Upwork CTO shares his advice for developers and IT pros who are considering a freelance gig

What’s it take to be successful as a freelance developer or IT professional? That’s what we are going to find out on this episode of Dynamic Developer.

I’m joined by Saty Bahadur, chief technology officer at Upwork. We’re going to talk about the rise of the gig economy, how it’s affecting the market for top tech talent, and some tips for devs and other IT professionals considering the jump into freelance work. The following is a transcript of this interview, edited for readability.

Listen to the podcast version of this Dynamic Developer episode on SoundCloud

Bill Detwiler: Before we get to what we’re really here to talk about, which is the future of work and how that relates to freelance and independent contractors, for folks who aren’t familiar with Upwork, tell us about what you do.

Saty Bahadur: Well, I’m the chief technical officer at Upwork, the work marketplace. My job is to build scalable systems and take Upwork on the next journey as we expand globally.

Bill Detwiler: What about Upwork’s operations? What is it Upwork does as a company?

Saty Bahadur: Upwork is the work marketplace, and we are truly disrupting the future of work. As most people know, COVID has changed perceptions of how work is done. There was already a lot of demand for people to work in different environments. So whether it’s hybrid or freelance, or it’s a different set of people coming together to solve a problem, the demand for different work environments was there.

There was always a problem of hiring the right talent as well. But what COVID did was to get businesses over that hump. It’s okay now to be working from anywhere, it’s okay now to be freelancing. It’s okay now to prioritize your life, because the pandemic showed us our mortality as well, versus the work that we do. So work became more of people trying to get something done and to achieve a goal—and how you do it matters less.

And so Upwork is the company that’s making it happen, it’s the centerpiece of what’s happening right now. It’s the perfect storm for Upwork to take off, if you will. We have been enabling the global marketplace now. We’ve been enabling people to find the right positions and right work, and we are enabling our clients and our companies to come and get them. So whether they are small companies with one or two people, or whether it’s a Fortune 100, it’s a Microsoft or Airbnb, or any of them, we are able to scale to meet all of their needs.

Which also means that we need to scale rapidly, because we went from a single product line company to a multiple product line company in the last couple of years, and we will expand more. Which means we have a really good team, but now it’s time to pivot to say how best you can go and deliver on or scale up as we expand in the next two years.

The accelerating gig economy

Bill Detwiler: So you’re providing that connection between people who are looking for work and the people who are looking to hire tech talent. Let’s drill down on that a little bit. We’ve really seen a rise in the gig economy over the past decade, but two businesses that I’ve been part of my whole career, tech and media, have really always had a tradition of freelance and independent contract work. However, at least on the tech side, that seems to really be accelerating more rapidly than in the past. What does that mean for IT pros, those individuals who are out there looking for a new job either now, or who will be in the future? How should they approach things?

Saty Bahadur: That’s a fantastic question. I think for IT pros, the time is now. There’s a significant demand and a very short supply of IT talent. So that means right now is the time for them to put their conditions forward on how they want to work and what they want to work for, and what it means for them and what their career goals are. So if companies are unable to match that, then it’s their opportunity to go to the next step or look elsewhere.

The great resignation is underway, and I’ll get to that probably later if we have a chance. But what that really means is people are finding the right opportunity for them, irrespective of the boundary that they had drawn for themselves today.

They are no longer waiting to climb a corporate ladder that’s defined by a company. They’re no longer looking at work like, “I need to work in this specific place and drive two hours to the job.” There’s no need to do that anymore. And they’re also finding that their talent has more value than what they were getting paid, or they were getting recognized for.

So freelancing is another term. I mean, a term that we used to use to define this kind of people, but really it’s about talent and lifestyle. The next generation, and even our generation, is trying to figure out that we can put our lifestyle in front and center of how we want to be, and the work and the value comes along with it.

Bill Detwiler: That makes sense. And drilling down on that a little more, for IT pros who are considering making that switch from what they’re accustomed to with the permanent position, to being a freelancer or an independent contractor, what should they know to be successful in this new world? And what mistakes should they avoid making?

Saty Bahadur: This is a “be bold” situation. This is a place for them to take risks. This is a place for them to recognize that it’s no longer the old situation. If I were in their shoes, I would be looking for my next position, that is, my “aspire-to” position. I could do it remotely or from wherever I would want to work, as long as it meets my requirements. I would also be recognizing the fact that the old shackles of work at work or work anywhere are no longer there. The boundaries have blurred quite a bit.

