Cloudflare TV

🎂 Hayden Brown — A Conversation

Presented by Michelle Zatlyn, Hayden Brown
Originally aired on 

2020 marks Cloudflare’s 10th birthday. To celebrate this milestone, we are hosting a series of fireside chats with business and industry leaders all week long.

In this Cloudflare TV segment, Michelle Zatlyn will host a fireside chat with Hayden Brown, CEO of Upwork.

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Transcript (Beta)

All right, excellent. Hi, everyone. Thank you so much for tuning in for the next Fireside Chat tonight.

It's five o'clock here in California. I have the CEO of Upwork, Hayden Brown.

Welcome, Hayden. I'm so excited to have you today. Thanks for having me, Michelle.

Oh, well, thanks for doing this. I mean, you run such a cool company, Upwork.

Can you maybe start by sharing with the audience, describe what Upwork is and your scale?

Yeah, Upwork is the world's largest freelance talent platform.

So we operate a global website, mobile apps, where clients can tap into a world of professional talent.

180 countries are supported with freelancers logging on, working with clients to do really high impact, high skill work.

And our clients include approximately 30% of the Fortune 500, as well as many, many small businesses who come to our platform to find the experts they need to do really high impact work.

Wow, that's amazing. 180 countries. That's a lot. So you're really helping find talent around the world, like literally.

Literally around the world. And just to give you a sense of kind of the full scale, last year, clients spent about $2 billion with freelancers on our platform.

So definitely, this is a significant amount of work getting done.

That's really helping businesses move forward, especially right now.

All of this work is happening in a remote work setting.

People are working from home. That's always been the model. And certainly this year, even more than ever before, that's critical.

Wow. So just give us a sense of like, so it sounds like a lot of small businesses, a lot of Fortune 500, I mean, 30%, that's an incredible number.

What sort of work or projects do they hire these people to do?

Maybe just help contextualize it a little bit. I'm probably not the first person to ask you that question.

No, we get that asked a lot.

And I'd say there's kind of three big types of work that happen a lot on our platform.

So one is clients come in looking for skilled mobile web and kind of IT professionals to help them with technology implementations, building websites, mobile apps, that type of thing.

A second big use case is clients looking for help with marketing, creative work.

So I need a designer, I need someone to do visual assets for my marketing copy, that type of thing.

And then a third big use case for us is around customer support and back office functions.

So I need a team of customer support professionals, maybe a global team, multilingual, all of those types of things are kind of big use cases on our platform.

And certainly this year, we've seen a ton of activity in those areas, digital skills have been on the rise before this year.

And then with the pandemic, it's been like giant explosion of digital demand, people just everywhere are looking for people to help their businesses become more digital.

And then our platform, because we serve 8,000 skills, and there's a long tail of activities that happen even outside of those three big categories, Michelle, there's things like e-learning that have taken a lot more traction right now, as you can imagine, why our instructional design, even game development, some of these things what you can imagine during this pandemic, people are leaning into the opportunities and the businesses that they're trying to rally around specific needs at this moment, which those aren't big categories for us specifically.

But again, we have this very large heterogeneous platform with people that do all kinds of high skill work.

And so people are coming to the platform to find those types of skilled freelancers as well.

You know, that makes so much sense as you said this, because one of the things we've seen is when this pandemic hit is the businesses that were able to pivot to a more digital first strategy are the ones who I think are doing better than ones who have been able to kind of caught maybe more flat footed.

And I've been amazed at how fast some of these businesses have been able to pivot and kind of take something maybe that was on the back burner or digital transformation project and move it to the front burner quite quickly.

And it sounds like maybe you're the secret weapon as why maybe they're just finding all this great talent at Upwork.

Maybe you are the secret weapon towards all these businesses kind of ones who are able to pivot during this pandemic.

That's interesting. It's so funny that you say that because we've had this running joke.

I mean, I've been at this company nine years and for since the beginning, I can remember clients talking to us as like, you're our secret weapon.

We don't want to tell anyone else that we're using you because we don't want our competitors to know or some of theirs like I don't want my boss to know how I'm getting all this amazing work done.

