Future of Work with Dropbox COO Olivia Nottebohm (CXOTalk #671)

As you mentioned, I'm the COO of Dropbox. I have an amazing leadership team that covers sales, marketing, customer success, business development, people, comms, and brand.

There is so much, Michael. It's been quite a journey, not only for our customers but for our employees and broadly in the world at large. For our customers, we saw early movement and spikes in trials and usage as customers and future customers were considering and using Dropbox in the quite quick shift, as we all know, to work from home. We saw them getting to know the technology and understanding the technology and also understanding the broader ecosystem that Dropbox leverages in order to provide a full solution to our customers. We saw Zoom integrations go up by 20x. We saw Atlassian and Slack all being used while on the Dropbox platform, so we could see, okay, these are folks that are working from home. They're using us for their inflow work and they're trying to focus and get their job done in the middle of all that's around them. Then we also saw immediate needs. We saw hospitals that needed us immediately to manage their beds and how to do patient intake. We had a hospital in Boston who we expanded overnight to make sure that they could do that. We saw the Red Cross out of Italy using us. All of these organizations that not only were in the world of move to remove but also in the world of actually responding to what we were experiencing globally at the time. In a way, the key theme was suddenness. It was quite an immediate shift. I'm sure you felt it as well, personally. I know I felt it. I joined Dropbox on February 6th, and on March 6th, I was sitting at home, and all that went with it. We're really here to help our customers go through that shift.

One of the things we're trying to do is be very thoughtful about what is this new reality. Drew, our CEO, has thought a lot about it and continues to really lead our thinking on what is it about this world that we want to keep for the long-term, to your question, and what is it the parts that we, when given the opportunity, want to go back to normal. I would say there are actually a lot of elements of this that we now have the opportunity to design the future of work. Obviously, we shifted and we adjusted, but there is also this opportunity to say, okay, what is the ideal end state? Of course, as a technology company, we think deeply about how do we enable that end state. We see that as an opportunity. We also see that as an immense responsibility because if we can figure this out, then we can help customers and users all over the world operate in this new reality. We take that responsibility very seriously.

We think about the different dimensions of it. We think about what are the important elements of people physically being together. What is the kind of work for which one physically needs to be with a colleague or a peer or in a team environment? This is, again, end state, right? In the U.S., anyway. In many places, we don't yet have the luxury of living that, but we really are trying to think end state. Then we think about, well, actually, what are the elements that are potentially better done in a remote and distributed way? What are the benefits that a company and a team has when they're able to work in a remote, distributed way? There are a lot of benefits. One of the ones that I care passionately about is diversity. I think, and the leadership at Dropbox believes, that the more distributed remote work that we have, the more opportunity we have to hire and engage candidates that otherwise might not want to move into the hub of the Bay Area or the hub of New York or some of these places that come with high living expenses, complexity in terms of work/life balance, long commute times, all of these things. For us, we see that element of it really as an opportunity to hire a much more diverse employee group as we figure out this long-term mixture of being able to work from home as well as being part of an office. This notion of being able to hire diverse teams is very heavily enabled by the remote distributed workforce, or the capability, the ability to work remote.

We play a couple of roles. The first, I would say, is choice. Our first desire is to make sure that people who are trying to get work done and trying to collaborate on the personal side or in a business environment have choice and ability to seamlessly do that collaboration. We view ourselves as a platform, a Switzerland platform, in which our customers and our users can use different applications that they need to do their job but in a very, very seamless way. They're able to be on the Dropbox platform but they're popping into Zoom, they're using Slack, or they're using Atlassian – you name it, any one of those integrated partners that we have. But they're coming back and being at home in Dropbox.

