Competing with marketplace giants — An interview with Connor Gillivan

How can a marketplace startup compete with platform giants? Connor Gillivan, co-founder and CMO of the freelance marketplace FreeeUp, shares their story.

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Connor Gillivan on competing with marketplace giants

Inspiration and insights from global marketplace experts and thought leaders.


FreeeUp is a freelance marketplace for the e-commerce industry. The company takes on established platform giants with a well-thought-out value proposition. Co-founder and CMO Connor Gillivan says building the tech from scratch has been the biggest challenge in their journey.

Connor Gillivan and Nathan Hirsch started their first e-commerce business in 2009. During five years, the partners scaled the company’s total revenues to over $25 million, built a team of over 50 people—and spent hundreds of hours searching, vetting, and interviewing candidates on major freelancer platforms.

—Don’t get me wrong, we found some rockstars from these platforms. But it could take weeks of interviewing and vetting to find one freelancer we could actually work with. It was an extremely frustrating process, says Gillivan.

—We decided we wanted to create a better hiring solution for other online business owners.

This became the founding insight behind FreeeUp, a freelance marketplace that connects e-commerce, marketing, and advertising freelancers with digital companies.

Three value propositions

Freelance marketplaces are a competitive field, where players like Upwork and Fiverr already have a strong foothold. Connor Gillivan, co-founder and CMO of FreeeUp, says their marketplace competes with the platform giants by focusing on a niche the founders thoroughly know.

—Our focus is the e-commerce world: businesses selling products through their own online stores, or through platforms like Amazon or eBay. We know how to talk to this niche. In addition, because we have had our own frustrations with hiring freelancers, we have a good sense of how we can make the process more efficient.

The FreeeUp founders identified three problems in the process of hiring freelancers on existing platforms.

First, employers have to spend a lot of time interviewing candidates. Second, despite their huge size, Gillivan says existing platforms do not offer enough reliable candidates to choose from. Third, employers often experience turnover with the freelancers they have hired.

Gillivan and Hirsch turned these three problems into value propositions that help FreeeUp differentiate from the competition.

To tackle the first problem, FreeeUp interviews all the freelancer candidates that want to join the platform. Only the top one percent of applicants get into the platform. As a result, the quality of the freelancers is very high and reliable, says Gillivan.

Second, FreeeUp is dedicated to customer service.

—Other platforms just leave it up to you. We want to be a platform where you can always talk to someone, ask questions, and get help if you run into issues.

The third aspect of FreeeUp’s value proposition is its no turnover guarantee.

—If a freelancer quits mid-project, we will replace them immediately and cover all replacement costs.

Three different products

Connor Gillivan and Nathan Hirsch launched FreeUp in 2015 with three different products. Along with the ability to hire pre-vetted freelancers, they offered e-commerce consulting and a course on how to sell safely on Amazon.

In fact, the first customers to what is now FreeeUp’s marketplace platform came through their consulting relationships and the Amazon course.

—They met with us and we started to develop a trusting relationship. After that, we pitched them the idea of hiring pre-vetted freelancers that we had personally worked with in the past. Most jumped on board.

Before marketing their product to the demand side, the founders had made sure they had a solid initial supply. In other words, reliable, skilled freelancers who would be able to fulfill the needs of the first clients. Overall, Gillivan says building supply has always been simpler than bringing in new clients.

—Freelancing is growing in popularity all over the world. As a result, there are thousands of highly-skilled professionals considering this path every day. They are also looking for a way to offer their services, says Gillivan.

—FreeeUp’s platform has significant advantages in terms of finding and landing clients. In addition, our hands-on support team helps freelancers as they grow their business. This is a huge benefit.

After a year of working on three products, Gillivan and Hirsch decided to dedicate their full energy to building a marketplace.

—We wanted to start with a very simple platform because that would allow us to work to prove the concept.

