On Fear and Leadership: Product to Sales CTOs & CEOs

with @martin_casado @armon @smc90 As companies evolve -- especially from product to sales to scaling operations -- so must the leaders. But can the same person transition across all these phases? When and when not; what are the qualities, criteria, and tradeoffs to be made? Two enterprise startup CTOs share a glimpse into their journeys on the question of to CEO or not to CEO; managing their psychology and tactics for managing transitions; and much more.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Sonal?

  Hi, everyone. Welcome to the A60Z Podcast. I'm Sonal. And in this episode, part of our ongoing Founder/Operator Series, which you can find more of at a60z.com/FounderStories, is about founders wrestling with how to evolve their roles from product to sales and the question of bringing in an external CEO or not. The conversation took place as a hallway-style chat and features A60Z General Partner, Martine Casado, who co-founded and was CTO of Nysara and shared his own journey, lessons learned, and advice for founders at a60z.com/ExternalCEO. And then the voice you'll hear after both of ours is Armon Dargar, the co-founder and CTO

• 0:43Sonal?

  of cloud infrastructure automation company Hashacorp, which enables enterprises to provision, secure, connect, and run any infrastructure for any application. And while the two share their own journeys, our conversation is really more broadly about the phases that all leaders and startups go through, though they may end up in different places. In this discussion, we touch on everything from managing one's own psychology to managing specific tactics, discuss swim lanes and what enterprise sales means for CEOs and more. But we begin by outlining different mental models for describing different phases of leading a company.

• 1:22Martin Casado?

  So I feel like leaders and startups go through three phases. And startups require three different types of leadership phases. The first one is a product phase. So if you're going to be a leader of a startup early on, like you have to be a product leader. And your goal is to find product-market fit, which is syncing up a technology and a set of technology trends with a user and a need. And so you have to be kind of piped into the nervous system of the technology, of the tech trends, and of the users, and how they use it, and of the problem domain. And if you're not piped into that nervous system on both sides of that, especially in core infrastructure, like Armon and I are both like core infrastructure geeks, then I don't think you can lead the company correctly.

• 2:07Martin Casado?

  So the first phase is the product phase. The second phase is the sales phase, which is now you've got product market fit. Over time, the economics of a company come down to go to market because that's your variable cost, right? R and D becomes this kind of sublinear cost. And then to get more customers, you need to spend more money. That drives your margin, which drives your valuation. That's go to market. And so if you don't understand how to do that go to market and becomes a sales leader, like you kind of miss on that stage.

• 2:32Sonal?

  What did you mean by the R and D cost trade off of variable cost? I actually did not understand what that meant.

• 2:37Martin Casado?

  Yeah, so this is in the spirit of what is the most important thing to accomplish very simply in each one of these stages? So in the first stage is finding product market fit. The second stage is getting a repeatable sales motion in a way that's solvent and has good unit economics. And the reason that that's so important is if you look at the valuation of a company, the valuation of a company is driven by growth, by margin, probably by things like net dollar retention. Those are the numbers that feed directly into the valuation and those are driven by go to market. And the reason they're driven by go to market is because that's a variable cost.

• 3:20Martin Casado?

  It's a cost that that you have to keep reoccurring in order to grow. Engineering, on the other hand, tends, especially in software, in order to like bring on that next customer, you don't necessarily need another engineer because it's pretty cheap to replicate bits, right?

• 3:33Sonal?

  Yep, yep.

• 3:34Martin Casado?

  So engineering tends not to scale linearly with the customers. What go to market does.

• 3:39Sonal?

  So the more salespeople you have, the more customers you can get.

• 3:41Martin Casado?

  Exactly. So you normally have relatively capped productivity of sales reps. It's very hard to increase that. So to get more dollars, you get more salespeople or you start to do clever things with like indirect sales channels. But that will drive your valuation. And so it's just very important to get those foundations right. And then the last stage is an operation stage. And the operation stage is you're trying to get something to scale. And now you've got all these operational challenges, like you go from a single product company to a product portfolio company. You start engaging the channel. You start engaging maybe these big partnerships. And so it's a lot more of the mechanisms of running companies or multiple companies that come into play. And so I think as a leader, you have to step up to each one of these stages.

• 4:21Martin Casado?

  And then you either have to make the transitions to these stages, or you have to bring in the people that know how to do that.

• 4:27Sonal?

  I love that framework. The first phase is about the technical product and of course, the market user fit. The second phase is about figuring out how to really sell it to the right customers. Sales and go to market motion. And then the third phase is really about scaling it. And when you say product portfolio, you mean expanding product lines, additional feature sets, other new product lines, et cetera.

• 4:50Martin Casado?

  Yeah, or increasing the customer base without cannibalizing your customers. You really get into like business operations at the third phase.

• 4:56Sonal?

  Right, growth is often where M and A will come in and a lot of the strategic things will come in.

• 5:00Speaker 02

  Yeah, I love that ontology. I hadn't heard it that way. There's a different sort of phraseology I've read and I like to use, which is it starts with a personality type that you might describe as sort of the pioneer, right? It's the person who likes high risk, high uncertainty. They're sort of forging the path. And I think that's sort of that phase one that you talk about of defining product market fit, right? Like there isn't a product, there isn't a clear market. You're sort of doing that pioneering work. And I think behind that person, you bring in the town settler. And their job is to say, okay, great, you forged the path, but now you need some process. You need some repeatability. You need some structure to how the company runs. It's no longer, you know, five people in a garage. And I think that goes to your point of like that town settling phase is very much the great, we have the product. Where's the go to market fit? What's that repeatable structure?

• 5:44Speaker 02

  And then I think that third phase that I've heard described is like who you need as a leader is a city planner.

• 5:49Martin Casado?

  That's perfect.

• 5:49Speaker 02

  Like you have a structure, but now it's like, great, it's not 10 houses. Now I want to build a metropolis, right? And you know, what I like about describing it that way is you can almost imagine in your mind, the personality differences, right? And it becomes so obvious that, you know, the city planner is a fundamentally different person than the pioneer.