Whether IT pros want to move from full-time positions to freelancing, there are multiple places out there that will help you get there. And Upwork is in the business of making sure that they are successful. And I am, for example, expanding my team globally. And as you know, most of my workforce is made up of freelancers. We have managed to deliver with the freelancing population that we have, and we are expanding like there’s no tomorrow. And so I would say, come out, reach out, it’s us that are trying to make connections starting with me.

Bill Detwiler: Thinking about the flip side and hiring managers, like yourself, how is the transition to more remote work and freelance work really affecting their searches for top tech talent?

Saty Bahadur: I think most CTOs and CIOs are spending a significant portion of their time just hiring folks. Hiring has become a full-time job. People are leaving, we know that, and everyone is impacted. So if you’re trying to keep ahead of the curve and you want to scale your business, you have to be in the place where you’re constantly hiring and constantly refreshing your talent, which becomes 100% of your job, if you’re not too careful about it.

Now, the boundaries that we had before, how do I connect people? How do I make teams? How do I make hybrid teams? All of this stuff didn’t happen in the past, either with FTE (full time equivalent) or contractors and some freelancers. But it has changed how CTOs and managers start thinking about hiring talent.

They realize, “I just need to get this done,” and it doesn’t matter if it’s done remotely or it’s done in a team that’s filled with FTEs plus freelancers. Whether it’s some hybrid model that I outsource that’s managed and is compliant with local laws. Those are all problems that they expect to be solved by a company like Upwork. They can work with us, and we can get them going on that. It gets them out of the position of looking for talent, because we provide them this highly skilled set of talent that’s pre-vetted on the platform and they can use for their needs.

And most of the people that we have on Upwork are highly skilled workers, especially our software development talent. The quality of the talent is something that is very different from other platforms that’s out there.

Shifting a company’s perspective on the importance of benefits

Bill Detwiler: One of the consequences of shifting to freelance, contract, or gig work is that some of those benefits, and especially here in the US, some of the really important benefits were often tied to your employer. How have you been helping both your clients, the job seekers and the companies trying to hire that talent, to bridge that gap between the old way of thinking about things like health insurance, here in the US, but other benefits like retirement or paid time off? Things like that, that people who have been in the workforce for a while may be more accustomed to getting through their employer as opposed to a third party?

Saty Bahadur: Great question. I think there are a couple of points there. One of the biggest things that employers talk about is culture. And I think every single time we’ve had this conversation in every company that I have worked with, they say, “We can’t do remote,” or “We can’t do hybrid workforce because the culture will not permeate down to them.” And there are different rules for how you work with your full-time employees versus your hybrid employees, or your remote employees.

The pandemic made all of us overcome it. The initial phase was all about brainstorming. And we all thought it was temporary, it’s going to be a couple of months, we’ll all be back. So we’ll all just move on. And then can the next part, which is that we suddenly got thoughtful about the new people that we are bringing on and how we want to do that.

We started documenting our processes and figuring out how learning and development works, so we could permeate our culture to the people that we are bringing on in a global workforce. That’s great, as many companies started figuring it out. That, for Upwork as a company, is a playbook. It’s a playbook to say, “if you want to disseminate information to employees that are global, this is how you would go about doing it.

The same thing applies for benefits, health insurance, compliance and taxation, because now all of that is now part of a package of how you manage your employees, irrespective of type. And as a business, when you’re trying to run it, you don’t want to think of them as FT versus non-FT, versus whatever. You think of them as a homogenous set of people who achieve an objective, and there are different requirements that they have regarding benefits, but that’s solved at a different layer for you. And each company can then optimize for what works best for them.

Bill Detwiler: And is that a hard transition to make? As you talk to companies, that sounds like a dramatic shift in thinking for some companies. And maybe not just a dramatic shift in thinking, but actually a dramatic shift in financial structure, depending on their processes and their backend systems. Has that been a hard change for companies to make?

Saty Bahadur: I think it’s a mental shift. The tools and processes come along once there’s a mental shift. And I think the mental shift is much easier now, simply because of the global pandemic. We now are open to the idea that this is a viable option. And the genie is out of the bottle.

It’s a confluence of two things. The genie is out of the bottle, and the people who are at home, many of them don’t want to come back. My wife, for example, would never want to go back to work, as the traditional work. She says, “Why didn’t we have this before?” And it’s just not her. It’s everybody else. Many, many people that I talked to say, “I want to work in this more permanently” And they also want to travel, they also want to do things that they didn’t do before.

