🌐 The Future of Work

All right, we're live. Welcome, Cloudflare TV. I'm Janet Van Huysse. I'm the head of the people team here at Cloudflare, and we're wrapping up our first ever Impact Week.

And it's been an amazing week. So many great things that we've shared that we're doing, not only to help make the Internet a force for good, but also an engine for global sustainability.

So I've been super proud and I'm really excited to cap off the week with an interview here with our co-founder and CEO, Matthew Prince.

Hi, Matthew. Hey, Janet. How are you doing? I'm doing great. How are you? Yeah, I'm good.

Beforehand, we were just talking about scuba diving and our experiences.

I've only been scuba diving twice, and I had sort of bad experiences both times, but it's amazing.

So yeah. Yeah, we'll talk more about that. Maybe I'll get you back tanked up again, Matthew.

We'll see. Looking forward to it. Swim with the turtles.

Great. So Matthew, we're going to talk today about the future of work, and you and Michelle published a blog post today.

And so I kind of want to go through some of the thinking that went into that post and what we've really learned, not just in the last 16 months, and also in the first 10 years of Cloudflare being around.

So before we dive into the future of work, I thought it would be good to give us some context about early days at Cloudflare.

We were very much an in-office company.

I used to describe our office philosophy as fewer, bigger ones, right?

So we wanted fewer locations with more people there. And that really served us well, I think, in the early days.

And so I just wanted maybe if we could set the stage a little bit with kind of talking through what were some of the guiding principles and thoughts around that approach in the early days.

Yeah. So I think that when we started Cloudflare, the challenges that we faced and the technology that we had to invent didn't exist.

And so I think we, from the beginning, had this very much, you go into the office, and that it was a place to get together and collaborate and exchange ideas.

And so much of the very early days of Cloudflare were when it was eight of us in a janky little office over a nail salon in Palo Alto.

I mean, we were all every day collaborating in person. And so much of how you start kind of becomes, whether you intended to or not, becomes the culture of what becomes the company over the long term.

And I remember when you started, we were a bigger company at that time.

We had three offices, I think. We had San Francisco, London, and Singapore.

And we unfortunately would have to say no to a lot of candidates that weren't in one of those three cities or weren't willing to move to one of those three cities because so much of how we had developed as a culture was around we get together in person, we build culture, we build community in person, we exchange ideas in person.

And we really valued the idea that engineers would sit next to sales people, would sit next to people on the marketing team, and there would be this sort of cross-pollination and almost learning through osmosis that was there.

It wasn't, we didn't think, I mean, we didn't have a strong held philosophy that remote work was bad.

In fact, we had seen lots of pure companies that had started as remote first companies and done very, very well.

But I think that what we realized was you really needed that to be part of your identity and part of your culture.

And that just wasn't how we had started. And it didn't feel like we could sort of switch tracks once we were on it.

And so we were on that path and it was working for us.

And so we continued to double down on it. And some of my fondest memories are the kind of non -work related, fun conversations with colleagues that would have never happened if we hadn't been together in the office.

And so I think that through March of 2020, that was very much what Cloudflare was.

And I think had COVID not happened, I think that's kind of what Cloudflare would have continued to be for the foreseeable future.

Yeah, COVID really turned that on its head.

And I think we learned a lot. I'm curious to hear, you talk about what's actually been better during this last 16 months of everyone being virtual and us kind of being forced to work remotely.

Thoughts on things that surprised you that were actually better than when we were all in person?

Yeah. So it was March 13th of 2020 that we shut down the offices globally.

We'd had some offices in Asia that had closed a little bit before that because the pandemic hit there first.

But March 13th, which was a Friday, was the last day.

And I remember the phone call with Michelle, my co-founder, that night.

And we were freaked out because we... I mean, I remember it was super emotional being the last day in the office and thinking about when are we actually going to be back?

And we spent a long time on the phone that night being like, what's going to happen?

