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Redesigning work in a crisis

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Most future of work conversations revolve around the “where,” but Upwork CEO Hayden Brown says it’s more important to focus on the “who.” 10% of the workforce at Upwork, the global tech platform for millions of freelance workers, was directly impacted by the war in Ukraine. Hayden’s people-focused approach to the difficult decision of how to manage remote employees there and in Russia is the same mindset she applies to meet the needs of all workers, from people feeling conflict to working mothers.

“The rules and behaviors around work have changed, and will keep changing a lot, as we redesign what this new world of work looks like. Be ready to experiment, be clear about what the experiment of today might look like, but then evolve that as you learn more.”

— Hayden Brown
About the guest:

Hayden Brown is the CEO of Upwork, the global tech platform for millions of freelance workers that counts companies from Airbnb to Microsoft among its customers.

About the host:
bob_safian

Bob Safian is the host of Masters of Scale: Rapid Response, and the editor-at-large for Masters of Scale. He’s the founder of The Flux Group, a media, insights, and strategic advisory firm. He was previously editor-in-chief of Fast Company, where he won the National Magazine Award for Magazine of the Year in 2014.

Upwork is a digital-enabled talent marketplace, which gives Hayden distinctive insight into the emerging future of work.

— Bob Safian
Transcript of Masters of Scale: Redesigning work in a crisis

HAYDEN BROWN: I was reading letters from customers saying, “We’re innocent civilians in Russia and Belarus. We’re not supporting Putin. Don’t turn us off.” And I 100% ascribed to that.

On the other side, we were getting lobbying from everyone in Ukraine — from the government on down saying, “How can you be supporting this war by continuing to operate?” Ultimately my conclusion was, as a business, we did have to take a values-based view. I can’t pretend to be blind to this.

And that was an incredibly hard decision. But we’ve seen record high numbers of Ukrainians working on our website, earning their livelihoods, not just for themselves, but often for entire pods of families and friends.

We would get these videos and photos. Landed in Dubai. Landed in Poland. Landed in Estonia. And we would literally be with the tissues out, in tears, seeing these happy families sending us messages of, “We made it. Thank you so much. We’re so excited to be starting our new lives.”

Every single one of these crises, as horrible as they are to live through, is this moment where you see your company and your team, the culture and the fabric is tested. And it’s either built stronger and better, or it comes out in tatters.

And I think this was another crucible where the team shined. They really showed up for every layer and every stakeholder in our business.

The rules and behaviors around work have changed, and will keep changing a lot, as we redesign what this new world of work looks like.

Be ready to experiment, be clear about what the experiment of today might look like, but then evolve that as you learn more.

BOB SAFIAN: That’s Hayden Brown, CEO of Upwork, the global tech platform for millions of freelance workers that counts companies from Airbnb to Microsoft among its customers.

Earlier this year Hayden made a bold move to pull Upwork out of Russia and Belarus, despite the fact that it comprised 10% of her business.

I’m Bob Safian, former editor of Fast Company, founder of the Flux Group, and host of Masters of Scale: Rapid Response.

I wanted to talk to Hayden because her business is directly connected to two of the most challenging convulsions in the economy: the war in Ukraine and the radical remaking of the workplace. In this episode, she digs into both areas.

She unpacks her decision-making and actions around Ukraine with unusual candor and specificity.

She also delves into the assumptions and evolving realities around remote work, hybrid work, and the fast-changing priorities that are recasting how talent is deployed.

She explains how, as a first-time CEO, she grappled with restructuring the business amid a pandemic, and the lessons she’s taken away about asking for help, setting high standards, and acting with speed.

Upwork is a digital-enabled talent marketplace, which gives Hayden distinctive insight into the emerging future of work. Ultimately, she says, if you take a people-centric view, the momentum toward a new system is undeniable and unstoppable. And that people-centric view? It also drove her decisions when it came to Russia and Ukraine.  

SAFIAN: I’m Bob Safian, and I’m here with Hayden Brown, the CEO of Upwork. Hayden is coming to us from her home in Silicon Valley, as I ask my questions from my home in Brooklyn. Hayden, thanks for joining us.

