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Episode 54: Interview with Matt Davey, COO at 1Password

As COO at 1Password, Matt Davey talks about eschewing perfectionism, being an empathy-led business, why it’s important that everybody in the company does customer support (even with 220+ employees!), and what exactly has helped them maintain their “organizational soul.”

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CLAIRE: Hi, everyone. I’m Claire Lew, I’m the CEO of Know Your Team, software that helps you, as a manager, become better with your tools to help you run effective one-on-one meetings get status updates and get honest feedback.

And today on The Heartbeat podcast, I am super excited because we have here a really special guest. Someone, an executive from a company that I’ve admired for the longest time, and they’ve been a very long time Know Your Team customer too, way back in the day since back we were called Know Your Company. So, an absolute true honor to have on the show, Matt Davey, who is the COO which, by the way for them, is the Chief Operations Optimist of 1Password. And for those of you who are not yet using 1Password, you are missing out. I use it every single day. We use it here on Know Your Team, but it is truly the best in class password management software that is out there. And so, I highly recommend using it if you haven’t. And the amazing thing about 1Password is they have millions of users all over the world, I believe over 50,000 business clients alone and got to that literally raising zero money and building the company from scratch over the past 14 years. And then only very recently, raised money for the first time, it was a $200 million Series A, which was super unconventional. And so, we can get into some of that if it’s [inaudible]. I know we have a lot of things to talk about. But then the other thing I think that’s worthy to know so many things about 1Password, such an interesting company, but they are also entirely remote. Almost 200 people, maybe even more by this time, located all over the world. And so, when it comes to leadership, so many different things that I want to ask you about, Matt. It’s a real pleasure to have you here today.

MATT: Thanks. It’s great to be here. Any topic that we cover, I think 1Password will be slightly different in how we do things. And I think that is a combination of growing organically and not constantly being fast-paced at hiring. I think within the 14 years that we’ve been running the company, we’ve doubled nearly every other year. And now, with our money, we’re going to double the company every year with the help and things like pipelines of candidates and stuff that we just didn’t have before, which is really exciting.

CLAIRE: So exciting, and I’ve got about a million questions I want to ask you about how you managed that growth. I know 1Password’s culture is super unique, how you sustain that culture through growth. But I got to start with the one question, Matt, that I ask every single person on this podcast that I’ve been doing this for the past two years. And so, are you ready?

MATT: I’m ready.

CLAIRE: The question is what is one thing, or it could be several things, that you wish you would have learned earlier as a leader?

MATT: For this to add a bit of context, I joined 1Password nearly eight years ago now. It’s been a long time. I joined as a designer, and I was kind of working on the apps or what we call the client apps which are kind of the end-user thing, what people use every day. And then slowly, I started working on the business end of it, so the management where you go for billing, where you go to add people to your account, where you set up sharing and configure everything. From there, I kind of started leading the design team. And then probably about four, maybe more years ago, we actually added a marketing team which we didn’t have before. Everybody before either supported our customers or built a product. We had basically pretty much three types of employee: a customer service person of which everybody in the entire company does customer service. So, just add that thing that we probably need to talk about at some point. And then all was a developer, all was a designer. That was kind of it. We had no management, we had no marketing, we had no sales.

Going back to your question, the one thing that I think I’ve tried to hold on to too long — that is how I’m going to interpret that question — is basically perfection. Coming from design, I always have the mentality that developers always want to start over, always want to go file new projects. And designers always want to have that second chance at perfection, that second chance to kind of add something and iterate. There’s limited people, there’s always limited people. That is what we found. And the ability to tidy up your stuff is not always there. So really, I’ve learned that it’s not going to be perfect the first time around. You’re always going to need that second round of feedback. And as I’ve taken on more things, like currently, my role oversees product marketing and design, kind of three areas, you donít get that day one. You donít get to that state of, “Hey, I can share this on Dribbble,” as a designer. Or, “Hey, this campaign worked perfectly.” That was my takeaway as I moved into more areas. I always expected it to have that pay-off the design has that is like, “I’ve done it. It’s good. Let’s go.” That is just not the case with other areas. Maybe that is more about me expanding into different areas than me managing more areas.

