Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (Sentry, VMware, Riverbed)

 Brett: Well, thank you so much for joining. I'm excited for the conversation.

Milin: Great to be here.

Brett: Yeah. Maybe 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?

Milin: You actually kind of set the framework really well on that. I think the way and the reason this has worked out is, David Cramer, 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 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. 

Brett: Were you looking for a CEO gig at the time?

Milin: I was not looking for a CEO gig. if you asked folks in the Valley, they would say, I was at VMware for a long period of time and I'd been asked, you know, to come out of VMware for a variety of different roles.

And I'd kind of, I'm happy. I'm, I'm enjoying what I'm doing. But this just kind of stuck out for a variety of reasons. And primarily because it ticked off all the boxes of like, Hey, it's product led growth. It's in a tool space that I care about. I believe, so my belief system was this is the decade for data and developers.

The one we are in the prior decade was cloud and SaaS. And the one before that was software defined everything. You know, VMware came about for the virtualization. We had software defined networking. Last decade was cloud and SaaS. So I'm like, wow, okay. There are no fix it elements to this. you know, yes, every company has things to kind of get done, but product wise, the opportunity that it presents were unique and great.

absolutely got along really well with David, Chris, Todd, who kind of were the functional leadership at that point in time. and so it worked out really well. And then, you know, since joining and we had so many other issues like COVID and everything else, which I never predicted. but what has worked out besides that is, our chemistry or our back and forth, Cramer and myself, you know, we, operate freely if that makes any sense, you know, so there is no like, you don't say this.

It's just like open communication there is no Delta in that. And he has, you know, accepted the role like, okay, this guy's the CEO. I brought him. And so I got to you know, delegate on certain things over there. So it requires that intellectual maturity, for that transition to take place successfully.

Uh, and so I always say, start with people, start with making sure the reason why, and then all the other things you said, which is, it was not a kind of fixed job, completely. We had to build certain functions, but the, the core of the company was really solid and continues to be.

And so I'm like, no brainer.

Brett: The interesting sort of dynamic that you're articulating is he's still very involved in the business. there anything you can sort of share about that in terms of how you sort of balance that in any way, or do you think about that? There is something about a founder being involved in a business. And obviously you've done something that's really symbiotic with that in some way.

Milin: if you lose what a founder brings to the table, which is. An extreme focus, on kind of what we want to get done, first principles of what made the company, what it is, values that kind of got us to a certain scale, in the case of, our current founder, David, and even Chris, a opinion about builders and developers and, how they think and what they bring to the table, which is unique because he is one of them, and so for me, I basically said, continue to be yourself.

And, uh, you know, there are sometimes I would say, even jokingly, that you might feel like, what the hell? Uh, he has a disproportionate voice. Who cares? It's bringing the point of view is super important. and continues to be even at the scale at which we are, because the journey is not over Even at this stage, 10 years in, him and Chris to be as involved, especially Cramer to be as involved and as passionate about everything from a piece of copy and marketing to, something that we didn't do well in the UX matters, right?

The intensity matters. It keeps us on our toes. and I've been fortunate because prior to this, I got to work with. other founders to acquisition at VMware. Martin, who is now a partner at Andreessen. got to see them and operate and you want to, leverage, what they bring to the table.

So I'm a big proponent that even as companies transition out, and I know some of the founders get tired, but how do you preserve their first principle thinking, the value thinking, the intensity of how they thought about the first product and where it could go. I highly recommend, keeping that element of energy in some form at a company, because you will see that is long lasting success, So part of it is getting your ego out of the way, and listening and letting kind of them be themselves. and, you know, through that, there is some friction, uh, not at my level, but it creates friction in the company. but. The end result, absolutely worth it.

Brett: do you mean by friction in the company?

Milin: Uh, 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 or whatever it is? but the articulation of that detail is somewhat the genesis of what makes Sentry Sentry. 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 tell teach that in on what 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, where you're 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, on a thing or a CEO.

Right. So I think that's the balance, uh, in that, but 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 create.

Brett: Before we talk more about Sentry, I feel like there's this, newer generation of founders, they may not be as familiar with what an extraordinary company VMware, is and was, and back when VMware was coming up, it was like one of the special companies of that generation,

and you obviously spent enormous chunk of your career there. Are there certain things that VMware figured out in any part of the business that should be, you think, an inspiration for more people building companies today, or like, big ideas that were, a part of what made the company so spectacular 

 I think if you take VMware, I think the biggest thing is their first product, was amazing, which is the server virtualization product. and the evolution of that from being running on your laptop to, as y'all have talked about product market fit, it was like, Oh, wow.