It's about that easy user experience, that it's seamless, it flows. You're able to stay in flow, so you're able to use the technology to make sure that you don't get notifications if you're trying to focus and that you're able to be interacting with only the people you want to be interacting within that moment of flow to do the work you want to do. The product teams think deeply about really starting with the customer. What is the customer experience? How do you take all the noise out of what otherwise seems to happen in our day-to-day lives? Very much the focus is that customer experience and that ease of use that we pour a lot of time and energy into to enable folks that are working on our platform. I would say our mission, as a reminder, is to design a more enlightened way of working. Drew and the leadership team at the time that they came up with that firmly, obviously are passionate about that as am I. It seems even more relevant now in this new world where we do, we need to figure out a more enlightened way of working as we find ourselves in the situation that we are in today.

We have hundreds of millions of users and we take that very seriously. We know that they're there because they love the product and they love the ease of use. For us, we want to make sure to continue to do that. You asked the question of how do we think about overall operating at that scale. We start with that organic adoption and we know that our job is to deliver an enlightened experience for those users as they use us in trial or if they sign up for a basic account or as they move to additional functionality that they need. Our history has been this bottom-up adoption of people all over the world that just love the product and we continue to be responsible and feel very accountable to drive that ongoing, amazing customer experience.

Well, we really think about it, Michael, end-to-end. As many folks are familiar with, there's this process called New Product Introduction, or NPI, in the tech industry. We think about how we bring and how we take the input of all of our customers and the usage that we're seeing on the product itself, use case, and jobs to be done. The design team, the research team, and the product team take that very seriously and really just do an amazing job of taking all those inputs and then also thinking in a visionary way about, 'Hey, what are some things that maybe our current users today haven't quite thought of but, in the future, we think this would be incredibly valuable to bring to our customers?' It's just a delight to see those teams in action. I would also say, we take very seriously what we call post-sale and the loyalty loop. Okay, now a customer is using us and they're giving us feedback. We provide these community forums for customers to provide us feedback at scale but we're also talking to customers. As you know, before this, I was just on the phone with a customer getting feedback. Those customers, we take that with great importance because those customers have taken time out of their day to tell us what's working and where they would love our help doing another job or expanding the functionality in some way. We take that customer feedback loop also very, very seriously as we think about how to design products for our customers and future customers.

Yes. And pretty darn quickly, too. Again, my hat is off to not only the product team and the engineering team, but also our infrastructure team and our platform team because, as you all know, there is a huge infrastructure engine that is so amazingly highly tuned to be delivering what it is that we're delivering from a product perspective. It's really an enormous task and ones that the team take very seriously and, I think, do a great job of it. It really is that ongoing input from the customer and we always have our ear to the ground in terms of what the customer needs and uses and how we provide that at scale in a way that provides value over time and also continues to provide value over time. We very much take seriously that our customers are here with us but we have a commitment to them to continue to increasingly deliver value over time and we're hard at work doing that.

The human element is really important. How do you build teams that feel a human bond to each other? I think, at the end of the day, people come to work most often for the people they surround themselves with. How do they engage with those people and how do they work as a leadership team? What we've been trying to do and really hats off to a number of teams at Dropbox that are so thoughtful about this. The people team and the comms team put a tremendous amount of thought into realizing that, okay, we need to be engaging much more frequently with our employees. We need to be communicating on a frequent basis. We've really upped our all-hands and the expansiveness of our all-hands. I know that we, as exec staff members, have been sending all out weekly emails to the entire set of teams that we work with. For us, we think about continuing to build that human connection and feeling a real sense of need to communicate. What in the previous world might have been felt a bit as over-communication, I think you can't overcommunicate in a remote world. I think that would be my primary thought. It's important to communicate on all fronts, both how we're going to set boundaries between work and everyday life; how we're going to focus the company, set goals for the company, and deliver on the things that we said we'd deliver as a company; what things we're going to do as a team to build the team and to drive people's development over time. There are a myriad of things to be communicating. I would say that that ongoing interaction, I believe, will continue to be one of the most important things for us as we operate in this new world.