• 6:06Martin Casado?

  I do think it's worth pointing out that often it can be the same person. But what I think people miss is how hard founders that make those transitions work to make these first-class problems. There are fantastic CEOs that come from deep, deep technical backgrounds and made transitions into great sales CEOs. When I speak with them, it's like I'm speaking to a salesperson. I mean, like, they're just obsessed with go-to-market. It's all they think about. It's all they talk about. It's the books they read, all the questions that I get. It's how the board is done. And so I absolutely think those are the three personality types. I think often, three different types of people can fill that. But when the same person does, they make almost a full metamorphosis.

• 6:48Martin Casado?

  If there's one takeaway, it's like, if you want to make these stages yourself, you have to be totally obsessed with the stage that you're in.

• 6:55Sonal?

  And you have to be self-aware. And quite frankly, this is where I think a lot of people bring in executive coaches and leaders to help them, train them. And there's so much value in that because it requires, A, awareness, B, willingness, and C, quite frankly, ability then to evolve. Because not everyone comes along on that journey. And sometimes you might also, four, make a choice, which we can talk about in a moment. I'm also glad you pointed that out, Martine, because what I also want to push back on a little bit, Arman, is, is it really that linear? We've had Jyoti Bansal on the A6 and Z podcast of App Dynamics, and he did a podcast on the evolution from a technical to product to sales CEO. Then we had our own David Yulovich, where he told his story from Open DNS to Cisco, et cetera. And it's a similar kind of thing. When David told his story, it feels like we talk about this journey as a bit of a linear journey.

• 7:38Sonal?

  And of course, I understand it from a growth and scaling perspective, but it seems like there's a phase where you're trying to figure out go-to-market and sales and technical product at the exact same time.

• 7:45Martin Casado?

  Right.

• 7:46Sonal?

  And so how do you kind of navigate that bit of it?

• 7:47Martin Casado?

  No, yeah, it's a good point. I don't think it is totally linear. The frameworks, I think, are a useful mental model, but they're not reality. And so I think the reality is, it's like, a company might be at a super early stage on the go-to-market, but actually might be at a mature place from a product perspective, right? And so there's this non-linearity of, like, you might be in different places in different parts of the company. One thing that Evav notices, even something as simple as a different geo can actually be a different phase of the company. It can actually... Have to do with product and not just sales. So for example, you sell in the US, then you go to like, say, Europe. And then the actual competitive environment is different, right? And so the actual positioning of the product and the problems and use cases you solve to, which actually roll back into product. So absolutely the case.

• 8:30Martin Casado?

  I do think it's useful to think of these three tiers as kind of like energy states. And then you can always move down and up into energy states. Like, let's say that you get to the sales energy state, but then there's a macro shift in the environment, and then now you're back down in the product market fit energy states. But here's the thing for a leader. First, you should know which energy state you're in. You should know, like, is the priority sales, is it operations, is it product market fit, et cetera? And then my number one test is if you wake up in the morning, if that's not what you're thinking about, like, you've not yourself made the transition. Your motions as the leader, particularly a CEO, should be 100% in line with like, that primary focus of the company.

• 9:03Sonal?

  So then I have a question for you guys. Is it always in the CEO's hands to make this choice? Did you have a choice to be the CEO or to be the CTO? Like, did you get to decide, or did someone decide that for you?

• 9:15Martin Casado?

  I got asked many, many times to be the CEO of the company. And I actually went through three CEOs. And there are long periods of time where there's transition, where there's no CEO. And then in which case, I was the de facto CEO. But what was interesting was, for me, I always thought that the CEO is kind of a clerical job. Seriously.

• 9:33Sonal?

  I feel the same way. I'm like, I want to be like, the person who's in the medal of the creativity. So I feel for you.

• 9:38Martin Casado?

  Right. I'm like, okay, my entire job is to find repeatability and find product market fit and to align this technical architecture that's researched to the market. I don't have time to deal with facilities. I don't have time to deal with like, IT and like, all these other things. I've got to focus on that. And in retrospect, it was my very naive perception of what a CEO does. I honestly thought that it would be a waste of my time. But then, we found product market fit. And then, we went to a transition. And then the question was like, okay, Martine, do you want to go do sales and leave that stage of the company? And I actually thought about it a lot. And then I realized at that time, we needed that knowledge in the company. I didn't have that knowledge. I started talking to people that had that type of knowledge. And my calculus at the time was like, you know, I can get someone who's pretty good as COO.

• 10:24Martin Casado?

  And do that, or I get someone who's really good and give them a CEO. And having created the technology, you know, like I wasn't worried about my position in the company or clout or credibility. I mean, I've been there for three years. It was my company, et cetera. But I love the HashiCorp story because they were actually solving their own problem, which is a real problem. I kind of had the more crooked path, which is we'd come up with a solution, which was kind of a grand unified theory of doing networking.

• 10:46Sonal?

  Software-defined networking.

• 10:47Martin Casado?

  Software-defined networking. And it could solve a bunch of problems, but we weren't exactly sure what was like the most important problem to solve. And like, having been trained to think about like, okay, like, we've got this kind of very elegant solution. Now, of course, all these problems will fall. It's kind of the wrong thing. And so, coming out of academia, we almost had to unwork that muscle and just really be very use case focused and then use that to figure out the mechanism as opposed to the other way around. And for us, it probably took two years. I see this get repeated all the time. It's like one of the major pitfalls of going from academia into startup land.

• 11:19Sonal?

  Well, I have a question about this because one of the challenges, and you've actually argued previously on other episodes of podcasts, that you actually think that computer science is now like more of an engineering discipline than even like science.

• 11:28Martin Casado?

  It always was, honestly.

• 11:29Sonal?

