Founder Confidential: The Top Things No One Really Tells You About Scaling

Duo Security's Doug Song and PagerDuty's Jennifer Tejada share how they scaled their companies through intentional leadership and culture. They describe concrete practices like quarterly board-report docs, appreciation rounds, and a "kinder than necessary" value, plus how they balance top-down intent with empowering teams.
Chapters
Alright, at this time we now have Doug Song, Duo Security Chief Executive Officer, and Jennifer Tejada, PagerDuty Chief Executive Officer. Please welcome them to the stage.
Hi guys! Should we go— oh, am I at the desk or are you at the desk? You want the green chair?
You sit there, I'll sit there. You should get the green chair. Alrighty.
I always wanted to be Jimmy Fallon.
Oh, like that? Oh, okay.
You want to do this? This is uncomfortable.
That's weird.
Okay. Oh, I got the green chair.
Yes.
Hi!
Hello!
How are ya? We in the food coma zone right after lunch?
Maybe. You guys awake?
Okay.
All right.
Well, there you go.
All right. Man, I thought Saastr was just a blog. Amazing.
I'm not gonna tell Jason you said that.
Well, I'm in Michigan. I don't get out a lot.
There you go. Go Blue! So we learned before we got here that University of Michigan grads have taken over Saastr. We are killing it. You just saw Jeff Lawson, also a Michigan grad. Doug and I both went to Michigan, not at the same time, but, uh, you know, have connected over our background from the Midwest and school. But more recently, we compare a lot of notes. We were introduced by a mutual friend, and it started this relationship where we would just immediately get into all the challenges and problems we were solving for and some of the small victories. And we've learned a lot from each other over the last couple years. Is that fair?
Yeah, absolutely.
So I thought we would kick off by talking about philosophy. I think both Doug and I have found some common ground on the intentionality with which we've designed organizations in terms of the way we think about people, leadership scale from the board to the culture of the types of employees that we're recruiting, and how we make the experience of being part of Duo or part of PagerDuty sort of career-making, life-changing experience. So why don't you share a little bit about your philosophy at Duo?
All right, sure. Well, before we get into that, I just want to say, you know, I've known Jennifer since before either of us were unicorns. And frankly, I think we've always kind of had, I don't know, some mixed emotions about that designation and what it represents. But I do want to bring you a little bit of a gift from Jennifer.
Oh, thank you. Oh, look, see? Now it's true. There you go. Now it's real. No, thank you very much. I want to be in any club you're in.
So in terms of our philosophy, we decided to build a company from the start that would really go after the largest opportunity in our space, right? And truth be told, I ran from security as an industry when I— probably 2 companies ago, because it had just gotten so crazy, so crowded. 1,200 vendors. A lot of customers who didn't know what was effective, and they're buying stuff that they shouldn't. But we came back to it when we realized that with cloud, mobile, all this kind of stuff, there was a huge opportunity for us to rationalize all that. And so the thesis we always had as a company was how do we come back and decimate basically the market, right? Could we go and take a lot of these companies that were building kind of one-feature products and kind of roll them up, roll up that value as part of a cloud-delivered platform at scale, and kind of become that Salesforce of security? And so for us, it was always sort of a mindset that we wanted to go and take on the industry at large, right? Not specific competitors, not specific markets. But that colored everything, right? From the very beginning, we, in order to do that, we knew that we would have to found the company on different kind of principles. And we really would take effectively a design kind of thesis, right, to how we'd, rearrange all that stuff. And so I think from the guiding principles of kind of what we start from, we're always there, and it kind of led from our strategy and product to the culture, right, and the operations really behind how we would operate, how we would disrupt product category after product category and entire industry to think about the consumerization of security in ways that I think in IT had come just ahead of us. And so that was kind of the idea behind all this, and for me, having— Duo will have been the fourth company that was part of Insecurity, second I've started, but the intention was for it to be our last, right? And really think about building for the long term. I think one thing that was maybe also a little bit different coming from Michigan was that most companies in Michigan the ones you've ever heard of, right, they tend to be very long-lived, generational. As I like to say, in the Valley, we generate lots of tech companies, but in Michigan, we've generated lots of industries. Automotive, furniture, kitty litter, pizza delivery, I mean—
Football.
