#163: Drift Is Going Digital First!

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This is a podcast episode titled, #163: Drift Is Going Digital First!. The summary for this episode is: On this episode of Seeking Wisdom, DC sits down with Dena Upton, Drift's Chief People Officer, to discuss the company's recent decision to go digital first. Together, they talk about what this means for company culture, hiring, and the fate of our office space (hint: Conversation Spaces are coming to cities near you). You're not going to want to miss this episode where DC and Dena uncover what the future of work looks like. Tune in! Like this episode? Be sure to leave a ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ review and share the pod with your friends. You can connect with DC on Twitter @dcancel @DriftPodcasts For more learnings from DC, check out his weekly newsletter, The One Thing. You can subscribe here: https://www.drift.com/insider/learn/newsletters/dc/

DC: Before we get to the show, did you know you can get more insights just like the ones you're listening to right here on Seeking Wisdom, delivered right to your inbox? Sign up to get my weekly newsletter, it's called The One Thing, at drift. com/ dc. And we're back. This is Seeking Wisdom. I'm going to talk to a special guest that we have today. Dena Upton, our Chief People Officer, is here to talk about the big news that Drift is going digital first. How are you doing, Dena?

Dena Upton: I'm good. I'm excited to be here with you, DC.

DC: I know, I wore my special whites for today. Look. Drift white.

Dena Upton: Nice. I can see them.

DC: White on white sweatshirt. So if you can't see, if you're listening to this podcast, go to our YouTube channel and you can see the white on white, the creamsicle.

Dena Upton: I love it.

DC: We call it the creamsicle hoodie. So I'm going to give a little background on this episode. When we founded Drift six years ago, we made it very clear that we value this in- office experience, and that stayed that way for five and a half years, until the pandemic hit about 10, 11 months ago now. I believe that that in- office culture created this environment that helped us achieve hyper growth and become to the company that we are today. But one thing that I kept telling the team when we went into this from the very beginning was that we weren't going to go back to the way the world was before, that we had gone through what I believed was this one- way door, and we couldn't go back to how it was before. That was hard to talk about, as we have for months now. But I wanted everyone to be in this mindset that we couldn't go back. What did you think when all that was going on back in March, Dena? I think you were ready to go on a sailboat and go around the world.

Dena Upton: Actually, I was coming back from San Francisco, a meeting in San Francisco. It was end of February. And San Francisco is a little bit further along, like two weeks along from what was happening. So everyone had masks restrictions on offices. So when you told the office we were staying home, I thought this was maybe a two month or three month thing. Oh, we're going to see everybody again. But here we are almost a year later and we're still in this virtual world.

DC: How do you think your own thinking and your own feelings, your emotions have gone? What have been the waves that you've gone through from the beginning to now, which is probably 10 or 11 months later?

Dena Upton: Well, it has turned my hypothesis or my understanding of things on its head. I always thought, okay, you can't hire somebody virtually with just doing Zoom calls. You've got to meet them. You have to interact with them. I thought, I'm not going to be able to connect as well with new hires or the team in the same way, but we've been able to do it effectively for three- quarters of a year. We've hired new leaders. We haven't met them in person. You can still get that connection if you do it in the right way.

DC: How many people do you think we've hired during this time since March of last year?

Dena Upton: About 130, I think.

DC: Isn't that crazy?

Dena Upton: Yeah.

DC: That many people remote.

Dena Upton: I know, that have never stepped foot in our offices, which we have always thought was the epicenter of our culture. The rituals that you and Elias put in place, we're realizing the value and the importance of putting our arms around the team twice a week. Those rituals were really important, but we've just doubled down on them now. Because when you start to live in this virtual world, you end up just connecting with the five or six people that you're working really closely with on a project. And I think Monday metrics, Friday show and tell has allowed the whole team to get together, so you have some sense of normal in the chaotic world that we're living in right now.

DC: And your own background, so before coming to Drift, you were at LogMeIn and various other companies before that. Have you ever been in a remote only environment?

Dena Upton: No. It's always been flexibility at my past companies. I mean, LogMeIn, we sold virtual software. So if we didn't eat our own dog food, then we couldn't really sell it. But it's always been hybrid. It's been hybrid models. And I think that's one of the interesting things. I'd love to understand what was going on in your head when you said," Okay, we're not"... You could go 100% virtual, you can go what we're doing, and then you can do this hybrid, just go back to the way that we were before with a little bit of flexibility, but you didn't want to do that. Why?