  Right, okay. Maybe we're just calling out the truth. The emperor has no clothes. Or maybe this is what the emperor's clothes are. But the point about the use cases is really interesting to me because the number one thing that a CEO or a founder of a company has to do, whether academic or otherwise, is sell their product and figure out who that customer is. And when you start with the use case, it's sort of a dance, a chicken egg thing. Do you get the use cases that that's what the product's gonna be? Or is it that it's, you know what, we're over rotating on the wrong customer? And actually, this is not the use case, but they're the ones who are paying us money?

• 12:02Speaker 02

  Yeah. When people ask me sort of like, what's the biggest advice you'd give people? Or like, you know, what was the biggest lesson for you? I think the thing that we got wrong was we actually didn't know who our customer was for the first few years of the company. When people would ask us, hey, who's the customer? We'd say, everybody. And what you end up realizing is that's the same as saying, nobody. What became obvious for us, once we actually started building a go-to-market, is the two-person, you know, garage team, they want to swipe their credit card and pay $5 a month and not talk to you. And then the person who's in a Fortune 10 wants you to sign a 300-page master service agreement. And if they're paying less than $100,000, they're sort of uncomfortable. You end up realizing that the go-to-market motion is so different. The pricing and packaging is so different. The features are so different.

• 12:47Speaker 02

  When we said, hey, we'll go right down the middle, there's nobody there. When we started the company, the focus was very much, hey, let's just build the products, focus on getting product market fit, doing the evangelism and building the community around things. And then I think when we had that sort of, I'll call it a crisis of identity, right? Which was-

• 13:07Sonal?

  As a company or as a person?

• 13:08Speaker 02

  Yeah, I guess both.

• 13:09Sonal?

  Okay. I guess there's no difference in you're the founder.

• 13:12Speaker 02

  I guess both. There was this sort of very distinct moment in late 2015 for us where we'd sort of finished building out the open source portfolio, the last few pieces were there, and the board sort of asked us and said, okay, well, what's HashiCorp as a company? And we're like, huh, that's an interesting question. And I think that kicked off a multi-month soul search for us to really say, okay, when we grow up, who do we want to be? Are we an SMB-focused company?

• 13:39Sonal?

  Small and medium-sized business.

• 13:40Speaker 02

  Yeah, are we an enterprise-focused company?

• 13:42Sonal?

  Right, the big customers.

• 13:43Speaker 02

  And where we ultimately landed was to say, yes, we want to be an enterprise business when we grow up. And then the sort of follow-on question is like, okay, if you're an enterprise company, what's the product? Like, you don't have an enterprise product, you just have a bunch of open source. And so there was a product discovery. And then I think the third piece of it was, to your point, who leads this? And then all of a sudden, me and Mitchell, Mitchell Hashimoto is my co-founder and the namesake of the company, look at each other and say, okay, well, neither of us has, we've barely worked in an enterprise company, let alone led an enterprise go-to-market. Okay, well, who's gonna lead the company in this next phase?

• 14:19Martin Casado?

  But at some point, you had to make a similar decision that I did, which is, you could have brought in that expertise in a different role. You could have brought in a VP of Sales and like-

• 14:28Sonal?

  Chief Revenue Officer.

• 14:29Martin Casado?

  A really good PM and a COO, or like, whatever.

• 14:31Sonal?

  Yeah, why did you not just stay CEO in the more technical but still visionary CEO and then bring in, because the whole point of a CEO is that David Ullivis describes it as, you don't have to be the one who has all the answers. You actually can draw on everyone else to be the experts. So why don't you take that model, like, bringing in someone else?

• 14:47Speaker 02

  I don't think we actually set out to bring a CEO. We started our search around saying, hey, what if it's a president, COO, maybe a super senior, other C-level executive that's not a CEO? And I think as we went through the search, we found David McJanet, who is now our CEO. And I think just the dynamics of his personality and the way him and Mitchell and I sort of work together, it clicked in this way. And what I love about Dave is he's so low ego that I think he also didn't feel strongly about like, hey, do you want me to be COO? Do you want me to be CEO?

• 15:19Sonal?

  But there needs to be some clarity around who does what and how. So how did you guys get from the moment of, well, this guy is actually not going to be our president or our COO. He's going to be the CEO. And hey, I'm OK not being that CEO. Like, tell me about that realization specifically.

• 15:33Speaker 02

  Yeah, I think when you talk about the process of trying to bring in a senior executive, certainly at CEO, COO level, it's such a serious hire that the way I describe it to people is like, it's almost like dating for a significant other.

• 15:45Martin Casado?

  You're like, do we have a culture fit? Do we have the same fiscal discipline? I mean, like, there's like multiple responses.

• 15:50Speaker 02

  Do we communicate in a similar way?

• 15:52Martin Casado?

  That's right. Yeah, yeah, yeah. Do we handle stress in a similar way?

• 15:54Sonal?

  Is that the assumption there that that person needs to be similar? Don't you want someone different?

• 15:58Speaker 02

  Not similar, but at least compatible, right? Like, if you feel like, hey, every time we talk to each other, it's like, we're talking past each other, or like, we're on two different brainwaves entirely.

• 16:06Sonal?

  Right.

• 16:07Speaker 02

  So, yeah, I wouldn't say we're carving copies of each other, but there's a certain compatibility in work style.

• 16:12Sonal?

  And why did you not want to be the person, to Martine's earlier point, to just say, hey, I want to learn and take on this skill and, quote, evolve in this way instead of going to more technical, other stuff? Why did you make that fork in the road?

• 16:27Speaker 02

  I think I'll echo Martine's point, which I feel like was incredibly naive. And I think what became clear is when we went through this dating process with David, that it was so obvious to me that his depth of experience was so much deeper than mine in so many of these sort of go-to-market areas, that, yes, could I learn from him and he could be a mentor and, you know, I could sort of come up to speed over time? Sure. But it became obvious that the enormity of that challenge became clear with the more time I spent with him.

• 16:57Sonal?

  Yeah, you basically saw someone who's like, really effing good at what they do. Why not let them be the best at them and you be the best at you?