Milin: So virtualization, I can do, you know, run multiple operating systems on a desktop and to transition that on the server side, and then to build that business out. it's this idea or iteration to product market fit, even with your initial product, and then scaling that, it's a perfect example of that, right?

not rest on that initial win, which was GSX, I think they called it, and then kind of iterating to what became ESX, Elastic Sky is the nickname for it, which became kind of the fabric of most modern data centers, in terms of server virtualization. So this general idea of, can your lowest package deliver the best value, right at the right price point. And then you layer in additional functionality to create like a three tier package, which now everybody talks about, Hey, you offer, um, small, medium, large, you know, back in the day, that was not very common. So this idea of a small, medium, large, was at a company like VMware, they did it really well, and getting the right price point. And then on top of that was this idea of bundling, which I would say was moderately successful.

you know, bundle a second product or third product. so that was kind of the combination we think of pricing and packaging. We could probably spend a lot of time just going in the details of it, but I use a lot of those first principles now, or have been using it for a bit: the other aspect which was interesting was this switch to

 this motion of Enterprise license agreement, which happens everywhere. but this idea that when you go from one to many products, so it doesn't apply really to early companies, but as you go to multi product instead of trying to sell skew by skew by skew death by skews, you could just say. committing a certain amount of dollars, which is called cloud commit now and everything else, right?

But this idea that you're committing a pool of money, and then you're going to use it across a variety of things, in that, right? So you're still reserving capacity for X, Y and Z. But this idea of an enterprise license agreement. over a period of time. That was another, I think, neat little kind of enterprise selling innovation that kind of helped the trajectory of the company in that regard.

So that was kind of, I look at that. and then the third aspect I would tell you is it is about people , I joined, I was an IC, things happened, I was doing well, two, three layers went off, started kind of working directly with the senior executive team, just do the right thing, you get taken care of, right?

And that is very rare in large organizations, but you will hear story after story after story of this happening at VMware, if you deliver on outcomes, you will be looked at, you will be taken care of.

there's so many such great stories. And from the early leadership to even the new leadership that came in, the people kept me there. Is what I'm saying. And the opportunities that they provided, they listened, leadership listened a lot. those three things I would say are long lasting attributes of building any great company.

Brett: In watching it from afar, it seems to be exceptional at turning technology into revenue, basically, which I think a lot of companies struggle with, particularly those that are trying to solve hard technical problems.

Was there anything interesting in the way the company was set up or the type of people that were there? technology

at company like VMware was just so high value, it just delivered on its value. once you have that, then everything else kind of fits in the puzzle, right? You can't sell something. I mean, you can always sell something that's okay, but if it's really good, then you can actually do something interesting and innovative on that.

Milin: Right. the First kind of level was like the technology was so good. The ROI was so good. And so as a result, you could actually be creative when it comes to delivering a message, delivering pricing and packaging, constructing commercial elements. Right. and so I think it was just kind of the, the Genesis of having a great product, which delivered value and to constantly innovate.

And all these functions, even though you could say the company was getting larger, were very connected. and that was the other fascinating thing. you know, product marketing, as you would call it, was involved as involved in kind of the day to day, building and, and, you know, interestingly enough, pricing and packaging was done by product marketing, at, VMware initially.

 Everyone was technical. They understood the product, they could actually, you know, demo and sell the product, which helps some of the same principles we're using now at Sentry, which is, you got to be technical.

It's a developer tool. And then you combine that with a vital product, a great message. And so I think the collaboration was always there. it was not thought of as here's product and then now here's go to market. It was always kind of this combined effort.

Brett: In a more tangible way, how was it a combined effort?

Milin: You know, just you build product as part of the building, everything from when beta took place to going live, all functions were involved. And so it was not done in silos. as soon as beta kicks in, you know, what is the message we want to kind of put out there? We would do. Onboarding and training internally, which would then get externalized.

so product marketing came early, came often product management is out there positioning and talking about it to understand it. you know, we would be out there. It is a classic enterprise selling motion. We would be out there selling as product managers, product marketing. 

You know, we were out there. I mean, I've got miles, uh, you know, my wife, post joining sentry said to me and it kind of caught me off guard, but I should have been more aware. She's like, you know, you were gone quite a bit, during those days, during the weekdays, right? And, You know, I reflected on it and that is true.

We would get on the plane, you know, and be with the customer, understand what they were doing, kind of hand to hand combat. especially as we started going to multi product, we had to kind of educate folks. So, just being in the building, of the product, but also the selling aspect of it, it was not like the sales teams or separate, you know, it was all kind of coordinated in that.

Brett: And so was it often when you were creating a new product offering, the product team were the folks getting the first million or 10 million in revenue 

themselves?

Milin: you have to, whether it's a startup or a big company, I think, the thing I say is like product management, or even like when the person building the team software team that is building, it's hard for them to go out and kind of position, I remember you are the first salesperson. So you need to message and sell. Now, this is very difficult by the way, because most folks are used to just going out there and saying, this is what our product does. Paul Merritt said this once, I think, which is if somebody comes and pitches to me, there's not a pitch that I don't like, I'll just change it to what I like, In a way. So if you go sell to a customer and say, I have this new idea, here's what I'm doing. Most times they're going to shake their head. Yeah. Yeah. You know, the question to ask is like, if you had a dollar or, you know, a hundred dollars, you know, would you spend this and in the next six months and the next nine months?

the art of just asking the question of where they are that selling process. Okay. You got a product. But even before you start getting to beta and stuff, you're asking the question, will this help you? And they're like, yeah, yeah, yeah. Will you use it in the next six months? I don't think so.