CLAIRE: So, there are so many different things that are fascinating about that response. One is sort of the reflection of that answer and, I would say likely, the uniqueness of your role on the growth of the company. Here you are as a COO, that [inaudible] designer. I donít know how many COOs I’ve met where that has been the case.

MATT: I think that attests to not many COOs not doing operations which I kind of donít really do. I understand why I have the title that I have. It’s because we have essentially a kind of three C-level people as well as founders in the company. And so, you can’t just have a Chief Design Product Marketing Officer. It just doesnít work. So, I see the title change there.

CLAIRE: Oh, absolutely. I only point that out because I think in your answer of trying to find or expecting almost that perfection to happen as the role expands matches up, I think, with just the fact that the role, it’s the transition from, as you’re saying, what you were used to seeing success as. It was the final beautiful polished pieces that you can then put [inaudible], feel like, “Okay, this is now done,” and management and leadership is not like that. And so, I love just how in the context of your progression that that’s been true. I was curious, Matt, for you, was there anything in particular that you found especially difficult to look at and be like, “This is so far from perfect right now.”

MATT: I mean, yes. We have a, I hate to say unique because I’m sure there’s other companies like it. But we struggle to find any. We donít have any analytics at all within our products, so we have no behavioral tools. We have no hotspots, we have no information from our platform that tells us how many passwords people have in different locations and what they’re for or what websites they’re for. That’s obviously a thing that people donít want. Your passwords and the things that you store in 1Password are private by the very nature of you storing them there. So, it’s difficult to build a product like that and to market a product like that when it’s all mostly based on intuition. I understand, like I said, the manner of building a software product is intuition anyway, but couple that with the fact that when we want to build something and we need to find out information about what we’re building whether it’s going to have an impact on the customers or anything like that. Basically, quantitative information is really difficult. I mean, what we end up doing is going out and talking to customers.

Customer service is one of the biggest assets that we have at 1Password. We use it for user testing. A customer has a problem, we’ll get together, we’ll think till we’ve solved that problem, we’ll present it back to that customer. It’s wild to see people’s reactions of, “Hey, I emailed in and I didn’t like this button here. I didn’t really know what it did.” And then they came to me with a whole new button [inaudible]. When that happens, that customer interaction is that close. People always find it really weird when — because we have a podcast as well. And when someone emails in from the podcast, I will email back because that is my customer service area. People find that really odd. [Laughs]

CLAIRE: I can relate.

MATT: When you have that from a product point of view, all of our product designers and product managers are all speaking with customers to find out their information. There’s no huge repo of analytics that we’ve [inaudible] from that. I’ve kind of forgotten your question now [chuckles] but I think that is like a massive challenge that we’ve overcome just for work really, just talking to the amount of customers that we have over the last 14 years has given us the insight.

CLAIRE: Matt, we can throw away my question, honestly, with the path we’re going now. Because what I’m so curious actually to hear is to what degree do you think, if any, the connection to customers has actually influenced your leadership style or how you approach managing your team at all at 1Password?

MATT: It absolutely has. The empathy points that you get from having a kind of customer champion over a feature is huge. There’s some entire projects we call internally after the customer that started that issue, like obviously first names only privacy and all that. But we literally named all project teams after the customers that have been involved. And I think it just speaks to the culture of how much we try and care, for the use cases of that customer. Like, they’re not personas. We try and really not deal with that because I think it detaches you from the problem. It’s really hard to detach yourself from a problem when right up in the [inaudible] is a link to the customer that had this problem almost the worst, maybe, or is just willing to give us a bit more time to talk to them and figure out. So, it’s really that empathy lead which has been really important for us.

When I joined, I think we were 23 or 24 people. I think we’re well over to 220 as of today. And scaling that customer attention has been really difficult, obviously in training, like we bring new people in. But that has always been at the kind of the core of where we look first when we think we know what a good solution is to a problem. It could be a situation that we had several years ago where we were like, “No one uses this internally. We’ll just get rid of it in the next release.” And then we had 10,000 emails the next week, and we were like, “Okay, we should put this back.” [Laughs]

I think it kind of stemmed from that, like a little bit of fear of getting 10,000 emails again. But also, having that customer really care about that problem that they had. Our userbase are really passionate, for a password manager seems crazy.