And so that term secret weapon has actually been something that has been kind of a running joke in our company for a long time because also working each other like, no, but we don't want to be your secret weapon.

Like you got to go tell other people you're using us because historically, we're a demand constrained platform and we're two sided marketplace.

And the way we grow is, you know, clients need to be telling each other and certainly word of mouth is actually our number one channel of growth.

But certainly this year, we've been leaning into the opportunity to really get the word out that we do exist.

And we are an incredible resource for companies who are trying to figure out some of these things like a digital transformation strategy that maybe they had sitting on their shelf, or they were kind of slowly, you know, inching their way towards completing and suddenly this year, it became a reality check that they needed to execute that strategy in a matter of weeks, not months or years.

And Upwork freelancers have been a huge asset to these companies to kind of execute on those plans, tap into a set of skills that quite often they either can't find, they can't find near them, they can't afford, like there's a million things that have been real barriers for companies to find the skills and the resources that they need to get critical work done for them and their teams.

And so definitely when they come to us, it's usually kind of these strategic projects, they're trying to find the talent for digital transformation being one of them.

And while we love being the secret weapon, we also love being the not so secret weapon.

I was going to say that's the new saying, the no longer not so secret, secret weapon.

Exactly, exactly.

So, you know, one of the other things you said is that you work with both small businesses in the Fortune 500.

I'm just curious, what are some of the similarities or differences between the skilled work on demand that they're looking for?

Yeah, there's certainly a lot of similarities. I'd say people usually come to our platform and whether they're a small business or a large enterprise, there's kind of a range of things they might want to get started with.

They might want to start with one of the smaller project types that we're, I think, well known for.

Although quite often, I think what people don't realize about Upwork is if they think of us, and hopefully they don't, but if they do think of us as that place where you go to get like a $100 logo for your business, that's great.

You can do that on Upwork.

But actually the majority, 80% plus of activity on our platform is actually around large complex projects, a long-term recurring work.

And this is where people are really forming relationships that are enduring.

It may not be a full-time work forever between that client and that freelancer, but they're doing kind of like a virtual bench.

And they find somebody, they start working together, they do a really great project, and then maybe they come back later, engage that person again.

And what our clients are saying to us is, you're kind of the strategic extension of my workforce that becomes something that's kind of my extended bench, my workforce kind of on demand.

And these are people who get to know my business, they get to know my brand guidelines or my technical stack, and become really familiar with me, my team, how we work, the ins and outs of our systems.

And that becomes a really great asset for them, because it's not about just a one-time transactional project.

It's something that becomes really a resource they can go back to again and again, to get meaningful work done and get it done quickly without having to kind of like re-educate someone for the first time, every time.

And so that's where I think there's kind of this wow moment, not just around the quality of the talent on our platform, which is I think often quite astonishing to people, but also the fact that they can kind of build up this capacity, which really does extend what's possible for them.

And so I say this is something that's a kind of a recognition from small and large customers about what's possible using our platform.

I think what's different is certainly our larger customers who are using more of our enterprise suite, our larger offerings, they have a lot more concerns around things like risk and compliance, and they participate in our worker classification offering, where we indemnify them against any risk around misclassification.

They have more sophisticated needs around reporting or around approvals and workflows.

They're larger organizations, they have more of those needs.

Maybe they want to take advantage of Power BI reporting where they can export all of the data about their programs on Upwork into tools that they're using inside of their workplace.

So our larger companies, they tend to use more of those sophisticated enterprise-grade tools and technologies.

Our smaller customers are quite happy with some of the more simple use cases that they don't want to be bothered with some of that complexity.

So we really have a range of things that we can give those customers, but I think all of them tend to start with some of those use cases and then build out that virtual bench and that more programmatic adoption as they kind of discover the world of Upwork that's available to them.

Yeah, I know that makes sense. What you were describing the enterprise is how they really want the control, the compliance features.

I feel like that's the a-ha of all, you know, even at Cloudflare, we start a lot with small businesses and developers and mid -sized businesses.

And as a larger fortune, 1,000 companies using Cloudflare, same thing.

It's like more, it's the richness of the reporting and the audit tools and the compliance, which is really important for these large organizations.