• 17:03Speaker 02

  Exactly. So it's like, am I going to be enabling him to be more effective as CEO? Or am I going to be in his way?

• 17:09Martin Casado?

  Well, it also seems that we had many similar ingredients. And I wonder if this has to do with it. So, for example, It seems like Ewan Mitchell didn't have any title fetishism. And in our company, nobody had title fetishism. Like, CEO, COO, didn't really matter. Like, there wasn't a lot of emotion behind the specific title. Now, job roles, there were, but like, the actual titles. The second one is actually ironically, so we brought in a guy named Steve Malaney, who's one of the core reasons we are successful. I've learned pretty much everything that I know from him. I'm so happy we brought him in. He also has a marketing background, just like Dave McJanet. So he knew go-to-market and positioning and how to launch a company and all of these other things, which is... I think when it comes to product marketing in particular, like, you can't intuit it. You have to have done it.

• 17:52Martin Casado?

  And it's way less systematic than sales. I mean, it really is kind of like art plus logic plus...

• 18:00Speaker 02

  Domain expertise.

• 18:01Martin Casado?

  But then also, Steve, and of course, Dave too, has incredibly low ego. So we spoke for months, and in no point in time did I think, oh, this person's gonna wanna take over the reins. He's gonna change the vision of the company. Like, you know, it's gonna do like a palace coup or whatever. And so, like, if you have these initial conditions where you're like, you just want the right thing to happen, and you don't have this kind of like insecurity about losing ground, and the person coming in, you know they're gonna work with you, and they're gonna be relatively low ego, then the question is, is basically, who wants to do what, right? And then who's in the best position to do what? Yeah. And in our case, and it seems like in your case, we kind of came to the same conclusion.

• 18:39Speaker 02

  I think that there's this moment where you're like, if you make this hire, you're sort of handing the keys over. That sense of comfort that this won't be a palace coup is so critical. And honestly, I had a moment. I ended up talking, I remember, to Glenn Solomon, one of our board members. And I was like, I need you to sort of walk me off this cliff, right? Like, I'm not ready to sort of hand over the keys.

• 18:59Sonal?

  What did he say that helped you walk you off that cliff?

• 19:02Speaker 02

  I think it was sort of a reaffirmation, like, ultimately, you guys are the product visionary. It's your company, the credibility of it's built around the two of you. And so it's like, we would obviously support whatever change needs to take place. But I think that was super important for us to hear from sort of the board.

• 19:17Martin Casado?

  I'm so glad you brought up the board support, because... I don't think you can do these unless the board comes to the founders and really are very clear about their position in the company. And certainly in my case, to a person, they said, this is your company. This is your vision. We're going to get someone that's compatible with that. And so I knew that they were kind of like on my team as opposed to, again, like changing the dynamics, right?

• 19:42Sonal?

  Right. Instead of making an adversarial pitting two opponents against each other in an arena.

• 19:46Martin Casado?

  Very, very accretive. And so certainly anybody that's facing this, I definitely think that having the board support is critical. And anybody that's on a board of a company that's going through this transition, I think really needs to support the founders in these sorts of transitions.

• 19:58Sonal?

  Martine, I think it's great that you talk about not having title fetish, but quite frankly, that's a luxury because in reality, in a lot of companies, you kind of need the title to know roles. Sometimes ownership is not so clear. So there's a lot of fuzzy things that happen in the real world with this. So tactically, did you guys like sit down and iron out like a plan, like a transition plan for how you're going to divide up who does what? I mean, I want the specifics. Did you just like dance your way around it? Because honestly, it's also not fun for everyone else in the company to watch that dance because then they get confused. So how did you navigate that?

• 20:27Martin Casado?

  So I've got a very simple answer, which is ours aligned with basically a transition from an academic platforming.

• 20:35Sonal?

  Yeah, yeah.

• 20:36Martin Casado?

  As Armon put it, like, we didn't know what we want to grow up to. We kind of had an idea of what we wanted to build and that we wanted to take to market. And so when someone comes in in that transition, there's just a bunch of new work to do that we weren't doing before in order to pick up. And so that made it much easier as opposed to someone coming in.

• 20:51Sonal?

  Mid-flight.

• 20:52Martin Casado?

  Mid-flight and then like hopping in the pilot seat or something.

• 20:54Sonal?

  So your point is that there was a clear demarcation in the phase of the company that brought in a whole new set of needs. So it was sort of like picking the right moment to like pivot into that next phase.

• 21:02Martin Casado?

  Or lucking into the right moment.

• 21:03Sonal?

  Or lucking into it. So not maybe picking it. Armon, any thoughts on that, on the tactical side of the how?

• 21:08Speaker 02

  It's amazing to me how many analogies I feel like there are between our two stories. You know, I'd say we were in very much the same boat of going from that phase one product market fit into great, we have the products, there's a community, there's a user base to that phase two of. Okay, we have a few customers, but it's not repeatable. There's not really a process. And so that whole build out of the go to market and sort of getting it from sort of phase one to the phase two focus was exactly when we brought Dave in. And so I think for us, it was really natural. It's like, hey, you and Mitchell, keep focusing on the product side of things, product development, you know, things like that. And Dave helped really focus on, okay, great, we need to bring in new leaders to run marketing and sales and go to market.

• 21:47Sonal?

  Okay, so then my next question. There's this tendency, and I actually call it the divide between the head and the hand. And the reality is that while you might say like, hey, this person's designated as a product visionary, this person's sort of the person who's going to scale and build the operation and the machinery. The reality is that there is overlap. They're not so clearly demarcated. And then quite frankly, the best people should not just be where one person is quote the head and one person is quote the hand. You want a hand who has a head and a head who also has a hand. So my question is, how do you, as a product visionary, make sure that person is empowered to still have insights into the product?

