All Things Upwork

Ever wanted to start your own business…while simultaneously traveling the world with your wife and two kids in an eco-friendly RV? Well, that’s what oDesk client Jay Shapiro wanted to do — and did. By tapping into online work, he was able to build Infinite Monkeys — a site that allows anyone to easily create a mobile app — while he remained happily on the road.

After creating and selling a Singapore-based Internet marketing agency with 175 employees and offices in Asia, London, and Silicon Valley, Jay set out to discover if it was possible to build an entire company in the cloud. Using oDesk as his go-to global talent pool, he created a super-nimble operational structure that relies almost entirely on online workers, and he has no plans to return to the old brick-and-mortar style of work.

“With my former company, I had offices and leases and had to negotiate with governments to be licensed in their country. I was dealing more with bureaucracy than I was with the creative process,” he says. “With oDesk, I can hire people from anywhere — wherever I find the best talent. I don’t have to open offices. I just find talent and hire them. And I go back to the creative end of running my business.”

Today, Infinite Monkeys is up and running, powered by Jay’s unique vision and a crew of about 35 freelancers from New Jersey to New Delhi. His business (ad)venture just passed 50,000 registered publishers, and Jay is currently engineering an expansion that could quadruple his workforce.

Along the road to success, Jay made some important discoveries about the benefits of online work and developed his own best practices for leveraging remote teams. Here are five of his best nuggets of advice.

1. Remote hiring opens up a global pool of talent that is deeper than your local resources.
Online work makes it possible to tap into the best talent regardless of geographical location. Jay explains, “What oDesk allows you to do is not hire the best person for the role who coincidentally happens to live within 30 miles of your office. It allows you to hire the best person for the role.” He adds: “We are totally global.…We have contractors literally on six continents. If there is a contractor in Antarctica, we’ll hire them.”

2. Project managers are well-suited to working remotely, and can smooth the transition to an all- or semi-remote workforce.
Cultivating a team of reliable project managers has enabled Jay to step away from what he calls “day-to-day hand-holding and operational issues” and focus instead on creative development and tasks he enjoys (including traveling around the globe with his family). His project managers decide on the frequency and means of communication with their teams. This often varies by job type and may include basic tools such as email or video chat, or more complex communication software.

3. Hire for skills or tasks rather than for personality or portfolio.
Interviews are not always the best indicator of who will be a great worker, and Jay has found that this is especially true when hiring international workers. “In a lot of countries where we hire, English fluency is not necessarily someone’s best thing and there may be shyness issues,” he says. “A great developer but might not be comfortable getting on Skype and talking in an interview.” Instead, Jay gauges whether to hire someone via email chatting and test projects.

4. Test your recruits with a small but meaty piece of work.
Breaking projects into small chunks allows Jay to test new hires and also helps his bottom line. He says, “Rather than hiring a developer and keeping them for 18 months, we’ll break it up into individual tasks and hire the best person for that task. So they tend to be bite-sized jobs and an individual contractor may have five or 10 contracts with me, but we start a new contract based on the work available at that time.”

5. It pays to focus on cultivating culture and loyalty.
Despite the transient nature of his workforce, employee retention is increasingly important and has driven Jay to focus on creating a good company culture in a remote setting. To foster loyalty, Jay gives his freelancers regular raises and bonuses. Occasionally he goes far above and beyond — after learning one of his freelancers was forced to stop working because she had been put on pregnancy-related bed rest, he sent her a “maternity bonus” to make up the lost income, help with her hospital bills, and just say thank you. Another team member recently asked him to be in her wedding. While he’s not sure if he can attend, the spirit of the invitation means a lot. “It’s a great testament to the remote work relationships that can be built,” he says.

For more about Jay and his best practices, check out our free eBook, our previous blog post about him, or our Client Resource Center. You can also watch his video below!

Catherine Raney

Marketing Coordinator

Catherine Raney is the Marketing Coordinator at oDesk, focusing on creating educational resource materials and building recognition programs. Before joining oDesk she worked with different international nonprofit organizations including Ashoka and Asylum Access, where she developed a deep interest in globalization and social change. Catherine recently graduated from Claremont McKenna College where she majored in history. She was just awarded a Fulbright Scholarship, which she… read more