Upwork's SVP of Marketing Explains What It Takes To Perfect An Offering That Relies On People
Elisabeth Brier and Rich Pearson

In modern society, it appears the role of the standard 9-5 job is quickly diminishing. With the recent boom in startups and the idea of working remotely becoming more hegemonic, typical “work hours” are being redefined.

This transition has subsequently spurred a shift in how companies shape their teams and where they seek top talent. As Rich Pearson, the SVP of Marketing and Categories at Upwork notes, “talent is distributed equally around the world, but opportunity isn’t.”

In aiming to resolve this, Upwork has become the largest freelancing site in the world attracting inordinate amounts of freelance workers as well as clients seeking to hire them.

Pearson sat down with TechDay to reveal Upwork’s strategies to fostering this level of growth and what it takes to perfect an offering that relies on people.

Upon Upwork's inception, what marketing tactics did the company initially employ to attract talented freelancers to use its website?

Upwork was formed as a result of the merger between Elance and oDesk, each of which had sizeable freelance communities. But starting each of those communities was a classic example of a ‘chicken and egg’ dilemma — we needed to try to balance marketing our website to both clients and freelancers. We built out both sides at the same time, knowing that clients wouldn’t join a network without freelancers and freelancers wouldn’t join a network without clients.

The concept of online work was quite new in 2005 and it attracted a lot of press, which we took advantage of to build our initial freelance customer base. At that stage, we individually reviewed every freelancer, which gave everyone a good chance of finding clients. We started a customer referral program early on and, to those freelancers that were successful, we offered a reward if they referred other successful freelancers. This gave our website another burst of highly-qualified freelancers, after which word of mouth drove increases in the number of freelancers.

As Upwork's popularity has grown so too has the influx of copycat sites. What strategies are utilized to ensure Upwork continues to attract both optimal freelancers and hiring clients?

The growth of freelancing is driven by a simple problem: Talent is distributed equally around the world, but opportunity isn’t. Technology has helped Upwork solve this, and, while we are the largest freelancing site in the world, the labor market is enormous, which allows smaller niche sites to target different segments of the market. It’s hard to keep up with all the different sites trying to attack the same problem. However, we have a big advantage in being able to analyze over $1B of work billed annually on Upwork to identify the unmet needs of our community. In fact, our community drove us to launch two new services last year: Upwork Pro, where you can have access to premium freelancers handpicked for your projects, and Upwork Enterprise, through which large organizations can gain direct access to high-quality freelancers in a compliant and scalable way.

How has the sort of modern 'startup boom' impacted the Upwork brand and to what extent does the company try to integrate itself into this community?

We actively engage with startups to help them use Upwork. Freelancers are a secret weapon to help early stage companies find product/market fit cost-effectively, then scale their success once they have found that fit. In fact, at the three companies I worked at prior to joining Upwork, we used freelancers to help scale our marketing, engineering and customer support teams.

Startups teach us a lot, too. We try to attend as many meetups and conferences as we can (example: Hustle Con) but the best resources are startups who are already clients themselves. The concept of remote-first companies came out of the startup world, and it’s a trend that we expect to accelerate. Enabling startups to easily communicate with remote teams is one of the reasons we launched our own messenger platform two years ago.

On the flip side, to what extent does Upwork try to relate to the community of freelancers in understanding their needs and encouraging them to join the platform?

We take a very similar approach to what we do with startups. We have a very active community forum in which freelancers can seek business advice from other freelancers and communicate with Upwork. Nothing beats face-to-face interactions, so we host meetups around the world on a regular basis. In fact, our local reps and other community members hosted more than 60 meetups in 22 cities around the globe over the last three months. Finally, we have a cool program called “Upworkers around the world”. When Upwork employees go on vacation or travel, they’re able to request and get funds and swag to host their own meetup in the city of their choice.

How was Upwork able to initially build trust amongst users that the freelancers marketing on its website were capable and effective?

Ensuring trust is one of the most important functions a company running a marketplace, like Upwork, can do. It’s critically important, and we have a large team dedicated to keeping the marketplace safe for both freelancers and clients. Our feedback system quickly became crucial: anyone hiring on Upwork can view a profile of the freelancer, which includes their education and work experience, skill level, feedback score and reviews. We have tried to make it easier by generating a Job Success Score for freelancers, which is a great way for skilled freelancers to stand out in our marketplace.

What would you say to entrepreneurs whose offering requires participation from both users and 'people as products'? What general advice could you give?

Offerings that depend on people are the hardest to build for obvious reasons, but once they are built, they are pretty hard to copy at scale. My advice is to make sure that you have someone accountable for the product experience and the people experience, then measure them separately. If you try to blend and measure these two components together, you can be fooled about where your real issues are. Of course, you need someone to be thinking of the overall experience as well, but I’ve seen a lot of companies stop at the overall experience and not take the time to get into the weeds, which is almost always a mistake.

Any exciting changes we have to look forward to from Upwork in the near future?

We’ll continue to innovate with new ways for companies to engage with freelancers - there are many different segments of the labor market that are inefficient, and we can help. On the freelancer side, we are determined to help talented people build their freelancing businesses on sites like Upwork, so they can have the flexibility they want.

Rich leads the marketing and categories teams at Upwork. Prior to joining Upwork, he led marketing and business development at Posterous through its acquisition by Twitter, and previously held senior marketing positions at Yahoo!, Attributor, Homestead, Segasoft, and Del Monte Foods. Learn more about Rich’s point of view on Chief Marketer and CMO.com.
Rich holds an MBA from the Haas School of Business and a BS in Marketing and Finance from UC Berkeley.