• 22:20Speaker 02

  Yeah, the way we describe it is like there's this very clear line in the sand where it's like you run this and we run this. Dave runs go to market and we run product. But I think the reality is we operate much more closely. Like, we probably spend hours every week. In some sense, hey, given the same data, we probably are going to come to similar conclusions about what needs to be done. And so that we just spend a lot of time staying in super close sync. And it might be, hey, here's what we're thinking about doing here in product, Dave. Does this make sense to you? You know, gut check us. And similarly, hey, here's what I'm thinking in terms of what we need to be doing from a marketing investment or a sales investment. Does this make sense to you and Mitchell? And so I think it's much more of a partnership as opposed to, you know, the head and hand never interacting.

• 22:59Sonal?

  Yes, that's great.

• 22:59Martin Casado?

  Yeah, so I totally agree with that. I'm going to add a dynamic to this question, which is, so you can bring someone in as to say a COO, like we've discussed, but one of the functions that these, you know, bringing in somebody that's a kind of a senior exec that understands the enterprise go to market, one of the primary functions is hiring a real exec team, right? And that's very important. It's hard to do if you just haven't done it before. And one thing that I've learned is it's very dangerous to give someone the ability to, say, hire without actually accountability for that hire. So if they're hiring somebody that would report to me, for example, and I had to manage them, because they don't have the accountability, you have a very different process. And so-

• 23:40Martin Casado?

  I think that creating your organization in the way that as you build out your organization, it's very clear that you're accountable for the decisions you make is incredibly important as opposed to none. And the reason I tagged it on to the previous question you asked, which is you're always working very close together and you share information and it almost sounds like a totology. I mean, of course, you're in the same company, you're in the same exec team, whatever you do.

• 24:05Sonal?

  Circular, right, right.

• 24:05Martin Casado?

  But you can actually really get it wrong. And the way you get it wrong is you have decisions without accountability and you have to bake that in somehow.

• 24:12Sonal?

  By accountability, concretely, what do you mean?

• 24:14Martin Casado?

  I mean, if I make, let's say I know something that maybe Armon doesn't know because I don't go to marketing, he doesn't. So if I tell him how to do it, but I'm not accountable for what I told him, then basically I don't have to be as conservative as if like my job depended on it.

• 24:29Sonal?

  You're right.

• 24:29Martin Casado?

  This seems to, in my experience, this materializes the most in hiring. Like if I hire someone and put it under Armon and they say it doesn't work out, I'd be like, "Armon, you're not a good manager."

• 24:38Sonal?

  Right. Even though you're the one who's like sort of has the luxury of being like, "Hey, hire this person," or whatever.

• 24:42Martin Casado?

  That's exactly right. So I would just say like, as you go into these partnerships, whether you're hiring someone as a COO or a CEO, just make sure that like these major executive decisions align with accountability.

• 24:52Sonal?

  Yeah. The more direct skin in the game you have, the more accountability you have for that.

• 24:55Speaker 02

  The way we've done it is basically the entire executive staff reports directly to Dave. So he has, you know, to your point, the accountability is paired with the autonomy, right? It's not, "I'm gonna go hire people and have them report to Dave."

• 25:09Sonal?

  Right. Because then he becomes a bigger head. You're actually making him empowered.

• 25:12Speaker 02

  Yeah, exactly. But at the same time, I wouldn't say that we've sort of been disconnected from the process. Like if he is the hiring manager on it, I'm sort of number two on that panel in terms of doing the interviews.

• 25:21Martin Casado?

  So we did the same thing as well. I did try kind of more of, you know, I hire and put it under somebody else, or they hire and they put it under me and like tell me like, "That's a mess."

• 25:30Sonal?

  Yeah, yeah. I have a weird tactical question. How do you handle things like all hands, where you explain what the company roadmap is and what people are doing? Like, do both you and the CEO do it together? Martine, did you as a CTO do it with the CEO? Do you take turns depending on the topic?

• 25:44Martin Casado?

  Well, this goes back to like these low ego CEOs that you bring in. The case of Steve, he was so fantastic. It was, we would do an all hands and he would be up there, but like I was always up there with him. And if we did press, like I was in the press. And often he wanted me up there and he didn't even want to deal with it. So like it was customer interaction, et cetera. So I mean, it was almost like the best apprenticeship on the planet because I was, you know, in the line of fire, you know, for whatever it was. And so I do think that If you're going to bring in a CEO, you want someone of that ilk.

• 26:12Sonal?

  I would say one thing on that when we say low ego, which I love that you guys are saying that, but I think it does a disservice to all the people out there who might be aware that they have huge egos. You can actually be aware of your own shortcomings and strengths and you know your swim lanes and where you're strong and not strong. And you can share the stage with others when people play to their strengths and you can be partners even if you have an ego. I just want to point that out because otherwise it feels like an insurmountable personality barrier.

• 26:37Speaker 02

  I guess that's ego paired with self-awareness.

• 26:39Sonal?

  Yeah, yeah, yeah.

• 26:40Martin Casado?

  Or maybe someone knows the right thing to be successful and is able to put their ego aside. They're playing the long strategic game.

• 26:47Sonal?

  Yes, the long game. There we go. And you were about to add something to his all-hand thing, I think.

• 26:50Speaker 02

  Yeah, when the company was super early and there really wasn't an executive team, it was, you know, me and Mitchell or Dave presenting at the all-hands on a weekly basis. But once we'd built out an executive team, we'd switched over to a new model, which is basically every week we rotate which function presents. The functional leader of, you know, let's say, sales and marketing present this week and then next week it's product and engineering and then whatever.

• 27:10Sonal?

  As it is, there should be room for all those groups to present. That's great.

• 27:13Speaker 02

  So really, it's like, you know, Dave presents maybe, you know, once a quarter in terms of, hey, here's the retrospective of what happened last quarter. Here's what we're sort of thinking next quarter will happen. And me and Mitchell actually have sort of an out-of-cycle sort of fireside chat with the founders every quarter or two. So we actually on a weekly basis aren't even necessarily the reporting face of the all-hands.

• 27:33Sonal?