BROWN: Thanks so much for having me.

SAFIAN: So you became CEO of Upwork in early 2020, and so your tenure has coincided with an unprecedented wave of crises. COVID-19, social justice, workplace convulsions, geopolitical challenges. It’s been a busy time. Take me back to the very start when you first took over as CEO. It’s the eve of the pandemic. You’ve been at the company for a few years. You had a plan for what you wanted to do, and then how much could you keep to that plan? How much did you have to change? And how soon did you realize that you had to be making those changes?

BROWN: It’s been an interesting two and a half years for sure. And I think as a new CEO in those two and a half years, I don’t know any different than this crisis-ridden landscape that we occupy. So going back to that time, I started in 2020 with this really clear idea of what I wanted to accomplish.

We were already a remote work company. We had been doing remote work ourselves for 20 years. Our customers were all doing remote work on our platform. So in that sense, we were kind of built for this moment. We kind of looked at ourselves and said, “Wait, we are ready to help.”

And the question we were asking ourselves in March and April was, “How do we serve customers?” There were things that we suddenly accelerated. For example, we had been working on the infrastructure we use to enable freelancers to get paid, and suddenly we realized, “Well, wait a minute. There’s so many freelancers who actually want to be bringing their clients onto our platform, and having the payments guaranteed,” which is the number one thing that freelancers worry about, is: “Am I going to get paid? Is the money going to be there?” Well, we could launch that product faster, and open that up for them ,and frankly, at that time, if you remember, a lot of kind of economic turbulence in the market, a lot of businesses that were pulling back and shuttering, and if we could give that product to them, they could know that their money was safe, that their own book of business would be safe.

There was just so much like that, in terms of our roadmap and our solutions, like, “How do we bring these things into more awareness or relevancy in this moment, where customers really need us most?”

SAFIAN: It’s an interesting moment for you guys, though, because it is a moment of dislocation and anxiety for a lot of people, including your own workforce. And at the same time, it’s sort of a tailwind for the core premise of the business, right?

BROWN: Frankly, a huge thing for us was we’re very people-centric. I’m a people-focused leader, and when I was a new CEO I had started doing this thing, kind of ad hoc — so that the company could get to know me better — of sending these videos to them. I remember my first day going into our office in the new year. I just stood outside and recorded a little video and sent it to them. I did this when we hit this milestone of the first $10 billion in lifetime earnings that freelancers had had on our platform. I realized, even though I’d been at the company for, at that point in time, about eight years, that I was in the product team and the marketing team, but a lot of other people didn’t know me, and they didn’t know me as CEO.

But then the pandemic hit, and I suddenly realized one day, “Wait a minute. My team really needs to know me, and they need to know me not just as the CEO, but as a human going through an unprecedented crisis.” And I switched from sending these videos as this fun, lighthearted way to kind of celebrate moments, to every Friday, there was a video from me in their inbox talking about what was going on, their health, their safety, some message from me about how I was getting through the pandemic, about what I was asking them to do, and connecting it back to kind of who we are, our mission, something really true, and personal, and important.

And I got so much feedback from our team about how much those videos meant to them, and I couldn’t end the week without shipping a video to my team, you know? And I did that for … I don’t know if it was 30, 40, 50, 60 weeks consecutively, where those videos went out, and giving them something that was so essential at a time when the paradigm had completely shifted.

SAFIAN: One of the things over the last two years has been this sort of rising expectation for CEOs to act or make statements about social and political issues, geopolitical and otherwise. And I had a guest recently who said, “Folks don’t understand how hard it is for leaders to deal with these non-business issues, and how much harder it’s gotten.” And I know you’re part of a CEO group, an informal group, sharing and learning from each other. And I’m wondering, are those the kinds of things that you all talk about?

BROWN: I think the responsibility of leaders in this arena is really great these days. I do use my peer groups, and that group that you mentioned, discussing how we collectively handle this responsibility, address this responsibility, share best practices.