It's so important, Michelle. And I think, you know, a lot of solutions are built to like help companies scale up and not a lot of solutions are built to help them really dynamically, like scale up and down and up and down and up and down, which our solution is built to do that.

And, you know, this isn't a comment specific to the pandemic, but I think a business in any dynamic environment, like they need to be very nimble, right?

And they have, whether it's seasonal demands, whether it's like a big project or a big launch, and they need to like kind of put a lot of resources against that.

And then, you know, those needs change and they need to like scale back those resources.

Companies, the reality is like, that's the business environment of today.

It's not about some fixed March of just like layering on, you know, more and more full-time headcount against, you know, some product roadmap or some, you know, plan that just kind of continues to get more and more bloated.

And so I think the realization that our customers have is that using Upwork gives them this, this control.

I mean, I love that you use that word because that's the word that our customers use.

Upwork gives us this control to like scale up, scale down, and really kind of map the talent resourcing that we have against exactly what our business needs are at this very moment.

And I think that for them is extremely powerful. Yeah, that flexibility, that's really well said.

You know, you are this two-sided marketplace where you've described, you have the freelancers coming, you have the talent, you have this broad set of talent who are coming back to work on these complex sets of projects.

And then you have the businesses, whether they're small or large, who, who are matching, who have the projects to match the talent to.

That sounds hard to get that right.

What, how does, what's it like to build and manage a two-sided marketplace?

And what are maybe some of the things that have changed over the last decade as that, that's matured?

You know, I think, you know, marketplaces have become more and more like popular.

You know, I think if you look at the data around like VC investments and things like that, they're kind of the rage and they're really hard businesses to build for a lot of reasons.

And a lot of people, you know, a lot smarter than me have written extensively about this topic.

But as someone who's been hands-on building this marketplace for the last nine years of my life, I think what's hard about it is the trust factor.

I think building a marketplace, you know, there's, there's a lot about like getting to scale and getting the flywheel going.

And yes, like certainly those things are true, but at the end of the day, what really matters is kind of trust and quality that people know that they can come in and have an experience that that's going to deliver for them, you know, what their expectations are and that they're going to, both parties are going to get the thing that they're hoping to get out of that engagement or that transaction, whether it's an e-commerce type of thing, or in our case, more of a services relationship.

And I think that as marketplaces grow and as kind of the e -commerce landscape and the world kind of matures and what I've seen over the last 10 years as consumers, and I mean that in the sense of even like business users of marketplaces, such as our customers, their expectations, you know, continue to be raised about trust and quality and curation and what they expect from any of the tools that they're using, including marketplace products, whether it's Etsy, eBay, you know, Amazon Upwork, is the trust bar, the quality bar just keeps going up.

And so I think the hard thing about running a marketplace business is continually staying ahead of customer expectations on trust and quality, which is paramount to really delivering a great experience for customers, winning that trust, establishing that trust, having that credibility, because at the end of the day, if you don't have that, you kind of aren't in the game and you aren't relevant anymore.

And so that's certainly, I think, something that we have been continually raising our own bar around what it means to deliver a trusted experience.

And certainly that feels to us like a huge differentiator versus a lot of the other, you know, startups or others who kind of like come into this space, but how do you establish that trust at scale while also doing all the other things that are required to build, you know, a giant marketplace?

It's a very difficult proposition. Yeah, no, that's, I mean, that's really well said.

And, you know, the thing about trust is it's a repeated, it's repeated action.

It's not, it's not one and done. You got to keep at it, keep doing it.

It's, it's, it's kind of a track record that builds on it. And so, right. Totally.

And it has to be on both sides, which is the hard thing about marketplace. I mean, it's one thing if it's, you know, more of a transactional experience like e -commerce, you kind of just need to deliver something for one party and you can kind of guarantee that in a certain way to build trust in a two-sided proposition is even more difficult.

And so, you know, this business is definitely not for the faint of heart, but the rewards for the participants, when you get it right, as I think we have done and are continuing to do for customers and for ourselves in terms of doing something extremely challenging and doing well, that makes it interesting.

And that makes it worthwhile. Yeah. And you probably, there's probably days you go home from work where you're like, it makes you re -believe in humankind.