  So a couple more quick tactical questions. How about the recruiting? So you alluded to this earlier. So Martine, in your case, when you were trying to recruit Steve, there were actually like three periods where you didn't have a CEO. At each one of those, you could have just stepped in and kind of default become the CEO. A, what made you resist that temptation? And B, how did you actually go about recruiting the right? Like, what did that look like?

• 27:53Speaker 02

  So when we first started the company, honestly, like the CEO title was just arbitrary. We had three founders, two professors and me. We decided to give the famous professor CEO title. We all just basically did what we did. And the only two of us actually had a day-to-day responsibility.

• 28:06Martin Casado?

  So when the professor, which is Scott Shanker, went back to Berkeley, then we decided to bring in an interim CEO while we figured things out. And at that point, I had a couple of the early kind of angel investors be like, hey, Martine, you should take the CEO. Like, this is your idea. This is your company. And I'm like, listen, like, I don't know this stuff. I really need to figure out, you know, this is the bottom of like, the worst economic recession. Let's get somebody in here that can help this. I would strongly recommend ever getting an interim CEO. We just never should have done it.

• 28:31Sonal?

  Why? That seems like a really reasonable thing to do.

• 28:33Martin Casado?

  For me, it goes back to accountability. You can't make the right technical decisions if you don't have to live with the consequences. So I think, docked my responsibility to the company because I didn't want to deal with it. And I really should have just stepped up and become CEO. I was, I mean, effectively acting as a CEO anyways, and I should have just done that. So I, I think I was trying to take kind of the easy path there. That was a mistake, though it was pushed front of the board. And so I would never do that to one of my companies. I don't recommend doing that.

• 28:57Sonal?

  Right.

• 28:57Martin Casado?

  But then, you know, it was actually Andy Radcliffe knew Steve Malaney, who was, funnily enough, interim CEO at Palo Alto Networks for a little while. But, you know, very famous and well-known VP of Marketing that had done a number of companies. And we just started talking. We did that kind of dating thing that went for a long time. And we spoke with so many that he was just such a clear fit. In the history of Nasira, hiring Steve as CEO was probably the best decision I made. Full stop. So these things can really change the trajectory of a company.

• 29:23Sonal?

  Well, you also had the confidence, though. You were the inventor. I mean, your name is like the first author on the paper.

• 29:27Martin Casado?

  Well, that was the thing is like, that was my research.

• 29:30Sonal?

  Right. It was your PhD work.

• 29:31Martin Casado?

  I was the only founder that was still in the company.

• 29:34Sonal?

  So I want to probound this a little bit because I want to just talk about the product visionary role and how that evolves. So as a founding technical CEO, I mean, you were the inventor of software-defined networking. Nobody can take that away from you. Like, that's just something you just have this visceral product market fit for. However, there is a point in everything where there may be conflicts, especially as you expand into different product lines or different areas. Who then makes the final call? As a product visionary, do you get that authority as, well, he was first and he invented it? But what if the company goes in a different direction? Especially if you're successful. Quite frankly, when you're successful, you do expand in a different directions. How do you negotiate that bit?

• 30:13Speaker 02

  Yeah, I think conflict is so interesting because what's nice about it, in some senses, it reflects that. We're going into it with probably a different set of data and a different set of sort of priors in terms of our belief of why do we think decision A versus B is the right thing to do? And I think what's happened for us is oftentimes when we, there is that kind of conflict, it's a, hey, let's dig into that and say, was the, why? Why do you think A? Why do I think B? Oh, you think there's a great market opportunity, for example, if we build this product, where I think, oh, actually, that's a legacy market that's dying as we go to cloud, as an example. And so I think that disagreement ends up being a good opportunity to sort of check yourself and say, hey, what are the assumptions we're making? And go deeper. And I think what has happened for us almost 100% of the time is as we drill deeper and

• 30:58Speaker 02

  say, let's figure out what these underlying assumptions are and where does our data disagree? Where do our priors disagree? Usually, we can reconcile that and say, oh, actually, you're right. Your data was right, or my data was right. And once those are correct, then the answer ends up usually being

• 31:11Sonal?

  The right one.

• 31:12Speaker 02

  The right one. Or it's, at least, we agree on it.

• 31:14Sonal?

  Yeah, totally.

• 31:14Speaker 02

  If it's the wrong answer.

• 31:15Sonal?

  So to me, it hits on something you said earlier, which is, it's actually about, I always say this, it's not what people say, it's how they say it. It's about communication. And you mentioned that you wanted to check communication styles when you were looking at hiring your CEO. And what I love about that discussion is when you say the word partnership, you guys are partners, et cetera, that involves a style of communication where both people can understand each other's points of view. And the core idea behind what you said is that it's about understanding the thing underlying it. Like, what is the rationale driving that thing? And you actually find in many situations in life, let alone company building, that there's actually alignment in people's values and principles on that thing, but they might get like very prickly if you can get past that prickly phase.

• 31:54Speaker 02

  Right. When someone says, I disagree, you can either take that at a personal level and say, okay, you're disagreeing with me personally.

• 32:01Sonal?

  Exactly.

• 32:01Speaker 02

  Or you think the idea is bad. That's one way to look at it. Or the other way is to say, you know, there's something more fundamental that we're misaligned on.

• 32:08Sonal?

  Yes, exactly.

• 32:09Speaker 02

  And let's go deeper and understand what that thing is.

• 32:11Sonal?

  And then it fuels opportunities and the idea on both sides that can actually become greater than the sum of the individual parts.

• 32:16Speaker 02

  And it goes back to needing that ability to have that honest discourse with one another. If you're not comfortable saying you disagree with someone, then you don't have a level of trust, a level of depth in that relationship. The partnership has to be at that level where you can say, hey, I disagree, let's dig into it, without that being a, you know, whoa.

• 32:31Martin Casado?

  I would love to actually tackle a related thing that's hard for founders to hear, which is, I totally agree with what you're saying, but sometimes that's actually a hard pill for us to swallow.

• 32:39Sonal?

