#167: The Culture Episode
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. We're back. We're back on Seeking Wisdom. What's going on? We're here to talk about something pretty interesting. It's been almost six years since we founded Drift and we've created many rituals. We've opened up offices. We've experienced the highs and lows of hyper growth, and we've grown to be over 400 people now. Just this year, we've gone digital first. Check out episode 163 for more on that, but the most important thing about today's episode is back by popular demand. It's been very rare for people to reach out as often as they have about this superstar guest making a return appearance, Drift's chief people officer, Dena Upton. How's it going, Dena?
Dena Upton: Thanks, DC. Good, good to be here.
DC: I had so much feedback on how many people loved you on the last episode we did together. I'm ready to give it up and let you run Seeking Wisdom from now on.
Dena Upton: I don't think it was me. I think it was because we were talking about digital first and so many people are curious about why we took the leap.
DC: See, she's humble, too. It's amazing. Dena, we started Drift for three reasons. I'm going to tell the audience what those three reasons are. One, we started Drift to make business buying frictionless and become the new way that businesses buy from businesses. The second reason we started Drift was to lean into the undeniable trend in the shift of power from vendor- centric companies to a buyer- centric world, and the third reason, which we're going to talk about today, is that we wanted to create an enduring company, one that could be a role model for future diverse corporate America, not only American but global companies everywhere, to create this equitable environment. I know we're going to touch on some of that today.
Dena Upton: Yeah. Achieving those goals requires having the best team in place, and that means that we need to be explicit about what we celebrate and what we don't tolerate, and I know you've thought a lot about this. You and Elias thought about this when Drift was two people. What are some of the aspects of our culture that have allowed the team to flourish and then will allow us to continue to flourish?
DC: There's five aspects of our culture that we're going to talk about today. The first is to cover our leadership principles, and I've touched upon that in the past a couple of times on the show, but really, we're going to dive into those. Leadership principles are a set of principles that we defined early, very early in the company when I think we were under 50 people, and we've used them in our hiring, we've used them in the way that we promote people, we've used them in the way that we talk about performance, inaudible. That's number one. The second aspect is high performance. Third aspect is hiring adults and autonomy. The fourth are our rituals, and the fifth is equity, which I touched upon as one of the three reasons we started Drift. One thing that you kind of highlighted there that I've said that can be controversial is that Drift is not for everyone, and people don't want to hear that. They want to hear about, how do we make it for everybody, but the truth is that in all organizations, or all groups, or all any kind of societal groups, they're not going to be for everyone, and that's okay. They're going to be for a certain type of individual that may find themselves attracted to that team, that approach, that organization, that group. I find, in defining our principles, and kind of the company that we want to create, is that we should be explicit about that. We shouldn't hide from that and try to become something for everyone, because when you're something for everyone, then I don't think you're anything.
Dena Upton: Right. This is one of the aspects of our culture that's been hard for people, I think. As you said, written words matter and the language that we use really matters, and the more authentic our language, the better, and the more that we can actually be incredibly transparent to our current Drifters, to future Drifters, to Drift alum, because it isn't for everyone. This stage of growth is not for everyone, and I think it'll draw the right people to our company at the stage that we're in right now and it will push away those people that might not be the right fit for the organization. I think it's a hard one to grasp but I think it's really important.
DC: Yeah, so, we have leadership principles that we define, that I mentioned that we defined at the beginning of the company, pretty much. Dena, do you know the eight leadership principles?
Dena Upton: I do.
DC: You do.
Dena Upton: I do, not because I've memorized them, because we just got through a 360 review process with our managers and they're woven in there, they're in peer reviews, they're in interviews. That's my life, so I live them. I think, I can rattle them off but I think the most important one is putting the customer at the center of everything we do. I see that in executive meetings and you challenge us when we're implementing something or changing direction, like, how are our customers going to view this. I think, every question that we ask for anyone that's managing a team here at Drift, do their goals put the customer at the center of everything they do? I think, the larger an organization becomes, sometimes you pull yourself away from that, but we're always trying to pull ourselves closer, so the more senior you become at Drift, the closer you should be to our customers. I think they're all incredibly important but all of them are centered around our customer.