Like where, where, where, when you get it right. And you're like, wow, like this is an example where you've been able to match up this super talented person with this really interesting project and they've created all this amazing thing and you, and it's almost those aha moments that make all of the other hard parts worth it.

Can I share two quick stories on that? Kind of like just teed up for me.

I mean, so I, I do calls with customers every week just to like talk to them about like, how's it working, what's good, what's bad.

And, you know, it's really, we fall down all the time on things that we got to get better at.

And I want to hear that firsthand from customers. And I was talking to one freelancer who, when I called her, she said, Hayden, I'm speaking to you from the house that Upwork built.

And I said, well, what do you mean? And she said, this is the house that, you know, I'm here in Long Island and we're Zooming together.

And this is the house that Upwork built because I've built my career over the last 10 years.

I started on your platform 10 years ago, earning $10 an hour. Now I earn over a hundred dollars an hour on your platform.

I started my own agency. I built this entire business.

I quit my full-time job. Like she told me her whole story. And, you know, it's a moment like that where you're just like, this is why I have been doing this job and continue to toil.

Or the client that I spoke to recently who had met this person on our platform, a freelancer in Macedonia, they had been working together for years.

They never met in person and ended up, he went to a Macedonian restaurant in his town, brought his iPad, had his Macedonian freelancer on the iPad, both of them eating Macedonian food together and enjoying this cultural experience that was only made possible because they had met through our platform and built this trusted relationship.

And so I think it's those moments, Michelle, where like, this is why it's worth it.

You know, these people are like, they're unlocking these possibilities for themselves only because of the technology and everything that's made possible by this platform.

And certainly that's what gets me out of bed in the morning.

Oh my God. I love those stories. I like have goosebumps.

It's like our hallmark moment this Wednesday afternoon. I love those. Those are, I think that is, that's when technology is at its best.

Like where you make these connections.

And so one more question to kind of looking backwards, then we'll look forwards is, you know, and you've just done a great job, but maybe there's some other things you want to add is, you know, you know, you've had this idea of connecting the talents with the businesses, but in, you know, we're a technology company, so we're kind of looking back to the last 10 years of how technology has shaped and where we're going to go from here.

So how big the role has technology played at Upwork?

Like how much of your day do you spend thinking about that?

I mean, all of it. I mean, it's the people and the technology. And I think all of this is only possible because of technology.

That's what drew me into this business, you know, to join it was really about seeing, like, you know, I looked at things 10 years ago and said, look, the Internet is blanketing the planet.

People have access through the Internet to learning opportunities. They should have access to work opportunities.

And yet that hasn't fully happened yet. At the time, you know, the thought process that I had and the people at what was then ODesk, the company that I joined now became Upwork.

The thought process of the company at the time was, look, people are being forced still to, like, relocate to other countries often to do the work and the job that they want to do or move to the big city to do the work and the jobs they want to do.

But we have the Internet. We have collaboration tools.

We have computers that process things very quickly.

Video conferencing even existed then. I mean, it's not it wasn't nearly as good then as it is now.

But, you know, the technologies that we're all using now for remote work, like those actually existed eight, nine years ago, Michelle, these are not new technologies.

And so if you think about what was true then and is still true today, these capabilities existed.

And yet the problem that people at our company saw and that I saw got me excited to join was we were not using them to their full potential to give people access to the opportunities that do exist and that are not evenly distributed around the world.

And it goes back to that famous quote that's attributed to, like, Bill Clinton and Gandhi and like everybody else of, you know, opportunity is not evenly distributed, but talent is evenly distributed around the world.

And so how do you use technology to bring the opportunities to the workers rather than force workers to move to where those opportunities exist?

And I think that that concept is so powerful and still true today and something that we have not fully achieved yet, where people, you know, are still largely expected to relocate themselves, whether it's an hour-long commute or, you know, a cross border move with their families to do the work they want to be doing.

And this year, and maybe we're going to shift to talk about the future in that context, but this year has been very powerful, I think, in reshaping a lot of our views as a society and inside of our businesses about, wait a minute, like these technologies do work.