And we we'd missed the quarter.

Productivity would slow to a halt. We'd lose our ability to recruit people.

And that was terrifying at the time. And to be honest, for the next two weeks, everything went wrong.

People didn't have places to work. It was tough for people to figure out what to do with their kids because their kids were all of a sudden out of school at the same time.

You know, a bunch of people just disappeared.

We didn't know where they where they had gone. You know, we didn't have the IT systems and everything in place.

And so and going into the last few days of the quarter in Q2 or Q1 of 2020, I don't think we were totally sure like what the future held.

And then it was almost like we found a different gear. I think that, you know, our IT team really did an incredible job getting people the resources they needed.

I think that you and the people team did a great job making sure that people had what they needed to continue to get work done.

And I mean, there are lots of ways to measure things.

But one of them was just looking at kind of our productivity of our sales organization.

And in that last like three or four days of the quarter, we closed something like 15 or 20 percent of all of all of our business and for that for that quarter.

And it was really amazing to see. And I don't think we've looked back.

I don't think we've looked back since. And so there are things that are worse.

We can definitely talk about those. But some of the things that really surprised me about being that are better are, you know, we're doing most of our meetings via Zoom or some video conferencing technology now.

We've done some work to look at participation either in all hands meetings or meetings in general.

And we see an uptick in participation from women. We see an uptick in participation from people who English isn't their first language, from offices that we don't think of as major offices.

And so that inclusivity, it turns out if we're all kind of if sort of the playing field is leveled, we're all in these little Brady box bunch of boxes.

And I don't think we totally understand why yet.

But I think that, you know, as I talk to folks like Eric at Zoom and and other CEOs, like they're seeing something that's that's similar.

But I do think that the biggest surprise for me has been how the move to a virtual environment for things like meetings has actually made it sort of reset some of the norms around how meetings work.

And I think we were a pretty inclusive culture before.

But, you know, I hear anecdotally now a lot more times where people are like, I feel if I'm a junior member of the team, I feel so much more comfortable sort of speaking in a meeting.

And I think that, you know, as we look out, one of the things that, you know, is the exact opposite of what we expected, our productivity as a team has gone up.

And and, you know, there are lots of reasons that could be the case.

You know, people aren't commuting and and other things.

But I think one of them is that if you can have every member of your team feel like they can contribute to their fullest, then that then that then all of a sudden you unleash, you know, and it's it's again, it's like another gear that you found in your organization.

And I think that's been that's been the biggest surprise and makes it so that, again, you know, had we not been forced to run this experiment, I don't think we would have ever figured that out.

But having run it, I mean, there's no way we're going to go back to the way way things were.

Yeah, I remember, you know, we have a management meeting every Monday, right.

And we had our CTO who's in Europe.

And I'm sure, Matthew, you remember, that's the thing, we're all scarred by it.

But he said, after, you know, after we'd had a few weeks of this level playing field on the Brady Bunch boxes, he said that his experience previously in that meeting as being one of the few leaders who was dialing in, that he felt like he was watching an episode of The Office.

Like we were all talk, sit around table talking, and he could hear most of the time.

And it's like trying to trying to participate, like trying to jump in, and he's like, Oh, forget it.

It's like, wow, yeah, if your CTO doesn't feel like he can participate fully in meetings, we're missing out big time.

That's right. And I think that that's, that's exactly the thing that that was, that was, that was the same moment where I thought, wow, you know, we, we always thought we were an in person company.

But because of the fact that we have, I don't actually know the count anymore, but like 17 offices around the world at this point, you'll know better than I that, like, we were remote, whether we wanted to be or not.

And, and I think one of the things we had done well, is that, you know, we had let offices that weren't San Francisco, lead a lot of our innovation and, and, and drive that.

But, but I think that at the same time, you know, even though we'd worked to not have this happen, there was still this gravitational center around San Francisco.