  Which is?

• 32:39Martin Casado?

  As founders. So I fundamentally don't believe in earned positions. I don't care what you've done in the past. That doesn't mean you're relevant today. That's why I don't like tenure, for example.

• 32:48Sonal?

  It's sort of like one of those logical fallacies. So instead of saying appeal to authority, it's like, appeal to my credible history.

• 32:53Martin Casado?

  No, seriously, I mean, I really think that like you should always add value and make yourself relevant. So I think that founders need to stay tremendously relevant. And just because you founded the company and just because you did the core work, doesn't mean that you get a free pass. And so in my case, I did the core research, I built the original team, I found the product market fit, I did the product definition. I mean, I did all of that early stuff. Well, you know, of course, with another team, I didn't do it by myself. But then it was sales time. Now, I didn't know the mechanics of sales, but I got in a damn airplane and I did sales and you have to make that transition. And I think if you don't, I don't think the CEO should listen to you.

• 33:34Speaker 02

  I really appreciate the way you put that of like, you have to continue adding value, which is as the company grows, your role changes.

• 33:40Martin Casado?

  Totally.

• 33:40Speaker 02

  And what I always say is like, every six months, my job is to rediscover what my job is, right? Because it's not the same job it was when you started. It's not even the same job as a year ago.

• 33:48Sonal?

  So that's also why people often say that being a CEO is like the greatest like professional development thing. I have a quick question about selling. What happens? You often start in the beginning with the founder and then Martin, you made the point that the second phase of the company is to have a repeatable sales process, which sometimes has product marketing materials and things that people can plug and play without having to have this charismatic person walk into the room and say, here's my vision. How do you scale that in this model? Like, what happens to sales in this model where another CEO comes in? Are you still sort of the showboat pony?

• 34:17Speaker 02

  You know, I think what I loved about Dave, still love, I should say, is Given his product marketing background, it goes to, I think, to Martine's point of like, that is such a tremendously useful experience because really, I think what Dave understood is like, yes, it's clear that there is a concrete problem we're solving. It's clear that practitioners use and love the tools. But what the company hasn't done a good job of, right? And Mia Mitchell were open and honest about was like, we haven't distilled the core messaging of the product, the core truths of how do we help someone who's not super deep understand? What is the problem? How does the product work? How does it solve that for you? What's the value of it? And I think he has that marketing mind in terms of, okay, I understand the product. I understand this landscape. How do we kind of distill that into the essential truth?

• 34:59Sonal?

  Yes.

• 35:00Speaker 02

  And that essential truth can be conveyed, whether it's by, you know, Mia Mitchell as the show pony, or whether it's, you know, a sales engineer and a salesperson.

• 35:09Sonal?

  So what I'm hearing in what you're saying there is basically the difference between turning it inside out, like here's a visionary selling the vision and making it more outward in where other people can articulate that vision and see it and make it more machine readable, make the task it more explicit so that other people can essentially pick it up.

• 35:24Speaker 02

  It used to be if you asked me, hey, what does the product do? And what's the value? I'd need an hour to explain it to, right? I'm like, do you have a whiteboard and an hour to spare?

• 35:31Sonal?

  Yeah.

• 35:32Speaker 02

  And I think what he saw is like, yeah, that's, it can't work like that. Yeah, you have to have the elevator pitch. You have to be able to explain to an executive in five slides.

• 35:40Sonal?

  Yeah, yeah.

• 35:41Speaker 02

  What's the value?

• 35:42Martin Casado?

  So I'm going to take the other side of this. So there's a very big difference between sales mechanics, which is like, how do you do pricing? How do you enable the channel?

• 35:50Sonal?

  Packaging.

• 35:50Martin Casado?

  How do you enable sales? You know, like, what is the packaging? What are the customers you go after? Like, you know, like the actual mechanics and then selling. Where selling is you walk in and you do the knife fight and you show the value and you paint the vision, et cetera.

• 36:04Sonal?

  Yeah.

• 36:04Martin Casado?

  Now, a lot of the mechanics is a repeatable sale. Like, what is the sales deck? How do you position it? How do you do marketing? How do you get in? But here's the reality for the world that Armon and I live in, where we're both hardcore tech infrastructure folks. And we've sold to the enterprise and generally about 20% of the deals are 80% of the dollars. And if you're asking someone for $10 million, which I've done many, many times, they have to be convinced on the totality of the solution from the genesis of the company to the technology, to the techno strategic landscape, to everything else. And that's done by founders who've seen that they've got the long view. And then, you know, the often the SE team, not the sales team. These are the sales engineers that will scale someone like Arman.

• 36:44Martin Casado?

  And so I totally agree that all the mechanisms, positioning and for that transactional business, that gives you a lot of predictability, it'll operationalize the sales team. But when I left with about a $600 million run rate and I was still doing, you know, 10 to $30 million deals. And I do think that that's a very, very important role for founders to continue to play.

• 37:04Speaker 02

  Yeah, that's a great point, which is I think the nature of enterprise sales hasn't changed that much. The reality is like, no, the person who's going to sign a $10 million check wants to know, hey, are you a partner that I can bet on are going to be here for us for the next five, 10, 20 years?

• 37:18Sonal?

  It's very different if you have a small deal size and you're just self-serve. But honestly, if you're paying that kind of money, you want the full red carpet attention.

• 37:25Martin Casado?

  And it's core infrastructure. I mean, like, this is like-

• 37:28Sonal?

  You keep saying that, just to make it clear to me, what does that mean that it's core infrastructure? Like, what difference does that make?

• 37:33Martin Casado?

  So core infrastructure means it's the foundation you're building your systems on. It's like rebar and it's like the value that holds up these amazing cloud workloads. This isn't like, I've got this productivity app that I'm using and then maybe tomorrow I'm not going to use. You do want to make sure that you have that relationship and then you just understand the totality of the vision, which always includes where things came from and then where they're going.

• 37:55Sonal?