You just realized that you're building something that may not get used at that particular customer. But if you have 10, 12 such conversations, from a prioritization standpoint, you may be building something that may be solving a problem, but no one will use it. And so this early validation is super important as a product team, whether it's the founder in a startup, whether it's a PM, Don't go and tell me what you're going to solve for me. the question to ask is. What problems are you trying to solve? Is this show up in your top three? Will you spend money on it? if so, when, And then okay, I can solve it now. Let's go. Right. can you get on my beta or whatever it is?

And most times we are in pitch mode, We are, we always try to sell something, tell our story. I am at fault about this too. So, you're going to pause and say, Hey, what are you trying to solve? And. Are these the top three things you would do and you will discover sometimes you're not building the right thing or the thing you're building may not be the right time, which happens quite a bit, right?

And, startups or should great idea a four years too early or, or whatever it is, right? So, that's why I think the product team, whether it's at a big company. Whether it's a startup, midsize startup, or a founder early on, you got to listen and you got to ask this most critical question. how important is this problem in your list of things in a stack rank?

and will you really, spend the money and time if I solve it for you?

Brett: When you're spending time with customers, maybe early on a new product, what are some of the things that you tend 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 drive the insights that ultimately will lead to great products and packaging and all the other stuff.

Milin: number one, I think most 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 these 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 that you're trying to solve? what is the experience you're looking to solve with, Because the actual solution may be completely different than what you're thinking. in the same vein, 

A lot of times when we go in, we get too caught up in the actual way we solve it versus what problem are we trying to solve and what would we experience the end outcome of solving that problem look like.

and so if you kind of bring that conversation to that level, number one, which is, Hey, what are you trying to solve? And then you dig deeper and deeper. And so it's a series of kind of back and forth, where they say, Oh, I'm trying to do this. Okay. Tell me more. And there's a point in time in that conversation where either you already know Oh my God, this is like the perfect fit. It's an okay fit or it's not a fit when it's not a fit. You bow out, you don't try to push. that's an art, by the way. Most people don't like to lose a customer or whatever it is. It's okay. It's not a fit right now. You know what I mean? So I think it's a series of iterative questions about Hey, what problems are you trying to solve?

so how does this relate to the business? tell me how this connects with other things I've heard at the company. If I'm talking to multiple folks. When I was at VMware, we had the unique advantage of seeing what they were doing as a company. And then when we bring in new things, then to relate back and say, Oh, I saw that you're talking to this person about this, how does this concept relate to this concept?

And then connecting dots it's an iterative process. There is no magic to this, but the biggest thing is You have to become the need, not a want. it has to show up in the priority list where they're like, we'll spend time on it.

Brett: So switching gears back to Sentry, talk a little bit more about what the business looked like when you joined as CEO for so years ago.

Milin: phase one is what I call it. We were just coming out of phase one. in your definition of product market fit, we were at that at scale for error monitoring. There was an excellent opportunity to just kind of scale the business out in terms of not only the number of users, but revenue.

and so we went from, I around 20, odd million to now north of a hundred, which we crossed last year, during this period of time. but it was primarily because of, uh, reaching that at scale. in your four level four level four product market fit for, error monitoring.

you know, we were able to kind of leverage it, push on it, and have that happen. And while in the past four years that was happening, we build out all the other functions, you know, our go to market function, our marketing function, build out the different, specializations in that. We built out a revenue team as we started meeting larger customers who want custom MSAs and stuff like that. we started thinking about, What else will Sentry solve? So back to the initial product market fit with a second product, which we did kind of get out. We have now three, four things in that early or level two of your product market fit, going into this year, right?

So, we kind of think of it as phase one was getting that at scale thing. I was not there for that. and the team made, did an amazing job. I helped kind of take that at scale. and make some other investment bets with the team. And now I think we're back, to kind of, initial product market fit.

And this is also very important in this whole question. You asked me, what is the role of the founder? you could say, Hey, we've got the early product, you know, with that at scale product market fit for product one. Now I'm like, everything is back. We're looking at not only the new things we're building, but what we have and making sure we continue to be the best at it. And that's where, Cramer, you know, he's building this whiskey app on the side and using the product and saying this is broken. This is not working.

the stack doesn't work in this scenario. That intensity is coming back to that question about why I'm so excited to still have someone like Cramer be so involved is he brings that intensity, that first day mentality, the first customer mentality, So we are in that phase three now of how do we get to a billion, just in your framework, think of us almost coming back to our roots 

Brett: you have very large enterprise customers now, how does the machine fit together?

And then I want to talk about The second product that you launched and sort of the process there, but maybe you could explain how the overall kind of business model architecture works.

Milin: I will start with this kind of core notion that, the persona that we care about and we want to serve is only one persona, which is the developer.