And, and I think that that was that that meant that a bunch of their team who are incredibly talented people just didn't feel like they were on the same playing field as they as they did.

You know, if they if they had worked work from there, it would, and it was amazing how just switching to being virtual, unlocked that potential.

And I think if anything, accelerated, you know, our rate of innovation and our rate of growth.

Yeah, yeah, I love thinking about the, just all this inclusiveness and what that unlocks, you know, I really haven't really heard many other people talk about that.

And I'm reading everything I can about the future of work.

Okay, so speaking of, we were, we describe our, you know, the kind of this next phase is our back to better, right?

So it was taking what was good when we were in the office together, what's been a positive, this inclusivity and other things around being all virtual, and really helping that shape this experiment that we're about to enter into or back back to better.

And I really love the way that you've been talking about us leaders about it, it's like, we have an opportunity to reinvent a better way of working.

And I find you kind of constantly challenging us to be like, I don't think it's going to go back like that, you know, or there's a we're gonna we've learned a lot, we're not going to go back to doing it that way.

So we're like, what do you think the big opportunities are ahead of us if we really do take advantage of reinventing the way we work?

I'd like to say we came up with back to better before the White House had their slogan, which is similar as well.

So, so we've been talking about this for more than a year now. And, and I think it, you know, pretty early on, Michelle and I, we really were having conversations like, is it, you know, is it going to go back?

And I think I was, I was more on the, you know, it's going to be everything's going to completely change.

And Michelle was more in that kind of, well, maybe we'll see.

And I think I'm sort of come back to well, maybe doesn't everything change, but a lot is going to change.

I think Michelle is sort of come, we sort of converged on a on a point and we've had and you've led a bunch of conversations across our entire team where we've talked about this.

And the first thing I think is, I don't think anyone knows what the what the future holds.

And what scares me a lot is, well, I think that you can build a very successful company where everyone is, is working in the office.

And I think you can build a very successful company. And I mean, like GitLab and Automatic are great examples of, of being fully remote.

We, what, what I think most companies are trying to think of, and we, and we're, we're included is how do you do some hybrid where you get the best of what was in the office and you get the best of what's remote and you kind of smash it together.

And I don't see a lot of examples where that's worked, worked well.

I mean, you know, Yahoo didn't work well.

Intel didn't work well. They have a great track record. No. And so, and so I think that if you just sort of just say, you know, the offices are open, come in when you want, it doesn't work because I come in one day, you come in another, Michelle comes in a third, Chris comes in a fourth, you know, someone else comes in a fifth.

We all wanted to be there at the same time, but we're all there at different times.

We all have kind of a crummy experience. And then none of us come in the following week.

And what, you know, what we've, as I've talked to peers who've, who've been in, in jurisdictions where they can open their, their offices, you know, they might get 60 or 70% of people coming in the first week, but by the end of the first month, they're down to three or 4%.

Yep. And that's just a terrible, that's a terrible experience.

And so, and so I think that as we think about it, you know, the question is, you know, how do you create a hybrid world that works?

And the reason you want to strive for that is, yeah, you can have more inclusivity in things like meetings, but, but more than that, if we can, you know, if we can hire from a greater pool of people, then, you know, we just can have a much, a much better, more, more diverse team.

And I think one of the things that you've been a real leader at, at the company is, it's emphasizing that, you know, we don't believe in diversity.

I mean, it's, it's nice that it checks sort of boxes on government reports and makes you look good in the media and those things, but that's not the reason to believe in diversity.

The reason to believe in diversity is that across almost everything you can imagine, whether it's, you know, genetic species, diversity, or diversity in your investment portfolio, or, or anything else, more diverse, the more diverse you are, the more likely you are to win.

And the more diverse teams are, the more likely they are to win. And it's, it's for a simple reason.

We all have a perspective that is shaped by our experiences that gives us unique insights and also, you know, unique blind spots.

And if everyone has the exact same perspective, then it doesn't work.

