have that very well drawn out. And then the second thing that helps a lot is the whole onboarding process. So you found this person, you would like to work with them, you like their skills, you’re like their experience, everything looks good on paper. And then some business owners forget to actually get them set up and set up ways that you can communicate and set objectives and kind of keep a track on everything.

So the ones that have a process for that and say, “Hey, you know, every time you work, you can just let me know what’s going on and then send me a summary once you’re finished.” Or, “Hey, every time you work for me, send me an email update at the end of your shift just to let me know it was going well. And every Monday we have a meeting and we’ll go over things and make sure everything’s on the right page.” So those people that set back communication loop, see success pretty quickly, I think. And then they’re more willing to add other people into that system as well.

Derek: Sure. What I noticed like observing the industry is, worldwide in every sector, things are getting more plug and play, turnkey solutions. You’ve obviously got the Netflix and some Uber and everything is almost to the point of absolute automation and, turn ON, turn OFF when you want to. And outsourcing is moving more towards that. The interface is getting easier and easier, but actually people then may be forgetting that it’s not a computer. It’s actually a person on the other side of that monitor. And it’s about training, it’s about onboarding. It’s about building a culture. It’s about having a respect between the two parties. So there’s a lot more nuances than I think people hope to understand from the initial point of view.

Connor: Yeah, totally agree. And what I like to tell people too is even though they’re not sitting right next to you, you should treat it as if they were. If you had an office and you hired someone, you wouldn’t just put them at a desk and expect them to become an all-star for your business. You take the time to put them through an onboarding program and you make sure they’re asking questions and you’re giving them enough information. So you should be doing that same thing with someone even if you’re outsourcing it. You want them to become an asset to your business. So you need to put a little bit into it at first.

Derek: Yeah, absolutely. And how do people, you know, I really encouraged everyone to give it a go, and FreeeUp is the perfect platform for them. What is an example of, if I want someone to get a quick win, if I want someone to try it, what do you suggest people try or do as a sort of inroad into the beginning of their outsourcing journey?

Connor: Yeah. So I like to start and encourage people if they are running a business online to have someone come in and work with them on their social media. I’ve found this to be a really simple way to get started. They help you create a content calendar. Either you’re creating the content or they are themselves and then they’re scheduling it out. And you quickly can see how many hours of work you can remove from your daily process and your daily habits. I know some business owners who can spend hours on all their social media channels on a daily basis. If you could take that and pass it off to someone and eventually trust them to do it for you, I think that’s a quick win. And that it allows you to then spend time on other things.

Derek: Yeah. Fantastic. And I know there’s someone in the Philippines right now, that the Filipino workforce really is highly, highly suited to social media there. They’re absolutely addicted to social media and have a sort of significant understanding of social media and also very creative, very communicative sort of people. So, there’s a lot of opportunity there. And also just on a side note, a lot of people and, I don’t know whether you agree with, but it’s kind of a lot of people think that customer service is the first thing to push off into outsourcing because it takes a lot of time. It’s annoying. But I suggests that people should go cautiously with that because the customer service people are really the face of your business. And you need to make sure that the people that are talking to your customers really are the closest to the business and really understand the business, and the product and the culture around it. Would you find that, agree with that? You can completely disagree.

Connor: No, very much agree with you. I think customer service is a great skill to eventually outsource, but you really want to have you’re your process down first and you want to have everything documented about your customer service and how you want it to function and how to handle all the different types of situations. Because like you said, it really is the face of your business. And it could have a good customer come through and it could turn them off and you don’t want that to happen. So I think it’s something you can get into after getting a good feel for outsourcing.

Derek: Absolutely. Completely agree. So thank you so much Connor. I want to get you back so we can deep dive into FreeeUp and how it works. But in the meantime, if people want to get in touch with you, how can they do that?

Connor: Yeah, of course. Very easy to get in touch with me, you can contact me at [email protected], that’s my email. You can also go to and there’s a button that schedules a meeting where you can set-up a phone call with me so we can chat. And then, you can also visit me at my own personal blog which is

Derek: Fantastic. Thank you so much Connor.

Okay. That was Connor Gullivan of FreeeUp. If you want to go to the show notes and learned anymore about this podcast then go to And of course, if you want to email us, or ask us anything, just drop us an email to [email protected]

See you next time.

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