How FreeeUp’s Founders Sold Millions Each Holiday Season with Freelancers


Did you know that the founders of FreeeUp, Nathan Hirsch and Connor Gillivan, sold over $25 million online with their first eCommerce company before starting FreeeUp?

My name is Connor Gillivan and I’m the current CMO of FreeeUp 🙂

I’m here today to tell you the story of how we did it and what made us so successful in hiring and managing remote talent as we sold millions with our first eCommerce company.

It was by no means simple and we went through MANY years of ups and downs before we found the secret solution that would work.

This is us celebrating at Myrtle Beach after a successful holiday season, way back in 2012.



By the time you’re finished reading this article, you’ll have a good understanding of how we:

1.  Made it through 5 holiday seasons selling over $1 million of product in each year;

2.  Surrounded ourselves with smart people to support our growth; and,

3.  Tapped into the power of remote talent instead of relying on traditional employees

Holiday Season Rush

If you’re running an eCommerce company, you’re about to enter the busiest time of the year.

According to studies conducted on the eCommerce industry, store owners can expect to experience 4 to 5 times their regular volume of sales during the holiday season from Black Friday through Christmas.

30 days where your business will experience an insane amount of sales, customer inquiries, and volume. It’s an absolutely amazing opportunity to capitalize and set yourself up for another great year in the books.

So, let’s first dive into how Nathan and I did it with our first business so you can see first hand what we went through to get to where we are today.

Selling Millions on the Amazon Marketplace from 2009 to 2015

Our Start Selling on Amazon

Nathan and I started working together on selling products on the Amazon Marketplace in 2009 as the Amazon Marketplace was really just getting ramped up.

At the time, it was still mainly focused on the sale of new and used books and text books.

It was around this time that Amazon was actually expanding the marketplace into selling toys, baby products, home goods, and everything else under the sun.

If you’re a newer Amazon seller, all of the hundreds of product categories are just a staple to the Amazon Marketplace today. But back in the day, they were a new thing believe it or not.

We saw the opportunity to follow Amazon into the new categories and we noticed that the new listings only had 1-5 sellers on each product because of how new it was to the marketplace.

There weren’t tens, if not hundreds, of sellers on every listing like there is today and it presented an amazing opportunity for us as young entrepreneurs ready to tackle the eCommerce wave.

Handling the Holiday Season Selling on Amazon

As we got the business off the ground and started seeing regular sales, we were approaching our first holiday season together (2010).

Nathan had been through one holiday season on his own the year prior so he had a rough idea of what we were getting ourselves into, but it turned out to be much more than what we could have anticipated.

We had more products listed than he did when he was running the business in the 2009 holiday season and more people were coming around to the idea of using Amazon to buy anything and everything for their loves ones in the holidays.

Needless to say, we found ourselves in a situation where we were overwhelmed with orders, customer inquiries, returns, and the like.

We found ourselves working all night for days in a row to keep up with the amount of orders that we were receiving.

Luckily, we were young and could handle not sleeping for 24 hours plus, but it wasn’t sustainable in the long run. We’d eventually burn out. And it certainly wouldn’t work for future holiday seasons.

Tapping into Freelance Talent to Help Handle the Holidays

After that first year of all-nighters, we knew that going into the holiday season of 2011, we needed to prepare the company better and be ready for a massive influx of orders and customer inquiries.

Starting at the end of September, we started to prepare for the upcoming holiday season. We wanted to give ourselves a couple of months of runway before the holidays started so that we could properly recruit, hire, and onboard the right people to help us handle the upcoming holiday season.

Here’s what we did….

1.  Outlined all of the roles that we wanted to hire freelancers for. The two main ones were order fulfillment and customer service.

2.  Went out into the Internet and used sites to find the right people. At the time, we were using sites like Odesk and Elance to try to find qualified freelancers that could help us in the process. We posted the openings and waited for applicants.

3.  As applicants showed interest, we put them through our standard interview process to see if they could be a good applicant for either order fulfillment or customer service.