And so, you know, I know companies who are like, we hire all of our engineers from MIT's engineering program.

Yeah, I think I've worked at a company like that. And MIT's engineering program, it's a great engineering program.

And we want some people from MIT's engineering program.

But if every single person went through the same program and talked to the same professors and had the same outlook and, and, and, and, and looked at the world the same way, then you're just getting so much less unique insight from everyone on your team than if you've got people who come from different programs across the way.

And so, we really want to, on every possible dimension, to say, we want diversity across our entire team so that we can, so that we can see things.

And if in the past, you know, we had said, we only want people who, who, you know, have through whatever pathway ended up in San Francisco, which again, there, there's, there's a, there's a certain set of, there's a certain set of schools that feed people there.

There's a certain set of, you know, characteristics of people who move there.

There's a certain set of, and you, and there's a lot of diversity in San Francisco, but there's a lot that's also missing in San Francisco as well.

And if you constrain yourself to that pool of candidates, then, then you're going to be much less.

And so I think we have sort of tried to solve that before by opening offices around the world.

But even then, you know, we were going to places that were largely sort of tech hubs and missing out on, on other locations.

And so I think that if, you know, we, we still think it's that people are going to cluster around where offices are, but if we can open ourselves up to places that we don't have big offices, you know, and, and recruit from those places as well, then we think we can actually build just a better team with more different perspectives coming from different schools, you know, coming from different, you know, backgrounds.

And, and that's the way you build a team, you know, that wins over, over the longterm.

And so I think that, you know, if we can make this work, then it, then we have the ability to, you know, just, you know, continue to accelerate the rate at which we're able to, to deliver innovative solutions, which is, which is what, you know, really drives, drives the machine at Cloudflare.

Yeah. It's definitely one of the things I'm most excited about as we have this much larger talent pool, we can now draw from because we're not so geographically constrained as we used to be.

Okay. So you talked about talking to some of your peers about, you know, bringing people back into the office and it not going so well.

And you talked about it internally as like, you know, cause we've kept our offices open as much as we could throughout the pandemic, because we knew that working from home wouldn't work for everybody.

So it was a good option for folks to have.

But you've talked about that, the experience, coming back to the office kind of suck.

And so, and so as we think about what would that, you know, kind of grand reopening of our office spaces be, you talked about using carrots, not sticks.

So can you talk a bit about your thinking behind that? Yeah. So first of all, I mean, so I, you know, I think that our philosophy to date is, as you know, has been opening offices as quickly as possible and then make it really hard to work from them.

Um, and, and the, the, I remember the moment where I was like, wow, we, we gotta get the offices back open.

And it was, um, when I, when I read, um, an article about how much domestic abuse had ticked up, uh, during the pandemic.

And, you know, unfortunately we have over 2000 employees. Unfortunately, you know, you would expect that some of those employees would have unsafe home life.

And so the office becomes a safe place for them to go and, and work and, and get away.

And, um, and so we wanted to make that available for them. Um, but I, you know, I told, I told you and our entire senior team, like none of you, I mean, unless you're, you have a, a, a secure physical, uh, issue at home, you're, you're all fortunate enough to be able to have, you know, a safe, a comfortable place to work from home.

Um, uh, but, uh, so you're not allowed to go in the office because if you go in, then everyone else is going to feel pressure to go in.

But, you know, we, we did, um, open the offices for people, but it's, it's been a kind of crummy experience.

You gotta wear a mask, you gotta be socially distanced from people.

Um, you know, we, we have tried to avoid, um, sort of mandating, you know, how people think about their own, own healthcare.

Although, you know, I think that, that we'll, we'll have to evaluate that, um, as time, as time goes on.

Um, but it's, it's not been a fun experience. And I think, you know, we've got to acknowledge that, um, because we want, we, we don't want to just sort of, um, kind of go back to work kind of just in a completely chaotic way, because then for sure it's going to be, it's going to be bad.

