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Future of Work: Why Drift Decided to Go Digital-First with Dena Upton

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About the Episode

As companies begin reopening their doors and reassessing how work gets done, there are a lot of work models to consider. Will your organization return to in-office, go remote, or instate a hybrid model? Drift decided to forge a different way forward: digital-first. Drift’s Chief People Officer Dena Upton explains why they made this strategic shift and how it helps remove inequities in the workplace, build relationships, and provide employees a better way to work.

Episode Highlights

Meet Our Guest

With 20 years of experience working in HR, Dena Upton has seen many changes in the course of her career. She’s helped run human resources at leading companies like LogMeIn, Norkom Technologies, and now Drift, climbing the ranks from a manager to a member of the C-Suite. All these experiences have prepared her to take on the biggest question HR professionals have seen in decades: How will your employees work in a post-pandemic world? As the Chief People Officer at Drift, she’s answering this question by putting employees first and building a strong foundation for their next iteration of work.

Episode Transcript

Chris Byers: The future of work is being shaped by the advancement of technology and the evolving demands of talent. What changes could be in store for the workplace, the workforce and the nature of work itself? On this seasos on Ripple Effect, we're continuing our series on the future of work, exploring the answers to these questions.

I'm Chris Byers of Formstack, and joining us is Dena Upton, Chief People Officer at Drift. A LinkedIn post, written by David Cancel, Drift CEO, prompted us to reach out to Dena, which you can read in our show notes to summarize his words for teeing up our conversation. The post stated that we can't pretend we're going back to the world we had before and we needed to find a way to thrive and succeed in this new reality. And a hybrid approach was never an option for us. Why? Because I still believe that hybrid leads to an inequitable experience. Drift is now a digital first company. Well, this inspired us to reach out to Dina and there's a ton to unpack here. Dina's worked in HR for 20 years, and I'm excited to hear her insights on how this function has evolved and why it needs to continue to evolve to meet the changing needs and dynamics of today's workforce. Anything our audience needs to know about you that I've missed before we get into the conversation?

Dena Upton: No, I think the big thing for me is HR has shifted over the course of my career. Chief people, officers are the title is On the Rise. And I think it's a statement to the importance of the people function across organizations. People function being a partnership with the business to drive outcomes. I think the use of the word people is very important because it drives it drives decisions. And so I think that the rise in that being chief people officers, the people talent leader, but I think our historical connotation with the word HR was very reactive. The association with the people function is a proactive part of the senior most arm of the organization. And so I think the word people instead of are sort of connotes proactive management of the people function instead of reactive management, as it was thought of 15 to 20 years ago.

Chris Byers: So describe a little bit what digital first is. I'm not sure everybody will know exactly what that means.

Dena Upton: There's a couple of different angles that you can go right there in the office, which means you're in the office five days a week, one hundred percent virtual, which means that no office footprint or all of your employees are in their home offices. That's one hundred percent remote. And then there's hybrid, which is a combination of the two of them and what we're calling digital first and the reason why there's a distinction. We want everyone to be on equal footing. The idea is the majority of the time spent for individuals working in a digital first environment is their home office. But there will be we have conversations, spaces that will be available for them, for collaborative work. But the collaborative work, they need to be pretty intentional about it. So I think of digital first as a mindset shift, whereas hybrid putting a stake in the ground to declare what you're doing digital first allows you to understand that majority of your time is going to be at home. But there will be opportunities is what we're calling conversation spaces to bring the teams together.

Chris Byers: Well, if we go into kind of current times, it sounds like you've done a little bit of probably reaction, but at the same time saying how are we going to kind of think about the future? So talk to us about the decision that went into becoming digital first.

Dena Upton: It was a really hard decision and something that we didn't take lightly. We were historically an office company, both D.C. and only our founders were very vocal about that. And it was something that was discussed and reiterated in the recruiting process when people joined Drift previously, we wanted to make sure that could be in the office five days a week. And that in and of itself was sort of a repellent to some individuals entertaining the possibility of joining us. It was something we were really deliberate about. We all think that it helped us to become the company that we are today, both from a growth and culture standpoint. But what's been amazing is how quickly the company has changed because of what's happened with Covid. And we started to think about what is this new normal look like? We recognize what you probably read in the post from DC. Our founder has been calling a one way door. Things have changed and people have changed. We're no longer traveling. We're no longer going to restaurants and we won't go back to the way we were before. So we entertained a few options. We could go back to the office one hundred percent, just as we had previously, which isn't realistic. You could you could have a hybrid model where you go back to the way you were before with just a little bit of flexibility. Or you could do what we're doing digital first and we've always picked an edge and didn't believe that the hybrid thing is the right thing to do. Our founders had had a past company and they recognized when they were in the past, company was a hybrid model and it created an inequitable experience for individuals. So those people that were remote missed out on hallway conversations or missed out on a quick impromptu meeting that sometimes can happen at headquarters. And so we didn't want an equitable experience for people as we're starting to recruit people from outside of those hub locations.

