Managing a Completely Remote Team of Over 250 Freelancers: Interview with Nathan Hirsch

Managing a Completely Remote Team of Over 250 Freelancers: Interview with Nathan Hirsch

February 9, 2017
7 min read

Working from home has become more and more attractive to experts around the world over the past 20 years as companies are seeking to increase efficiency and lower costs of their payroll. With a simple Google search, you can find a handful of leading platforms where business owners can recruit, interview, and hire freelancers. With the craze of the remote workforce, I wanted to sit down with Nathan Hirsch, the CEO of, to hear his thoughts on the topic.

Nathan has been hiring remote workers for over 5 years and built his first multi-million dollar eCommerce company through the use of a remote workforce. Nathan now runs his own online hiring platform, FreeeUp, focused on the eCommerce industry. He is regularly featured in leading podcasts, i.e. Entrepreneur on Fire, and publications where he shares his knowledge of remote workforces. Here is what he had to say.

Q: In your view, why are so many online businesses turning towards remote workforces?

A: If you limit yourself to only hiring employees in your geographic area, you’re not only limiting what talent you have access too, but you are also competing with all the other businesses around you. There are also plenty of extra costs you end up paying for as well, such as gas, overhead, payroll, etc. Hiring remote workers gets you access to talent around the world at different price points and that is a huge factor.

Another huge benefit is that you have people that work under different time zones. Many argue it is a negative aspect of remote hiring, but you can turn it into a positive. You can have someone or a particular team work at night or at times when you normally won’t be on.

Q: How has your experience hiring, firing, and managing hundreds of remote workers impacted the way you run FreeeUp? How do you keep track of that many freelancers?

A: I started FreeeUp because of my past experiences hiring online. I have made some great hires over the past 7 years, but like anyone else, I have also made some hiring mistakes. I took the time to reflect on why some of my hires were so good and worked out so well and why others failed. I realized the main factor was communication.  Even the lowest skilled workers can have a role in your business if the communication is there. Similarly, the most talented will fail to create a positive ROI if they can’t communicate.

So I made this the basis of FreeeUp. We care about communication as much as we care about their attitude and skill set. This makes tracking 300+ freelancers easiest and efficient. Workers know that in order to stay in our network we can’t be chasing them down, constantly reminding them to do things, or even asking for updates.  The workers in our network know that it’s on them to communicate at the highest possible level. This leads to a good client experience across the board.

Q: What must business owners know and practice in order to recruit, train, and manage their own team of remote freelancers?

A: The biggest thing to know is that people are going to be different. They have different cultures and they have different ways that they communicate. So, the way that you communicate with your in-house staff might be a little bit different with how you communicate with your remote worker. For example, I find Filipinos to be a little more sensitive so you have to alter the way you normally talk and your tone to fit the situation. Going along with this theme of communication, you need to be constantly getting reports and know when your workers are working. The best way to do this is to create strong policies and guidelines that all of your workers follow.

When it comes to training, its best to use videos or written guides rather than one on one audio/video chats because they need something to reference back to. You’ll never know when Skype is going to cut in and out if you’re talking. It’s much better to give them a reference point and something that they can look back on as they are getting into their new role.

In terms of managing, you should a similar culture to what you are creating with your in-house team. If you keep your all of your workers separate and no one communicates, no one works as a team and no one knows what’s going on in with the business. Have meetings where everyone gets together and works at the same time. Put teams together so people are communicating and people know what each other is doing. Clearly communicate your goals and how the company is doing so your workers can feel a part of the long term vision. If you find someone good and you want them to stay, you have to make them feel like part of the team.

Q: Why do so many companies have poor experiences when attempting to outsource aspects of their business?

A:  The major reason for poor online hiring experiences happens in recruitment and setting expectations. Many business owners will focus on finding someone with the skill set that they need, but that is not good at communicating or able to commit to the schedule they want. I have a lot of clients who will say, “Hey, I have a flexible schedule,” but then they are always asking, “Where is my worker? I need them right now.” I try to consult people and help them figure out what they want and what’s important to them so that when they hire a remote worker, they actually get everything in that package that they want…not just the skill set that they’re looking for. I’ll mention it again, most of the frustrations people have with remote workers or even in-house workers come down to some kind of communication breakdown. Communication is everything with freelancers.

Q: Many people argue that remote workforces can’t be as efficient and specialized as in-house teams. What are your thoughts on that?