I call it B2D. so we have business to business software. I would categorize that we are probably a B2D and B2D is very close to B2C. So if you're a consumer, as you know, when you're buying a shirt or something, it's word of mouth, you read a ton of stuff, you do kind of a lot of research, and then nowadays you can evaluate something and return it, so that's kind of what B2D is, which is you have to win the mind and heart of that user, uh, and they have. To love the product, and so that's kind of the genesis of everything, which is build a great product, make it accessible, uh, and affordable, right? And so that's kind of the genesis of all of it.

if it's great, they tell other people, And then not take for granted. The second principle in our businesses, similar to the consumer, if you're not happy, they'll never come back. and so how do you keep a persistent. connection of quality on product, but also by being authentic in the community.

and so I'll now connect the dots into your question about open source. what we would now call, there's a lot of kind of talk about this, is eventually open source. we crafted a new license FSL, basically says that, you know, after two years. You can use the code, but there's a period of time where you cannot use the code, and nobody else can run the service.

but the code is fully available all the time. Number one, the software, a SaaS offering is exactly the same as the open source offering. There is no feature Delta. So as a company, you can run the fully functional up to the minute value of Sentry on your own without paying us anything. We have built for that.

We built the idea that democratize access to the software. You want to run it on your own, run it, That's just the philosophy of how we build the company, which is this idea that open source has many different connotations. actually I should clarify myself. it has one mindset about code and access and, elements of that.

When we thought about it, we said, software, Should be accessible to everyone. And the community we are serving, which is a developer, likes to try software, wants accessibility in terms of not only having to pay for it or running it as a SaaS, they should have access to all of it in totality on their own.

And so again, coming back from that persona, the developer and how they think and who we serve, he said, if they want to run it by themselves, Let them have it. So this came from that mindset of make access to software easy, or free, and then, from there came everything else. And so SaaS our SaaS version is nothing but affordable.

And for the most part, it brings this, inherent value where people are like, I don't want to run it myself. I'll just pay them $29 a month. That's the cheapest plan. It works for most of our customers. so I think that's kind of the element, which is this idea of starting from the persona, acutely understanding how and what we want to do for them.

the trend line, which is more you know, like B2C model, open source, not for the sake of open source, but in terms of accessibility to software. and then. Also participating in this community. so one of the things we do is every year we give back to all the different projects we use on open source.

So we fund the, builders of open libraries and stuff like that. You have to sustain open source. This is a message we're trying to get out there. If you're a company using open source, you better allocate some hard dollars, or you're allocating time or code back, but you got to give back. You can't just be taking, And there's so many individual people who spend time building. Let's sustain this, motion of open source. So those are kind of the core elements of how we think about this world. and think about a persona, which is the developer and serving them. And so when you start thinking about that, that's gotten us to the scale of, we've just crossed a hundred thousand SaaS because of the sustained kind of commitment to building a great product.

Being in the community, making sure, access is easy. and then participating in the community

Brett: Is this something that's sort of come out over the last handful of years as companies are trying to balance how do we both build a company that's open source, but also build a company that can generate sustained revenue?

 right when I joined, we changed to BSL, for the primary reason that nobody else should be able to build a service. It's open source in every other way, shape or form, in the definition that we see, which is it's accessible code is available but we had to go BSL so that nobody else could run a service because we had folks wanting to ride, on top of Sentry without actually contributing to Sentry. So the unique thing about Sentry is, we have pretty much owned and written most of the code that's out there. So it's not like somebody else is contributing to that, user base or whatever it is, it is not a community project that we have then made BSL, right?

Milin: This is a project we started because of this idea that we want it accessible. Everybody should have access to it. And then as we became successful. Folks started thinking, Oh, let me take the work they've done and just package it up and host it or monetize it right. Without giving credit back.

And we actually had those conversations and we realized that we needed to protect ourselves against that aspect specifically. And that's the reason to transition to BSL and then eventually to FSL, which is a license we announced this past year. And so, yes, the short answer is, I think there is element of that.

now there are different shades of this. In this case, Sentry was fully a piece of software that we primarily built, managed and contributed. if your project was a community source project and then everybody else contributed and then you took it, in a different direction. I can see why the community uproar takes place and that has happened recently.

so there's a balance in this, but it all comes down to the fact that somebody else is trying to take and build a service on top of it and you can't monetize it as the original creators of it. In our case, we continue to be the main and only contributor to core Sentry, So it's a little bit easier from a market standpoint.

If it's a community project, it becomes a little bit harder.

Brett: To your point, there are certain open source projects where one of the main benefits of being open source is you have thousands or tens of thousands of people around the world that are making the widget or whatever better.

there's more your version of open source. which makes everything out in the open, I assume in an enterprise context, 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 and 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

and how we want to operate, which is this comes back to the premise of for the people we are 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, what you said, and we don't think of it as, enabling or helping us build a business.

Milin: 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 hosted.

and so the idea was about, uh, 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.

Brett: It seems like in the way that you've constructed the business, it's not, we can be open source and support our customers and developers in a certain way, or we can generate revenue, like you're trying to do both.

but maybe you can talk about more, why you think it works.

Milin: The interesting thing on this is that number one, it works because most folks have realized that I want to get the value of what Sentry delivers, as fast as possible.

because it delivers extremely high value to me, and then the question becomes, okay, how much is it? And so that's where the affordability piece comes in. $29 a month, gym membership. . that's kind of the mindset. And so what's worked is Hey, you know what?

I see the value most folks are no longer think about, I want to squeeze every dollar, it starts maybe with that mindset, but eventually it's how quickly can I ship my own product and my own value? I want to keep building my thing and Sentry supports me in building my thing faster and with higher quality.

