CEO of oDesk, Gary Swart, and the Revolution of the Online Workplace

Photo: Marc Levin via Flickr

Gary Swart, CEO of oDesk

Gary Swart is the CEO of oDesk, the world’s largest online workplace—on which more than $1 billion has been spent cumulatively on work done.

Gary is passionate about helping small businesses thrive, fueled by his extensive experience working with startups and small businesses that use oDesk, as well as by mentoring entrepreneurs and business school students.

Previously, he led SMB Sales for the Americas at IBM’s Rational Software Product Group, and also served as VP of Worldwide Sales at Intellibank, where he was responsible for leading the sales organization. Gary holds a B.S. in Business Administration from the University of Maryland.

1. What was the catalyst for the creation of the world’s largest online workplace?

The idea for oDesk was originally born of a problem our two co-founders had: they wanted to work together, but were halfway across the world from each other. One, Odysseas Tsatalos, was getting a Silicon Valley startup off the ground and wanted to collaborate with the other, his childhood friend who’d become an expert engineer, Stratis Karamanlakis. So they did what any enterprising tech-heads would do—they created a digital platform that would allow them to work together via the Internet as if they were in the same office. And that’s how oDesk began.

2. What is one of the biggest challenges you faced at oDesk?

In 2006, we made a bold decision to lower our 30% commission (the industry standard at the time) to 10% of the freelancer’s desired pay rate. In the short-term, this change obviously reduced current period revenue to ⅓ of its current level but it was this forward-looking vision that skyrocketed oDesk to market leadership in 2009. “By 2009 oDesk surpassed the nearest competitor, and they are now the clear leader (larger than their top competitors combined) in the rapidly emerging “online work” industry.” (Bill Gurley, Benchmark Capital)

3. How has oDesk redefined the way that people work?

Work is no longer a place. With more than 180 countries and $1 billion in work done on oDesk to date, we are bringing freedom and opportunity to businesses and independent professionals around the world. oDesk is the world’s largest online workplace, connecting businesses and freelancers so that they can work together via the Internet. Removing the “Industrial Age” limitations of traditional staffing, we are empowering businesses to get access to the best talent on demand and be more profitable, while bringing the work to the worker, rather than the worker to the work. This redefinition of the way people work is helping to get more work done and effectively expanding the labor market—without the ability to hire online, only 17% of oDesk clients would consider local hires (Genesis survey of 7000+ oDesk clients).

4. What is your advice for businesses that are working with freelancers for the first time?

In order to be successful, businesses need to think about how to effectively manage a distributed team. Make sure everyone on your team can answer the questions: “Where are we going?”, “How are we going to get there?”, “What is my responsibility?” and “How will my success be measured against this responsibility?” Just like hiring on-site talent, managing freelancers is centered around responsibility and each team members needs to know exactly what they’re responsible for and what key metrics will determine success. Managing these relationships online requires constant and consistent communication—whether it be daily check-ins via Skype or regular screenshot shares—it’s imperative to make sure all players are on the same page and that they understand the short and long-term goals.

5. What is the most interesting project you have seen someone use oDesk for?

The skills people hire for on oDesk are incredible. Recently, I heard from clients who hired for bioinformatics projects, and another who hired a theoretical physicist. Olivier Hainaut, an oDesk client, is one of the world’s leading observatory operators and he hires photo editors on oDesk to retouch his images of outer space.

More broadly, we’re seeing especially rapid growth in demand for specialists as a “long tail” market for them forms online—logical given the ability to find specialists online for specific project needs. While just four categories of skills represented 90% of spend on oDesk in 2007, 35 categories represented 90% of spend in 2012, with another 40+ categories growing quickly. A visualization of the long tail of specialized skills on oDesk is available here and more details on it are here.

6. What are the types of projects would you suggest to avoid?

The types of jobs that are tricky to hire for online are projects that require in-person and on-site touchpoints. Jobs like plumbers, painters, and window washers are a few good examples.

7. Where does your passion for the entrepreneurial lifestyle stem?

I have had a number of mentors in my career and the good fortune to learn from great leaders as well as peers and direct reports. In addition to learning significant lessons from the teams around me, my grandfather was one of my most significant mentors. He was an entrepreneur and taught me the value of hard work, old fashioned customer service, and the importance of paying attention to details to get it right the first time. Most of all I believe I inherited a strong work ethic and entrepreneurial drive from him.

8. Outside of oDesk, what is your biggest passion in life?

My passions include spending time with my family, swimming, biking, and cooking. One thing I also love to do is give back to the community by talking with students and mentoring startups. I make a point to lecture at universities (including my alma mater—University of Maryland, Stanford, Harvard, University of Utah, MIT, Berkeley, Santa Clara University, Columbia and INSEAD) once a quarter. I have hosted several student groups like UC Berkeley Center for Executive Education and the Sloan (MIT) Entrepreneurship Club at oDesk over the years to give pitch guidance or feedback on business plans.

9. What is the best piece of advice you received early in your career?

“You can teach a chicken to climb a tree, but you might as well get a squirrel in the first place.” Speaking to the importance of having a best-in-class team, I think it’s critical to hire motivated people who are eager to make an impact.

10. What is one app that all FoundersCard Members should be using?

I am a fan of services that over deliver like Dropbox and Amazon. Anytime an app works as advertised or even exceeds expectations, that is what all FoundersCard Members should be downloading!

11. Apart from the success with your company, what are you most proud of?

At the end of the day, I’m so proud to be able to help those in oDesk’s community achieve success around the world. We receive daily tweets and Facebook posts from clients and freelancers thanking oDesk for changing lives and improving their future. We are giving our clients boundless opportunities to grow and develop their businesses and giving our freelancers the freedom and flexibility to work whenever, wherever and however they want.

I wake up every morning and feel really good about the positive impact oDesk is making.

Give us your best plug/brag a little about as to what you’re working on now/next.

And risk giving the scoop to our competitors? Not a chance!

Online work is just getting started; to use a baseball analogy, I think we’re only at the top of the first inning. In August 2013, we announced that $1 billion of work had been done via our online workplace and Staffing Industry Analysts predicts that the online work market will reach $5 billion in 2018. oDesk is growing into this potential and very excited to revolutionize the way we live and work.

Last but not least, as a FoundersCard member, be sure to activate your exclusive oDesk offer to take advantage of our oDesk credits and recruiting services package. Log in to your FoundersCard account today to get started!


Are you a FoundersCard Member that is interested in being interviewed or submitting content?  Click here.