EP #4: A Glimpse in the Mind of a Tech CEO With Toffer Winslow (StackState)

35 min listen

Toffer Winslow - CEO at StackState

5 months ago, Toffer Winslow joined StackState as the Chief Executive Officer. It doesn’t happen very often that we hear first hand from a CEO (1) why he or she chooses to join a company, and (2) what prepared them for their first CEO job. Therefore, we thought it would be a great idea to invite Toffer. We're excited he said yes, which makes him the fourth guest of the StackPod!

In this episode, Anthony talks to Toffer about:

  • How his previous experience in consulting, sales and marketing were the perfect basis for his current role as CEO

  • Why he said yes to StackState - even though the observability market seemed like an awfully crowded market

  • How building a sustainable company culture can be challenging, especially during covid times

  • How to tell if someone went to Harvard Business School (just kidding)

Toffer & Anthony's book recommendations:

You can find a written transcript of the episode below. Enjoy the recording!

Episode transcript

Toffer: [00:00] I got my early start doing strategy consulting with a company called Monitor, which is now part of Deloitte, through the classic strategy consulting firm. And it was phenomenal training for a kid who had come out of a political science degree, from the University of British Columbia, Vancouver, where I grew up. It was amazing business training and a great growth opportunity for me, but also helped me realize pretty early in my career that I wasn't interested in just advising people. I wanted to do stuff and have accountability for implementing the plans that I was responsible for devising as well.  

Annerieke: [00:38] Hey there, and welcome to the StackPod. This is the podcast where we talk about all things related to observability because that’s what we do and that’s what we’re passionate about, but also what it’s like to work in a tech company. So if you are interested in that, you are definitely in the right place. 

Annerieke: [00:55] So the next guest of this show is quite the special guest, he recently joined StackState as the Chief Executive Officer and his name is Toffer Winslow. Anthony and Toffer will talk about how Toffer started his career and how become a CEO and why he joined StackState which is of course something we’re very curious about, so - without further ado - let’s get started.  

Anthony: [01:20] Thanks for coming on, and thanks for doing this. I know you're a very busy man. But again, thank you for taking the time to come on and giving us the opportunity to get to know you, your journey, a little bit about yourself, a little bit about why StackState, a little bit around some of the things you're doing in and out of work. And let's just get to know each other, and see what we can do from there. 

Toffer: [01:49] Sounds great. 

Anthony: [01:50] So, obviously, Toffer, you're the CEO of StackState. Do you want to give yourself a little introduction? 

Toffer: [01:56] For sure. Yeah. So, I'll start with a little background about me, where I come from, and maybe segue into how I got to StackState, and talk a little bit about the opportunity I see in front of us. 

Toffer: [02:09] So, I've been doing enterprise software in various forms for probably the better part of 25 years, I hate to say now. I got my early start doing strategy consulting with a company called Monitor, which is now part of Deloitte, through the classic strategy consulting firm. And it was phenomenal training for a kid who had come out of a political science degree, from the University of British Columbia, Vancouver, where I grew up. It was amazing business training and a great growth opportunity for me, but also helped me realize pretty early in my career that I wasn't interested in just advising people. I wanted to do stuff and have accountability for implementing the plans that I was responsible for devising as well. 

Toffer: [03:01] So yeah, that pretty quickly led me to an operating career. This was the mid to late nineties, the early days of the internet boom. And I went and joined an early, early startup. I think I was employee number seven for a company that was making Java-based, rapid application development tools. 

Toffer: [03:22] We were on stage with Scott McNealy and Ed Zander, the executives at Sun Microsystems, when they announced Java to the world. And we were one of their showcase companies that were doing cool advanced things. We had built a scripting language that if we had figured out how to do the licensing deal that Sun was trying to do with us, it would have probably become JavaScript and used broadly today, but instead it's now a defunct proprietary language. 