If that means at some point in time, I have to pay them 29 or 39 or 49 or whatever the amount is, it's absolutely worth it versus me trying to self host it. just from a user standpoint, that is what I have seen, which is it's affordable, on the other end of this is, there have been times where customers have self hosted at scale and they're like, why am I spending time doing this?

I can just. Pay someone to do it. and so we've had extremely large scale customers just transition and say, take it off me because you do it better and you do it cheaper. that's kind of the value play that has worked out, but again, inherently comes back to, are you delivering value? And in our case, yes.

Are you delivering it really fast? Yes. maybe it's just the affordability piece that most other companies miss out on because they always try to kind of squeeze that last dollar from everything. And we've tried to kind of really focus on can we make it affordable for that first software team, and then scale proportionately as they grow.

Brett: you not spend time thinking about how do we translate this product value into sort of economic value for the company?

Milin: you know, coming from VMware, where we did a lot of ROI, business value, and all of those things, which is enterprise selling. by the way, when I was interviewing, I was talking to my developers and they're like, man, this is magic, this just works, right? And I'm like, okay, how do you articulate value? And they're like, yeah, you know, I don't have to look at logs and dah, dah, dah, dah, dah. I can save a couple of hours an issue. it's super easy. and so the ROI is just a developer getting to their outcome and getting to it repeatedly.

high value, one project, two projects, three projects, you know, additional value in that. there is nothing in the product that actually has any kind of ROI calculator. although those ideas have been brought up, we should tell them the value we bring, you know, in net dollars.

no, we literally focus on deliver value, focus on adoption. If those two things happen, things compound over time, a little crazy, but that's how we think. And that's allowed us to iterate and, be hyper focused on value delivery. And then the last part, which is different enterprise buying motion, pricing, packaging, typically extract the most dollars When we are thinking about it, extract, the right amount, very different mindset.

Brett: How do you figure that out?

Milin: through a combination of, you know, data, what is the market doing in that space, through our own, because again, we use Sentry for Sentry and we kind of operate as that, software team, so to speak, and so our intuition on that.

And so there's always a discussion about, you can sell it for X. Others are selling it for X. So you could sell it for one third of X. And simple example of this recently was, something called a session replay. Everybody has one now, but we kind of built it hyper focus privacy focus for developer to solve.

And there was art from pricing and packaging prior art, which is it's X dollars and we're like, no, for the way we operate. We don't want to be at X dollars. We're going to basically focus on adoption. It helps kind of solve this problem, which is our core market. What's the right price X by three X by three it is.

we are not maximizing on every element, but we are maximizing on value delivered to our existing customers. Adoption continues to be at a steady clip. So more customers are using it. And the combined value. Multi product. Enables us to grow at a sustained pace,

Brett: why in one of your meetings when someone is like, we're delivering all this value, customers are very willing to pay a dollar. Why are we charging 30 cents? what's the rationale and the ethos that's woven through the company?

Milin: Yeah. I mean, it comes to, you know, how we, again, operate from a, what are the things we think about, which is when somebody thinks about pricing and packaging, we have this discussion, it does come down to this point where somebody, this is what the market bears, right? And we say, okay, but the market bears that what is our perspective on this, right?

Which is. to deliver it at the right price point so that we enable the persona, which is a developer who does think about, am I getting the right value? So if I was selling top down CTO, as I've done in my prior life, the conversation is business value ROI, dah, dah, dah, dah, dah. And then you sign a big ELA and, whether it gets used, not used different discussion, right? the levell of discussion at that point is very different than a individual developer in a software team who is basically out there trying to ship software and for them to basically look at this and say, Hey, it solves my problem, fair price, let's go, So again, thinking from that lens. of enabling them to use the product, get to their outcomes.

And then imagine so many developers in the world doing this at, scale, people say we are an observability company. I say, we look, smell, probably do everything that an observability company does, but we are not that We have north of a hundred a thousand Saas orgs Look at any other player in the space in that regard, right? where are they? Right. So we just generally speaking, we're thinking of this opportunity, the persona comes back to that main thing. Developer, developer, developer

Brett: When you joined the company, were you tempted to take your decade plus at VMware, these ideas around pricing and packaging and, come in and say. What are we doing here? We're charging 20 cents on the dollar. I'm going to be a genius. I'm going to come in here. We charge a dollar for this.

We're not going to charge $5. it seems like it takes a certain amount of curiosity and open mindedness to not want to come in with your VMware playbook and apply it to Sentry. 

Milin: the way I look at it is it comes back to in everything you want to kind of understand what are the first principles of a company?

and through this conversation, hopefully that came out the most, which is it's about who we are serving. It's about the community. It's about the approach that we are taking you know, I bought into that, right? And once you buy into that, then the decision making process becomes significantly easier, and then I always say this, which is, there are so many executives out there who have such great experience, super smart, but they're not a right fit for a majority of the companies they end up joining. You'll see that constantly. And that's because A lot of them either are unable to adapt or choose not to adapt or are like, I don't want to deal with this shit.