The team had a technical co-founder who started building FreeeUp’s Minimum Viable Platform. Their first solution was a time clock program that allowed freelancers to bill hours from clients, and clients to view the hours billed by freelancers. As the team was building the platform from scratch, a highly limited feature set was needed to launch their platform as quickly as possible.

One big challenge

FreeeUp’s platform hosts, as of this writing, over 1,200 freelancers in 30 countries. More than 10,000 clients are listed to the service. Achieving these numbers has required constant development. To sum up, Connor Gillivan says the platform continues to be a work in progress.

—Our aim is to build a platform that truly competes with major marketplace players. Also in terms of functionality.

A lot of the platform's features have been built based on feedback FreeeUp got from clients and freelancers.

—With marketplaces, it’s very important to listen closely to users on both sides. There’s always a new opinion that can help you improve! We highly value feedback from users. That's why we meet with them regularly to understand their experience.

The platform's feature set has evolved a lot during the years. Now, businesses can submit jobs, and freelancers can view them. After that, the two parties are introduced and can communicate with an on-platform communication tool. Later, if a contract is made, the billing and hours tracking takes place on the freelancer’s and client’s personal accounts.

According to Gillivan, developing FreeeUp’s software to the needs of a growing number of users has been the biggest challenge throughout the company’s journey.

—As a young company, we’ve always been slightly behind in terms of software experience and design. It’s been a constant challenge since the beginning.

The founders have worked to solve the challenge by hiring more developers to help work on the software and add key features to the user experience.

Today, FreeeUp has a team of three developers and a project manager, and they publish new features and design updates on a regular basis. The developers—as well as the rest of the team’s more than 30 members—have been hired through FreeeUp’s own platform.

—We’ve had a clear policy from early on to only hire freelancers that have made it into the FreeeUp marketplace and worked well with clients for some months, says Gillivan.

Gillivan shares a tactical tip on making a great hire: always vet candidates for skills, attitude, and communication. He says that in addition to know-how and experience, it’s essential to ensure the candidate’s values align with your company culture and that they’re easy to communicate with.

—Particularly if your employees work remotely, great communication skills are the absolute key to your success in working together.

A balancing act

Similarly to the software, FreeeUp’s growth strategies have constantly evolved as the founders have tried out new ideas. The foundation for FreeeUp’s growth, however, is the relationships the company built with its early customers.

—We offered our first clients an amazing experience, so they soon started referring their colleagues and other business owners to FreeeUp as well, says Connor Gillivan.

When the founders discovered referrals taking place organically, they decided to lean into the dynamic by introducing a referral program. The model of the progra673m is unique. The company is committed to paying $0.50 for each hour billed to a user that came to the platform through a referral—indefintely.

The referral program quickly became one of FreeeUp’s best growth channels. It also generated some visibility in relevant media.

Since then, Gillivan says FreeeUp has diversified its marketing mix. Now, they focus on building relationships with e-commerce and marketing influencers and honing their content marketing and SEO strategies. In terms of marketing opportunities, Gillivan thinks there is a channel many entrepreneurs neglect to take full advantage of.

—One of the most impactful marketing strategies for us has been to be featured in podcasts within the niche industries we target. We definitely did not expect that to be as useful as it has been. I think there might be many other entrepreneurs that don’t take this channel as seriously as they perhaps should.

When asked about growth, there is one thing Gillivan emphasizes over everything else.

—We'll continue to focus on what makes our clients happiest: fast hiring process, hands-on customer service, and high-quality freelancers. Those are the pillars of our marketplace. 

For this reason, the founders are not thinking about backing down from their rigorous freelancer vetting process, even though scaling the business will require constantly growing the team in charge of recruiting and interviewing freelancers.

—This is such a core part of our value proposition, so we’ll continue to invest in it, Gillivan says.

—You should always think about the next steps your company can take. At the same time, though, it’s crucial you don’t lose sight of how you got your customers to fall in love with your product in the first place. It’s very much a balancing act.


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