Early in my tenure as a CEO, I had a kind of a lightbulb moment. I’m going to ask for help every single time I need it, and can learn something. And the worst thing that can happen is someone says no. And this is one of those areas where I am so fast to ask for help, ask for advice. And similarly, on the other side of that, always try to pay it forward  and share what I can. If I have a tip, or a suggestion, or something that I’ve done, that feels like it might be working, share that with others.

And that was actually one of the reasons that Dr. Erin Thomas, our head of diversity, inclusion, and belonging, who is phenomenal, and we brought on board in 2019, we actually made some mistakes through the social justice events of the last couple years, where early on, when Ahmaud Arbery’s death came to light in March of 2020, within Upwork, we did not address that within the first 24 hours of that hitting the news.

And we got feedback from our internal team and our team members were upset about that, and understandably so. We discussed that in my staff meeting. We talked about how we need to show up differently in these instances, and much more quickly address these types of topics.

And so unfortunately, it was only a few weeks later when George Floyd was murdered, and immediately, we sat down, wrote a letter to employees, sent it to them, and then Dr. Thomas, and I actually decided, “You know what? Because we’re in these conversations with so many other leaders who didn’t know what to say, we published our internal communication on our website, and she annotated it, and said, ‘Here’s the line where we said this, and this is why we said it this way.’”

And I got so much positive feedback on that, because again, people are struggling in these moments as leaders, or as employees. What do we say? What do we need to hear? And these are new conversations, that we don’t have 20 or 50 years’ legacy history to draw on. So it’s not that we’re perfect or we know all the answers. It’s more, how can we contribute here, help other leaders, give them a toe hold, and maybe they can build on top of our thing and tell us even how it could be better. The only way it’s going to change is if we’re out there kind of putting our neck out and trying to help others in the process.

SAFIAN: During that time period, you also chose to join the advertiser boycott at Facebook, right? You went on CNBC, as I remember, to sort of explain and defend it.

BROWN: Yeah, that was really an easy decision for us. I think it was so consistent with our principles and values, and it wasn’t an anti-Facebook move so much as it was just using our voice to say, “Look, we have to shine a light on this topic, and there needs to be more transparency around the tools and the actions that Facebook is giving advertisers and being held accountable to in this area.”

When that boycott was announced to me as an option that we could sign, I think it was a Friday night. There was one other signatory, and I looked at it, I was like, “This makes perfect sense. And we should totally do this.”

SAFIAN: Earlier this year, you made a decision to pull Upwork out of Russia and Belarus. And how did that decision come about? Was that a harder decision?

BROWN: Yeah, that was on the other end of the spectrum, Bob. That was a completely diametrically opposite decision. So to set some context on that one, 10% of our business is in Russia, Belarus, and Ukraine. And 10% of our own team members are in Russia, Belarus, and Ukraine.

And so when the war broke out on February 24th, I remember vividly seeing on the news the tanks rolling in and knowing that life would never be the same. Our roots in that region go back to the founding days of the company.

The first thing on our minds was the health and safety of our employees. We needed to make sure that our team members had funds if they needed to relocate, buy gas at some exorbitant price, food, et cetera.

I was on vacation that week, but I was like, “I will be there in the team meeting.” It is an all-hands meeting we have every Thursday.

Went into that meeting, and there was a question that somebody asked, and the answer was, “Well, we’re preparing some options for the executive team.”

And I could hear from her answer that in her mind, the answer would be in a few days. And I could see we needed to get an answer in the next few minutes or hours. And there was just a disconnect. This is a new crisis. Everybody was kind of trying to figure this out.

So on the payments topic, we made the decision within hours to push a month’s advanced pay to everyone on our team in all three countries, not just in Ukraine, because we didn’t know what would happen with the banking situation in Russia or Belarus either. We got those funds flowing by the end of the day. Gave us a moment to breathe and then say, “Okay, what’s next?”

Can we evacuate people out of the region? It became very clear that getting people out of Ukraine was not going to be possible because the borders were closing.