Maybe we just need to change some of our mindsets and behaviors to take advantage of what the technology can give us so that we can work together remotely and not require people to make some of these really tough personal sacrifices that, frankly, you know, may not be adding up to something that's better for people or for business.

And I think that that is like a very powerful concept who's, I think it's not a new idea, but it's an idea that finally is kind of getting its due.

And I'm very excited about, I think, what that can do for people and for businesses, because there's so much potential that can be unleashed when you put those things to work together.

Yeah, no, what you were saying was, I was taking some deep breaths because I would say that, first, I am definitely guilty or where we were definitely very much a come into the office every single day company.

And we had many offices, but you had to come and move to be near one of our offices.

And to the credit of our wonderful team, a lot of people did.

And then personally, I was also one of those people who moved to the opportunity.

I moved from Canada, the Bay Area, and it's been amazing. But it is a lot, you know, immigration, work authorization, family, you know, you're raising your own family, you don't have a network of extended family around.

And you kind of realize it is a big disruption to people's lives.

And, you know, what I thought might have been a couple year project has turned into a 10 year experiment.

And now all of a sudden, I'm like, wait, where's home, I guess this is now home.

And so a lot of that really rings true. And so this does lead me to the future.

And so I think you said that it's kind of having this moment of where do people need to work from.

And obviously, predicting the future is difficult.

But what parts of this moment that we are all going through together, this rarely happens, I guess, in a global penta, we are all doing this together, which things in life, we don't do that, maybe the Olympics, but that's about it.

And the World Cup, like, maybe that's it.

But what parts do you think are maybe fleeting?

And just kind of right now? And what parts do you think are maybe here to stay when it comes to how we work?

I think a lot of these things are here to stay. To be honest, I have to think about what's fleeting.

I mean, I think what's fleeting, I hope, I mean, it has to be fleeting is this idea that we have, like our children home from school, and we don't have, you know, a social system around, you know, childcare, and things like that, because that's not sustainable.

And there's no way I mean, as much as I believe in this idea of like work life integration, I don't think any of us meant like that when we talk about like work life integration, right.

So certainly, those things are fleeting. And I do think there's a risk of tarnishing the potential of working from home with the kind of a naturalness of working from home during a pandemic, which has like all kinds of things to it that are very unique and situational to that.

I think what's here to stay are really companies finding and workers finding a new balance that isn't doesn't have to be all about like everyone at home forever.

Like even, even us, so we're very, like, you know, work from home oriented company and culture ourselves and for our customers, like that's something that just is very natural for us.

But it's not about, you know, let's all lock ourselves in our homes forever.

This is about being very intentional.

How can we be intentional to really recognize the benefits that a distributed, more work from home oriented culture and set of practices can give workers and businesses, which include a lot of the things that we talked about.

And also, by the way, I think include some very powerful tools towards addressing some of the diversity challenges that all of our companies face, because it suddenly opens up pools of talent, potentially, that we can tap into, again, outside of the places where potentially we've traditionally hired and means we can tap into those people.

And they're not second class citizens, because they're not the only ones working remotely.

They're not the ones who are kind of marginalized because everyone else is back in the home office.

So, you know, because we are working in a new way where lots of people are distributed, lots of people may be working from home, lots of people aren't necessarily near a home office all the time.

We can suddenly, I think, tap into some things very powerful to solve diversity challenges, which are so important, as well as address workers needs, which have been stated for well before this pandemic, wanting more flexibility, wanting to reduce commute times, wanting to access great work opportunities that may not be in the cities where they live, and other things.

So I think there's something very enduring about those needs that, again, predate the pandemic and can be addressed going forward, as well as businesses, when we talk to them, and the studies showed before this crisis, number one challenge was, we can't find the talent, right?

We don't know where to get these people. Like we're fighting against Google in the Bay Area to get these engineers out, like we can't compete with Facebook or whatever else.

Well, guess what, let's look outside the Bay Area for these people, remote work provides a solution for that.

So I think that's where a more hybrid strategy that may include face to face interactions, sometime in the office, on the occasions where that's really valuable and necessary, like, absolutely, let's do that.

But let's not revert back to and I don't think companies want to revert back to, you know, the kind of work that was happening before there's kind of a new hybrid world available to us.

