Gigster Makes the Case for a Freelance Economy that Works

January 11, 2017

If the freelance economy was a startup, its founders would be very (very) happy. Between 2000 and 2014, the freelancing segment of the US workforce grew by 500 percent. And according to a 2016 survey by Edelman Intelligence, there are 55 million freelancers working in the country today – altogether they account for 35% of the total US workforce. The same survey also found that this substantial workforce represents an estimated $1 trillion in annual earnings. What’s more is that the data shows a growing trend (up 10 points since 2014) of people getting into freelance as a matter of choice rather than a matter of necessity.

There are a number of factors contributing to the growth of the freelance economy, including the expanded sophistication and availability of software that enables remote work, the expansion of co-working spaces, the cost savings companies reap due to reduced overhead and flexible staffing, and – last, but certainly not least – the proliferation of platforms that pair talent with employers.

Roger Dickey, founder and CEO at Gigster, is a leading innovator behind one of those platforms. Founded in 2014 and growing strong, Gigster matches elite software development teams with both traditional entrepreneurs and intrapreneurs within enterprise organizations. To date, the company has handled projects for more than 500 clients and has earned a remarkable client satisfaction rate of 93%.

High satisfaction is due in large part to the quality of freelancers Gigster’s platform attracts. The company’s growing global network of invite-only professionals includes more than 400 developers, 200 product managers, and 100 designers who come from some of the most respected brands in the business, including Y Combinator, Google, MIT, and Stanford. The caliber of Gigster’s talent reflects a phenomenon that the Harvard Business Review calls The Rise of the Supertemp. This trend has been growing for a few years as greater and greater numbers of experienced and exceptionally skilled professionals are choosing to join the freelance economy instead of taking traditional corporate jobs, thus making their highly sought-after expertise available to more employers.

Maintaining this level of excellence is a critical element of Gigster’s success. “Some of our clients have experimented with other outsourcing vendors, but found that the quality wasn’t good enough or the time-to-delivery wasn’t fast enough or they weren’t getting access to product manager-level talent,” explains Dickey. To earn Gigster’s high satisfaction rate, Dickey’s team employs a stringent vetting process. “The acceptance rate for folks that come inbound is extremely low, about one percent,” he says. “Primarily, we take referrals from existing members for people they think are exceptionally talented. We still screen all those candidates, of course, but there’s a higher acceptance rate for that pool.”

Dickey focuses on hiring freelancers who have a deep understanding of the software / app domain and professionals who will fill the role of strategic partner. “If you’re a busy, Fortune 500 executive, you don’t want to have to manage a grab bag of random freelancers,” Dickey says. “With Gigster, it’s more of a turn-key, white-glove experience. We provide an entire, self-sufficient team led by a top-tier product manager who makes sure the software gets built, manages the timeline, and handles the day-to-day team management.”

This dynamic also appeals to Gigster’s freelance talent. Many of the people driving the freelance economy are in younger demographics and value independence, success, and a sense of entrepreneurship. Gigster engages talent in these areas in a uniquely manageable way. “Even developers who work for a company like Google or Facebook can get bored when they are working on slow cycles with a large team. They feel like a small cog in a big machine,” explains Dickey. “But, on a Gigster project, developers get to be the CTO of their own effort for two to three months and the project manager gets to be the CEO or COO. We’ve found it’s pretty fun for our freelancers.”

The “fun factor” is one of the things that keeps Gigster’s talent churn rate in check. “We haven’t had any talent churn issues beyond the ordinary,” Dickey says. “Our approach is pretty flexible. We have some developers and product managers who are each working as many as ten projects at any given time, and we have some people earning in excess of $500K per year because they’re able to take on a lot of work. But then we have other folks who don’t really want that much work and only want to do one or two projects a year. It really varies.”

This spectrum likely correlates to the makeup of the freelance economy at large. According to the Edelman study, 40% of freelancers are independent contractors who work steadily from gig to gig, 27% are moonlighters who have traditional jobs but take on side projects, 18% are diversified workers who manage multiple revenue streams (such as some freelance plus a part-time job), 10% are temporary workers, and 5% consider themselves freelance business owners (often subcontracting to other freelancers).

Interestingly, the fastest-growing business area for Gigster is in the enterprise segment. “We have more than thirty enterprise clients now,” says Dickey. “We originally thought enterprise clients would feel completely different than our entrepreneurs, but they really don’t because what we’re doing is going into an enterprise organization and helping executives within that organization start new business units or break into new markets. We help them build technology when they can’t find internal technology talent, and – so far – it’s been a fun ride.”


Brian is a Partner at OpenView where he is responsible for identifying and evaluating investment opportunities for the firm. He particularly enjoys assessing new markets/technologies and connecting with passionate founders.