Football, yeah, yeah, we're getting back to that, finally. Finally. But it's a longer-term sort of thinking. And I do think that when it comes to scale and kind of thinking about how we set up for where we're headed, having a north star like that is so important. So I don't know, what was your philosophy? Like, what did you see in PagerDuty when you came? You know, you could have done a lot of things.
Yeah.
But what was interesting about that?
Well, I was really fortunate. When I joined PagerDuty, Alex Solomon was the founder at the time, and he had made a decision to put the company ahead of his own personal ego and interests and bring in a leader who could scale the business. And oftentimes when a new leader comes into a business, they feel like they need to fix a lot of things. They feel like they need to change a lot of things to prove that it was the right thing to do. And I just found at PagerDuty, so many things about the business were going in the right direction. There was such a very strong foundation, a deep interest in making the lives of our users better. And in many ways, PagerDuty is like a consumer company in that regard. You never heard people talk about our company customers. You heard people talk about our practitioners, our users. So our philosophy has always been to start with the user experience and solving problems for the user and trust that that is gonna benefit the business and the company. And it means that, you know, it changes the way you think about design. It changes the way you think about culture. It changes, who you invite to your summits to speak, et cetera. You want people that are gonna resonate with the folks that are doing the work and the work that's really important. So it wasn't so much my philosophy, it was recognizing the strength that we needed to build on that I wanted to make sure we didn't accidentally hurt.
Yeah, having a purposeful culture, I think, right?
Totally.
It's so important because the things that you do when you're small, right, I think I've heard said, you get amplified as you scale. But they also provide the guardrails for it in so many ways. And I feel like, you know, as we thought about why we existed, why we brought the company together to prevent others from harm and all this kind of thing, through all the gyrations and all the things we try, it was always going to be important to have, again, a very explicit culture, right, of how we work with customers, of how we look at the business from the outside in. And I think, as you referenced, do the right things by customers leading to the right things for the organization.
Totally.
I think the former coach of the 49ers, before we stole your last one, Bill Walsh, I think he had a book called The Score Will Take Care of Itself. And I've always believed that to be true, that if you did the right things for customers and so forth, that all good would come from that. And so those kind of things, I think, writ large, have continued to carry our business in ways that, again, customers can connect with deeply, that we partner authentically with them, but also written in a way where as we onboard and bring other folks into the company at scale, can follow those trails and adopt that as their mission, as their purpose, in ways that are actually operational, right?
And I think— how many of you are founders? We have founders here? Ooh, see, that's so cool. Where the cloud meets, apparently. SaaStr Annual. One of the things that I think is really interesting about that is, as you scale your business, you're gonna bring on investors. You're gonna bring on board members and advisors and influencers. And there's this very strong gravitational pull to try and please those people, to really understand their agendas and try and do right on their behalf. And I think one of the things that has set Duo apart for a long time is that just laser-focused on getting it right for the customer and trusting that then everything will fall in place. We say this at work frequently, like, "Get it right for the customer, get it right for employees, and everything else will come together the way it should." But you're gonna feel that. You're gonna feel that gravitational pull of investors comparing you to their other portfolio companies, of giving you help and advice in thinking about what you do next, and just keep that customer at the center of everything you're building and everything you're designing for.
So in many ways, a lot of the operational practices of how we preserve the alignment of our organization toward those kind of goals, I think, are things that— it's interesting— date back to the second year of our company, when we first started writing our sort of culture decks and understanding—
Which was when? How long ago was the second year of your company?