Chris Byers: Well, I'm curious, your early on in this, if you kind of learned any lessons already that are maybe new or surprising.

Dena Upton: Yeah, I think we have lots of lessons, actually, but I'll highlight a couple. I think that we did survey the organization. So we said, would you like to go back to the office? One hundred percent? Would you like to be one hundred percent remote? And and we asked, would you like a different model? So the survey feedback was split. So a third. A third, a third. I think part of the problem was we didn't really paint a picture for what Digital First could look like when we asked that origin. Survey question, we've done a lot of work internally to explain, like, what is what do we mean when we say digital first? What does that mean internally? So we spend some time creating and talking about what are these conversational spaces. We don't have them. So people can't visualize what it means, what is digital first actually mean and why did we pick an edge? And so we've had internal conversations about what that means so that our team can visualize what will work look like when we go back to some sense of normal. Our teams, always known drift is in office culture where music was loud and people were connecting and there was activity in the kitchen and there was just a lot of energy that that was part of those office spaces. And it did kind of define our culture. And so we've got to double down on what will we gain by going digital first and what does it mean to the team here?

Chris Byers: Yeah, you've coined a term conversational spaces, which which is a bit how did you come about that and what makes that important?

Dena Upton: We're in the business of changing the way businesses buy from businesses. That's what we do. And we do it through conversational marketing and conversational sales. It brings the human element back into the buying process world. That was where the term came from. We wanted to make sure that we were deliberate about why we were using those spaces. So again, when I think about Drift going digital first, the majority of our drifters will experience in their office will be their home office. But when they are using what we're calling conversational spaces, they're intentional around why they're using that. So they're collaborating with customers, with other drifters or future drifters. So just really intentional. And that's why we've called them conversational spaces, because they're conducive to conversations with your manager, your teammate, most importantly, your customer.

Chris Byers: Well, the way you describe that reminds me of how pretty much every decision in business kind of happens, which is everybody translates it differently. I love that you're kind of beginning to share that experience. What advice do you have for people who are thinking about this conversation right now? What advice might you give them?

Dena Upton: I think the reason we were able to pivot successfully is because we had doubled down on some aspects of our culture. Our drift leadership principles were really understood across the organization. Our managers were trained on them. Our people were trained on them when they first came into the organization. So we had these solid aspects to our culture that were ingrained in the organization. Right. This idea of high performance, how we measure performance, we do calibration sessions, we take that very seriously. So high performance is felt and operationalized across the organization as well as as Drift ritual. So we bookend the week. We start the week off with what we call Monday metrics, and we end the week with what's called Friday show and tell it to town halls. What happens, I think when you go remote is you end up working with seven or eight people that you're specifically working with on a project or customers. And you don't have that opportunity because you're not going into the kitchen and you're not bumping into people who don't have that opportunity to collaborate with other people that are outside of your work zone. And so these drift rituals that we have with Monday metrics and Friday show Intel allows us to put our arms around the organization twice a week in town halls. So I think those aspects of our culture were ingrained when we were together and we've been able to double down on them in this remote world.

Chris Byers: Well, I love those kind of cultural assets that you've created. I think those are important for every business to think about. How how are we going to operate in a way that's effective? One of the things that's clearly a part of your culture is an attempt to make sure that you do provide an equitable experience. And so why do you think you mentioned earlier? Why do you think hybrid is not equitable?

Dena Upton: Well, I think what happens is a couple of things that I've seen in previous organizations is there isn't that foundation for why you're going digital? I think the the important things is that foundation of equity. And what happens is when you pick an edge, which is what we did and we said we're going to go digital first, it forces anyone that is a leader in the Organization of People manager to really work on their digital footprint. So if they're communicating in a meeting, they're calling a meeting. Everyone's on the agenda is done ahead of time and then reinforces what I call the digital footprint internally across the organization so that everyone, regardless of where they're located, if you're running a sales forecasting meeting and you're the sales manager, you're going to make sure everybody's on video and sure that there's an agenda ahead of time so that anyone who's experienced that meeting has the same equitable experience. They're given data, they're given preparation. Side conversations aren't happening. And so it's a mindset to ensure that you're thinking about everyone in your team, regardless of where they're. Located what happens in a hybrid environment is sometimes the foundation isn't set in, those habits aren't developed, and so you get a little bit lazy because you can just turn around and talk to someone who's right next to you if you're not thinking about all the other people that might not actually be in that physical office.