Toffer: [03:50] But yeah, we were doing all the things you needed to do to transform a browser into a front end for a tiered application. So, it was cool stuff back in the day, but a bit of ahead of its time. 

Toffer: [04:04] That startup started to crater. And I left for business school. I went to Harvard. I met my wife there in my section. And I've been living in Boston for, gosh, since 1996. So, 25 years now here, and all the while doing various forms of enterprise software jobs, originally on the product management, product marketing side. And then as my career developed, took on more and more of the whole marketing function, then marketing plus BD, plus sales. And then most recently, including those things, plus a strategy and overall operations role. So, StackState is my first CEO job. And I'm psyched to be here. 

Anthony: [04:55] That's great. I do have a question. So, you left school, you had political science, you then went into contract or consulting. Right? And then, you'd made it almost into the tech industry, right? Working with a startup. You were already in the industry. What made you decide that you needed to go back to school? And of all schools, it's a great school, don't get me wrong, Harvard. But what made you decide to take that as a step, as opposed to just using what you'd already learned and propelling off of that? 

Toffer: [05:28] Yeah. You know the old joke about how to tell if somebody went to Harvard Business School, they tell you in the first five minutes of meeting you. 

Anthony: [05:35] Yeah. 

Toffer: [05:36] I try not to be that guy. Let's see. I went back to business school, in part because I wanted to have a broader tool set to try and build companies with, right? The political science degree I did was great, I guess, in some regards, but it wasn't particularly practical. That first startup taste that I had working, it was both, someone responsible for strategy, but also for operations and execution in the tech world, gave me a great taste of what this life was going to be like and made me realize that's where I wanted to be long term, but it also made me realize that I had a bunch of learning to do, that maybe I could acquire on the job. But I thought the more efficient way to go get that was through a degree and do it through a degree at a place that had a fair bit of practice in delivering a really strong educational experience, and also had a great brand with it. Plus I was in Boston at the time, it seemed like the place to stay. I love this city. 

Anthony: [06:45] Well, you met your wife there, so who knows what would've happened, if you hadn't taken that leap? I mean, one of the things I find with a lot of people in tech, is that they get into the operational side. And the problem with the operational side of tech is that's where you get a lot of the just the hard graft and the hard work. You got to usually with technology, you sell your customer something that may be is in beta or alpha at the time you sell it. And then ideally you get two or three customers who help drive the revenue, who then also drive the R&D to a certain extent, as well as the operational side. 

Anthony: [07:32] So, I find a lot of people who start out on the execution side, end up staying there just simply because of the amounts of work that there always is, right? There's always a demand for somebody to sit behind a keyboard and to just deliver whatever it is, whether it's a deliverable, whether it's code, whatever. But it's I think healthy in some respects to identify that you want to be in tech, but then that you don't necessarily want to do what you were doing. And in order to expand from what you were doing, you probably needed that broader skillset. Right? So, that you could have more of an impact. Is that an accurate summation around some of the mindset and the thought process there? 

Toffer: [08:19] Yeah, that's a good description of it. I think the thing that I'm good at is integrating information from a bunch of different disciplines. So, having real operational experience, building a demand generation organization and a full marketing organization, doing a bunch of biz dev deals, running a sales organization, selling, carrying a bag myself, doing fundraising. Having that breadth of experiences, and then being able to put it all together in a single role is something that is, I think one of the things that I'm good at, and also one of the things that I really. It gets me going, figuring out how to combine different disciplines in the pursuit of trying to build something cool. 

Anthony: [09:08] Yeah. Yeah. And that's also the reason why I love working at startups. Right? I feel like I've been ruined in terms of, I wouldn't be able to just take a role where I'm just doing pre-sales or I'm just doing support, or customer success, whatever it may be. I like to do a variety of things, and that's what drives me to companies like StackState, right? Because you have the opportunity to drive the company, as opposed to just driving your own agenda or your own career. 