  If it's such core infrastructure, honestly, my takeaway is you're kind of entrenched. The switching costs are too high, they're not, they ain't going to move, so don't bother. You're going to send other folks on the road.

• 38:04Speaker 02

  It's not just the initial investment of, hey, we want to partner with Haji Corp. And sort of use this as a foundational technology. It's as they adopt other pieces of their portfolio or new features, it's sort of the same conversation you're having, which is great. Maybe we took a bet on you for this piece of our stack and technology, but hey, this is a different piece of technology. And as we adopt more and more- The criticality of you to them increases, right? And I think if you look at companies like Microsoft, almost every business in the world, Microsoft is absolutely critical to their functioning, right? Like, they would implode if Microsoft didn't exist.

• 38:36Sonal?

  So basically, every new product line that's significantly different than the existing thing that they bought is essentially like a new startup within your company?

• 38:43Speaker 02

  It is. The way we talk about it is we're almost four companies in one. And I think with every new product that a customer adopts, there's another degree of dependency or criticality that they're taking on our relationship, right?

• 38:54Martin Casado?

  Expanding account leads to basically net dollar retention, which is one of the most important numbers to the valuation of a company. And net dollar retention is how much an existing customer will expand their spend, net the churn, the amount that decide not to do it anymore, right? So that drives valuation more than like ACV.

• 39:13Sonal?

  Annual contract value.

• 39:14Martin Casado?

  Annual contract value.

• 39:15Sonal?

  Right.

• 39:16Martin Casado?

  And so any company that's not focused on making their customers successful and then increasing their value in the account is not going to build a

• 39:24Sonal?

  Right.

• 39:24Martin Casado?

  large company. You just can't do that anymore.

• 39:25Sonal?

  Right.

• 39:25Martin Casado?

  So this idea of like, oh, it's based on the infrastructure, I'm going to walk away and not do it again, it's a path to failure, right? I mean, you have to have that relationship and increase.

• 39:33Speaker 02

  You have to be invested in the success of the customers.

• 39:35Sonal?

  Yes, that makes perfect sense. Okay, so we've kind of covered, you know, the timing, that there's actually, both of your guys' cases, there's a common timing when you guys made this choice, so that was a key factor. The idea of partnering, we've talked about the importance of being self-aware and having a mental models, even if it's not necessarily linear. We've talked about some of the specific tactics, including different aspects across the board. How do you diligence in this marriage dance? With marriage, as you actually have dating, you can reference people, you could do credit run checks on them, I guess, and do other background checks.

• 40:03Speaker 02

  In many ways, it's actually not that dissimilar. Do you spend a lot of time backdoor references, right?

• 40:08Sonal?

  Yeah.

• 40:08Speaker 02

  People who've worked with them, right? Whether, you know, above them or below them or adjacent to them, right? Getting a sense of how do they treat their peers? How do they treat their reports? How do they manage upward? I think a lot of it is bringing them into your problem space. I think that was an important part for us was like, hey, let's not talk about hypotheticals. Let me really lay out, hey, here's how a product works. How would you think about doing this? How would you structure a go-to-market? Because you're not doing it in a, it's not a 30-minute interview that they come in and then you make a decision, right? Like, it's a multi-month process. So they have time to really soak in that context and sort of make an informed analysis. You learn from them, and I think that for us was the really big thing.

• 40:44Martin Casado?

  I mean, you really need to show everything. I think you have to. Almost anti-cell, because like the failure mode is hiring the wrong person, having to fire them. It's so much more disruptive to bring somebody in that doesn't work out. You really want the right person. There was an anecdote that Stephen Laney, the COI, hired afterwards. He's like, you know, when we were doing this dating dance, here's what I would do, Martine. I would basically keep asking you the same questions. And then I would pretend that I didn't understand, and I just wanted to see if you'd get frustrated with me.

• 41:10Sonal?

  Oh, how funny.

• 41:11Martin Casado?

  Yeah, yeah, yeah. So he's like, I was testing.

• 41:12Sonal?

  I thought he was looking for alignment, but he's just seen your reaction.

• 41:15Martin Casado?

  I mean, I think there's a general rule in startups that's just so useful to implement, whether it's creating a board or hiring people, is like, you should do it with the bad times in mind, not the good times. You normally like hire based on the good times. You're like, oh, I want to have the best board ever and this and that. But it's really the bad times when these things kick in.

• 41:29Sonal?

  So any parting thoughts for those out there who are negotiating with themselves or others, whether to be the CEO or to bring in an outside CEO? Any parting pieces of advice?

• 41:38Speaker 02

  I think you have to just be super honest with yourself and like what motivates you. That level of honesty with yourself of what do I want to do and why do I want to do it? Is super critical, because I think if you can answer that, then it becomes pretty obvious of like, hey, if you really do get energy from being CEO, you really are motivated by that growth and that sort of challenge, then maybe it's right for you to do that. But if you have a different, not a worse, set of motivations, right? Like, in our case, I think it was a different set of motivations, which was like, we love the products. We want to see the technology succeed. And the best way for that to happen was for us not to lead the company.

• 42:09Sonal?

  Yeah.

• 42:09Martin Casado?

  If there's one piece of advice I'd give, it's don't make a decision out of fear. And that can operate on both sides. I think I brought in an interim CEO out of fear as opposed to actually stepping up. And I think a lot of people don't bring in a CEO out of fear. And I think fear, more than anything else, clouds this decision. It's very clearly an insecurity fear issue. And that's a total failure mode.

• 42:29Speaker 02

  Fear of loss of control.

• 42:30Martin Casado?

  Yeah, exactly. And I made this mistake myself, brought in somebody because you were afraid that you couldn't do it. And I really think that this is an abdication of your responsibility as a founder. And so I just like step aside from the fear, make the right decision.

• 42:42Sonal?

  Well, Martine, Armon, thank you for joining this episode of the A6MC Podcast.

• 42:46Martin Casado?

  Thank you.

• 42:46Sonal?

  Thanks so much.