CLAIRE: I’m like a total fan of a password management system. I think it’s one of the many fascinating things about 1Password. I do want to come back to this idea of the challenges may be that you would have faced around that growth from having 23 employees to now over 220. But before we do, one of the things I was curious and the reason I had asked the question around to what degree do you think does a connection to customer has influenced leadership style is because I was thinking about how a lot of times sort of from an organizational scholarly perspective or however you want to think about it, a huge motivating factor for why teams coalesce and align and actually work well is because they are rallying around some sense of vision, some sense of a picture of a better place. And oftentimes, what most companies and teams struggle with is just the fact that that vision isn’t very clear. And so then to peel it back one more layer is that vision usually isn’t very clear because not everyone on the team and especially actually leadership, the bigger the team gets is as connected to the people who are benefitting directly from the work that they’re doing. And so, it was almost sort of my academic hat was on, I’m just wanting to understand to what degree, if any, is that connection to the customer actually interweaving and connecting everyone at 1Password including leaders as this company is growing rapidly to say, “This is what we’re always about. This is why we’re all on the same page. This is sort of our true north is that connection to our customers.” Less so of a question, Matt, and more just sort of an explanation of why. I was so curious to understand that.

MATT: I really think it is that element of everybody in the entire company doing customer service, obviously to varying degrees. And as we grow, the varying degrees have gotten bigger. But everybody is in there somewhere. And so, when we have things like something goes wrong — I think a couple of years ago, we put out an app and had a faulty certificate. So when you install it, [inaudible]. Our customer service numbers went up significantly. Everybody in the company was like, “Okay, down tools. I’m going to go and answer and reassure some customers.” Thankfully we have checks in place for stuff like that now. Everybody has that in the back of their mind. It is the backbone of the company that is treating our customers how we would want to be treated under customer service because everybody’s had a bad customer service experience and they’re not very nice. Especially with something like 1Password where not accessing it makes you feel completely helpless. And so, I think that is where our customers are so passionate, it’s because about what you store in there and the amount of trust you have in the product. And that is not something that we take lightly.

CLAIRE: Yes. Matt, let’s circle back around then to one of the many different areas that I was so eager to dive into. So, this growth, insane. Doubling every other year. I mean, this is literally purely off profits and money reinvested into the business. You hadn’t raised money to date while you were doing that. And just absolutely incredible organic growth that no marketing, no sales team while this is happening. So, I’m so curious, and you alluded to this, what have been the biggest challenges in that growth in terms of the relationship and team dynamics and culture as youíve scaled that quickly. And especially being remote too, and those might be separate questions. Those are sort of big questions, but we’d love to hear your observations on that.

MATT: I would say that the biggest pain has never been growing the areas that we’ve already had. Finding designers to work on the product and having them understand how we work, that wasn’t really a problem. Finding developers, that hasnít been that much of a problem. Finding customer support people who are really passionate and really kind hasnít been that much of a problem. We’re finding a lot of them and I think that is maybe the problem. Growing new areas — and again, some of these areas like our customer success team, our sales team, those have been grown from our customer service team. So, people have expressed their interest and we’ve kind of grown them out from there.

CLAIRE: Fascinating.

MATT: That is how we grew those areas. How we knew how to grow was hire customer service people and if they express an interest, train them up and move them on to development or sales, or anything like that. A lot of people who are [inaudible] company have moved through customer service, who joined answering customers and then wanting to do something about the problems, not just say ‘sorry’ and ‘here’s the fix’.

I think those areas have been okay. The ones that we didn’t really know what we were doing are the ones that we’ve added very recently which is things like HR, finance, the people that donít really work on the product. We didn’t know who or what to wear to do anything there. I’m a designer. The CEO, Jeff, is a developer by trade. And the two founders, Roustem and Dave are developers who still work on the product. They literally go to work every day and develop. That is what they want to do. So, I think that is, where we’ve struggled, is the areas of the people that donít work on the product because we donít know what to do there.