2012. 2012, OK. Yeah, so some time ago. Hard to think back that far, but, you know, for us it was a lot of that kind of stuff. Like, what do we stand for? What are the pillars going to be of our business as we grow? And just like Amazon has these pillars of its business of, you know, widest selection, lowest prices, convenient delivery, you know, what is the basis on which, you know, you really choose to compete, right, in sometimes very crowded markets? But also some practices that would carry a lot of that forward. Like, how many founders here still are involved in the onboarding of their employees? Right. So that's something that I still do. Right. Over 700 employees, right. We do an onboarding orientation, and there's always a founder session, right, where we catalog kind of all the decisions we've made and talk about that shared history and journey we've been through. And again, it's just important, I think, to impart that kind of orientation and knowledge. Other things that we had done also to get board— our board and other folks in line with our journey was to write a board report. And so all of you probably who have boards probably write investor updates and so forth. But for us, every 6 weeks— and this is something I learned from Luke Kenneys over at Puppet— we would write a board report, 3 to 5 paragraphs for every department leader of all the plans, progress, and problems in their business. And they would complain to me all the time, like, oh, do we have to do this again? Been a month ago. I said, well, if you can't write to me sort of an update, and not just for me, but for our team, because we shared the board report with the entire company, in basically the span of an email, then you don't actually know what you're doing. You don't actually know what you've done or don't know what you need to do. And so we basically shared that as a Google Doc with comments enabled for board to, you know, have conversations with us and focus then our board meetings on the 2 or 3 topics of most strategic concern. But those kind of things, you know, practices, over time, we built an entire sort of body of knowledge and practice that, you know, when we onboarded new employees, when I'd interview new executives, I'd give them the last 8, right? Every 6 weeks, you know, kind of octave basis, I'd just give them basically the last year's worth of history of the company, all the major successes, failures, learnings, and see how they'd react or internalize or— and have a really meaningful discussion about this. But it was so useful. In so many ways to capture a lot of that. But again, a lot of the things, I'm sure you have other practices that are similar, right, to sort of inculcate a team and—
Definitely, I mean, having, I'm on the Puppet board and have been for several years, so I've been a consumer of that board report, and the thoughtfulness that goes into that ahead of time means that your board members come into the room already with a perspective of where the business is at, and you can dig in and have a meaningful conversation about special topics that really require strategic thought, that are gonna have a big long-term impact, et cetera, as opposed to spending all of your time on the operations tactics, the read-through, or the read-out, as a lot of people call it. So I think it's a great practice. I think every company has its own ceremonies and things that they do, and they do very well. We both share green as our brand color, and green tends to stand out amongst a lot of the blue and the red that's out there. Our Duttonians, as we call them, are very proud of their green, and I think engendering this idea of being proud of where you're from and what you do actually creates heavy responsibility on the leader because you've got to make sure that you continue to build a culture where the behaviors, not just the words on posters, not just the names of your cultural values, where the behaviors are going to to demonstrate day after day a place and a culture and an organization that your teams are proud of.
Right, every company's gonna have those demotivational posters like teamwork, you know, all this kind of stuff, right? And it's all the same stuff, but it is about the lived practices, right, of how we put our values, right, into action. And I think you do have to create the space and the framework, right, for that to happen. So other ways, like we would do border ports for us, as leaders to be able to tell the company at large what we thought was important. But just as much, we needed ways to surface what was important, right, across the org in the opposite direction. And so one of the ways we did that was maybe a little bit different, but we took it from a Jewish deli called Zingerman's down the street from us in Ann Arbor. Those of you—
Oh, yeah. Awesome.
Yeah, it's a force of nature. But anyway, Zingerman's has a cultural practice that we just stole. Call it appreciation. So we open or close every large team meeting with 3 to 5 minutes of specific thanks, thanking each other for the things that we've seen each other do that have made the team successful. And we train on how to give feedback more generally, right? Hearts, diamonds, spades, clubs. Hearts are positive but unspecific feedback. Diamonds are positive specific feedback. Clubs are unspecific critical feedback. And similarly, spades are specific critical feedback. And spades you always give in private. But diamonds, diamonds we want to be surfaced in public and all the time, because that's how we actually model the behavior that we want to see. And in a company that's growing at hypergrowth, where, as we say, we push decision-making down with a similar kind of decision framework— like I said, I don't care about the quality of any individual decision, but I care a lot about the quality of our decision process— you know, we would make sure that every decision was guided by the same thing. Is it the right thing for the customer? Is it the is the right thing for the company, is the right thing for our community. But at the end of the day, we would never, there was no way to stay on top of all the right decisions that were made. And all the things that we would need to elevate and standardize in order to scale. And so by CUSP, by our employees actually thanking each other in the very public setting, we would actually surface that in ways that we would be able to crowdsource and understand. And so, you know, half of the challenge of scale is just staying on top of what's actually happening in your own organization. And certainly things like Slack have helped. Even before Slack, every company—
How many Slack channels are you stalking on a given day?
I have no idea. But we have more Slack channels than people, right? And maybe your organization is the same. So it is hard to stay on top of everything. But at the end of the day, figuring out ways to surface all those nuggets of goodness, right? And again, level it up and make it repeatable is half the challenge of scale.