Chris Byers: So this is probably a little bit of the weeds, but I think it's important. Maybe just curious how you're thinking about it. So imagine the person joins they're not near one of the conversational spaces. How are you trying to promote that? At times you'd love for people to get together and learn to create whatever that happens to be.

Dena Upton: Yeah, I think for us, what we're thinking of, the cadence of how we're thinking of bringing the teams together and the new normal is going to be it's going to look a little bit like this will have kickoff at the beginning of the year in February when our flight twenty twenty three kicks off. We'll have everybody across the organization there so they understand at a high level we're together. There's also there will be content distributed as well as team collaboration and team building happening in those in that initial kickoff. We'll also do a halfway kickoff in the summer. So those two times the whole organization will physically be together. And then at the other quarters we'll have team meetings. So product will get together physically together, sales team will get together, et cetera. And then the same thing. And the other quarter we're anticipating and planning that we will bring the whole Drift team together twice a year and then departments together twice a year on the off. So every quarter there'll be an opportunity for you, regardless of where you're located, to be brought to a spot for a full team collaboration.

Chris Byers: And I'm curious how, as you kind of taken a dove into it, how is it impacted hiring already?

Dena Upton: Well, it's opened up access to talent that we wouldn't have seen or connected with in the past. There's two things that have opened up the top of funnel activity for us on the recruitment side. One is flexibility. And that, as I was talking about before, when we were very much in office based company, there were some people that self selected out. They could have lived an hour away. We're talking about Boston or San Francisco, an hour away. And the commute was too large and they knew that we were very much an office culture that wouldn't even apply. I think the other thing, too, is we have gotten to talent that may not be even in the states where we were before. And so it's opened up access to talent that we wouldn't have seen before or that talent wouldn't have been interested in exploring opportunities with us before.

Chris Byers: As you think about onboarding, something you talked about earlier and some of those new team members are coming on. Have you tackled a different way of onboarding to do that more remotely?

Dena Upton: All of our onboarding is run digitally so remotely. And we're starting people we've got a team of about 12 in London and a couple in Australia. So all of the onboarding, what we call Drift foundations, which gives you a framework for conversational marketing and conversational sales revenue acceleration, you're understanding the concepts of how we even teach our customers. So if individuals go through Drift foundations for three days when they join the organization, all of that is done digitally. But our head of onboarding has been able to use Drift video for learning opportunities as well as inside Drift. So there's some things that as individuals are going through foundations that they're doing on their own sort of self based knowledge, and then there's opportunities for the team to virtually come together over zoon to understand our culture.

Chris Byers: Well, it's great. I know the experience we give team members, especially those first days, are really important for setting the stage for culture and their success in the long term. As you think about the broader set of OK, I can now hire anywhere. Sounds like your offices have tended to be in potentially higher cost areas. How are you thinking about pay and that looking different or the same across locations?

Dena Upton: Right now we do market pay essentially, which is driven by location. Obviously our office footprint, you're right, have been in high cost areas. So Boston, we have the majority of drifters in Boston, we have an office in San Francisco, an office in Tampa, a small office in Seattle, and we're in London. In Australia, we build our salary bands based on market data so that market data is driven based on location. So to answer your question, if somebody is interested, they live in Boston and they're interested in moving to Kansas, for example, we would look at a couple of things. We'd look at performance and we'd also look at market data. So not cost of living, but market data in that location to see if there is a multiplier that would bring that down a bit. There's other factors, right? Like performance is another factor. But what I think is going to happen. Over the course of the next couple of years is you're going to see that location based market data come down as people start moving out of those general areas like San Francisco, New York, etc., The city has been the most expensive place to live. But as people start leaving those centers of influence over time, the market data, which is where we drive our compensation bands, will start smoothing out.

Chris Byers: Yeah, you know, as we have watched remote over the years in our own organization, I've always been amazed at the volume of moves that take place across our company. And in fact, it's a beautiful thing to be able to allow someone to keep their job or they need to say him and to go be near family or make a decision that's a little bit more personal but still get to do my work.