DC: Absolutely. That's the most important one, and the way that I think about our leadership principles, are not that they're rules, that they're a process necessarily, that they define a process, but really they're kind of this idea that I love that they're guard rails that help keep us on the road, from driving off the road, and they help steer our actions when hiring, when we're doing reviews, when we're doing promotions and even exits. These are the things that really guide us, but number one is put the customer at the center of everything you do, like you said. Number two is creating a culture of respect and trust, and what do you think that means to you, Dena, or what's a good example of that?
Dena Upton: I think it's respecting other's opinions. I think it's also respecting diverse opinions, seeking out diverse perspectives. It's ensuring that the team that you're developing, either your close team or your expansive team, you're surrounded by people that are going to challenge your thinking. That's what I think with that.
DC: All right, and number three, which is some people's most favorite, especially some of the early Drifters who witnessed Elias's baptism with this book, and it's called practice extreme ownership, and look back in the old episodes of Seeking Wisdom to find the episode where we talked about the book Extreme Ownership and what we kind of tricked Elias into doing that kind of transformed his life.
Dena Upton: Yeah. I think that one's, you have to take control over what you're walking on, and we practice that with DRIs, responsible individuals that are on the hook to deliver something, because if you don't assign someone something and if it's in a volunteer department, it's not actually going to get done. This one, we ask for individuals to demonstrate this in the interview process. As you said, we test on it as we're evaluating internal Drifters. This one's really important.
DC: Number four, which I think is, actually, internally, it might be the one that people default to the most, and it's called have a bias for action, deliver daily results. I think this one is the one that people... The good side is that people default to this one the most. The bad side is probably that this becomes the bogey man that you have to always deliver everything on a daily basis. What do you think of this one?
Dena Upton: Yeah, I think this one's easier for Drifters because there's so many tools that we have in place for showing your work, Slack updates, the lattice tool that we use for showing what you've actually accomplished that week, even Monday metrics, where we talk about what was accomplished last week, we're able to point to specific ships. I think it's this idea that 80% shipped is better than perfect. We have a ton of people that are able to do that and we foster that through different channels of communication across the organization, but I think the only pitfall for that one, as you said, sometimes you have to move slow to go fast, and we have a tendency to do more instead of sometimes mastering the four or five things that we want to do really well. This is the yin and yang of that leadership principle.
DC: Exactly, and sometimes just moving fast inevitably makes you slow, because you have to pay off that debt. The next two, five and six, I think, are the ones that we need to work on the most, that we don't do enough, at least at Drift, and number five is seek feedback, not consensus, and number six is push for high standards. Those two are ones that, I think, are super important, which I don't think we're there yet in terms of where we need to be with both of those. What do you think of that?
Dena Upton: Yeah. Seek feedback, I think it's in place to get to the best idea, but it's not to slow us down, so we're not a consensus- driven organization. I think, sometimes this one is the hardest part for people that join Drift that came from a larger organization that was very consensus- drive. You don't have to display 10 or so PowerPoint presentations to make your point, or going to a meeting is not a badge of important. I think, for people that come to Drift from larger organizations, this is the muscle they have to exercise, that I am responsible for a particular task or strategy or whatever, and I don't need 10 other people to tell me that it's okay. I need to seek feedback, but it's not a vote. I think, there's the other thing that you see this in the recruiting process a lot. You get feedback on a particular candidate, everybody doesn't actually have to vote yes for that candidate to start. The DRI that's hiring that particular person, in most cases is the most senior level person in our department for those positions, makes the decision, based on the data that they pulled from individuals that interviewed the candidate, but we're not consensus- driven organization.
DC: I love the way that you put that, but number seven is also a bogey man one, at least at Drift, which is called stay scrappy, which crosstalk.
Dena Upton: Oh, yeah, it used to be stay scrappy and frugal, right?
DC: Yeah, used to be stay scrappy and frugal. I think it got modified because everyone interpreted it as, like, we're cheap.