DC: That's probably one of the more things that we get asked about when it comes to the digital first announcement that we did, which is, like you said, there's an option to go back fully in office, which is not an option today, but you could imagine maybe that would be true in the future. The other option is to go fully remote. And then there's this middle option in the middle that is some combination of remote and in- person office. And I will say that just a general way that I try to think about things is to always pick an edge. In this case, the edge would be office or remote, and try not to compromise and be in the middle because you usually don't get anything or you don't actually produce anything remarkable when you're in the middle, when you try to compromise and blend the two. That's just a background framework, how I always think. But then when it comes to this decision, I'd go back in the past and just say, and I know things can be different each time, but I had a hybrid company at one point. I had a fully remote company that I worked with. This is the first place that I worked with Elias, my co- founder, and it was fully remote. And then it over time became hybrid as we had more and more of the concentration of the company in Boston. So we got an office here and then we had the other less than half of the team in San Francisco, but they were fully remote. And we had a couple of people throughout the country, throughout the world. And what we saw there was that it was almost impossible, and the tools have progressed since then, but it was almost impossible to not make the people who were not in the," HQ," which in this case was Boston because that's where the most people were to feel left out, to feel out of the conversation, and the conversations that they were often referencing weren't conversations that weren't like strategic conversations or the company meetings or things like that. They were just like the water cooler, the relationship building, the shorthand that develops when you're with someone in person all the time, like all those things, they were missing. They always felt left out. So, I think about that experience. I think I don't want to recreate that if possible again, because one of the things, one of the founding reasons that we started Drift was that we want, and it has been one of our goals, has been to build this new type of this new face of corporate America, when we think about diversity and equity. And it was really the equitable part of it that really wanted me to stay away from hybrid because I think in the case of that past company I described, it was not equitable because what would happen over time was that not only did those people feel left out, but naturally when you're spending more and more time in- person with a group of people, those are going to be the first people that you're thinking, even if you're looking on a performance base and whatever, those are the people that you're going to tend to favor when it comes to, even unconsciously, to promote, to give new opportunities, to ask them to try out a new project just because they're there, just because it's easier. It's the path of least resistance. And the important thing... This is a long answer to your question, but the important thing to me for Drift is really to create this role model of an equitable company, where it is a level playing field. And I thought a hybrid approach would not create a level playing field. And in a lot of ways, I think diversity, we talk about diversity a lot at Drift and outside of Drift and in the world. But diversity isn't the goal for me. That is like one step. The goal for me is equitable, which is way beyond that, which is level playing field, no matter where you come from. Diversity, and I think often can be lost in today's conversations. Diversity can be we need three more of these and four more of these and five more of these, but often those are junior roles. Those are roles that don't have the same access for progression within the company. So the real conversation I think is about this, and this is not the conversation for today, but is about equity.

Dena Upton: Yeah. And why now? We've got some time. We don't know exactly how much time we have. The end goal keeps moving, but why announce to the team now?

DC: We debated that going back and forth. We had told the team, and now the time that we're filming this is January of 2021. And we had told the team that we weren't going to come back into the office, and we had announced this a while ago, until at least June of 2021. So we had in theory six months, five and a half months left before that expired. One thing that we saw happening was that this uncertainty hurts when people are trying to make life decisions. A lot of people, a lot of our team, especially our younger team, live in the city and they have roommates. They have very small spaces that they're all working from home now. And it's hard to do, be on Zooms, like we're doing, Zooms or video calls or things like that, when you're have a whole bunch of roommates in one room, especially if you're in sales or support, where you actually have to get on the phone often or on video conference. So they were starting to make life decisions about, do they want to stay in the city? Do they want to move? And we thought if we could announce earlier and give them some certainty that they could make those life decisions, maybe they would move out of the city. Maybe they wouldn't. Maybe they would move out of the state. Who knows? But they would make bigger life decisions than they could right now.

Dena Upton: You were talking about Drift being very intentionally an in- office team. It's how we recruited. It's how we talked about it. Do you think the team was waiting for permission from you on this new... I mean, we surveyed the organization. But I don't-

DC: Yeah, tell me about that.

Dena Upton: ...I don't think they fully could visualize what, when we asked them," Okay. Would you like to come into the office? Would you like to be remote?" I think they could only visualize Drift in the office. I mean, the people that were part of Drift prior to us-

DC: Yeah. Not the 130 we hired.

Dena Upton: Right, right. How did you announce to the team and get them comfortable with this new way of thinking? I think we're still working on it a little bit.