What about our team members in Russia and Belarus? The rumors started that maybe those borders would close. Those team members might be trapped in the country. And we had these extraordinary team members; there was literally a three day period where none of them slept. They were literally booking and rebooking flights for people. And you had to have a two-way ticket to get out, and social media deleted from your phone and all these things.

And I’ll never forget all of us on pins and needles being like, “Okay, did the three-year-old get his passport yet? Did the grandma get her papers?” Because it wasn’t just about getting the team members out, we were getting their whole family out so that they could relocate and start a new life somewhere else.

And extraordinarily, through this, we got 75% of our team out of Russia and Belarus because those are the people that wanted to go. And we went through a period where flights were all grounded and we thought we lost it. Their borders are going to be closed. I mean, this was a drama.

Then on the other side, we would get these videos and photos back from the team. Landed in Dubai. Landed in Poland. Landed in Estonia. And we would literally be sitting here in this room where you see me now at my desk and with my team members on Zoom with the tissues out, in tears, seeing these happy families sending us messages of, “We made it. Thank you so much. We’re so excited to be starting our new lives.” So this was the whole focus of our health and safety, the Ukrainians on the ground, all of whom are safe and still trucking amazingly. And our Russian fellows who we’ve relocated.

And then the final piece was around our platform. You asked about: could we continue to operate? And that was an incredibly hard decision. I joined this business to create opportunity, not ever to pull that away, but as we evaluated the situation on the ground in Russia and Belarus with our payment partners, the expectations around sanctions, as well as the situation with the just the values of operating in that region, given what Putin has done, we went from thinking we could continue operating to knowing we could maybe do a partial operations, to realizing there’s no way. We have to do a full scale suspension of operations.

And that was an incredibly hard decision. But the silver lining, I think, has been seeing the Ukrainian resilience and strength coming through all of this where we’ve seen record high numbers of Ukrainians working on our website, earning their livelihoods, not just for themselves, but often for entire pods of families and friends whose jobs have completely vaporized through this conflict.

Realizing that the portability that our platform offers has meant that they can take that work with them even as they’ve had to move across the country, or in some cases out of the country completely. I mean, this has been tremendous to see the resilience and the power of this platform for them at an unprecedented time. And so that has really been, I think, this guiding light for us.

SAFIAN: And when you make the decisions to pull the operations, the platforms, out of Russia and Belarus, where you’re generating revenue, I mean, it’s valuable, is that a moral decision? Is that a business decision? Are they the same?

BROWN: I mean, for us it was informed by both. I felt it was very important not to make the decision in a vacuum. I wanted to talk to customers. I wanted to talk to outside experts on how they thought the short and long term of what would happen in the region would play out.

A wide range of folks, not over-index on one point of view, but get all the inputs and say, “Okay, what does that mean in terms of the ability for us to operate and the appetite of our customers on the client side, talent side, to be able to continue to use our platform successfully?”

And that’s everything from cybersecurity risks, and can we operate in that scenario? Electricity and internet being up and operational, and can we operate a business if that’s going to be super unpredictable? The diplomatic situation. All of these things had to be taken into account.

And so that informed our business assessment of the viability of operations. And for us also, in terms of the sanctions’ expectations. What is going to be the operational complexity and cost for us of following and implementing the sanctions’ regime? What’s the burden there? And by the way, does that become so unpredictable for our customers that basically it’s just a nightmare for them because the rules are continually changing?

So all of those things were factoring on the business side. The moral thing is also so important. We’re mission-centric; we’re value-centric. And when we looked at our customer base, we had customers advocating on both sides. I was reading these letters from customers that were saying, “We’re innocent civilians in Russia and Belarus. We’re not supporting Putin. Don’t turn us off.” And I 100% ascribed to that.

On the other side we were getting lobbying from everyone in Ukraine, from the government on down saying, “How can you be supporting this war by continuing to operate?” Ultimately my conclusion was, at some point as a business, on a topic like this, we did have to take a values-based view. If I go back to a World War II analogy or something like that, I can’t pretend to be blind to this.