There are a lot of challenges to scale. I think that's why this has become such a popular event in and of itself. And one of the things I think our companies had in common from an operational standpoint or have in common is the high velocity, you know, land motion, the flywheel effect in the expansion motion. And one of the things that I found when I came to PagerDuty was in an industry where we're constantly looking for best practices that we can appreciate and copy and reapply, there weren't best practices that we could go just steal. If we tried to bring in kind of the Oracle Splunk elephant hunting motion, it didn't work for the way our users, who tended to be developers, wanted to engage with our product. And so we really had to build our own model, and it was a lot of experiments. We burned a lot of pancakes, before we got it to sort of golden brown. And we've got some of our go-to-market team here today. What were some of the biggest challenges you found in scaling that model, particularly given you're not sitting in the center of the Valley? There's not 10 companies around you doing the exact same thing.
Well, to be frank, I saw it sort of as a benefit because I joke about SaaS being just a blog. But for us, that's what it was. I'd never been a SaaS-er. None of us had been.
Is this your first time as a SaaS-er?
My first time as a SaaS-er, yeah.
Let's give it up for Doug speaking at his first time at SaaS Tour.
Very happy to be here. But I certainly read everything that Jason ever wrote. Like, that was kind of the Bible, right? We called him Brother Lemkin, right? That was the way we kind of referred to a lot of what we ever read there. And, you know, but just as much we read, like, David Cummings, we read David Kellogg, we read, you know, Tom Tanguy, we read Alex Clayton. We read so— just like venture capital, all this stuff has been demystified. It's no longer the realm of the black arts. And so that's where we sort of got a lot of our kind of grounding. Talking to a lot of other founders, right, was where we got the rest of it, frankly. And particularly at this stage of the journey, when we were achieving, you know, big scale, preparing for maybe potential entry to the public markets, all that kind of stuff, you know, guys like you just saw, right, Jeff Lawson.
Oh yeah, amazing.
So generous with his time with me, not just because of our mission connection, —Samir Dalakia from SendGrid. I know you spent some time talking to him as well. Totally. And Toby at Shopify, Matt at Veeva, like all these folks. Scott Dorsey out of Indianapolis and ExactTarget. One thing you shouldn't be shy about, and this is something that we've talked about too, is about asking for help or reaching out to other founders to get some perspective.
Likewise, returning that call when someone reaches out to you. Because you think about it, I remember calling Greg Schott from MuleSoft once, I had a question, he called me straight back, that's turned into monthly coffees, we compare notes all the time. Lucerne, same thing. You and I, Doug emailed me, says, "I'm gonna be in San Francisco on Monday." Monday is Memorial Day. I'm like, "Okay, well, drop off the 13-year-old at David's Tea and we sit down." We start talking about our businesses, but it is, no one can know or understand the pressure that a CEO is under, 'cause it's not just about work, right? It's also your family, it's your board, it's your customers, it's your investors, et cetera. And so that bond that I think sort of naturally develops is a really important one and not one that everybody knows is out there and available.
[Speaker] Yeah, it's a lonely job and mental health is health, right? It is very important to keep yourself in the good spirits of other folks who've got your back.
Speaking of health, what happened here? You can guess. Skateboarding.
There you go. Exactly. Doing something really dumb. But at least I got the picture. Check my Twitter if you want. So when I think it came to us thinking about scale and building out in Michigan, The other half of it was the fact, the opportunity to actually do it differently. Like you say, all these things are inputs, but they're not directly tactics and strategies you can often apply, and so you have to be adaptable. And like, for instance, tomorrow you'll see, hopefully, my VP of inside sales, Jennifer Lawrence, who joined Duo from an enterprise SaaS company selling just healthcare, like big, massive healthcare deals, and she had never done inside before, But she joined Duo working under the tutelage of my head of worldwide sales, Jim Sibb, who'd just come out of the Zendesk IPO and had plenty, right, to kind of shape for her, but also said, "Do it your way." And what's so important about that is that, you know, for companies like us, for any small startup, right, you're not better resourced, you're probably not smarter, and you shouldn't necessarily work any harder, right, than any of your competitors. Competitors, but the most important thing is to learn faster and outrun anybody in terms of finding new routes to success that your competitors won't. And so what we were optimizing for, because we're the same thing, high velocity, high volume, high margin, but what's most important is that we need to do that not just in terms of our commercial, you know, design, but in terms of our organizational operation and learning faster. Faster. And so that's why I say we push the decision-making down. We needed to have sort of a commander's intent, or what have you, borrowing from military analogy, which I hate doing. But we need everyone to sort of have that North Star, know what we're running toward, but be able to go and try lots of things until we found ways, again, that we could do things better, or at least differently. Than our competitors would. And at the end of the day, all that kind of summed together made for a very different customer experience and journey, right, for our market than they'd ever seen before. And that's what actually has led to kind of the larger ongoing scale for us, that it, you know, the feedback loops within our business that all tie together were born sort of out of a lot of efforts from our teams cross-pollinating each other, working together to find all those points of intersection, but again, with a grand design that we could all align to. So anyway, I just encourage that for those of you who might be more command and control or top-down or whatever sort of leaders, that you let go a little bit. And you have to have ways in which it comes back and you sort of preside over it. I'm not sure if you feel like that's the same thing.