So we have talked about how let's, let's have when it's safe to do so.

And when we can do it as a company globally, let's have a grand reopening.

We actually is, um, originally, as you know, use, use the term homecoming.

And I remember our German team turns out that homecoming is a metaphor that doesn't, doesn't, uh, translate very well internationally.

And our German team was like, no, no, you don't understand. We've been coming home plenty.

We want to go into work. And, and so we had to send them a bunch of eighties movies to explain what homecoming was.

Um, but a grand reopening, I think everyone, everyone understands and we want to do that.

We want to do that when the office can be the thing that we all want it to be again, which is you don't have to wear a mask and you, you can see your friends and you can give them hugs and you can, and you can meet people you haven't met.

And it can be a, it can be a good, a good piece.

Well, what we really don't also want to do is impose these arbitrary rules.

So I hear about big companies who are like, you know, everyone is going to have to come in Monday, Tuesday, and Thursday.

And, and I just think, I'm thinking, you know, why those days?

And then, you know, wow. You know, bizarre incentives that creates because now the Caltrain and it's going to be busy on Monday, Tuesdays and Thursdays.

And so maybe Wednesdays and Fridays are the days that, you know, you want to optimize for it.

And, um, and I think we've tried as hard as not to force what feel like, you know, arbitrary rules because our, our team are adults.

And, and again, we've seen that they're able to perform when they're fully remote.

And so let's, let's figure that out. So we want to create ways that the office is a place that not that you have to come to, but that you want to.

Um, and, and I think a couple of things are going to be necessary for that.

But first is like, again, you can't just open it and hope for the best.

Like, I think we're going to have to be really deliberate.

And so we've talked about this concept of onsite offsites where teams will say, you know, we're the marketing team.

We're going to bring people in from across the company for a week of brainstorming.

We're going to do that whiteboard, have dinners together, socialize, have, have some time.

And then we're going to scatter back to the wind. And some teams like our, you know, might be like our junior salespeople might, might come in more frequently.

You know, some of our engineering teams might come in less frequently.

Um, but I think teams should set that pace, but they need to be very deliberate, um, about that.

Um, we expect that 10% of the team, um, is going to come in just every day.

Cause they like working from offices. Uh, but, but then we were trying to figure out what are other incentives that make it really interesting.

And so we're lining up a speaker series that, you know, we were only going to do if you're actually in the office, because we want to create incentives.

And if we can get, you know, big deal speakers to come in and talk, then, you know, that will, they'll have people come in.

And we're also trying to think about things about, um, you know, my, one of my, my pet project internally has been this thing we're calling orange cart, uh, orange card, which is how do we turn every employee's ID badge into essentially a charge card that will work to buy, you know, meals, uh, but only activates when you scan into the office and only, um, and only works at restaurants that are within a 10 minute walk.

And I think that, you know, that hopefully will get, you know, folks who are the most motivated by discounted food, you know, which is actually a very large group.

Yeah. And, um, and it'll hopefully get them to the office, which is in our interest.

Like that is, we're not doing that as a perk. We're doing that because we want people to come into the office.

Um, and then at the same time, instead of, you know, I I've always been very hesitant to build like the big Clio Cloudflare cafeteria, because literally one of my favorite things about Cloudflare is that we didn't build the campus and the, you never need to leave.

We actually want encourage people to be part of our support our local community.

And right now, I mean, restaurants are dying.

Um, and so if we can do something that incentivizes our team to, you know, eat lunch at our, at our local restaurants, that's great.

I mean, we, we do lunch, we bring in lunch on Wednesdays.

And I remember talking to the Subway sandwich, the owner of the Subway sandwich store in San Francisco, their, their business drops between 10 and 15% every Wednesday.

And like, so I think that as, as you think about it, so listeners to know, because we served lunch on Wednesday on free, a free lunch on Wednesday.