We spend a real portion of time on it. Yeah, it's because people are what matter the most. Making sure that our employees have everything they need to do work, are able to focus, and have the resources they need, we take that very seriously. There are teams at Dropbox who really spend countless hours thinking deeply about it. It's really across all functions. We're coming together and making sure that we're making decisions at the right pace. I saw that early on. I would say I was a little bit more of an observer. It was month one in my job and this crisis management team came together. It was across all functions. We were meeting daily and making decisions daily about what our employees needed, what guidance we should give, what communications we should give. I have to say it was a delight to see that cross-functional team come together and just be running through the paces to constantly be thinking about all the elements of what the employees needed.

Collaboration is at the heart of Dropbox in the sense that our goal, again, and our mission is to design this more enlightened way of working and engaging with each other as humans, as individuals, and as team members. The technology we use on a day-to-day basis is obviously on Dropbox, right? We're on the Dropbox platform, so we're living and breathing that very much so. Of course, we use other applications, which is what we expect, right? We do want to give our customers choice, and that's why the Dropbox platform is designed in the way it is, very open, integrated broadly into the ecosystem. We live and breathe that reality as well. The teams very much feel like it's by dogfooding our own products that we're able to really make sure that, yes, this is in fact what we're testing for our customers. By the way, if folks aren't familiar with dogfooding your own products, it's kind of trying them yourself before you release them into the world. As one board member said at Dropbox, you could also think about it as drinking your own champagne, which I thought was a nice way of framing it. It's really the humans at the center. Dropbox has a very unique culture and we take that very seriously, so it's less about tech or non-tech and it's more about putting the individual and each other in a way that we really are coming together as a team and working together to drive to an outcome.

Very much so. If you look even back into our history, there were other players at the time that were offering ways to share folders, collaborate on folders, and share content. But again, I wasn't here. Real kudos to the innovation and the leadership of Dropbox that just came out with an amazingly technically complex and very advanced way of solving that problem but, from a user perspective, it was simple and easy to use and you just couldn't help falling in love with it.

If I were to just break it down, one of the dimensions in terms of the future of work is, again, this intentionality of when do you need to get in a car and drive to the office and be with other people in a physical room. Then when actually are there immense benefits of working remote and distributed, really being purposeful about that and mapping that out? Where are the ways in which we support that in-person work and how are the ways in which we support that more distributed work? The other element, of course, is this diversity element that I mentioned before, which I've been very passionate about. How do you get the benefits of, 'Hey, is there a much higher ratio of in-office to remote? How do you use that to a company's, a teams, and really the world's advantage in engaging more diverse talent and bringing those folks into your thought process?' We all know that you come up with better ideas if there is more diversity. That also is a really important element of the future of work. I would also say that because we believe that there is a higher level of remote distribution in the future of work, then how do you really make sure that your employees have everything they need? How do you make sure they have all of the technology it takes to work from work, not only Dropbox itself as a platform, which obviously we believe plays a huge role, but also the screen, the keyboard, the chair, and all of that sort of stuff? We've had to think about that. We've obviously provided that to our employees to make sure that when they are working remote, they're comfortable and they're able to do it in a really seamless way. Then also, the other elements of that work/life balance, so how do you start to build norms around, okay, yes, you're at home, but you also do need help from your teams and others around you to set boundaries so that work ends at a certain time and then you get to go be with whoever it is or do whatever activity that you want to do. I think that's also an element of the future of work, which is how do you enable and reinforce this boundary-setting so that people can be in flow, get amazing work done, and then turn it off and go do things that rejuvenate them or reenergize them so that the next day they can do some great work again?

Exactly. Yes. Obviously, we listen to our employees. We are asking our employees, 'Well, how often would you think about needing an office experience?' We really want to make sure that this is something that we're thinking about intentionally. Obviously, you see many companies in The Valley doing the same, but we're really, really trying to be thoughtful about the intended end state.

Very much so, yes. It's a team effort, I would say.

