How Upwork turned the traditional leadership model on its head

Sometimes being a leader means recognising when old and familiar methods are more limiting than they are helpful, and trying untested approaches to uncover better solutions. That’s what the co-founders of Upwork did when they chose to work together whilst living an ocean apart. The result? Not only did they build fantastic technology and lead their company to the top of their industry, they’re also helping to lead the paradigm shift in how we work worldwide...

I spoke with Shoshana Deutschkron, Vice President of Communications and a veteran at Upwork, to get the details on the inner workings of the start-up, the leadership model that sets teams up for success and the unique culture that has helped them grow so rapidly. 

As a person in a leadership position at Upwork, what would you say a "leader" is?

I think a leader is someone who sets an example through their actions and, by sharing their vision and by inspiring others, they help guide a company or a team.

Would you say management and leadership are the same thing?

No, management is about ensuring the team is functioning; it's more operational vs. sharing a vision and setting an example for others to follow.

What are some key problems with the traditional hierarchical management model?

The hierarchical model feels kind of like a child and their parents, as if "you are in this position, I will tell you what to do." That devalues the contributions that each team member can make. We really want to hear from everyone, and often the best ideas come from people you wouldn't expect. I myself am learning through our culture how surprising the contributions are that people can make, once you give them the chance, and how every type of team member has such a unique perspective that they think of something you might never think of on your own.

Do people have managers at Upwork?

Yes, but also they are supposed to have their own individual plan, which feeds up to their team's plan, which feeds up to the department's plan, and then the company plan. And within each individual's plan are the projects they own.

How does management and leadership work at Upwork?

We have very little hierarchy. Our belief and tagline is  "work without limits". That manifests itself in many ways, such as flexible work in terms of location and hours. We believe there should not be strict guidelines on who can do what, or at what level. Everyone is empowered to share their opinion. The way we approach management is we give guidance on our mission and objectives so everyone has a unified sense of purpose. Our cultural values serve as the guiding compass for making decisions, and then we let each department and each individual figure out how they can support those objectives. We also try to have really flexible teams and roles that play to each person's strengths so we can be agile, and so everyone performs at their best within the company.

So it’s really about leading people towards an objective, and then giving each individual the autonomy to achieve that objective in the circumstances most effective for them. Why choose this kind of management approach among all others?

It really goes back to our founding story, which is based on the idea there shouldn't be these traditional limitations on who you can work with and how you work, because they don't make sense today. Technology is knocking down those barriers, and people want that to happen. They don't want to be constrained to a nine to five or long commutes, and companies are better off if they're able to access the talent they need from anywhere.

Just how much flexibility is there under this kind leadership model?

It depends on role; for content, for example, if you know when you're going to deliver a piece, you don't have to do it within certain working hours. Our culture is very supportive of what work-life balance someone needs. Also, our offices don't have assigned desks. There's areas generally labeled as a certain department so people collaborating can be close to each other, but everyone has the ability to just pick a desk on any given day. And there's a lot of open space so people don't typically sit at a desk or in conference rooms all day; they'll spend a portion of the day on the couch or at a fun lounge area. There's even a "beer garden" with taps in it and you can just park yourself in there.

How have teams and the company benefited from this flexible culture?

Quite a few ways! First is loyalty and longevity of employment. Many of the original freelancers who helped create this company still work with us, which is unheard of in Silicon Valley because engineers are so in demand and get stolen away constantly; it's really, really hard to keep talent, especially tech talent.

Second is performance. It’s harder to measure, but people are obviously more motivated when they feel supported, not just for their professional goals but also for their lifestyle goals through how they're able to work. So I am confident we get better work products out of the team members.

Thrd is agility. We are much more productive as an organisation because we can find the talent we need quickly, and we can find different specialists, who we probably wouldn't be able to find locally.

Read: Why social media matters for modern leaders

Do you think any kind of organisation would thrive with this flexible model?

I think every organisation can adopt it to some extent, and the extent might vary depending on the organisation. A big part of this is trusting you have the right team members in place and that they’re being responsible. There's so much technology today that, as long as both sides are making the effort, your communication is still ongoing - between texting and Skype and all the different chat systems. We have video conferencing in all the conference rooms. And our co-founder, Stratis, actually never moved from Greece, but he has a constant live cam on as he works. So, it's kind of like he's sitting next to you and his team can see if he's working or if he's taking a lunch break, and they just ping him if they have a question.

What has made managing or leading people remotely work well for you?

Having incredible team members! People need to be self-driven. Also, as a remote manager, it’s important to help set priorities up front so people are clear on what they're working on. Regular check-ins help provide guidance on any challenges the team may experience.

Some people might say that thriving with such a flexible culture is an exception and not the rule. How would you respond?

Many models like this have existed for quite a while and show it does work. Take, for example, open source, which has been around for years and has been the source of amazing software that was born of distributed people working together because they were passionate about a project. That's a model for lots of IT today, but somehow people don't think about the fact that open source is a distributed team. Also, take for example movie crews. The movie crew model has existed as long as the film industry, and that is always a freelance structure, not necessarily distributed, but freelance ad hoc teams that come together on a project basis.

There's also a really interesting, more current example, and that is the VC firm Andreessen Horowitz. They have a Hollywood talent agency model, so they basically rent out a staff of sales and marketing teams to their startups. And according to Money Source, they are the number one VC firm, which says something. Also I think consulting firms, like McKinsey or Gartner, for example, have distributed teams. They have these really senior specialists in specific areas of expertise, and there's no way they could find the best people in the same location. For example we were scheduled to speak with a Gartner analyst this morning who was in Sweden! The more specialized an industry, the more distributed the people tend to be, because you've already encountered that barrier of, "I can't find the people I need locally," so you had to think creatively.

What evidence is out there that demonstrates companies with alternative cultures may outperform their more traditional counterparts?

McKinsey Global Institute did a report on online platforms, like Upwork, and the efficiencies they are creating. They found that such platforms can add $2.7 trillion to global GDP by 2025. So that just shows there's huge efficiencies and opportunity to boost productivity when you change how you're finding the people you need to do work. There’s also the fact that companies like Upwork are doing it well. Our freelancers are earning over $1 billion a year through our platform.

Is there anything else you would add on how the mentality is shifting about life and work?

I would just repeat that we believe in "work without limits". Because of technology today, there is no reason for traditional work models to remain pervasive. They were born of a need from the industrial revolution to have people in the same place, at the same time, at factories. You just don't have the same need anymore. Technology should be our road into work, rather than these long commutes and price-intensive offices.

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