I know everything. Right. And I think you do need to be constantly curious, to kind of eventually succeed or eventually be kind of part of something bigger than you. I didn't sign pre joining that I will agree to these terms, but there was some first principles, This open source one comes up a lot. Open source is great. people can use the software for free, the SaaS offering should have differentiated features.

I was comfortable with this idea that, in general, I don't believe in self hosting software at Sentry. So I'd rather pay someone for a service they deliver of high value, the right price, then actually have a couple of engineers build something so that I can save a few bucks.

So I've always believed in that mindset through whatever I've led. that made it easy for me. I'm like, we're just going to build a great service. We're going to innovate. We're going to move fast. It's going to be the right price point. No brainer. that's how we've thought about it. And so all of those things helped, some of the, the kind of concepts that I learned over the time at Riverbed and at, VMware, then still bring the core concepts of product has to deliver easy value.

There is no substitute for that. We've had some hits and misses at VMware too. Pricing and packaging is a art. You don't delegate that. to an external agency, but you got to have a sense of intuition of what the market bears, what the customer's thinking and, and doing the research.

that's my one recommendation is think deeply about packaging, forget pricing, pricing can change packaging, how you bring your different packages to bear,.

Brett: So, do you not think about Customers and normal customer segmentation. We have our startups, we have our mid market, and we have our enterprise. We have a roadmap. We're trying to land with a developer at, Coca Cola. And then once we have a group of developers that like Sentry then have an expand motion and we ultimately want Coca Cola paying us $1.5 million a year. that's not the way that you think about both pricing and packaging and product strategy. 

Milin: there is a part to what you said, which we do, absolutely align on, which is we are for the fortune 500,000 is how we say it. and then we've identified this idea of a developer who is, call it forward thinking or builds often, right? Shipping often and working on the latest and greatest technology stacks, right?

So whether that developer is a new startup, in Latvia, Or they are in Coca Cola building their next mobile app. They're the same person and the same target and we're building for them. the Genesis of everything starts from there, which is we are for the fortune 500, 000.

And that's who we want to enable. Now that I have that software team at Coca Cola, and maybe there's a second team, out there, can we. see if there's a broader opportunity there. So Chris, our CRO and his team then works through that to enable that concept, right? we start from this base construct of what you said, there is a developer or a set of developers independent of size of company or anything else.

They just need to be. shipping iteratively, forward thinking, care about their users, working on a certain set of modern stacks, although we support everything. but there's a kind of lineage to taking and moving fast, right? Or forward thinking. So let's go get them. And then we get a few of them at a company and then that scales from there.

Brett: so do you build product with the goal to have an enterprise wide deployment at a company like Coca Cola or the company doesn't work like that?

Milin: this may be controversial, but, uh,

Brett: that.

Milin: if somebody came to us, and said, 

Brett: We want the widget 

Milin: yeah,

Is this widget important to just 10 or it will apply widely and the ability to then say, no, we can't do it because it doesn't apply widely is something we do, by the way, this is something the art of saying no is the best thing a product manager can do, to actually eventually win in a product, right?

Because you typically have like one company, you're basically jamming their features. I'm paying you $10 million. You got to do this.

If it doesn't align to where you want to be long term, you should not change your plan. we don't build for a few, we build for the many. So in those kind of scenarios, we will not kind of optimize for the few. Number one. Number two, you asked an interesting question about scale.

We build for scale. So we've got some of, the largest streaming platforms, delivery platforms, B2C sellers, SaaS platforms who depend on Sentry, At scale, we absolutely support that scale element, that collaboration element you need to, go enterprise wide. But we are not that classic enterprise motion where go build me, My personal favorite widget.

And we'll just go start scurrying towards that, because we want to make sure, again, we are for the fortune 500, 000. We're doing the right thing. We're making the right bets and moving that needle.

Brett: What do you think a lot of people don't appreciate about what it means to be truly developer centric if you were 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.

Milin: 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 like, Oh, wow. They are actually good with the overall kind of community. Well, 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 

Brett: what does that mean to show up well, then?

Milin: Depends on what the team is looking for, right?

Which is, as a simple example, you know, if you're a developer, you care about a certain stack. are we in that community enabling that stack? How does that work out? not only kind of thinking of Sentry, Sentry, Sentry, Sentry, Sentry, we are kind of out there working with others for the broader good of kind of the developer community. Right. So that's kind of one element of it. you know, I would say like what I did not appreciate. this is one of those things which you coming from a larger enterprise company and coming in, it's so obvious, but this idea of.

if you are taking from the community, are you giving back? So sustainable open source, I continue to believe we need to make it the mission of everyone building out there. You use something you give back. and so I think that's kind of another way where you participate in the community.

Brett: Are there rituals or ways that you are constantly bringing people back to that?

Milin: Repetition, repetition, repetition

and so like, it starts with alignment and so making sure you have the right people, you're aligned, so coming back and saying, no, sorry, we've said this always, right. we are for the fortune 500, 000.