Dena Upton: It's been a source of stress for people when they know that stress has been lifted it out. If they're moving to a low cost area, there might be some kind of adjustment, will have to be made on their compensation, but it will be the cost for them to rent a place will be lower, too. So the idea is to take the take home pay is the same regardless of where you're located.

Chris Byers: Absolutely. Well, drift isn't the first to make the shift. You are a company that tends to be ahead of the curve when it comes to innovation, whether its product, culture, whatever. What do you predict other companies are going to do in light of last year and the new normal?

Dena Upton: I think that companies have a lot to think about in the coming months. It's hard to predict because it really comes down to what works for them specifically, and that's going to be different for each company and even each individual. But I believe that whatever people decide increase flexibility has to be part of it. And I think it's possible that we go back to the traditional five days in the office work week. We're not going to go back to that. And so I think one of the positive pieces of it has forced companies to a lot of their hesitancy to sort of embrace this flexibility. I think because we've had two organizations have seen it being successful and they've also seen the flexibility that it's been able to give to their employee base. When people think about what they want to do, I would encourage them to do their research, ask their employees how they're feeling, look at the data and then decide. The tough thing is that, of course, employees want answers because they want to be able to make decisions. But it's not always a decision you can rush. We tried to be open and transparent with our team about what we were thinking, the thought process behind it. DC was very vocal as we migrated through the coronavirus and what was happening as to what he was thinking about teams set up and this idea of digital first.

Chris Byers: So how do you think this will actually change? The drift culture over the long term

Dena Upton: is something that we're working hard every day. It helps, as I said before, that we had a strong culture to begin with. Our team really enjoys each other. They enjoy spending time with each other. They like to talk about books that they're reading, food they're cooking, pets that they have. But we quickly also try to make those things virtual. We have what we call mentor series, which is we bring someone outside the organization to speak to our team about things that they've learned. We've quickly moved those online. So where we had those guests in the office with us, they're now available on Zoom. It's very interactive session. So we've been able to move some of the things that we did together, book club, remote cooking classes, some events that our employee resource groups do. But we've had to be creative and thinking of ways to move those remotely. We've also just recently wrote our own culture deck and we're making it really clear to employees and candidates what we celebrate and what we don't tolerate adrift. And that's that's really helped us kind of put into words where the culture is moving, where the team is moving. It's been helpful for our own employees to really understand. How do you define the culture of the organization?

Chris Byers: Well, and I guess as a technology company, you're likely embracing some new technology as part of this, the shift. Can you give some examples or an example of how you're doing that?

Dena Upton: We're big Drift video users. It allows for asynchronous communication. If there's something, then I can get across to my team with a recorded video with my my face and sort of details that I want to describe. I'll do that. Instead of calling a meeting, we use video a ton for asynchronous communication as well. It's I think we have broken slack multiple times. So slack donut dates, a lot of slack channels, engagement in those channels. Zoom again when we do our all hands. The Zoom chat feature is blowing up. So we've been able to to double down on the technology that we were using before and then using it in a different way throughout the organization, which has been great for our teams to feel connected to to each other in the remote world.

Chris Byers: And are there any technology predictions that you have as it comes to kind of. What's needed for more companies to become digital first?

Dena Upton: I think that's the thing is thinking about different ways of communicating with your team. I think you have to. It's funny. I think you probably heard this right. If you want to communicate something to the employee base, you have to say it about seven times, but you have to meet them where they are, which means posting on Slark, an email, a PowerPoint slide, a video. You have to go. You have to try harder because you can't pull the team together and jump on a desk and talk about what the direction of the organization is or whatever it is that you're communicating out. So internal PR is incredibly important. And I think before maybe we took that for granted. Right. You always had internal communications as a function of marketing organization. But for us, our PR leader, Lacy, she does internal communication as well. So the rigor that she puts in external communication is the same with internal. So we when we announce things, we make sure there's an FAA cue, a video. If it's a video from D.C., it's a video for myself or our CFO or whatever it is, the content that we're trying to get out to the organization, that we treat that release of information the same way that we would release information to our external team, because you can't rely on communication channels that you could rely on before when you were doing it in person. You have to be a little bit more deliberate with that.

Chris Byers: What do you actually think the biggest kind of barrier to organizations making the shift is going to be?