I think one of the benefits of partnering with someone like Accel who are the people involved in the investment round really comes down to the expertise of how to run an actual operation or business to scale. Things like finance, HR, and everything like that. Scaling that department when I think I could count on one hand how many finance and HR people we had.

CLAIRE: Absolutely. Matt, I think it’s so intriguing that essentially, and please feel free to push back. But what I received was this almost identification of the growth of just new and unknown functional areas being sort of the biggest pain points. What I find so remarkable about that is, because I’ve talked to so many leaders, whether through this podcast, and thousands and thousands of managers that we work with through Know Your Team. I also hold a very small number of executive coaching clients still to this day, and it’s so interesting because what people usually say, you did not say. What people usually say is the cultural piece. It’s finding and maintaining sort of the, for lack of a better word, organizational soul as the company gets bigger and as you hire new people. And that did not come up. And so, what I’m curious is one, did you or have you struggled with that at 1Password? And if not, what do you feel like you guys do that’s different?

MATT: That’s a tricky one. I couldn’t write down on paper what we’ve done, but I could tell you like what is the secret sauce, almost. Our real values, I would say, are security, privacy, community, and kindness. I would say that the community one is a new one I’ve tried to kind of spare us on, but security and privacy, we’re a very private company. Before the announcement of funding, no one really knew how big we were. No one really knows that much about us, how many customers we really have. We almost donít know that ourselves. It’s a long story there. We’re very private internally, as well. How we treat customer data is like nuclear waste. We have as fewer people that touch it as possible, the right storage containers and all that kind of stuff. However you think about it, we treat that stuff really carefully. We don’t slap customer emails around. We will send the link to the thing that you need to log into in order to get there. And we’re really careful about this. And in bringing on all these new people, we’ve instilled that as a practice, as kind of a thing that you need to absolutely abide by because this is our core. It doesn’t really strike us as, “This is our culture and you might want to do this.” Or, “Hey, let’s get on a call and we’ll drink this kind of coffee.” To us, it was a fundamental and I think that’s kind of different than some other values.

And then, security is exactly the same thing. You are responsible for a huge amount of customer data in terms of when someone sends you a diagnostic report or something from their device. It has things like their device name and some people might say secrets, but it’s still personal identifiable information that you’re holding. So, securing your own laptop again is one thing. And again, this feeds into the remote thing. We absolutely instill that as a fundamental, “Here are the things that you absolutely must do.” Because we have a pretty good security track record and we want to maintain that.

And then I would say on the kindness thing. When I joined, Dave, one of the founders of the company, was the one to teach me customer support. It was a very — the way that we do customer support is incredibly empowering as an individual. You’re not going to get told to go through three manager positions in order to approve someone getting a small discount that they want, or someone wants to move this. We really do try and make absolutely sure that someone has the tools that they need too in order to make a customer happy and to go almost to the extra distance as they need. And so, I think that comes into it as well. We’re very generous with time and everything like that and it just feeds into this whole thing of really another foundation that was — there is most of the time, and especially when I started, there was no one above you to go to, to say, “Hey, can I give this customer 10% discount?” You are told how to go and generate a 10% discount and then you went and did it. Like that was the chain. And I think we’ve tried to keep that to a certain extent. We’ve tried to keep the kindness surprises customers. It really does.

Actually, I spoke to the developer and we fixed this thing in the next build. “It’s going to come out here, just go and download it.” They look on people’s faces, I imagine when I’m writing a reply like that. It is just like nowhere else, at least we like to think it is.

So, I think those fundamentals are really instilled in the culture because that’s how you do your job, not what you try and believe in while you do your job.

The community one is a little more kind of me trying to push stuff. [Laughs] We have lots of small communities internally and I think that’s kind of how we’ve kept it to feeling like a small company. We have a room to talk about coffee beans. We have a room to talk about books youíve read. We have a room that is our water cooler that seems to pass around songs of bad recordings of me today. [Laughs] I was recording a podcast. I said something slightly amusing and someone added a drum and bass track to the back of it and put it in the water cooler. That might make its way out eventually.