These workers are willing to negotiate. And depending on where the company is in their thought process, they’re willing to negotiate on whether that’s a full-time position, an hourly position, an independent contractor, a freelancer, or whatever you want to classify it for that company’s current mindset. Which means, all of them at some point need to start thinking of how to manage the change?

Now, either they can figure it out themselves, if they are large enough. Or, they could take the playbook of a company like Upwork, who tell them, “We looked at the best practices of everyone, here’s the right playbook. It’s absolutely customizable to the people you have. And we will plug in your tools and processes so that now you manage your workforce that you have.”

That could be anything, it could be all FTs (full time), it could be not. We want to be in that mode of providing you the right talent to get your job done.

The pandemic and our new approach to work

Bill Detwiler: You’ve on touched the pandemic a few times, and of course, we’ve all lived through. I’d like to think about going forward. How significant do you think COVID and the variants that we’re living with now, in particular, will be to this search for top talent in the months to come and next year?

Saty Bahadur: I think COVID forced our thinking on how we approach work in general. I think the tech challenge was still there, hiring the right tech set of people was still there. The demand for freelancers was still there. The demand for independent talent was rapidly growing. All of that stuff was already happening, but the pandemic changed the mental mindset of a lot of people. Rather than seeing an advertising campaign or a brand saying, “Hey, you need to go do X,” the event forced everyone to start thinking.

Once this event is done, I would not think we had to go back. I don’t see anything materially changing on how we behave going forward. I think many of us will have to go and solve this problem. The future of work has already changed.

Whether we like it or not, this is how it’s going to be. And the great resignation is a result of it. Because people are like, “Wait a minute, I just realized I am not tied to this stuff anymore. I can do more stuff. And I don’t need to go back to my employer and ask him for the same constraints.” So the conversation goes, “Hey, come back to work.” “No, I don’t want to.”

All of those things are making people think about where they want to be in a post-COVID world. And so what we are seeing is the beginning of folks setting up their careers higher. They’re trying to go test the market, because they are finding out they’re highly valuable.

It’s like the housing market. You’re finding out a house is super valuable now. The talent is finding out that they are super valuable right now. So it’s causing a change where talent will go and try new and different things, which means that more and more people will be on a hybrid workforce or a remote workforce. Or just working a certain hours at a time, not working full-time. It’s like part-time, but it still gives you the position and financial security to move forward in your lives.

How The Great Resignation impacts hiring trends

Bill Detwiler: On TechRepublic, we’ve been writing about something you mentioned, the great resignation, for a long time. We know that people are leaving their current positions in record numbers for, like you said, better opportunities, which don’t always just mean more money. It’s a lot more about balance and being able to travel, and doing those things that you feel that are meaningful in your life. How is this trend affecting the market for freelance tech workers, and those considering that jump from being a permanent employee to a freelancer?

Saty Bahadur: I think this is a very positive development for the freelancer market. We now have significant talent who realize that they are very valuable. They’re getting really good benefits, whether it’s financial or whether it’s life goals, for the work that they’re trying to do.

Companies starting with Upwork are looking to hire this talent. The great resignation is both a curse and a boon. This is a great place for companies to go out there and pick the right talent that they need, who would not normally be looking for jobs in different places.

The mode of working, whether it’s freelance or not, is relevant but not that relevant either. It’s what people would prefer to do. And look at me, I mean, I joined Upwork as their CTO. And I’m the only guy in Seattle, and this was unimaginable two years back.

If you talked to me two years back, or talk to any company and say, “You’re a publicly traded company, are you going to hire a CTO that is remote and doesn’t even interact with the people personally,” you’d have laughed at it. And here we are. This is the new normal.

I have access, and so do companies, to talent that is remote, that is in different parts of the world. Talent who is fantastic. That can work to better themselves. As Upwork, we provide economic opportunities for everyone, that’s part of our mission statement, but that is now global. This is where everyone is getting to. Not only would I love to be hiring that talent today, I’m sure every CTO out there is looking for that talent today.

Bill Detwiler: Saty, I can’t think of a better place to end it. I think that’s a great statement to wrap up our conversation. Thank you again for being here, sharing your insights, your knowledge and telling us about Upwork. I really appreciate it.

Saty Bahadur: Thank you, Bill.