And my conclusion was we can’t continue to operate in that region. That as much as I want to support the civilians on the ground there, by continuing to operate in that region, I’m making a value statement that we’re in some sense supporting what’s going on in those countries and with those governments as well.

So both of those things together combined for us to say, “You know what? We’re going to suspend for now. If the situation changes, we would love to reopen, we would love to continue. But in the meantime, if you’re a freelancer on our platform and you are from Russia or Belarus and you relocate, you can reactivate your profile from another place. We are operational in 180 other countries.” So that is the stance we took. And I think that was the right one that we felt would stand the test of time.

SAFIAN: For you personally, you go through these two years as a CEO and you’re dealing with COVID, and you’re dealing with George Floyd, and you’re dealing with a lot of different business challenges. And then this comes along. Were you just a little bit like, “Give me a break. What’s going to come next?”

BROWN: There was a presentation I gave in probably February before this conflict broke out, and I remember I had framed the first two years of my tenure as kind of, like, more playing defense. And I was like, “2022, we’re going to go on offense.” And then it was like, “Q1, Ukraine war.” And I was kind of like, “What? Are you kidding me? We’ve been building all this stuff, this is going to be the year,” and then Q1 hit.

We did have to pull our guidance. The business impact was actually minimal. We estimated it was $1 million in the whole quarter, which it was kind of like, “What? After all of this?” So it was actually a very minimal business impact, which was a testament to the resiliency of our platform and our customers, frankly.

Every single one of these crises, as horrible as they are to live through. Is this moment where you see your company and your team, the culture and the fabric is tested. And it’s either built stronger and better, or it comes out in tatters.

And I think this was another crucible where the team shined. They really showed up for every stakeholder in our business, from our internal team members, to our customers on the ground, in a way that, I mean, I’ll never forget this, that I could not be more proud of.

And I think everyone in our business who was here for that feels the same way. I mean, they were in awe of what we were able to do for our team members and our customers at a time that was just so unprecedented for the world and for us. So yes, as painful as it was, and as much as we would never wish it on ourselves or anyone else ever again, I think there was a beauty in what people were able to do for each other and the power of those moments of connection and building that has made us stronger. I’ve said this to my team, if we were able to get through that quarter and prove our value-centeredness in that way, our people-centeredness in that way, we’re unstoppable. I think people feel that and they know that. There’s no question about that.

SAFIAN: Before the break, we heard Upwork CEO Hayden Brown talk about her toughest decisions since taking over in early 2020, including shutting down operations in Russia and Belarus earlier this year.

Now she talks about the evolving workplace and offers specific advice on how to navigate new remote-work realities. She argues that full in-person models will have trouble surviving, and suggests specific ways to cultivate a compelling organizational culture without relying on regular in-office presence. 

Plus, she shares two key lessons about setting high standards and acting with speed that have propelled her and the company through a crisis-heavy landscape.    

For a lot of the listers in this show, one of the crises is sort of the convulsions underway in changing workforce patterns. The move to remote work, the Great Resignation, or the great awakening, or whatever you want to call it. Your business is right at the center of that. I can imagine that some of the CEOs in your group and others, they come to you for advice about it, like, how do I think about this? What do you tell them?

BROWN: First of all, I’m such an optimist on this, partly because I think my company’s been living in the future for a long time. I’ve seen firsthand that this is not the boogeyman, this is the solution. Remote work is fantastic. I think it’s a win-win for businesses and for talent. The other thing that I really want to remind folks is the experience of the pandemic, that’s not the experience that we’re going to have going forward around remote work or the next wave of the future of work and rewriting the rules of work. I think the pandemic was so unique with the stressors of the pandemic, kids home from school, people locked up at home, no social outlets. All of these things were pandemic-specific.

The opportunity we have to redesign work in this much more human centered way with more trust, more accountability, and flexibility versus policing people in offices or expecting them to do these commutes, there’s so much opportunity in that. So I think trying to decouple the opportunity ahead from the experiences we’ve just had is very important. I think the other thing is we need to move beyond the conversation about where the work is happening, which I think people are so obsessed with and caught up in. It’s a real trap to much more focusing on who’s doing the work because when we move past this obsession with where the work is happening and start to focus on who can be in our workforces when we do embrace a remote work model, and how we reconstruct work so that it does achieve the outcomes we need as businesses, but also work for the constituents in our workplaces, so much more is possible.