[Speaker] 100%. I mean, it's funny you say that. So PagerDuty started, journey in the DevOps community. And one of the core tenets of DevOps is to empower individuals with information so that they can make the big decisions closest to the action, right? Which is the direct opposite of command and control. You know, if you've got a customer or company that's burning because of a technology issue or an issue with a customer experience in an app, right, one of the challenges that happens is if you've got to float that decision through a linear ticketing platform up to a senior leader and wait for it to come down, that customer is gone, so are a couple hundred thousand others. And so I had to change my leadership style. I had to learn to listen to the individuals in our organization who were closest to our user community. And even when something's going down at work and you have an incident, you know, and something's not working, learn the incident commander during that incident is my boss. When I come into the war room during an incident, they call it the executive swoop and poop.
So— The seagull, right? Flying through.
Yeah, exactly, that one. And so, you know, just learning, like, I've learned a lot from our community and our employees. And, you know, part of that is checking your ego at the door and being open, like, being open to the fact that everybody around you probably knows more than you do about something. And being open-minded to that.
I'm usually the dumbest person in the room.
100%. In most of my meetings.
Meetings, and it's the same thing coming from the, you know, where I came from, because before I did any companies, I was something of a software communist doing open source, and in that community, right, it's all just volunteer. You can't tell anyone what to do, but even at this stage, right, this scale of our company, everyone has choices, right? There's so many great SaaS companies to go and join, so we have to offer something different. And so when we thought about, you know, the platform we're building, not of the technology and the product, but of the company, could we build a platform opportunity where understanding deeply every person's story arc of their career and life, and how to align their opportunity— our needs as opportunities, what they wanted to do, we could all grow together, was the most important thing we were looking for in terms of our management style and leadership style. And so we spent a lot of time really looking for employees that were deeply self-aware, with a lot of behavioral learning questions, like tell us the biggest misconception about you, or have you— we look for leaders who have had a history of traveling distances with teams that grew with them. Because there are many ways to be successful. We just chose, in a very intentional way, how we wanted to be. And I'd say it looked a little bit more like— to choose two extremes in the SaaS kind of leadership model— You know, Matt Wallach from Veeva had, you know, and the Veeva team had sort of one Peter as well. And then I'd say like Godfrey from Splunk had another, right? And like Splunk was— Godfrey was like, we want folks who've been there, done that, we don't got time for this, right? Veeva was like, we're going to grow all of our leaders from the inside. And, you know, on balance, we were a little bit more of Veeva than we were Splunk. But by the same token, we knew that there were things that we would have to have to really be able to accelerate and introduce the right perspectives in our company. And so while we weren't in Silicon Valley, we needed a little bit of Silicon Valley in us. And so we did seek out very specifically, you know, in certain roles, some of that leadership that came with that experience and perspective to share. But again, you know, one of the benefits I think we had in Michigan versus maybe in the Valley is that there wasn't so much an echo chamber. Of everyone sort of seeing and reading and kind of following exactly the same things. We had a much greater cognitive diversity of all the folks we were able to bring in, and arguably a greater diversity overall. That's something you've done extremely well. Well, we're trying.