DC: I think we're still working on it. I will say that I try to have this continuous conversation for the majority of the time that we've been in this lockdown to say that we weren't going to go back. This idea of the one- way door, the two- way door. The one- way door meaning that if you go through it, you can never go back to the way it was before, it only works in one way. The two- way means that it's an easy decision. You can go in and out and it's not a problem. So we had gone through a one- way door, but I think no matter how much you say that, it's hard to reset people's thinking. They're still thinking about the Drift of before, the Drift that was in- office, the energy that we got from being in- office, when they were going to see their friends. The more extroverted they were and the more social they were, the more that they missed that connection and that bonding. So I think it was really hard for people to even imagine a world where we didn't have an office and that that option was gone. So I don't think there was an easy answer. I think we're still working on it and it's a progression. I've heard from a lot of people when I announced it, when I sent an email announcing this and a video, internally messaged me privately, a long list, but I'm sure there's an equal number of people who aren't happy that there is no office. But the truth is that the office is not... We're talking about fictional things. If you're not happy that you can't go back to in- office, well, we can't go back to in- office and we can't go back to in- office anytime soon, even if we wanted to right now.

Dena Upton: Yeah. I think they're missing the way that it was, the way the world was, not necessarily what it's going to become. And so I think there's a little bit of a loss of that. Whereas you and I have been able to digest it because we've been talking about it for a while. I think others, there's a bit of mourning. I think there's a little bit of mourning.

DC: There's definitely mourning. And it was funny. I think even from our leaders, we had a lot of questions when we were announcing this about, well, how are we going to do onboarding? How are we going to hire?

Dena Upton: Well, we've been doing it.

DC: How are we going to have energy? And I think you said, your reply was like," We've been doing it for 10, 11 months. We did it for 130 people so far." But in their mind it was a temporary thing. They didn't think we were actually doing those things, and the truth was that we were successfully onboarding and bringing on new teammates every single day, every week since this started and in some very, very senior, the most senior hires that we've made as a company.

Dena Upton: Right. Well and I think it frees the mind to think of what is possible instead of holding onto what was before. And I think it opens up a whole new network and way of communicating with people through asynchronous communication, some of the things that we used even when we were in the office.

DC: Yeah. It's a progression. Even like I was talking to Maria, who's our Chief of Staff about some announcement things and some stuff inside company meetings and kickoffs and stuff like that. And one thing for her and Lacey, who's our Head of PR, that I talk about is to try to reframe their thinking because they are both social. They miss the office. They want this energy. And each time that they think about doing something, like an internal company thing, they want it to be live. They're like," Let's have a live this and a live that and a live that." And my push is we've got to think more about asynchronous now, because we now have... and because of this going digital first, people are moving to more locations. We're across more time zones. We have people in Australia, we have people in the UK, we have people all over the place. We no longer to think about Drift as this Boston thing of let's get everyone live. And it's like, no, we now have to think and lean into some of the tools that you were talking about. And luckily we created one of them, Drift video, which we use extensively to communicate asynchronously when you have people all different time zones, but also people who are juggling because of this digital first reality, kids at home, taking care of people, schedules conflicting with roommates, all sorts of things that people are dealing with now, we have to take into account in the way that we communicate.

Dena Upton: Talk to me a little bit about outcome based thinking, I think this coincides with focus on outcomes, not face time, not desk time. We're doubling down a little bit on that.

DC: Yeah. I mean, it's funny how things converge over time. It's been a progression in our stages as we grow, that moving from a place where we were all in one office and it was really important where that everyone was there so that we could have shorthand and osmosis could happen and we didn't have to have everything formalized from a training and onboarding standpoint. So we just learned and worked. So face time was important. And as we've grown and as we now cover more places throughout the world in terms of where people live who work at the company, now we're starting to think, and we become more mature, things are more measurable. And now we can think in terms of, okay, now let's measure people on output or their outcomes versus if we see them, if we don't. That takes time. That took us years. And that also takes a maturity that has to be there from a leadership standpoint, to be able to coach people through that, especially because we hire a lot of people straight out of school into some of our roles. There's a lot of coaching that needs to happen.

Dena Upton: What about people have asked, okay, does this mean you're going to lessen your real estate footprint because you're going digital first?

DC: The reality is that we're not, at least in the short term. We still have all of our leases and we will keep those offices as something that we're calling conversation spaces. So a place not to work from, but a place to collaborate from. So with teammates, with customers, with people in the community to bring people together with the purpose of collaboration. Very different than bringing people together to work from the office.

Dena Upton: Yeah. And I think it just makes that interaction just much more intentional. So when they know, I know I'm meeting with a customer, I know I'm meeting with a teammate. I'm working on something together. Solo work will still be done at home.

DC: What are you worried most about with this switch?