Dena Upton: Yep. It's funny. We had one of our onboarding managers... We recognize people every quarter as you know for demonstrating these leadership principles, and our onboarding manager, Allie Winkelman, was recognized for this leadership principle. The quote was, " She makes the scrappy classy." I think it's doing more with less resources, and not always using headcount to actually get something done. It's prioritization. It's intense, it's ruthless prioritization. I think that, as I describe this leadership principle. It's always thinking that your resources are scarce, and how are you going to get more done with less, but it can be misinterpreted as a money saving leadership principle. It's not about that.
DC: I love that story about Allie. I love the way that you articulated stay scrappy. You really know these. We're on number eight, which is the last one, which is my favorite one, and the whole reason that this podcast even exists. Be a curious learning machine.
Dena Upton: Yes, yes. I think this is... People say, " Is Drift for me? Am I going to be successful at Drift?" You have to always be getting better. You have to make an investment in yourself. I think I described coming to Drift as, like, getting my PhD in Drift when I first got here, because you were always... I've got five or six books going right now, I'm reading part of them. I think it's this curiosity and voracious reading and exploration of new ways of thinking, that those are the successful Drifters here, because there's so much to learn, from our advisors, from the team that you're surrounded by. You have to be the kind of person that is comfortable with being uncomfortable but being uncomfortable drives you to learn more.
DC: Yeah. You mentioned two things right there, that, perfect segue to talk about high performance, or the idea of high performance. You mentioned being around the best people, and then you also mentioned performance in that last description. I think, the way we think about it is the way to become the best is by hiring the best, not just because, obviously, you're hiring better people, but because you're leveling yourself up as you start to raise yourself up to the people that are around you. We think that, you mentioned reading, the book that I gave out to the entire company at kickoff was Reid Hastings' book on Netflix's culture, and we think Netflix said it best, because Netflix said, and this is from Reid Hastings, the CEO and founder, " The best office perk is working with people you respect and can learn from every day. We are a team, not a family. We're like a pro sports team, and it's not a kids' recreational team. If we're going to be a championship team, then we want the best performer possible in every position. Team members are playing to stay on the team with every game. For people who value job security over winning championships, Netflix is not the right choice, and we try to be clear and non- judgmental about that, but for those who value being on winning teams, our coach provides a great opportunity. Like any team, successfully competing at the highest level, we'll form deep relationships and care about each other."
Dena Upton: Yeah. I know. I think it's ...
DC: I don't know if everyone loves that, but I love that.
Dena Upton: I think it's like, when you're on a successful team, you're watching your video, you're watching what you can improve on, you're always getting better. I think that mentality is really important for individuals to be successful at Drift. You got to earn your spot every quarter, every month, and that means that you've got to invest in yourself and you have to learn as much as possible and challenge yourself to do things that you might not have done in a prior role.
DC: Something you mentioned earlier when we started the leadership principles is that we just went through this performance review cycle, and one of the things that's super important is that nothing in a performance review should be a surprise. How do we go about making sure that nothing is ever a surprise to the person being reviewed?
Dena Upton: Correct. I think the thing that we try to instill is, it's that seek feedback... It's embedded a bit in the seek feedback component, that feedback is a gift and we give it freely. We give it and we receive it, and I think we instill in individuals who are coming into Drift, that important component to our culture, that it feeds on itself, so you're right. We do formalized reviews twice a year, but people are working with their manager on a weekly basis, or they're working with their teams, and if something's going wrong, you go right to the person that can be working on that particular thing. If I flubbed a presentation, I hear from the Drift team about it. " You read that presentation, Dena, it didn't sound like you. It wasn't authentic. You got to alter..." I think, the beauty of it is we get it from all levels of the organization. It's not hierarchical here, so a software engineer...
DC: Yeah, that's for sure. We do get it from every part.
Dena Upton: We try to get it from everybody.
DC: Every part, get it from every part, believe me, all day, every day.
Dena Upton: I think that's just how we do things here, and so I think it becomes a habit, as you start getting exposure to it, and it feeds on itself. I think the comment that you made about semi- annual reviews not being a surprise, they shouldn't be, because you should've been getting that feedback constantly from multiple people.