That’s when we start to have the real conversations and address the real problems that are holding us back in business. These are the shifts that we need to start to make in the conversation and in problem-solving and in the tooling and in the composition of our workforces that really are going to start to unlock the potential and the real future of work that is ahead of us.

SAFIAN: One of your colleagues cited you as saying that businesses have to choose your sides in some ways in this battle and that systems have to be redesigned from the studs up. Can you explain what you mean by that?

BROWN: Yeah. I think it’s easy for companies to get caught in this muddled middle of hybrid work where they haven’t necessarily picked their poison. I think it’s important for companies to say clearly, “Here’s what we’re solving for.” If we really want you in the office, I think if you want that as a company, you need to be very clear with your team members about what you’re asking them to do and why — why is very important here. Then on the other side, if you’re ready to embrace a remote work or a hybrid model, really articulate that and the specific covenants. If that means hybrid meetings have cameras on each of the laptops so that people’s faces are still visible or whatever else, you really need to spell that out.

But, the worst thing companies can do is kind of be in this messy middle where they say, “Well, we’re hybrid, but come in when you want, and there’s no ground rules around how meetings happen.” Then everyone’s having a miserable experience. Clarity is really important. Choosing an approach is very important. Then, the other thing I say is experimentation is very important. Making a declaration today about we’re going to do X, Y, Z policy, and that’s going to be it until the end of time I think is a very dangerous place to be, because this is a time of change. It’s a time of evolution.

I think as a leader, it’s a mistake to lock into a model now that, frankly, might look very archaic or out of touch with what work is changing and evolving into being. My advice would be: be ready to experiment, be clear about what the experiment of today might look like, but then evolve that as you learn more, as you get feedback from your team, as you observe what the real patterns are, which frankly can be very different region to region, city to city, et cetera, et cetera. I think that’s where companies can really be successful, is being clear and then being ready to experiment and evolve as they learn more and get more data.

SAFIAN: If you’re Jamie Dimon and you’re saying, “Everyone’s got to come into the office.” As long as you’re clear about that, that’s okay. If you’re Brian Chesky at Airbnb and you’re saying everyone can work remotely, that’s okay. With both systems, you should be testing your own premise even while you’re not giving uncertainty to your workforce in the near term.

BROWN: I think that’s right. If you’re Jamie Dimon, you’ll start to see: Is this working? I’ve clearly stated my position. I can attract the people who are attracted to my model and not have confusion in hiring people that thought they were getting the Brian Chesky model. Then see if this is working. My personal bet is that it’s going to be very difficult for these in-person models to survive in the long-term because I think that the tides are moving away from that.

But I think it’s possible. There’s a fraction of the workforce that does want that model. I think the question for businesses is, is the talent that they need going to line up with the fraction of the workforce that wants that model? Or are they going to be forced to move to a more hybrid or distributed approach just because they have a talent need? The jury’s going to be out on that, but yes, I think clarity is the starting point. Then, see if you’re getting the results you want.

SAFIAN: I saw some interesting data that 80% to 90% of people don’t want to return to a 5-day work week, but there’s a lot of variation in that. Some people want to work at home all the time. Some people will say, “I’ll come in two days a week,” some four days a week. All of that makes it super complicated for managers who are just, they’re not used to that kind of variation.

BROWN: It is. Ultimately, a lot of aspects of work are a team-based sport. You do need to define for people what are the aspects based on the role or the function where team-based collaboration is going to be important. By the way, I firmly know that can happen remotely through tools like Zoom and Google Hangouts and all the rest of it. You do need to define kind of what is the expectation around what are the team-based aspects where people have to interlock and maybe get together once a quarter or once a year for an offsite or whatever.