Dena Upton: I think it's a mind set, really. We we struggled with the same thing. How can we possibly create that same kind of energy that we had when we were all together? Like you miss people. It's people interaction, right? Like you can't read a room. If you're jumping into a presentation, you have to give. You can't it's harder to read a room on Zoom, but that means that you've got to track a little bit more ahead of time. And so I think that preparation is going to be really important as we move forward. And I think but I do think some organizations were stalled because it's the way they've always done things but gone through a one way door and it's hard to go back. People aren't traveling as much as they did before. So I think successful organizations are going to have to embrace the migration.

Chris Byers: I'm curious if you actually had to put some rules in place that almost prevent people from going into the office too much, because if I think about mindset, everything flows down often from an executive team and people want to emulate the way they do things. And they can be the toughest one to say I'm committed to not going back into the office in a way. How are you guys thinking about that?

Dena Upton: We tried to paint a picture of what does this look like in practice? OK, what are conversational spaces? How can I use them? Some of the feedback that we've gotten is for individuals that have three or four roommates. Right. They've been making this work. They've tried to find and carve out a spot in their apartment. But the challenges, they want to go back into the office. And what we've tried to communicate is the majority of the time spent in these spaces is going to be for collaboration, work, customer calls in person, virtual meetings, brainstorming sessions. However, we do recognize that there'll be times when those who are able or want to need to have a space outside of their homes just to focus. So we're going to make sure that solo spaces will be there for people that need them because there might be a challenge in their space that they're sharing at home. So our hope is that anyone using the conversation spaces will structure their day so that they're intentional about using the office and collaborating with fellow customers or drifters or future drifters, new hires, etc. We just want people when they're using the space to be deliberate about collaboration when they're there.

Chris Byers: Well, that's the beauty of digital. First, it actually allows for quite a bit of flexibility and being in an office at the right times, but also at home. What are some of the negative aspects of digital first, from your experience already, or what do you expect to happen that that can actually be a negative right now?

Dena Upton: Many of us are going through these phases of kind of isolation. We miss people. We miss getting out to see individuals. And I think when we first announced digital first, there were many that were very excited about it. But there were others that were like, oh, I was hoping that we would bring the whole team together five days a week because I'm really struggling with isolation, with what's happening with Covid. And so we've had to combat that by talking about the benefits of digital first. We've also ensured that our drifters are equipped. We're sponsoring sort of home office set up so they can ensure that they're in a comfortable set up in their home locations. But we've definitely provided for that, as well as shifted some of the benefits that we offer to support having your main office or your main desk be your home location. So we've been able to shift some of the money that we were spending on benefits to support individuals in their home office setup.

Chris Byers: Well, as we kind of wrap the conversation and thinking about the future of work, I've got a couple of questions. What's one thing you wish was solved for digital first companies?

Dena Upton: I wish that Zoom would default to hiding yourself. You I think what happens is you end up distracted either in your hair, fixing your hair or you're doing something. I wish that Zoom would just default to hide, sell view. And when it kicks it off, because I think what happens is it takes individuals a while to realize that function is there and you get exhausted staring at yourself all day. And I think I also think that it would be great for individuals to resort to go back to an audio call. I end up doing a lot of my one to ones with sort of walking just audio one to one, because it's tiring to sort of look at video camera and not get distracted. It allows for active listening when you do that.

Chris Byers: I love that thinking. What do you think the number one kind of soft skill is people need in this future of work?

Dena Upton: I think it goes back a little bit to the digital footprint that I was talking about before. But the soft skill that's associated with that is thinking about yourself as a leader, a manager, a leader. And I don't even mean you're managing people, but I think that you have to put yourself in the perspective of your audience. So you have to be really good storyteller, regardless of whether or not you're telling a story to a handful of developers as a product manager or you're telling a story to a team of recruiters, whatever it is, individuals need to double down on good storytelling. And then you use the platforms that are available to you in the digital first world. So could be a video. It could be PowerPoint slides. But I do think this remote environment is going to challenge all of us to be better storytellers because you have a small chance. Your chance to make an impression is limited. And I think that's going to be an important skill to get better at.

Chris Byers: Thank you for listening to this episode of Ripple Effect with Dina Upton. My biggest takeaways, digital first is not just about location, it's about a mindset shift and putting your people first. The future of work is not about going back to the way things were, but embracing what they can be. For us, the future of work is about enabling workers to be as efficient and productive as possible. For non-technical workers, this can be accomplished through harnessing the power of no code workflows and process automation. We cover this no code revolution in our comprehensive report, The Rise of the No Code Economy, which explores how no-code tools can help you achieve more. To learn more, visit

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