DC: Mm- hmm( affirmative), absolutely, and what do you think about the idea of someone in the company owning their career? What do you think that means?
Dena Upton: I think it means that a career isn't always linear. It can move cross departments, cross teams. You could do different things, but you as an individual have to drive it and not expect that your manager is going to lay the foundation for how you can gain additional skills. If you want to move into a leadership role and there isn't happen to be one in the sales organization, for example, well, be a leader in one of our ERGs, or connect with a new project that's happening across the marketing organization. There's several examples that display leadership responsibilities without being told that you're moving into a leadership role. It's what I believe that comment is, and if you are a curious learning machine, that will be a natural thing that you will do when you join Drift, because you've always been the type of person that paves your own way and is not waiting for somebody to tell you what to do. It's hiring fully formed adults, which is one of the things that we talk about. It means that you, DC, are not going to tell me how to run the people function. I'm going to tell you some of the things that I think we should be doing differently. I'm not waiting for you to give me permission to speak about something or get outside of Drift and talk about the digital first movement that we've made. I naturally do that and I'm always challenging myself to do that, so that's what I think we mean by that, but you have to come in with that drive. We can't necessarily teach that.
DC: Mm- hmm( affirmative). There's one thing that you might not know about me, Dena. I may be known for saying polarizing things, Dena. All right, and one of the polarizing things that I've said is that we believe in hiring adults, and that we're not here to babysit you. We define being a responsible adult this way. You're self- motivated, you act like a leader and you don't wait to be told what to do. You dive right in and you have this willingness to roll up your sleeves. You carry the water and never think to yourself, " It's not my job." If you don't know the phrase, " Carry the water," that's one of the most famous Seeking Wisdom episodes.
Dena Upton: It's a great one.
DC: We'll leave a link to that below.
Dena Upton: Yeah.
DC: Number five, you're focused on outcomes, and outcomes because, versus your own personal outcome, the overall outcome of the mission or the project or the thing that you're working on. Those are the things that we think are critical to being a responsible adult, and we try to hire responsible adults so that we can build this idea of an autonomous environment, where people have a high degree of freedom, but a high degree of responsibility on the other side, so we call it, autonomy comes with the equal portion of accountability. How do you think we can create an autonomous company? What do you think the ingredients for crosstalk?
Dena Upton: I think, we talked a little bit about this earlier and it's in our leadership principles. I think, the outcome piece that you were referring to is, by being customer- obsessed, so customer- driven, all of our teams need to commit with spending time and energy on fixing our customers' issues. It's why we're here. We're never too busy to get on a call with one of our customers. We're never too busy to solve their problems. I think that's one of the most important ingredients to it, I believe.
DC: First is being customer- driven. These are the ingredients for creating this culture of autonomy. One, customer- driven which Dena mentioned, but number two is accountability, and I think this is the ingredient that most people get wrong. They try to create a model for autonomy that has very little accountability built into it. I always say, autonomy with no accountability is anarchy. It's not autonomy. That's just anarchy. That's just I do whatever I want to do because I want to do it. That's not autonomy. Autonomy comes with this responsibility, this accountability, and each person needs to be fully accountable for their decisions for autonomy to work, and the finger pointing and excuses destroy this idea of autonomy. Number three is this idea of transparency, that we have to default to transparency. Number four is this idea which goes back into our leadership principles about shipping daily and showing your work. It's this, have an iterative approach, that you're not just focused on big, giant changes but that you're delivering value to the customer, again, number one, all the time, and number five is this idea of ownership which again ties back to the leadership principle of extreme ownership and that there's a clear owner or DRI, directly responsible individual on something, and that we can't get things done if there's not clarity around who owns this decision. Doesn't mean that they have to be a manager or a leader or anything like that, but they might be a DRI who owns a decision on a specific project.
Dena Upton: Then, I think, sometimes we get criticized for micromanaging, but... I don't think you have to micromanage, but there would be times... The foundation is set in motion so that we don't have to micromanage, but sometimes things can go off track if you steered away from the customer or you weren't outcome- driven, then we might have to micromanage for a period of time and then back off again.