Then, what are the aspects where they do have the full freedom and autonomy to define when, where, and how the work happens. Again, I think business leaders do need to be ready to set some contours around that, but I think many of them believe they need to set many more of those parameters and define many more aspects of where the work is happening than they actually need to. Most people did an amazing job through the pandemic. We’ve seen the data on this, actually managing and delivering productivity. That’s where I think there can be a big unlock.

SAFIAN: How do you generate and maintain and extend the culture in an organization when everyone’s remote or there’s unevenness about who’s remote and who’s not. Do you have any insights or suggestions about how to manage that element of it?

BROWN: I think companies that thought their culture was posters in their office, or just the activity around the beer keg or whatever, probably this is a good wake-up call for them to reconsider what culture really does mean to them. What we’ve seen is we build culture in a distributed team. There’s different tiers of those touch points we do a weekly all-hands. It’s short, it’s 30 minutes, and then there are things like fostering smaller communities inside the company, and we’ve had Upwork belonging communities since … I think the first one that we started was probably five or six years ago with a women’s group. Now we have, I think, six or eight Upwork belonging communities of different types, a veterans group, Upwork UBC for our Black team members, our Asian Pacific Islander communities, and so on and so forth. Those groups are really powerful ways that subgroups are connecting, finding community inside the broader group of Upwork.

I think this is the dimensionality that can really come to life and then be augmented with these in-person events. We got together with our vice presidents two weeks ago in Monterey, California, for one day. It was such a high-impact day. We spent half the day just on people getting to know each other and then half the day on our strategy and our vision for the next five years, and people’s minds were blown. Everyone walked away with people’s cell phone numbers to not just connect on Zoom, but to call each other. You can do so much I think with both digital connections, subcommunities, and then in-person events in a really thoughtful way that has a ton of impact.

SAFIAN: I wanted to ask you, you created a Motherhood Works ad campaign, and it caught my attention. I wanted to ask you why.

BROWN: Moms need jobs. These moms are under-recognized in the workforce, and this is something — I’m so sick of it. We looked at the data, 1.6 million mothers left the workforce during the pandemic. It’s a staggering number. That’s in the U.S. alone. These moms have amazing skills. Think about the skills that parents have developed. I think you’re a parent; I’m a parent. We know that these moms have amazing abilities that they have developed both as parents and as professionals, and yet time and again, they are not just overlooked by employers, they are penalized. That is unacceptable. We developed this campaign to really shine a light on the amazingness of these parents and to challenge corporate America to really bring these moms who are ready to be back in the workforce, as the pandemic is coming to a different chapter, to bring them back. We are really excited to shine a light on them.

We have a page where these amazing moms are featured. Employers can come in and check out their profiles and get started hiring them. And I think, I don’t need to tell you the deplorable stats of women’s equality in business, in this country, and globally, and how many years it’s going to take to move the needle to a place where we’re 50-50 on that. But, this is one effort at kind of chipping away at some of those numbers.

SAFIAN: Parenthood is a skill, and it’s a valuable experience. And yet, for some reason, the workplace doesn’t necessarily recognize that value, or place value on that.

BROWN: It’s extraordinary. Because if you think about the skills that parents develop around things like multitasking, around creativity, around discipline. Would you want your employee or your team member to have those skills? It’s like, yes, yes, yes, absolutely. I think we all see these powerhouse women constantly. So, we wanted to put them on a pedestal, and really challenge corporations to really be bringing them more to the forefront in their hiring practices.

SAFIAN: When you look back over the last two-plus years, are there lessons that you hark back to, lessons that our listeners maybe should keep in mind as they’re preparing for whatever the world brings us next?

BROWN: When I stepped into this role at the beginning of 2020, I was governed with two big emotions. One was optimism about this amazing vision, and opportunity for this business that was not yet realized, and excitement about that. And the other was frustration. I was kind of pissed off. I’d been at the company for eight-plus years. I had been the chief product and marketing officer for a while. And I didn’t feel like we were getting where we needed to be. And largely because we were getting in our own way. And I knew where all the bodies were buried. I was ready to attack that challenge head-on. And I started that year with three big priorities. One was to sharpen our long-term strategy and broaden it out, so we could really move the needle on stuff.