Um, and, but that's bad, right? I mean, and what would be actually better if we said, Hey, how do we, how do we actually support the community that we're, that we're a part of and, and encourage our team to, you know, go out and, and patronize those restaurants.

Cause we, cause we want to make sure that they survive and the communities are happy and friendly.

And that's where people want to work and they want to work in places that are like that.

So can I tell, can I tell our listeners how you asked everyone in the company, if they thought it was a good idea to email our CIO.

I've started to learn that at all hands meetings, I have this, this, this dangerous new superpower, which is that I can basically, um, rally the troops in this.

And the latest one was we're doing these summer socials.

And, uh, and I, and I said to our head of infrastructure, I said, if you, if you think it'd be fun to go on a, uh, on a tour of Cloudflare data centers as a summer social, um, you know, email our, our head of infrastructure and his, his inbox was flooded as well.

So it's, so I know I'll be on the receiving end of this at some point.

I'm getting such a kick out of it until it's me.

But yes, Matthew, you do have that power. Yes. It's, uh, it's a, yeah, there you go.

It's, it's a, it people is, is a company gets bigger and bigger.

People less listen to less, but that is a, that is a new way. That's my new, my new trick to get things that I want.

Do you want to talk about your czar of serendipity?

Well, so, so again, I think that one of the things we all love about the office and the crazy, the crazy sad for me is half of our team at this point has never stepped foot in.

And most of them have never met another Cloudflare employee in person.

And so as we've done these summer socials, like, it's really great to get, you know, different teams together where you have engineering and sales and marketing and they go to, they go to lunch and they're like, wow, you're so cool.

And like, and they learn from each other. And I think that makes everyone better at their job.

And so I think as we think about how we use the offices as these sort of onsite offsite locations, um, one of the things is, is we have, you know, the marketing team and, you know, the BDR blue team and, and, you know, maybe a few people from sort of the intellectual property legal side, you know, all in the office together.

How do we say it wasn't there? We've got reservations for lunch for six people.

How about the six of you go out and do it? And I think ideally you'd want to, um, you know, have that happen spontaneously.

And I think it, it will a lot of the times, but some of the times having somebody who, you know, helps coordinate that and helps pull it together, um, makes sense.

And so we're, we're playing with this idea of can you have a czar of serendipity that kind of sits over, looks at who's in the office on any given day and then make suggestions of, Hey, you know, I don't think you two have ever met each other.

Why don't you, why don't you go out and, and have, and have coffee?

And I think that that's, um, again, I think what all of us that there's, look, nobody misses commuting.

Nobody misses, um, you know, uh, that a lot of the things about, about being in offices, but I think all of us miss the community that it can create.

And so, you know, again, I think if we're thinking about what the future of work looks like, it's, well, how can we get the best of being virtual?

And then also, you know, bring back some of that, that community as well.

Yeah. I can't wait for the czar of serendipity and to wear shoes that aren't flats.

I was wearing shoes. All right. We only have one more minute left, Matthew.

So I want you to pretend it's 2026. So we've had a few years of our opportunity to reinvent a better way of working.

What is the thing that you're most excited that has changed or most surprised that we're still doing the same way?

I, you know, so I, the one thing I know for sure is that whatever, wherever we start, isn't where we're going to end.

And, and what I'm excited about is that there are going to be literally tens of thousands of experiments run by other companies everywhere, everywhere else.

And so, I mean, I can see a world where we decide we all go back.

We actually going back in the offices better.

I can see another world where we say, actually, why are we paying for all this real estate?

We should all just, you know, move to completely virtual.

And so I am, I'm pretty, I really don't know what the future holds, but I'm, but I'm excited to help invent it.

And I appreciate you and all the work that your team is doing to, to shepherd us through this.

Yeah. Thank you, Matthew. I'm excited to be a part of it.

I'm excited for what the future holds and I know there'll be grapefruit La Croix in 2026.

Don't have one with me. All right. Thanks, Matthew.

A lot of time. Take care. Bye -bye.