>Leadership>The Next Workforce

A startup veteran, Roger Dickey has moved on from his last success—selling a gaming company to Zynga and founding the game Mafia Wars with 100 million users—to become the founder and CEO of Gigster, a five-year-old company that allows enterprise clients to tap into an elite pool of independent developers for building and maintaining their software. Today, they’re working with over 1200 clients, including 6% of the Fortune 500.

Tell us about Gigster and how the idea came to you.

We started Gigster about five years ago. Every executive is interested in digital transformation, but they don’t necessarily have the resources they need to make it happen. We wanted to solve three problems with how companies worked with outsourced software developers:

One was around user experience for outsourcing. My background is consumer internet, and I wanted to take a consumerization angle with the problem—to have a team with full product management, development, and design. Basically, a ready-to-go team for our clients to build whatever they need. We wanted it to be as easy as pushing a button, the same way that Uber transformed the taxi experience.

Number two was talent. The best software developers in the world don’t want to work for agencies. They don’t want to sit behind a desk and do client projects and not have their own freedom to explore. We found that some of the best freelancers in the world were actually the most talented people. They were always tinkering, always learning new technologies. We found that by building a model that creates the best place to work for independent talent, we attract the right people.

Number three was a vision of automation. In software development, there’s a ton of duplicated work. You could rebuild 99% of what is found on the internet with a small, finite set of components. Search boxes, landing pages, profile pages–we see a lot of repeated patterns. We’ve always believed that if a centralized group was doing all of the software development in the world, they could find a way to economies of scale. So, we set out to build technology that allows us to scale across projects—and not just in software development, but in project management, design quality assurance—everything through the lifecycle. We build tools and use data to optimize how that happens.

From your viewpoint, what changes are happening in today’s workforce that CEOs need to know about?

We’re already seeing with the millennial generation that job tenure is declining. People used to keep their jobs for decades, now it’s more like years. In the future, I could see the trend moving towards months or fractional, micro-work systems.

What we’ve learned is that people value their freedom. A lot of the best software developers are in that young generation where they’re learning new technology all the time. I think companies want a way to harness that new technology talent to get the digital transformation they need. The challenge is that enterprises don’t want to work directly with freelancers. We’ve been responding to that gap, and put together a talent pool of extremely smart developers with a management layer on top. We provide quality guarantees. The customer knows exactly what they’re getting. So, from their perspective, we serve the best of both worlds.

You recently pivoted the focus of Gigster from corporate to enterprise. It’s a shift not all companies pull off smoothly. What are the lessons you’ve learned there?

It wasn’t an easy process. Our investors were a big help, making a lot of introductions, getting us first meetings. Then it was a learning process of figuring out how to have an enterprise conversation with a customer. How do you brand yourself? How do you position yourself over the competition? It all boils down to building trust. If someone trusts you, they’ll want to work with you. It was hard at first, and for the first six months we spun our wheels. We didn’t see much success, but we powered through. We made it work and built off of a few key clients that were passionate about what we were doing and willing to be advocates.

“I’d like to see executives embracing the
transformation side of digital transformation.”


How do you measure success for yourself as a leader?

It’s highly correlated to how well the company is doing. There are a few main things I care about. First is the business metrics: revenue, strong financials, getting the right ones to move up and to the right. Repeat business is a big one—if I had one metric to keep an eye on, it would be repeat business.

The second is the vision and how we can use technology to think long-term and lead the industry forward.

Third is people. You have to pay attention to make sure people are engaged and listen to the questions they’re asking. There are so many opportunities in Silicon Valley that competing for the best talent is everything. We run a morale survey every quarter and look at voluntary attrition and overall performance. Smart people don’t want to work somewhere they’re not getting a lot done, so measuring overall performance is important to us as well.

Every CEO seems to have a unique relationship with their board. What’s the best approach you’ve found?

My philosophy has always been: this is the company that I founded, I want to bring in the best possible board members to help advise me how to move the company forward. One of our values at Gigster is the best idea wins. In the spirit of that value, if someone on the board has an idea, suggestion, or recommendation and it’s the right approach, we’ll do it. I think that kind of meritocracy of ideas should extend to the board and CEO relationship. Ideally, it’s a healthy two-way relationship where I’m learning from them, and they’re learning from me.

How do you know when you see a good idea?

Most people would say it’s a combination of data and gut feeling. In an ideal world, your gut just knows the right answer. I sold my last company to Zynga. People used to always say to Mark Pincus, the CEO, that he only gets it right about 60-70% of the time. But that’s good enough. There are certainly things we’ve tried that didn’t turn out to be right. I think the idea is to try things out fast and shut them down fast if they don’t work. Use your gut, plus customer data, to inform the roadmap. We’re very customer-driven. Everything—every feature, every initiative, every strategy that we launch is informed by what we’ve learned from our customers and our gut sense on how that translates into our business.

What opportunities and trends do you see in the industry that business leaders aren’t jumping on today?

One of the biggest needs out there is to embrace change, because change is coming. There’s a lot of trepidation around the topic of change management. People are afraid of the topic. They don’t know how to do it well. That leads to leaders hesitating when it’s time to make a hard decision. But transformation is never easy. I’d like to see executives embracing the transformation side of digital transformation. We can’t build software to magically improve your business. Leaders need to follow through with adoption strategies. That’s when they’ll see the benefits of the symbiosis of machines and people. That’s the future of work.