The second was to really bring in the A team. Talent density was going to be the only way we could get to where we wanted to be. And the third was really upping our game on operational excellence. I felt like we were kind of still operating like a start-up, even though we had gone public in 2018. Early in my tenure on the advice of Brad Smith, who was a mentor of mine, Brad Smith, from Intuit. He basically advised me to go on this listening tour. I would advise any new leader stepping into a new role or a new company to go on a listening tour. In this case, I spoke to over 125 people in my first 90 days in the job. It was board members, customers, internal employees, smart people in the industry.

And two of the pieces of advice, in particular, really stood out to me. One came from Auren Hoffman, the CEO of SafeGraph. And he said to me, “I can’t think of any CEO of a truly great company who doesn’t hold herself and her team to an incredibly high standard.” And I thought back to my last eight years at the company. And I realized I had always held myself to an incredibly high standard, but I had not always held my team to that same high standard. And I regretted that. And I had saw that that had led to many missteps.

So, I vowed not just to hire the best team in the world, I had to hold that team and my entire company to incredibly high standards. The second piece of advice was from a dear friend of mine, Fritz Lanman, who’s the CEO of ClassPass. He said, there’s going to be a lot of moments when you know instinctively what’s right for your business. And yet, you’re also going to be tempted to do a lot more analysis, and talk to a lot more people, and take like three or four years to do what you could do in one year. Don’t make that mistake.

And so, I vowed that I would do as much as I possibly could in my first year as CEO. We have this running joke that we did like three years’ worth of work in my first year, and we keep doing that. Like every year it’s like, can we do three years’ worth of stuff in this year? I knew I needed to do a major reorg of about 600 people.

I also wanted to offer a severance to every single employee in the company. And basically say, you know what, you’re either on the bus, or take a severance package and go, you have a choice. But there’s going to be a line, and you’re going to either go across that line with me or move on. And there was a moment where we were debating, should we do this in February? Or should we wait till the end of the quarter, and do it in April? It might feel more natural then, and da, da, da, da, da. And it was my executive assistant who looked at me and said, “You know what, Hayden, you’ve been talking to us about how important speed is to you. You know you can’t wait till April.” And I was like, “You’re right. I can’t wait till April.”

So we did that where we offered everyone’s severance. It was a bold move. We were able to execute that plan. And that need for speed was huge. So, those were two pieces of advice that I literally thought about every single day of my first year as CEO. And I still think about every single day.

SAFIAN: You’ve done so many different things through just two years, six years’ worth of stuff, by your calculations. Where is Upwork now? And what’s at stake for you, looking forward?

BROWN: So we’ve really evolved from being a talent marketplace to being a work marketplace. We’ve launched several new products for customers. So now they can work many different ways inside of our business. We’re still innovating every single day with and for our customers. And really rewriting with our customers the new rules of work. We are at this amazing moment of work awakening. Everyone spent the last two years themselves, redefining what they want out of work, how they want to work differently, and starting to realize that they can get different things out of work.

We’ll keep building to serve them very differently in a world of work that is more flexible, that is more distributed, that really empowers them with the tools that each side needs, to really be a win-win, but to get more of what they want out of what work can be today. Which I think, looks very different from how work looked even in 2019, just a few years ago. The rules and behaviors around work have changed, and will keep changing a lot, as we continue to partner with our customers to really redesign what this new world of work looks like.

SAFIAN: Well, Hayden, this has been great. Thank you so much for doing this. I really appreciate it.

BROWN: Oh, absolutely. Thank you.

Masters of Scale’s mission is to democratize entrepreneurship. Launched in 2017 as a weekly podcast featuring Reid Hoffman, we’re now two weekly podcasts — Masters of Scale with Reid Hoffman, and Masters of Scale: Rapid Response, hosted by Bob Safian — as well as an award-winning daily learning app, a best-selling book, virtual and live events, and more, serving a global community of founders, funders, and leaders looking to innovate at scale.
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