Stuff like that happens in small communities and I think that helps people with the idea that we are growing so fast. The people that have been here as long as I have and several people have been here a lot longer than I have to help that kind of, “Oh, there’s a lot of people there.” That kind of feeling. And I think hanging around in multiple smaller communities, you realize, “Actually, I know a lot of these people. It’s just I interact with a smaller number.”

CLAIRE: Absolutely. Thank you so much for sharing that, Matt. I would love to go almost one level deeper because I think, first of all, everything that youíve shared is immensely applicable when you just think of actually operationalizing values versus just saying that this is something you’d aspired towards. So, you’re talking about very tangibly how are the ways that people are acting are actually reflecting each of those sides which I think is amazing. What I would love to do is just get in one more level deeper, because I know for myself and so many other leaders who are listening is exactly how does one do that and specifically in a remote team. For example, very tactically, do you rely on a lot of written communication and asynchronous communication to communicate this? Do you put a lot of emphasis on onboarding and training? Do you have, for example, a buddy system in the company? Do you focus a lot on in-person meet-ups? I’m just so curious, just sort of on that tactical level what you feel like, “Oh, these things actually seemed to really work just for us.”

MATT: We do a lot of things. And I never feel like we do them in a way that feels like, “Oh, here’s one of these [inaudible],” or something. I think we try very carefully to not do many things but do them well. I think one of the weirdest things that we do, I’ve never heard anyone else do, is we meet up once a year and we get the whole company together. For the last, I’m going to say eight, maybe seven times, we’ve been on a cruise. So, the problem with 200 people is when you put them in an area, they’re all going to want feeding, they’re all going to want to go to different places, they’re all want to go here. Then we need meeting stuff like we need a projector because there’s too many people sitting in front of the telly and you can’t just shout at them, so we need microphones and all this kind of stuff. And the easiest way that we found to do that is a cruise ship because it kind of keeps people in the same — in relevant news, not such a good thing. But we literally all go on a cruise ship at the beginning of this month and had our kind of annual get together, in which we do things that we think that is the only time that we can do them. So, it’s for a huge kind of company-wide effort. Last year, what we did was we decided that the customers [inaudible] responses weren’t fast enough. We were taking a day or two or three, where we want to take a couple of hours. So, what we did was we completely reorganized the customer service team in terms of when you joined before, you answered customers. Maybe you were in the billing area, maybe you were in this area, maybe you were in that. No one really had a specialism. And so, that was kind of important in the early days because you had this kind of pillars of wisdom that were here for a long time and they knew everything about 1Password. “Oh, it’s not WiFi synching over three networks. Here’s the thing that we’re going to do.” As we move to service and the product came a lot less complicated, we found that people really could specialize in one area. So yeah, specializing in an area really helped. And that was a huge deal. We had to get the whole company in order to do that just because everybody has an investment in customer service.

And then, what else do we do? We do a “Secret Santa” which is kind of fun, in which we end up with something — you kind of add a little information about you and then the fact that we’re worldwide remote makes secret center really fun because you get Russian poetry like I did last year. And then I was like, “I’m pretty sure I know who this is,” because it’s from Russia. That’s quite fun.

We also very adaptive, I think, as a company. I’ve worked at small companies, I’ve worked at kind of really large, massive institutions. We are obviously slower to change at a couple of hundred people, but we’re still pretty fast. We can roll it all out and just have people start using it in no time. [Chuckles] So, I think being adaptive and changing this kind of stuff is another thing that we do. If something isn’t working, we just change it. If we want to bring in another tool, we just do that. If it has no worth, we just get rid of it. And I think that flexibility has really helped and is one of the things that has kind of kept us communicating well internally, I’m going to say.

We have problems like every company. “Where do I put this in this tool?” That type of thing. But slowly, we’re starting to understand that we do need multiple places based on how long that information is applicable. Slack is great for what Slack is great at, but if you want permanent new information, it probably shouldnít go in there. So finding those other places and putting information in there, I think that is the adaptiveness as we’ve grown, and probably going to the most popular tool, but we’ve kept that steady over the last 14 years. I think we moved from HipChat to Flowdock to — I think we moved chat tools until we got to Slack about ten times in a matter of months. I think that type of thing, people come to expect now.