Let's find that place, because boy, that's going to be amazing for people and for businesses.

Yeah, I love that.

I feel like we need a new term, like it's going to evolve, because I don't, I don't believe in it being radically different, because I just think humans aren't like that.

But, but if it all goes back to how it was, better and more flexible and access more pools of talent, like, we got all the things we've learned.

Exactly. That's the, that's a great thing. So we have about five minutes left.

And I want to I want to talk to you about, you know, if you go to your Twitter handle, it says believer or passionate about tech for good.

And that really, like sparked an interest in me.

And I said, Well, what do you mean by that? So maybe we can start by sharing?

What do you mean by tech for good? And why are you so passionate about that?

Well, it's definitely not tech for bad. Um, tech for good, you know, I think it goes back to this idea that, you know, for us at Upwork, our mission is to create economic opportunities, so people have better lives.

And I signed up for that mission, you know, nine years ago, because when I was growing up, and frankly, still today, my mom and my parents both do international development work.

My mom is a women's empowerment specialist. She has dedicated her career to furthering the lives of women and really focusing on issues around gender equality.

I felt strongly I wanted to do something with my career that was purposeful, that was, you know, something bigger than about me, and was about kind of trying to create opportunities for other people.

I didn't really know what that would be for myself.

But I also fell in love with technology. And the idea of the scale that technology can kind of change people's lives, you know, working at Microsoft, like, what a thrill to be able to touch products that, you know, have the scale that Microsoft's products have.

And that was one of the things I did earlier in my career.

So I fell in love with technology. And I also was on this mission to like, find a place where I could do something that felt like it really was about having impact.

And so when I think about kind of tech for good, for me, that's about using technology in ways that really is about opening up opportunities, doing things that really are transformational with technology for people's lives in ways that really engage them deeply.

And when I go back to, you know, talking to this freelancer in Long Island, who said, this is the house that Upwork built.

That's tech for good, like right there. Yeah, no, that's amazing. And I love this.

And I'm with you. It sounds like you're a little bit of an optimist too, where it's like, can do, let's do it, find all the good.

Although it does feel like recently tech could do no good, like where like the headlines and you read and there has been some bad.

And so it's hard to balance that. How do you, how do you balance that as a leader in this industry?

I mean, you're CEO of a large publicly traded company.

I totally believe in the sentiment of tech for good. So do I. How do you not get discouraged by some of the, some of the cynics who think about all the bad things, speaking about balancing home and work life.

This is the witching hour of hungry young kids running in and out of my office right now about five times.

You know, I think you're right.

I'm an optimist. And I feel like, you know, in the tech space, we have a lot of work to do.

Clearly we're not, tech is not all for good.

Tech does not equal for good. I think it's how we use tech. There's a lot of abuse and misuse, and there's a lot of ways that technology can be used that is not great.

And so I think as an industry we have to take some steps forward, some of which are being taken.

I think there's more work to be done there. And certainly from a regulatory perspective, there's probably, you know, real questions that we have not yet addressed as a country in this area.

But for me personally, and when I think about the work at Upwork, the beauty that we have is we can keep focused on driving forward our platform and our mission in a place where our platform is a true meritocracy.

People come on our platform and they compete based on their merits, based on their skills, based on how excellent they are at serving their clients.

This is not about, you know, identity-based politics on our platform or, you know, anything else.

This is truly a place where people can compete based on their skills and their capabilities.

And so when I get discouraged or feel down about what's going on in the industry, I think, you know, we just try to stay focused on what we're doing to really further a place where people can come and find that tech for good and create those opportunities for themselves.

I love that when you feel discouraged, what you do is you go to work because you get reinvigorated by what you're doing, which is probably should be everyone's career or life goals.

That's pretty awesome. I feel to say I have something very similar at Cloudflare and I just sometimes think, wow, we're so lucky to have that.

It's an awesome feeling.

Okay. So we have 30 seconds. So this was awesome. I love this. I can't wait to talk to you again in the future.

Good luck with everything. And thanks for matching opportunity to talent and talent to opportunity because that's the way it should be.

Absolutely. Thank you. Thanks everyone for tuning in. Bye.