We couldn't be here where we are today without Sylvie, who is our CIO. She's incredible. Her team is incredible. It was almost awe-inspiring and almost unbelievable. One day, we were in the office. We had a meeting. We decided, okay, we'd be working from home. I didn't notice any difference. That just is a huge testimony to an IT team. It was really, really incredible how our entire employee base was able to be remote within 24 hours. That's a huge testimony and I would say it's a strategic asset to have an IT team that's able to do that and pull that off is really, really impressive. They continue to be very purposeful in the rollouts that I see, in the simplicity that they're driving for Dropbox and on behalf of Dropbox. It's great to see the thought leadership there and we wouldn't be able to do this without them, for sure.

I've heard many stories, amazing stories like yours, of these rapid transitions to work from home. But now, people are trying to figure out what to do next and it's really hard for all the reasons that we know. As you mentioned, we operate at scale, a tremendous scale, and that's fun and we have a huge responsibility. It also means that we have very different types of businesses, companies, and individuals. We have individual consumers. We have professionals. We have small teams, market teams, enterprise teams. It is really an amazing thing that because of the love of the product and the organic adoption, it shows up kind of in all customer segments. All to say that it's not a simple answer to your question in terms of how they're thinking about the future. I think it comes in many different flavors for many different types of companies and customer segments. But we are seeing that there is a bit of a new normal, for sure, this need to use technology as a platform and at scale. I'll give an example of the University of Michigan. Now, their students are all using Dropbox because now they're taking classes remotely. They're onboarding remotely. It's truly a new world. You can imagine a scenario in which, in the future, that's kind of standard. Whether people are going into schools physically or not, there's an understanding that there is this technology platform that offers choice and creates choice in how people interact and go about their business, their education, or their nonprofit. I think that element that has been now kind of driven by this reality that we're in will take on a more permanent place in how companies, nonprofits, and educational institutions operate, for sure.

Sure. If we think about the class, what does it mean to go to work? I think, at least five or so years ago, we would imagine it as you get in your car, you show up at the office at 8 or 9 o'clock, you spend the day there, you work all day, you leave the office at 5:00 or 6:00, you come home, and that kind of repeats itself. Obviously, you throw the realities of life in there and people start to opt-out. For whatever reason, maybe people can't get child care, they can't get someone to take care of their elderly parent, or the commute is just physically too long to make it worth being in the office for that amount of time – all of these things. I would say it affects a lot of people. It's not just a certain population that it affects, but it does affect certain populations more than others and you see that in the numbers. For me, this increase in flexibility is really what it comes down to. I firmly believe, and as the leadership at Dropbox, we firmly believe, should give us and we see it. When we offer more flexibility, we get more diverse candidates. That's really important to us and we have that as a key value for our company.

Accountability is key. I firmly believe that. In life, even if it's setting self-goals for yourself or setting team goals if you're on a soccer team, like my daughter is, or at work, you set goals because that holds you and the folks working towards it accountable to try to achieve those goals. Not only do you set the goals, but you check in on those goals and you say, 'How are we doing against these goals?' If it's not working and you're not pacing quickly enough to the end state that you're trying to get to or that goal that you've set, then you take the time to say, 'Okay, why aren't we where we need to be? What can we do about it?' All of those things. I think the same holds true for the topic of diversity because it's a fundamentally important topic in our lives today. Yeah, I'm all about, you actually have to set goals, and the leadership at Dropbox is all about it. We set very clear – we really are thoughtful about where we want to be and it's not haphazard or, if it happens, that's okay. We're very intentional and thoughtful about that so that we can really continue to move the ball forward.

Yeah, we're checking in on how we're doing. We want to make sure that we're moving that ball forward and the team does an amazing job of that. Also, I would say the second element of that is resourcing it. It's not enough to set the goals and to try to move the ball forward, but actually putting the resources against it that are necessary to do that.