CLAIRE: Matt, do you feel like as a remote company with over 200 people that there’s anything in particular that you feel like is absolutely critical to the team working well as a remote company?

MATT: I’m bad at this but it’s good that other people are good at it, and it is asynchronous. It’s the management of issues and keeping things moving forward.

CLAIRE: Interesting.

MATT: And I think another thing is ownership. Anytime we start something, it better have an owner. [Chuckles] It’s all right me saying, “Okay, we’re going to do this marketing experiment,” or, “We’re going to build this page on the website.” If there’s not someone who owns that and feels responsible for getting that done, even if it’s me or someone I want to get excited about that task, I think ownership is a huge one because it means that regardless of time zones, regardless of location, that is their goal. They’re going to make that happen. That’s what they’re really excited about. Making sure that that person is then excited about that is also pretty key. Yeah, I think that’s the key to me. It’s trying to leave an audit trail is accessible. We use GitLab and everything is an issue. Everything that anybody works on, be it a marketing product, be it an email, a newsletter, or a web page, or even going down to the product itself, server level, anything, everything is an issue. And that issue then gets a common trail and you can kind of lookup where projects are pretty instantly. You donít have to kind of ping five people in Slack. It’s key to have it all in one place, I think. As soon as your marketing department starts to use a calendar in here, that’s when things get difficult, I think.

CLAIRE: Absolutely. I find it so interesting because I would say that that is true, not just for remote teams, but any team. You need ownership and that audit trails so that when new folks come on board, that’s that transparency. Matt, thank you so much for sharing all of your wisdom and incredible insights into just the really remarkable path that 1Password has taken and the way that youíve helped contribute to that and led that. I’ve learned so much actually in listening to it. I have one perhaps the last question here before we sign off if I can squeeze it in, which is, is there anything that you wish personally just based off your experience from 1Password and keeping in mind that the folks listening to this are managers themselves, that you wish were more true and that more managers embraced, embodied, or did.

MATT: On a personal level, I think the products that we build, they affect the people who use them. I know that sounds ridiculously straightforward of like if you’re suggesting that you use information that perhaps you might not want to be used about you. From a standpoint of privacy, there are so many products out there that donít stand by some basic rules that they would want to be treated as. We, as an organization, donít do any retargeting. We have Google ads, we spend the same amount as everybody else does on Google ads, but we know we leave money on the table by not retargeting. But I donít like it. Loads of people are comfortable with it, that is fine. Stuff like being targeted on the internet gets out of hand really quickly. It’s a really slippery slope of kind of the desire to capture that last customer. I find that there is something that slips away from a product every time it does that. I feel like you have kind of a level of trust in a product. And as privacy becomes more and more important, that trust is finite. You never get that back again from a customer. So, the more that you do in terms of retargeting or even to a certain degree, personalization and [inaudible] people to web pages, it destroys this underlying trust and it might make your conversions go up. But it might not make those conversations feel very good because those conversions are, at the end of the day, people.

The one big thing that I would say I really would love more people to take hold of that build products, is just be careful with people’s information. Sometimes, it’s really damaging.

CLAIRE: Absolutely. I so appreciate that emphasis on privacy, Matt. And I think you’re the perfect steward to champion that message. Thank you so much for really setting that example at 1Password. It’s been a real treat to have you on the show. For anyone who’s been listening and who’s been admiring the way that Matt’s been describing the way, theyíve thought about building the company and now growing the company even more. I know at 1Password, you are continually hiring for your remote positions all over the world, so be sure to check that out. And in addition, thank you all so much for listening here on The Heartbeat podcast. You can always watch all of the episodes that we’ve had over the past two years at KnowYourTeam.com. And as always, be sure to support us and make sure to check out our product, Know Your Team, to help you become a manager too. So, thank you so much again for everything, Matt. I appreciate it.

MATT: My pleasure. Thanks very much.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.