DC: Yeah. Some people have called this old saying, trust but verify. Especially earlier in a person's career or early in your tenure within the company, and that's just to help them along the way so they don't stumble and make obvious mistakes. Other people call it different things, but it's trust but verify. Sam Walton used to call it, the founder of Walmart, over the shoulder management. It's like trust, but every once in a while you reserve the right to inspect.
Dena Upton: Yeah, and I think those are the types of things that we're ensuring our leaders are fostering.
DC: Yeah, and that, to me, is part of this idea of accountability, part of the accountability, because you need to be able to inspect to have that accountability. One thing that we've talked about in the past a little bit and we've done some episodes on, is this idea... It's funny, we get so many questions, especially now in this digital first world, that everyone's kind of been forced into this idea of rituals, and that we have all these rituals at Drift. Our rituals, I believe, keep us focused and centered around our goals. They're not just a meeting. They are something that's important that people can count on to get something that's specific to that ritual, whether they're a new person, an old person, everyone can count on these. We have three main rituals. Do you want to talk about them, Dena?
Dena Upton: Sure. I think, the benefit of them is we're also able to put our arms around the company twice a week. Every week, we kickstart the week with what we call Monday metrics, and then we bookend the week with Friday show and tell. Monday metrics is, it's 20 minutes, it's led by our VP of operations, Will Collins, who's amazing at it. He's the metrics guru of the org, but we have a leader in the sales organization talk about deals that are in play, somebody senior in our CS organization is talking about what our customers are retaining and what's happening with the metrics from a customer success perspective. Head of product talks about product launches, marketing campaigns that are running that particular week from someone from the marketing organization, so there's no excuse for anyone across the organization, regardless of position, for you not to have a high level understanding of the metrics of our company, and then we bookend the week with Friday show and tell which is my favorite Drift ritual. One person from each department talks about something that they shipped that week, a problem that they worked on, something that they were challenged with. They offer a solution and then there's a CTA for the company. It's MC'd by one our product leads, Matt Bilotti and it is...
DC: Mm-hmm (affirmative), and cohost of a Seeking Wisdom podcast called Growth, if you subscribe to it.
Dena Upton: It's great, and Matt is in Matt Bilotti form, but it's animated, the Zoom chat goes crazy. We vote on those presentations. There's usually, sometimes there's a culture corner component to the presentations, as well, and then we have open mic for our executive teams, so what's on your mind, and a lot of people have come to Drift because they want to see what it's like to be part of a hyper growth company, and so we share a lot about decisions that are being made broadly across the company, our competitive landscape, so, those two rituals are incredibly important and we've doubled down on them by going digital. I think they've actually become better as a result of...
DC: crosstalk think so.
Dena Upton: I think so. I think it's helped our digital footprint, internally. I think we've had to double down on internal PR and communications across the organization, because everybody doesn't see each other. We used to run Friday show and tell in the backyard in Boston and you could get up on a chair and throw the microphone. You can't do that, so you have to create that same kind of energy remotely, and so I think we've been able to do that, and I hear it because new hires that come into the company will Slack me during the show and cannot believe the energy that they feel from the room. Matt's been able to replicate that same energy that we had in Boston which is really cool. I think it also gives... It doubles down on that storytelling skill that we really want our people to master and be very good at. You have five minutes to catch the whole company's attention, tell a story about something they're really working on and there's also a call to action from the whole team, so we've really gotten into those. I think the other ritual is company meetings. This is an interesting story to tell about this one. We've always had company meetings together, in person. We flew everyone to Boston at the beginning of the year, and then we also got everyone together at one point in the summer, and we've had to shift those to virtual meetings. I thought the one that we did in February was incredibly powerful and I think it was also really powerful because it wasn't completely live. I thought that we might miss the magic by not having you speak live in a Zoom call, but we prerecorded that meeting, and the slide in and out and the professionalism from our video team, everyone who was participating in that, and you were on the Slack, you were on the chat, I think people were blown away at the professionalism of the production. We spend so much time producing with rev growth and a lot of our other external events, I think individuals that participated in that kickoff felt the same kind of love and attention and professionalism in that internal kickoff as they would feel at any rev growth or external summits that we've had before, hyper growth.