A: I would say the opposite. I think remote workers are more efficient. If you just think of an employee that works 40 hours per week on salary, how many hours are they actually working? There has to be unproductive time that is going on in those 40 hours. For people that are contractors or remote workers, the best ones are very focused as they are juggling multiple positions each day. They don’t have any distractions as they are working at home or in an area comfortable to their habits of productivity. In my opinion, I think a remote workforce is better and more productive as long as you run it efficiently, you emphasize communication, and you keep people informed.

Here is another way to look at it. You can go out and find someone that specializes in a particular skill set you need for each area of your business. You can put them together into teams where each person has an advanced knowledge of their niche. Or you can hire someone for 40 hours a week. With 40 hours each week, they will naturally need to work in areas where they are not an expert. This can create inefficiencies and learning curves that can slow down your business. With remote workers, you have the freedom to limit them to the amount of hours that you actually need them for.

Q: What’s the worst experience you’ve had while hiring online? How did you overcome it?

A: The worst experience I had was hiring a two sisters to handle customer service for my first eCommerce company. We set each of them up with their own schedules to answer customer emails, which is how we would handle hiring anyone in the position. However, they took advantage of the situation and only worked half of the hours while billing us for all of them. It took us a week or so to catch on before we let them go from the team.

This was back in my early years of being an entrepreneur and it was definitely eye opening. I’m glad that we caught what they were doing and fired them, but it was a very poor experience that I still think about today. We overcame it by hiring very separate customer service freelancers that didn’t know each other. We trained them separately and then introduced them once the training was complete and had them work together. We also had them split up shifts and it worked out much, much better.

Q: What has been the best online hiring experience you’ve had?

A: The best online hiring experience I’ve had is an extremely talented freelancer, Chiqui Ann, who I continue to work with today 5 years after we first met. I first met Chiqui when running my first eCommerce company. We were looking for someone to help with a new tracking job we had and she was one that applied. We interviewed her and hired her. She quickly impressed us and starting teaching our other VA’s how to be more efficient with their time. Within a couple of months, she was running the entire team of freelancers that we had for the company. When we decided to start FreeeUp, it was only natural that she help us start it. Since the start, she has been the Head of HR bringing in top talent from around the world. I couldn’t imagine not having her on my team.

Q: How does FreeeUp help online business owners realize the potential and efficiency of remote workforces?

A: FreeeUp takes a lot of the most frustrating aspects out of the hiring process. We handle the recruiting we conduct the interviews. We make sure that the worker cares about more than just money and has a good attitude. We make sure that communication is there for clients at all times. We have our own communication policies that we enforce at a very high level to make sure that our client is always in touch with their workers. On top of all hat, you get access to the top online workers with particular skill sets that you need without having to do the vetting. You don’t have to worry about implementing the communication policies and making them follow your rules because by the time they get to you as a client, they already have these rules from FreeeUp.

We also offer a way to track their time and billing through our custom software. We handle all negotiations about the worker’s rate so that you can get right to the work you need completed. Instead of you having to negotiate with the worker, we say: “Hey, here’s the most reliable worker. Here’s the rate. Get right into the project.”

The final aspect is that our hiring process is speedy fast. If a client needs a new worker, they can request the worker and we’ll can introduce them within hours or even minutes in certain situations. If a client says, “Alright, I’m ready to go!” The worker is ready to go. There is no onboarding process. No signing documents or getting them set up into the systems. All of that HR organization is handled by us and you are ready to get started working.

Q: What’s the best piece of advice you can offer to companies thinking about hiring remote workers?

A: If you’ve never hired a remote worker before, start small. Whether you’ve signed up to FreeeUp or are trying a different marketplace, interview a few people, meet with them, and see what the differences are. When you are open to what options are out there in terms of online talent, doors will begin to open for you. Figure out a selection of small tasks you are doing that might not be an efficient use of your time. As a business owner, should be focused on sales and marketing while hiring team members to do pretty much everything else unless it’s your core strength.

The biggest thing is just giving it a shot. Hire a worker to fulfill one of those menial tasks and learn from your first experience. You’ll see that there is a real opportunity and it can really change your business if you tap into it as a resource. Think of how much time you could free up if you just gave it a shot. I bet the potential outcome is worth the initial hour or so to try it out.

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Michael Brenner

Michael Brenner is an international keynote speaker, author of "Mean People Suck" and "The Content Formula", and Founder of Marketing Insider Group. Recognized as a Top Content Marketing expert and Digital Marketing Leader, Michael leverages his experience from roles in sales and marketing for global brands like SAP and Nielsen, as well as his leadership in leading teams and driving growth for thriving startups. Today, Michael delivers empowering keynotes on marketing and leadership, and facilitates actionable workshops on content marketing strategy. Connect with Michael today.

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