At Dropbox, we take that very seriously, and our people team take it very seriously and really do put in that investment because you can't have one without the other. You can't set the goal and then not resource it. It's really important to us and we put our resources where we say our intent is. Those two things need to come together and I'm really pleased and honored in seeing how it comes together at Dropbox. There's always more work to do. I would not say that, check, we've figured it out. I think there is always more work to do. We take that very seriously as well. We keep, keep pushing.

There are a couple of elements of this. One is your processes need to be very explicit and very well documented. They need to be as simple as possible because it needs to be easy to communicate to someone who is joining in a remote world for the first time to your company. We've really thought about what is the onboarding process. There's been great work on that. But then, what are the processes that we think are key processes that stretch across the company and make it so fundamental to how we do work that really everyone needs to be trained up on it and have a very clear understanding of what the roles and responsibilities are. A hundred percent, those processes are really important and we've been doing work on that at Dropbox to really make explicit, even more explicit, some of those processes. I would say the other element is figuring out the way to do human connection—and I know we all know this—is not stopping in the hall, grabbing lunch together, peering over someone's shoulder at their desk and saying, 'Oh, that's how you do that model!' or whatever it is, that level of apprenticeship that in-person played a large role in. How do you make sure people are connecting on a personal basis, that the apprenticeship is occurring, that the development is occurring. We've been also thinking a lot about that. How do you create forums for people just to be relaxed and hang out? At my staff meetings, we think about how we're doing professionally, but also how are we doing personally, going around, and sharing that and being really open with each other. This is an example from my world. I have two kids who are at school remotely, and so it's a battle for wi-fi sometimes. There is a whole reality of that person that you're just seeing as a two-dimensional image on the other side of Zoom that you really have to get to know in a very intentional way because that in-office or that in-person interaction is not happening. That's an important way as well. How do you do that that isn't necessarily more videoconferencing because there is also this reality of there is only so many hours of videoconferencing someone can do in one day. Do you just jump on the phone and have a chat? Go for a walk while doing a one-on-one on the phone. Really, mixing it up so that people can have the personal interaction but they're also not tethered to the videoconference.

Well, I would just say there are certain elements that we might want to go back to the future on, picking up the call. I know I did a couple of one-on-ones yesterday and I was on a walk with my dog for all of them. The folks that are on the call, I'm sure, were doing other stuff that they kind of just needed to do to get their head cleared. Giving each other permission is really important that, yeah, we're going to all figure out our own way of doing this and it's okay. It's okay not to be sitting there perfectly on the other side of the screen. If you've got stuff to do or you just want to go outside and need a bit of a mental break, I think we do need to figure that out and be kind with each other about what that looks and feels like.

Very much so, and I do believe that one of the things that we take as the kernel of Dropbox is the humanity of our products, of meeting our users where they are, and meeting our customers where they are. How we engage on a day-to-day is a bit of that as well. If I decide that what I really need is to go on a run at 7:30 and I show up in my running outfit to my 8 o'clock staff meeting, I think that can start to be okay, right? I mean that's what I do. I think, especially at this time where there is a lot going on, that people just want to be themselves as much as possible. To the extent that companies and cultures can allow that, I think that will be healthy and good, both for the employee and the individuals. You've just got to believe if you do the right thing for your employees that that's also great for your company, but really starting with the individual and the culture first.

I would say, just be kind to yourself. It's a hard time. There have been a lot of changes. I know I make mistakes every day. We all will make mistakes as we're on this journey. But learning from those mistakes and understanding, okay, this is a new world for me. How do I operate in this world? As a mother, I have a lot of adjusting to do, as I mentioned in-home school. As a wife, right? My husband is also working from home. Obviously, as someone who is trying to really do what's right for Dropbox, I have those elements as well. Of course, you're not going to always get them all right. That's just me. People have other elements that they're focused on, whether it be other family members or things that they do that are important to them. I think kindness, kindness to yourself is probably one of the most important because it's different times. We'll get to that end state, that very intentional end state. But until then, we'll be kind of bumping along a bit and that's okay. It's not meant to be perfect.

Thank you, Michael.