I mean, it's a journey, right? And I, you know, we're sort of trying to focus on the I in D&I, the inclusion. Like, how do you make discovering PagerDuty, becoming part of PagerDuty, you know, having impact at PagerDuty, but also PagerDuty having a positive impact on you? All feel equitable and everybody having the same opportunity to kill it as opposed to certain groups having privilege over others. It's meant that you have to operationalize a lot of behaviors. It starts with leadership. Our leadership team is gender balanced. That was not easy to do. 65% of our leadership team is born outside the US. Also not easy to do because there's lots of brilliant people just hanging around SOMA. It would be easier, quicker to just bring— South of Market in San Francisco, for those of you from out of town. It'd be easier to just bring those people in, and frankly, the whole system sort of works against you because the recruiters, your investors come to you with athletes, and those athletes tend to be white males. And mercenary. And mercenary.
Which is something that, again, there are many ways to be successful. I just never could do that. I would never work with a team of folks who were continuously rotating. That were kind of out mostly for themselves versus kind of the team and so forth. Totally. And so there's— for those of you who aren't in the Valley, you know, I encourage you— I mean, great that you're here, but I encourage you not to be discouraged about anything that you might be lacking from, you know, being in this region. There's something strategic, right, about every place you could set up. And the real work in actually building a scalable organization is to figure out what that is. What is strategic? That you can apply. In our case, one of those things was the fact that Michigan and Ann Arbor is—
You're like the king of Ann Arbor now.
Well, Ann Arbor's a pretty small place, right? We can fit everyone in Ann Arbor in the stadium, right? So it's pretty small. But one of the nice things about what the culture of Ann Arbor is is learning, right? That's learning, the team, the team, the team, right? And those, as we talked about before, are the elements of what drove our success and how we chose to go about building something that would be highly disruptive. You'll figure out, again, what those things are for you, but I encourage you to draw upon what that looks like and institutionalize it, because, you know, again, like, again, the small things you do when you're small, if you do them well and they really are strategic values to you, they will help you scale. So in terms of those learned behaviors, right, you know, We did a lot of that stuff at a micro level, where we would talk about assuming positive intent. One of our core values at Duo has been to be kinder than necessary, which is not a statement about being just nice. It's not like, say nice things about Detroit or whatever. It's going out of your way to help each other be successful. And so those kind of behaviors have led to so many of the deep innovations we've had in the business at every level, right, including how we do— it's the most effective team selling I've ever seen, right? Our legal team gets kudos all the time, right, from how they're, you know, in how they kind of move deals alongside, and everyone can celebrate and own that together. What are things that you did that might have been, you know, like behavioral, right, like defined sort of V?
Yeah, I mean, one of the things I did when I first came to PagerDuty, I, I'm a little bit of an extrovert and I like to have fun. And I actually have been intentional about making sure the work stays fun for me, that work is fun for our teams. We like to— we have a party or a celebration. There's a cupcake almost every day for something at PagerDuty, making sure that we never lose sight of if you're gonna spend 80% of your Waking time somewhere, you know, why are you doing that? Like when you get out in the morning, out of bed in the morning, what are you excited about? So sort of trying to build fun and laughter and joy into everything that we do and seeing some of the big ugly challenges as the big ugly problems as fun challenges that you want to tackle. So not taking ourselves too seriously because we're founded by Canadians. We're already nicer than necessary. We're almost Canadian in Michigan. Yeah, and I'm from Minnesota, so it's like nobody's mean at PagerDuty. It just doesn't happen. So I think that was a big part of it, was like bringing joy into the work that we do with our customers, with our users, et cetera. And then also being really explicit about what winning looks like. So we've got company kickoff next week, and we'll stand up there and we'll not just talk about what the long-term goal and what the numbers are. We're gonna envision like at the end of this year, What will it feel like to be PagerDuty? In the end of 3 years, what will that feel like? What will it feel like for our users? And how do we continue to disrupt ourselves?
Yeah, leading your teams through change is the hardest part of this job anyway. Oh yeah, particularly in hypergrowth, right?
How many times have you had to sort of change and tweak your leadership team as a part of this?
