The Exchanges

Q an interesting place to start would be you joining as the CEO of Sentry. Obviously you're not, you didn't found the company. What I've noticed is it's a rare Situation to have an external CEO come into a relatively early stage company and have it work both for the CEO coming in and for the company sort of itself. What was the story about you getting involved in the company?

A I think the way and the reason this has worked out is David Kramer, the founder, who was the CEO through his journey, being CEO, adding different functions and getting it to a certain scale, had the maturity to realize that This is something I don't want to spend time on. Managing the other aspects of scaling the company and all related aspects of being a CEO. I did rather focus on building product, and so I think it started with him just having the intellectual kind of maturity to say, hey, this is where I am in my journey, in the company's journey, and so I'm okay bringing in someone to help drive our next chapter, right, as the CEO. So I think that actually has been one of the most critical pieces of success because it's the realization of the founder that this is the right time and it was not forced, right? So that's number one. Specifically why this worked out for me is when I kind of looked at it and I'm like, wow, okay, this is a developer tools company, has a great PLG motion and an amazingly good product.

AI assessment note: “Specifically why this worked out for me is when I kind of looked at it”

Q Maybe to wrap up, we'll end where we always like to, which is when you think back to the arc of your career, are there specific people who shared a specific way of looking at something that's like still part of your tool belt?

A So in my case, I would say the person I've learned the most about what I call is just leadership and being a good person is my dad. Super good human. Family man. And on the business side, he's done extraordinary things. So I kind of started learning from him of how he operated and carried himself, and there was a little, you know, swag to him. I always kind of think, like, my dad is really cool. And so that's kind of where I learned some first principles of a human interaction about caring. Charity begins at home. This construct of family and, and kind of in that. My first cousin is a Lifetime Achievement Award winner from NASA. He sent the rover to the moon. He inspired me to get into computer science. And he was the one who told me, hey, you're a good engineer. I'm in like undergrad building websites in India. He said, you're a good engineer, but the way you are able to communicate with humans on the technology front, you may want to think about life beyond coding. So that just kind of showing you the roots of kind of how it all started. So he's constantly inspired me to, he was the kind of the, the trigger. So those two are really good examples. Mike Speiser, he probably doesn't remember me, but Mike was basically at Veritas. And he transformed and helped transform our kind of backup unit with Jeremy Burton. And I'm like this IC engineer thinking about business, and I'm like…

AI assessment note: “the person I've learned the most about what I call is just leadership”

Q What do you mean by friction in the company?

A Points of view, right? When you are a founder or a CEO, by the way, When you're participating sometimes at a very kind of low level, it may come across as everything from, like, why the hell do you care to micromanagement to whatever it is, but the articulation of that detail is somewhat the genesis of what makes Century Century. The attention to detail on a copy, is it carrying the same kind of mindset that we've always had a sense of humor in how we present ourselves? And as we add more people, sometimes they don't have all that context. You can't teach that in onboard. We try, but you know, so having that presence of saying, Hey, this, you know, we don't do things this way, or this is how we do it, or you don't sell to developers. You know what I mean? Like there's no selling to developers. You have to just show up in the right way. So I think all of those things, sometimes, you know, as an IC who's removed from the process can create a point of like, my goodness, the CTO and our founder, Speaking to me or calling me out on a thing or a CEO, right? So I think that's the balance, uh, in that. But I, I personally believe it's worked out for us because I'm kind of leveraging that. And I would say every company should figure out a way to harness that in perpetuity. That is really, uh, what's the most important thing if you think about founders and what they bring and how they cr…

AI assessment note: “it may come across as everything from, like, why the hell do you care to micromanagement”

Q to spend time talking about? The specific questions you ask, how you architect that time that makes it sort of the most high impact? Because I think a lot of people can spend time with customers, but if you don't do it in the correct way, you're not going to be able to derive the insights that ultimately will lead to great products and packaging and all the other stuff.

A Number one, I think most At times, it's a longer process with a customer, right? So if I meet you once, I'm not going to be able to extract all the signals necessarily in that. Now, Sentry is a very different case because we are directly talking to the community at scale, and so in that case, it's a constant iterative process around what works, what doesn't work, and it's almost constant experimentation, but it starts in-house with our own developers. Are you going to use it? Are you using it? If you're not going to use it, why the hell do you think some other developer at Another company is going to use Sentry for solving that scenario. And by just asking that question, it changes the entire dynamic of, oh, yeah, because most times people have apathy, right? A team member is building something. I'm giving you a Sentry example, then I'll talk about the other thing. But if a team member is building something, in this case, we are building a developer tool, right? There's a set of developers at the company. You're like, yeah, they're building something. I'm not going to use it. The question is why you're not telling that person that you're not going to use it or what should they change? And so that's the constant kind of conversation we have both internally and externally, which is what's broken. Tell us more. Tell us what you're trying to solve. Not the technical how. What is it…

AI assessment note: “what's broken. Tell us more. Tell us what you're trying to solve.”

Q it means to be truly developer centric? If you are building a company that is a product that is being adopted, and actually in a lot of cases physically paid for by an end developer, other than building great products or having a great developer experience or whatever, what are some of the important things that you need to get right if that's what your business is in service of?

A Assume you've already landed the developer. I'll kind of correlate this back to how we deal with the consumer world. It is a constant maniacal focus To make sure that they're consistently and constantly happy. When they hear about you through the ecosystem, they hear the right things. And it cannot be fake, right? So it's authentically right there. It is very hard, number one, what you said. And so it's not a one-time thing. Oh, this developer is using it. Great, they're using it. It's a ongoing retention story. And it starts with product, but doesn't end there. It's how you show up in your community. It's how you present yourself to the ecosystem. It's all these other things that come into play, that collectively then, the developers are like, oh wow, they are actually good with the overall kind of community. Oh wow, they work with these other ecosystem cool players, whether it's the latest new stack, and then the last thing they're looking for is, what are others saying, or are we on the bleeding edge when something new and cool comes in, are we there? So that's kind of the combination that you need, and it's not just product, it's how you show up every day, All day in the community.

AI assessment note: “It's how you show up in your community. It's how you present yourself”

Q a lot of enterprises like to know that they have control over everything, even if they're using a hosted sort of solution. How do you articulate the value, like as a thought exercise, if tomorrow you decided we're going closed source, aside from end developers being frustrated or whatever, like what is lost? It's sort of like the opposite question of what is gained in sort of being open source.

A So, you know, it's, it's a philosophy of how we want to operate, which is this comes back to the premise of for the people we're building, which is a developer, it's free access to software. And I think for us, that just is like, we don't even think about this to what you said, and we don't think of it as enabling or helping us build a business. So the thought process is not about how does it generate leads or how does it create that it's about like, Hey, if somebody has a new three-person startup, Decides to put software out there daily. Sentry is available to help them ship with confidence. Whether they use the free cloud edition, they pay us, or they self-host it. And so the idea was about, you know, for us is, it's not a lead generation or anything else. It's a, it's the way we want to operate and build. And it comes from this base premise of access to software and community. And so that's how we think about it. And, you know, when people ask me like, hey, what does it mean from a, you know, Leads or conversion. We don't even have a campaign necessarily to say convert from our open source to opt in when you're ready or never. It's completely okay with us.

AI assessment note: “it comes from this base premise of access to software and community.”