DC: I think you're right. It was an incredible thing that we'll have to do an episode on, how we did that company meeting, and we really wanted to go to a different model instead of sitting on another Zoom call. We really wanted to up the production level and blow people away, and I think our video team did an incredible job there and we made some really great steps there. These rituals that all of them used to be physical, we have created new digital first approaches to them. I think, some of them, all of them will continue to refine over time, but really the work that Will has done with Monday metrics and then Matt with show and tell, they continue to raise the bar each and every time, and it blows me away just being a participant and watching what they're doing. The fifth thing that we're going to talk about is equity. With everything that we do, we are on a mission to create an equitable company. We are just part, and we, being Drift, we are just part of just 2% of the VC- backed companies led by Latinx founders and we take that responsibility seriously, and that is why my co- founder Elias is launching his own podcast which will be debuting soon and we'll have in the feed here at some point, and it's called the American Dream. It's really to highlight underrepresented people in their march towards the American dream in order to create a more equitable environment for all of this. This idea here really shaped what we did with becoming digital first and we wanted everyone to be on a level playing field, for no one to feel like a second class citizen here, and that we would create this equitable experience. What do you think we can do, Dena, before we go? Leave the people with some wisdom, some nuggets. What can we do to create an equitable environment, not only at Drift, but also in their companies?
Dena Upton: I think this is a big one, because I think people resort back to what's comfortable for them. I think, as you start to visualize what does going back to the office look like, a lot of people are migrating toward, I'm just going to go back to the way that things were with a little bit more flexibility, but the problem with that, and I believe the power in what's happening right now, is we're very productive because we're all on the same playing field. I think, it's a mindset shift, and I think that if individuals realize that you're kind of crossing a chasm. Like, we are going digital first. We're not going to go back to the way things were, inaudible ensure you're creating an organization or a team that is very equitable, you're not going to pass the next project to the guy or the girl that's sitting right next to you in the office. You're going to pass it off to the most accomplished person in your team. They could be in San Francisco, they could be in Tampa, so location, I think that's where I'd like to get us to, but it's a mindset shift, and I think some organizations are struggling to cross over to that area.
DC: Exactly. Drift is for the curious, the determined, the creators and the problem solvers out there. If that sounds like you, we'd love for you to be here. We are hiring every single place, and you can learn more and apply at drift. com/careers, but Dena, a quick question for you, how many people are we hiring at Drift right now?
Dena Upton: We are about 415 Drifters globally, and we have about 140 positions open right now. We're going to add 200 more Drifters, well, 100 crosstalk.
DC: A lot. Wow. Mind is blown, jeez. That's a lot of people. We need your help.
Dena Upton: crosstalk globally.
DC: Globally, yeah, wow.
Dena Upton: Yeah. We've got people in London, Australia, Drifters all over the globe. It's really exciting.
DC: Wow, that's a lot of people. Remember, if you're curious, you're determined, you're a creator and a problem solver, then Drift is for you. Apply at drift. com/ careers. I need you all to do one last thing. If you want the great, the amazing, world class Dena Upton to make it back on this here podcast, I need you to leave a six star review. I need you to go, open up, leave five stars and then leave an extra star in the rating and then leave a shout out to Dena, tell her how amazing she is, how you want her to replace me as the host of his podcast, and let's see how many six star ratings we get. Dena, thanks for joining me today.
Dena Upton: Thanks, DC.
DC: All right, see you soon. Let me know what you thought of this episode by texting me at 1- 212- 380- 1036. Again, 1- 212- 380- 1036. 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. Hope to see you there. Text me. Hit me up.
This week on Seeking Wisdom, DC is joined by Drift's Chief People Officer, Dena Upon. Together they talk about the five aspects that make up Drift's culture including autonomy, high performance, equity, and more.
Tune in now to hear what Drift celebrates (and what we don't tolerate) and to learn how to build out your own culture of high performance.
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 or text him to share your feedback at +1-212-380-1036.
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/