We are not for the few, we are for the many, we are not going to kind of go into this narrow aperture for one thing, but it has to apply. And so we show that with action, but it also requires kind of rhythm of repetition, number one. this kind of idea of engaging with the community starts with all of us.

so in this case, I'm fortunate that, Cramer is relentless, So he's out there, our early engineers, you know, Ben Armin, they are out there. helping, uh, with the team and the community, so through action, people see that, and we are making it kind of increasingly part of how we want to operate.

That's really hard by the way, you're right at scale. and we continue to try to get better at it every day

. 

Brett: One of the last things I wanted to dig into, you mentioned this in the context of, packaging is so important, but you started to talk about the product evolution as you've launched the 1st, few products that have come outside of the core product. It's entry. Maybe you could talk in a little bit more fine grain detail around the story behind the 2nd product.

what that process was like, how you landed on it, how you brought it to market.

Milin: the idea of the second offer, in simple terms, this idea that tell me when my code slows down, Traditionally, this market is called APM. New Relic pioneered it. Everybody's jumping on it now. Very large market. And then if you kind of look at this market for the longest time, it generates a lot of revenue, but think about who uses it, it's typically very large companies who use it sporadically to find deep problems.

So it's like. lots of agents, lots of time. It's a special project, lots of money spent. but if you look at where we are now, we're building every day, we're shipping every day, maybe three times a day. the user is the one who matters. And so two things we thought about as we were building about it, like start user in, and again, our persona is a developer, so they're not going to have ample amount of time to kind of go figure this out.

So it should be super easy to use. And again, as with errors, can I get to the answer of what's slow really, really quickly. 

Brett: Was it obvious that that should be the second product? how did the company know that it was time for a second product?

Milin: I'll take the second question first time, time, right? So I'm not going to shill your framework, but when you have reached, 

Brett: should . be delighted.

Milin: when you've reached a at scale on your initial product, okay, there's a pull, the business is moving, It's good. Right.

However, it might be too late if you start after that. And that's why I said, you know, as we were getting to that stage, the team started thinking about where else could we go? and where is the opportunity to disrupt? if you think about this APM space at 10 years old, people are still doing it the same way, 10 from 10 years back, and the shift to developers are taking place.

So there were two trend lines, old, model of operating, uh, Plus new persona emerging, that's how kind of this idea emanated. It was always in Cramer's mind, like this would kind of be the next play. and so we started sowing the seeds for that while that was happening.

And as we are kind of looking for that. Product market fit from level one to level two, which is where we are. 18 months back, we're like, Hmm, I think we're still only at level one. We need to make changes. So we made some changes. We got to level two, six months back. We said, Ooh, we need to get to level three.

What we had built initially was successful, double digit millions. In like 18 months, it was growing thousands of customers and everything else. But what we realized to capture the broader opportunity to expand the market, we needed to go from. what we had done, which was like solving very easy to solving a little bit more, in a little bit more detail? So I'll give you a couple of examples. we realized that we were a user and kind of offering, there's a concept called web vitals, which tells you how your user is experiencing your product coming in.

and we said, everybody has one. But can we make it more pointed where when we offer it, it absolutely has a beautiful workflow to get you to the answer. went and did that. Built a very curated workflow for that. built this concept for mobile. We said app start times are a problem. So let's go just show how to constructively solve that in a curated workflow.

So first one was like, Hey, easy to get going API performance, blah, blah, blah, curated workflows. And now we're like, Oh, wow. Now that we have all this data, we can do something even more interesting. So just kind of building up and making those investments to kind of continuously say, how will a user use it?

Will they use it? And that again, comes with this idea of, I'm going to use Cramer and others were saying not good enough. this product is shit. You know, we're selling in double digit millions. You'd be like, Oh, wow. You know, and he's like, nah, others are like, nah, So that internal focus to understand and appreciate that there are levels to this, is super important.

And so we've been iterating on that. And I think we're somewhere between, you know, we're at level two, Figuring out kind of how to expand to create your level three. And then that's when kind of some of us realize we need to get, back and see what's happening, take a deeper look, the surface level success, may not get us to where we want to be. So all part of this phase three of the company, which is let's get back to product market fit, right?

. and so this is constant, reflection, introspection, making sure you're aligned. And that's where the early engineer founder mentality combined with the new people who have joined has really helped, that's kind of helping drive that, change and momentum.

Brett: when you're building a second product and then a third product, are you thinking about it as a standalone successful product in the eyes of the developer? Or are you always thinking about it as an extension of the first product into the second? 

Milin: the mistake that most folks make is this assumption that we want to ride on the coattails of the first product. That is an incremental, expansion of market. And so we definitely have new SKUs that build on the core construct of error monitoring.

And I call them basically incremental bets, in just expanding the core platform as you would call it, very important products in themselves can make a move, have a big impact, are having a big impact, but they are in that realm of supporting that first product, integrated experience and everything else.

When you are trying to be a large sustainable long term company, you have to go after new net new opportunities. they have to be adjacent though. So they can't be completely disconnected. So the way we said it is this needs to be able to win as a standalone product first. So you have to build a great product.

 We constantly talk about this idea that you have to win on your own merit. Then you can unify the experience. Then you can leverage the fact that you've got this first great land product and errors that kind of pulls the other, but if you don't maniacally think about building the best product.

you know, on a standalone basis, you will not eventually get those outsize outcomes that you're looking for.