4.  After interviewing and testing handfuls of people for each role, we finally decided on a set of freelancers to join the business.

5.  The next step was to get them fully onboarded so that they would understand our processes and the Amazon Marketplace.

For order fulfillment freelancers, we got them familiar with the process then got them to start practicing on real orders.

For customer service freelancers, we introduced them to how we handle every aspect of the customer service process (emails, returns, cancellations, refunds, etc.). Similarly, they worked sample cases to see how they performed in real situations.

6.  As we approached the holiday season (say around mid-October), we started to put together a holiday season calendar. One for order fulfillment and one for customer service.

Our calendar broke it down so that each freelancer worked 1-2 hours, allowing us to have order fulfillment and customer service going almost around the clock for Black Friday through Christmas.

7.  Once the holiday season hit, we communicated clearly with everyone through Skype and email making sure that everyone was handling their role properly and that we were staying up to speed with the orders and customer service inquiries.

After we created this system, holiday season sales started going more smoothly.

Don’t get me wrong, we still ended up pulling a few all nighters every holiday season that we were running the business, but it was much less of a regular thing due to the freelancers that we had hired to assist in our operations.

Lessons Learned from Selling on Amazon with Freelancers

1. You can’t do everything yourself when running and growing a business

While you may want to believe that you can do everything, every business will eventually reach a point where the founder is not enough to handle everything.

And to be honest, we learned early on that you, as a founder, should not be the one handling everything.

As businesses grow and mature, more tasks and projects naturally arise. For the most part, you should be the one handling those new projects and growth tasks instead of the daily tasks that you’ve already perfected.

When you reach that point, it’s critical that you find someone to hand it off to that you can trust and push to grow as you continue to grow the company in new ways.

2. It’s better to overprepare than not to no prepare at all

That first holiday season that we went through selling on Amazon, we weren’t anywhere close to being prepared.

We didn’t take the process of planning for the holiday season as seriously as we needed to and we paid for it.

We lost sleep, sanity, and potential profits that we could have gotten if we had the right people supporting us.

Don’t push off planning for the holiday season. Make sure that you have a good plan to maximize your profits and keep operations as efficient as possible months in advance.

I think the sweet spot is to start planning for the holiday season on Oct 1 as the fourth quarter starts. That gives you about 45 days to get it all organized and ready for the onslaught of Black Friday, Cyber Monday, and the month of December sales.

3. Everything can be delegated and automated if you want it to be

As entrepreneurs, our initial instinct is to keep things under our control. We built it, we have possession over it, no one else can do it better than us. So why would we pass it off to someone?

Through the years, we’ve learned that everything in your business can be delegated and automated so that you, as the business owner, can stay focused on where you add the most value.

The secret to delegating and automating everything is to break it all down into small pieces. Look at a group of ideal people and pick out the individual processes that they must go through on a day to day basis to keep everything moving in the right direction.

Document a step by step process for each one of those tasks then find the right people to pass them off to.

As the leader of the business, keep things organized. Know who is working on what. Know what new tasks need to still be passed off. And have clear communication channels so you can stay updated on what is happening within your business.


Be prepared for this upcoming holiday season by having your systems and processes and people prepared first.

If you’re reading this article and you’re worried that you are already too far behind, don’t panic. Set up a meeting with us and we’ll talk through how you can get freelancers ready to maximize the holidays.

If you’re reading this article and you feel good about your current plan for the holidays, take some time to double check it and make sure that all the holes are filled. You don’t want to regret your lack of double checking your plan when you get into the madness.

Everyone reading this article has the power to build their own eCommerce company that is fully automated and run by an amazing group of freelancers from around the world.

The key to making it a reality is understanding every moving part of the business so you can clearly document the processes then fill those tasks with the right people.

We can of course help you find the top freelance talent that you need for growing your business this holiday season. If you haven’t already, take the time to create a FreeeUp account and submit a request for anyone that you may need to hire.

If you have any questions about how we hired freelancers for our eCommerce business, feel free to share them in the comments 🙂

Cheers to an amazing holiday season everyone!