Upwork is the largest freelancing platform, operating across 180 countries. It’s a company that deals in human resources, so its own HR department needs to model best practices. Upwork’s Head of Human Resources and Talent Innovation, Zoe Harte, keeps the department at the cutting edge. Making sure that the right people in the right places are equipped with the skills and tools they need to perform at a high level requires strategic decision-making, so it makes sense that the person responsible for that core work would serve much more than an administrative role.

Managing human resources happens on a few different levels at Upwork. First, like any company, Upwork has its own employees. More than 450 full-time employees work alongside around 1,100 freelancers to make Upwork work. The team is fluid and flexible, an ever-shifting combo of corporate employees and independent professionals, with distributed project teams swelling with freelancers when the need arises and contracting just as quickly as projects end. Secondly, there’s the open marketplace of freelancers the company maintains, millions strong. Upwork hosts a platform that connects these folks with all kinds of employers. Thirdly, Upwork partners with enterprise clients like Microsoft and GE, who rely on them to quickly provide trusted cadres of freelancers. 

Distributed Podcast: Hear Matt Mullenweg in conversation with Zoe Harte and Han Yuan.

For big short-term projects that require many workers, Upwork can activate several hundred qualified workers quickly. This approach is well suited for simple projects like document processing and translation. But according to Zoe, freelancers are no longer just for peripheral roles or rote jobs requiring little strategic thinking: 

[We use freelancers] for everything. We use freelancers to help us design learning programs. We’re moving some of our compensation to a different philosophy. We worked with a freelancer to do a video explaining the why and the how that impacts everybody. We work with freelancers when we’re looking to bring in different skills or scale in our organization. 

Even departments that might be considered core to the functioning of a business, like finance — and yes, HR — are partially populated by freelancers at Upwork. 

The HR Leader as strategic decision-maker

The head of HR in a large, globally-distributed company isn’t just a facilitator but a strategist, a high-level change agent who can articulate goals and opportunities to the C-suite. These HR heads are uniquely equipped with an understanding of how different types of workers located in different places and with different skills can come together on projects to achieve efficiency and success that would otherwise be impossible. Think of this role as an orchestra conductor — someone who wields pools of labor like instruments, carefully considering the timing and positioning of each in order to draw a symphony forth from the noise.  

HR leaders in distributed companies can also provide insight to the C-suite on big decisions, like whether or not to open up a physical office in another country. Zoe says that there are a range of factors to consider in a move like that: how many employees would be required in that country and for how long, the kind of work they would perform, the country’s political and economic climate, whether the company has a sizable customer base there, whether there are other physical offices in the region, and whether the perennial legal and financial hurdles are worth overcoming to set up shop. If the costs outweigh the benefits (or if the need for long-term dedicated workers isn’t a clear imperative), then freelance may be the way to go — which also gives the company the freedom and flexibility to scale up and down as needed. Because distributed HR leaders are attuned to the flow of human capital internal and external to their organizations, these executives can provide essential information for decisions like this.

Communication and camaraderie 

Maintaining and facilitating a distributed workforce is no small feat; it requires constant reinforcement of strong communication best practices. Zoe recommends a flexible but strict calendar of check-ins among teams, and between managers and their reports. 

That means saying, “Okay, our entire organization will connect this many times a year in this many ways. There will be an all-department meeting once a month, once a quarter — whatever is appropriate — and that we will cover these three priorities and in broad progress and how it’s impacting the business overall.” And then the expectation would be that the smaller subsets of teams are meeting in this way. The leadership team is meeting in this way, and you, as the overall leader, are connecting with your direct reports on this regular basis, and then making sure that you connect with every single person in your organization at least once every [blank] months.

This cadence helps ensure strong communication across Upwork’s teams and departments, which is especially crucial when many employees are working remotely. Upwork developed its own internal communication tool, Upwork Messenger, to help workers maintain ongoing conversations. 

These tools are used for more than just work-related logistics. They’re also used for the bonding and connection that’s crucial for high-performing teams. 

But there is also the check-in about like, “Hey I know your daughter should be hearing back from colleges she applied to. Is everything going okay? Did she get into the one she wanted to get into?” And just building that camaraderie and that understanding. That’s not something that’s unique to us, it’s something that is drilled into us that we will continually make sure that we are connecting on a personal level as well as a professional level with individuals.

Some teams also have virtual happy hours, where team members hang out at their computers and have a drink (alcoholic or not!) without discussing work-related matters. 

Upwork reinforces relationship-building by making it a top priority, first thing in the morning. Before the team discusses work, they check in on a personal level. Then, the conversation moves toward work, and everyone has a chance to discuss their priorities for the day and voice their need for input from other team members. 

Digital communication tools are invaluable for remote teams, but they aren’t (yet) a replacement for face-to-face communication. That’s why Upwork, and many other distributed companies, maintain a regular schedule of in-person team meetups. Upwork hosts long meetups, some lasting as long as two weeks, that are a mixture of work and play in various destinations around the world. 

Fostering employee safety and a culture of help

After almost two decades in HR, Zoe has developed keen antennae for workplace situations that might make employees feel unsafe or marginalized, and distributed teams aren’t immune to this. In fact, they come with their own unique issues that HR leaders have to resolve in a sensitive way.   

Personal physical and cultural needs abound: Maybe one employee doesn’t eat meat and won’t want to eat at the Argentinian steakhouse, or practices a religion that prohibits working on a specific day during a meetup. Maybe one team member is a nursing mother who needs to reserve spare time and a spare room during meetups. If an employee feels uncomfortable enough to communicate their feelings about a situation to HR, Zoe feels an imperative to think outside the box to resolve the problem. Sometimes it’s as simple as booking a hotel room for an employee who doesn’t feel comfortable in a shared living space, so Zoe keeps a buffer in meetup budgets for these occasions.

All of these measures are about making people feel comfortable — something that’s important year-round, not just at meetups. When communication is just words on a screen, it’s easier for meaning to be lost in the transmission, which can lead to remote employees feeling as though their voices are not being heard. These employees can feel alienated from their teams, or afraid to ask for help when they need it out of the fear that they’d be perceived as incompetent or lazy. Zoe tries to tackle this problem at the root. 

I point them to learning as much as they can about how our business works and the different roles that people have organizationally. I point them to not being shy and just proactively communicating. Like, “these are the four things I’ve been asked to work on, I understand these two really well, this one I think is like this — can you help me figure that out? And this fourth one, I’ve got no idea, I’ve never even heard of this before, who can help me?” And then really making sure that they understand how their piece of the puzzle is impacting this incredible mission. I think every person who is associated with Upwork believes in our mission and our vision. And you feel it when you work here. And hopefully you feel it coming in and visiting us.

That mission, says Zoe, is to create economic opportunities so people have better lives. If the gig economy continues to grow at its current pace (The share of the U.S. workforce in the gig economy rose from 10.1 percent in 2005 to 15.8 percent in 2015), companies like Upwork are going to have a huge role in defining what the future of distributed work looks like.

For more on Upwork, read “The American Dream is Broken, and I think we have a shot at fixing it.”

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