Yeah, there's always— Growth curve. Yeah, leadership errors of any company, right? And we've talked about every year Here we're basically a different company. Now we're not all different leadership, right? Typically we kind of have at least 2 years sort of span in which we kind of have a fully committed and locked leadership team. But you do have to think about that stuff and paint the forward picture for teams in ways that they can understand and internalize the change that's to come. Because, and again, maybe other folks do this differently, but for me, I don't know how to tell people to kind of take something if we haven't socialized a lot of it and brought them in, because I think for decisions to stick, they have to have two things, right? Clarity, but also buy-in. And folks have to have an understanding of how they can own a lot of those decisions, create their own commitments, and help align their efforts to them, you know, as much as leadership. So I feel like the best teams that I see really achieve that scale have a way that that basic kernel of how that works within a team really cascades and cascades really well. And so you guys wear it on your sleeve. Like, one thing I see companies like yourselves or our team have to do well is employer branding, is creating a truly an employee value proposition, which again, my former head of people, Ambrosia Vertesi, did an amazing job of. She has a whole HR open source kind of movement she's kind of built with all these CHROs talking about this stuff. But more and more, that same challenge of how do I manage sort of an inbound funnel, right, of sales and marketing, applies actually to talent. And you want to have talent self-select its way to you. You want to manage basically, again, that flow, and have ways in which you have those kind of feedback loops of what's kind of worked well and what hasn't. You know, we used to ask these very interesting questions of all of our hires, you know, like, "What makes you unique?" Because what we were looking for was a cultural contribution they would bring to our company, not a cultural fit. [Speaker:MALE_SPEAKER] Yeah. [Speaker:JASON_M_LEMKIN] You know, they need to share our values, But more than that, they needed to bring something new, hopefully, that we didn't have already. Because if they didn't have that, you know, what was going to drive the scale, right? We need those alternate sort of mental models, frameworks, skill sets, and experiences. And so, you know, we built hiring practices. We had, you know, a lot of, I remember Matt Kohler from Benchmark talking about how in hiring, maybe you take a product or product marketer and have them take the challenge of actually operationalizing that whole program, because product marketers think this way. How do I talk about the key value proposition? How do I kind of, and all this stuff, and so we worked really hard to operationalize those things in ways that made it completely repeatable, made it inbound, 'Cause that's gonna be hard, some of the hardest parts of scale, like finding the right people.
There's a lot of hard stuff in scale. We got like 2 and a half minutes left. You wanna do a little speed round? Right, let's do it. Okay. What's the most important decision you made in the $0 to $50 million in ARR run?
Decision of the first level of our leadership change, where at about $10 million, I brought on board effectively the nucleus of Zendesk, Fisk's go-to-market engine. I brought on board Jim Sibb, Jeff Wyss, and Zach Urlocker. And we basically went from 1 to 3 to 10, from 10 to 30 to 73, and then I'm not supposed to be talking about the rest of those numbers and hundreds, but at any rate, that's—
OK, so 100 plus. 100 plus is interesting.
I think it was about finding the different overlapping S-curves of growth, because in the early product market fit, right, in Series A product market fit, Series B, it's about making things repeatable, and sometimes with a foolish consistency. But in Series C, where you're looking at kind of the larger strategic risk, right, you're big enough that people care about you, and you've got to worry about that, but you need to figure out how you sustain the growth when your initial strategies might have reached the point of diminishing returns. You have to manage a portfolio of growth. And so we've always thought about different parts of our business in startup, growth, and scale mode. And of course the latter, you know, you're finding different people, you know, for, 'cause they will, you know, you have builders, you have growers, and then you have operators. And for different parts of our business, right, we would be, and we still are, right, in all those stages across different segments of our business at a given time. And being thoughtful about how we would set up size our investment, look at managing, basically the life cycle of learning. What's the next increment of learning or success? As you say, we would win or we'd learn.
So on that note, we have 47 seconds left. Yes. What are you most proud of? You've built an incredible business. You've delivered an incredible return back to many investors, employees, and friends of Duo. What are you most proud of, knowing that this is not the end of the journey, this is is just the start of another one.
The legacy of creating a different model for what a successful business can be in our industry, and one that is really people-centered, both from a product perspective and customers, but also from employees, and also leaving a legacy of, again, a bunch of our folks all having had the best experience in their careers with us and beyond. And so that's— we'll see. We'll see what happens with Duo over the long haul, and we're certainly very excited to contribute to all of Cisco's transformation. But I think as we look back, that's what we're most proud of. Awesome.
Well, thank you for hanging out with me today. Thank you, Jennifer. Cheer for Doug.
Thank you. Well done. Jennifer.
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