Brett: share more about why you think that way, because I would say conventional enterprise software wisdom is, we are happy to have each one of our other products be 80 percent as good as the category standalone leader, and we're just going to cross sell this all away.

the suite will be better than the standalone because it's a suite, but each product is not going to be as good as the best of breed sort of solution, I'd say, is maybe more conventional wisdom. And it seems like you're oriented in a different way, that you actually want the standalone product to be the best product in the market for that use case.

Milin: So you absolutely nailed it. I mean if you take a VMware or any other enterprise company, they package it up. It's all good enough. We'll be number two, number three. Distribution, ELAs, life is good. Whether it gets used or not, can't afford to do that if you're in the developer land. I can't afford to be a mediocre offering, right?

Like, ah, good enough Sentry. Oh, it's from Sentry. I'll just use it. No, you have to care about the art of what you're building, especially for the persona of your building. I would say the same applies if you're trying to build something long term and sustainable. I think it's okay to say I'm happy to be a number two in the second category, Which is more of an outcome, a business outcome. you should never say that I just want to be a mediocre offering. Now, what I mean by that is you could say, I'm not going to match the best product, pound for pound. I don't want to be them. I'm going to actually figure out what makes sense for my community.

You know, typically people say best means you're matching everything pound for pound and I'm like, no, best is, you could actually be 80 percent of the best product, but then you win out because your errors plus, tracing experience is perfect.

And then the synergies of everything works out. But if I seek to kind of just say, I'm going to be 80 percent good, I'm not going to build the state of the art, So go for solving. the problem correctly, comprehensively, not the same way. And you win out in the market.

Brett: 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? 

Milin: 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, 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 are two are really good examples. Mike Spicer, 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. thinking of ideas, sending him notes, and they would respond back, both of them. And I'm like, wow, this is, I learned a lot through watching them in action about this idea of how to think about strategy. I know that sounds crazy, but through those interactions, they would tell me, eh, ooh, you know, and then I would see their actions, the investments they made, and the way they kind told stories.

Brett: Share more about what you learned about business strategy from watching Spizer.

Milin: So he's in product management. Some, you know, I don't remember his title. He was some head honcho. I'm like this IC guy writing code. when they would do all hands and they would talk about our product strategy and how to kind of expand that market. And at that point in time, email archiving was a really large market.

And so there was these discussions or synergies and how to think about it. And so they would kind of present at all hands. And then I would write back and say, Hey, have you guys thought about this? Just kind of like ideas around like product ideas and stuff. And they had the time and the patience to respond back and either validate or invalidate things or say, Hey, this is a good stream of thought.

And just that interaction to tune my brain of how the art of kind of building out what we build product strategy selling, so I would just ask them and they took the time to respond to me. Right. And running a very large organization. So that was the other thing about if they have the time to respond to me, that's why when people say, don't respond to my email, which happens a lot, by the way, I'm surprised.

I will tell you this, if I sent Pat Gelsinger, who's now the CEO of Intel. He will respond. He has the time to sometimes, you know, it takes a little bit, but he will respond. People who are not as busy or, you know, I don't want to say like not as important or whatever it is, but they won't respond.

So like this art of communicating back or acknowledging the other person changed the trajectory of how I operated, It's important. I feel like anybody who listens, it doesn't take too much, even if it's delayed, say, sorry, I don't have the time right now. Maybe later. Is that okay? And I think that's super important to get them.

So like that interaction changed. it inspired me to make the transition to product management? And so at Riverbed, it was Eric Woolford, who essentially exceptional leader, his, ability to connect, go to market product, the way he kind of led the company, he's now at Excel as you know, And then VMware, as we talked about as this phenomenal set of people. Raghu Raghuram, Priceless. The man just understands strategy and product like no other. And then, you know, folks like Karl Eschenbach, man, that man has achieved so much. Humble, humility shows up. He's side to side, always combat, And then I had the opportunity to work with Martine, changed everything about how I operate because it became like, figure out the story.

Anything you do, write down your thoughts, figure out the story arc. What are we trying to achieve? How will you tell the story? You know, almost like how you write a movie script. Kind of write it down, write it down, let it marinate when you're running, when you're hanging out on the weekend, you know, nonlinear, thinking kicks in.

And then that, that work of art becomes how you then come out, right? So product strategy is not product necessarily. It's the story arc of, you know, where you saw the outcome, so that's kind of the habit I built with him. saw that in action with him. So these are a few people that are few, I'm probably missing out, but I would tell you, like, there are people around us, that teach us so much.

including my wife who, who teaches me attention to detail. I'm not very good at it. she continues to kind of hone in on that, but I think we try to seek these superstars all the time. and I would tell you there are people around us that we can learn from a lot.

And I, these are all people I reported into indirectly or directly. but have kind of different things that I've learned and picked up from them. and even, I would say there are, there are folks at Sentry who I'm constantly learning from, which is like, oh, wow, I'm new to this developer space.

So it's been really fun. and so if you're curious to your point and you're humble. there is a lot around us and people around us to learn from.

Brett: Good place to end. Thanks so much for spending the time. Thank you. this was great.