Dena Upton: Well, for us on the recruiting team, I mean, we have a ton of positions to hire, and this helps us. It helps us to get to talent that would have normally not seen us. So, diverse talent. It also will allow us to get closer to customers. So that time zone differences, that's all going to help. I think for me, the biggest thing is just thinking differently on how you bring teams together, how we communicate, how we connect. I think part of the conversation that we're having earlier around having an equal playing field, I think the move to go digital has reinforced the general hygiene around connecting with teams to make sure you're deliberate and why you're connecting, why you're running meetings. My only worry is I hope that we stay as disciplined as we always have been around a lessened meeting culture. I think we need to make sure that people are not just replacing meetings with interactions in the office. So that efficiency piece is where I just want to make sure that... and I also want to ensure that our team is... Your office is always there if your office is at home. And so compartmentalizing when you work and when you shut off creativity is needed. That's the piece that I just have to ensure our... and that's a good management, that's good leaders, making sure that they're connecting with their teams, that they're not overworking because work is, you can always see it.

DC: It's always there. That is true. Do you think you're working more?

Dena Upton: I mean, I'm more efficient. For me, the commute into the office was only about 25 minutes, but now I can go for a walk or I can go for a run. I can pick the kids up at school, where I couldn't before. So it's providing me flexibility that I didn't have. I don't think I'm working more. I think that I'm spending a bit more time connecting with the team than I did before, because I do have team members that are outside of Boston. So I feel like I'm spending... When I was in the office, I would see those teammates that were in the office a lot. And now that I have teammates that are in Charlotte and New Hampshire, in San Francisco, I'm spending an equal amount of time socializing with them, so to speak, I mean through Slack and through connecting and through video, I think I'm more equal with wherever my team is because I don't see anyone in the office, if that makes any sense.

DC: No, it totally makes sense. How do you think, and are you excited for, how do we drum up excitement? We had the in- office excitement that naturally came with the loud music and the gongs ringing and all sorts of crazy stuff and people filming stuff and visitors walking through and this kind of thing. Do you think we need that? And if so, how do we create it?

Dena Upton: I think we've been able to create it with some of those... For our team, I think we've been able to, we have the excitement and music that we... For Monday metrics and Friday show and towel, you've got that same excitement. Our Zoom chat explodes when we do Monday metrics, which is time where we bring the whole team together to go through metrics. And then show and tell, I think show and tell attendance and Monday metrics attendance is ramped up because it's a big part of getting to know the team. So I think that that excitement is there. I think it's going to be really interesting when we bring the team together. So if we fast forward to we're in a normal world, non COVID times, and we can actually get the team together. I'm super excited. I mean, I haven't met Todd, our CRO. I can't wait to meet him.

DC: None of us have.

Dena Upton: No. I mean, I can't wait to get... I feel as though I'm going to be super excited. When we have a new hire gathering, or whatever we're going to call it, to bring new hires together, I'm going to be super excited to actually see those people, where sometimes when you're in the office, if you need to stay a little later for a new hire gathering, it's like, okay. I think there's just going to be a lot more excitement for when we do get the team together than when you're always in the office and it's an added activity or an added event. I think those events are just going to be a lot, they're going to be special and treasured. And we've just got to bring the excitement when we have those opportunities of bringing the teams together.

DC: Well, luckily the team has you and you're super exciting, unlike myself. This is the most exciting I get. So, thank you for joining me, Dena. This has been amazing.

Dena Upton: Thank you.

DC: Don't forget, you can find Dena Upton on LinkedIn, on the Twitters, on all the places that you'll find. I'm DCancel on Instagram, Twitter, et cetera, et cetera, and LinkedIn. And you know what to do. Please, don't forget, this is the universe's only certified six star podcast, so leave a like and leave a six star rating for us in the comment. Leave a little shout out to Dena. Let's see if Dena can get some shout outs in the comments. Thank you for joining us, Dena.

Dena Upton: Thanks, DC.

DC: All right. Cheers.

Dena Upton: Bye.

DC: Let me know what you thought of this episode by texting me at 1( 212) 380- 1036. Again, 1( 212) 380- 1036. Now if you're looking for more leadership insights, sign up for my weekly newsletter, The One Thing, at drift. com/ DC. Every week, I'll share a habit, tool or mental model that's helping me reach my goals. I hope to see you there. Text me, hit me up.


On this episode of Seeking Wisdom, DC sits down with Dena Upton, Drift's Chief People Officer, to discuss the company's recent decision to go digital first. Together, they talk about what this means for company culture, hiring, and the fate of our office space (hint: Conversation Spaces are coming to cities near you). You're not going to want to miss this episode where DC and Dena uncover what the future of work looks like. Tune in!

Like this episode? Be sure to leave a ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ review and share the pod with your friends. You can connect with DC on Twitter @dcancel @DriftPodcasts

For more learnings from DC, check out his weekly newsletter, The One Thing. You can subscribe here: https://www.drift.com/insider/learn/newsletters/dc/

Today's Host

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David Cancel

|Co-Founder & CEO, Drift

Today's Guests

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Dena Upton

|Chief People Officer