Toffer: [09:42] I totally agree to that. I think that's been one of the things that I've observed with you at StackState that is a huge asset for us, is your both, ability and willingness to go pick up whatever needs to be done, whether it's coming up with interesting new marketing opportunities that we can pursue, helping build a program that lets tap into the voice of the customer, driving a bunch of work with a key partner in AWS and getting us listed in the marketplace, or doing what people would consider the traditional sales engineer job of doing demos and understanding customer’s requirements, and getting them through POCs. I think, the breadth of what you've been doing here has been super helpful. 

Anthony: [10:25] It's fun. I actually enjoy it. I really can't stand people that have a mentality or an attitude where it's like, "That's not my job. That's somebody else." Or, "We don't have a marketing team, so we don't have marketing." Well, that's not really a helpful attitude, especially when you're trying to pivot. And especially when there's a dependency on maybe singular individuals for a whole department in some cases, right? Because then if that person quits, then you lose everything. 

Anthony: [10:58] So, by building almost like a, I wouldn't say it's communist, but building out a socialist level of responsibility, where it's like, "Hey, just because you don't have a marketing title doesn't mean that you don't contribute to marketing. Or just because you don't have a sales title doesn't mean that you don't contribute to sales." Because at the end of the day, if any of those functions don't work, then you're at a stage where the whole company won't work. 

Anthony: [11:24] One of the things I've had to learn is to be less, and this isn't from StackState, this is just in my career in general, is that you move from the young person who knows everything and is always right, and is always pushing what they want, which you look at yourself after five years of doing that and you're like, "Why don't people listen to me?" And it's because you're the irritating youngster who thinks he knows it all. And so, going more into my thirties where it's like now, okay, I can contribute things. I've got enough self-assurance that what I'm providing is going to help in some way, shape or form. But let me do it in a more politically correct way, allowing people to take the lead, and all that kind of stuff. That's where I've really been trying to mold myself in terms of where I can fit, as opposed to just being somebody who drives everything, because you can get too busy as well when things do start to kick-off and the business does start to become successful. 

Toffer: [12:29] For sure. Yeah. I think that's one of, you touched on it a minute ago, one of the things that I think can make or break a startup, is whether there's enough people who have that mentality that, "Look, I see a problem and I'm going to go solve it because nobody else looks like they're solving it right now." So, that's one of the things that is great about being a little company and allows companies like StackState with 50 employees to out-compete bigger organizations with 500 or 5,000, or 50,000 employees, because you have that agility and willingness to just do what it takes to solve a problem, even if it wasn't in the job description that you signed up for when you started six years ago. Right? 

Anthony: [13:13] Yeah. Yeah, exactly. Exactly. So, speaking of that, why on earth did you decide on StackState, and what made you join this group of observability people? 

Toffer: [13:26] It's a good question. When I first got the call from a recruiter about StackState, my initial reaction was, "Gosh, this feels like an awfully crowded market." It's one that I knew reasonably well, and my knowledge was starting to get a little dated from my days as the early CMO at Dynatrace. I joined them when they were a small Austrian company that had just taken on some institutional money, and put out a shingle in the US, similar in size and scale in many ways to where StackState is today. 

Toffer: [14:06] But the thing that got me super excited about joining Dynatrace, 10, 12 years ago, was this core technical innovation that I saw. For them it was dynamic bytecode instrumentation. And that innovation had been harnessed in a software platform that was delivering what customers who were building at the time were cutting edge, n-tier, microservice-based applications. They needed to see how every unit of work was traversing the whole application infrastructure in order to figure out when problems were popping up, what was the underlying cause? Yeah, that was a big innovation at the time. And to be able to do that in a low overhead way, so that you weren't degrading the performance of the application, you were supposedly monitoring and optimizing, that was a big deal. And Dynatrace had done that. And it was clear to me, when I figured that out that this was a company that had huge growth potential. 

Toffer: [15:08] When I got to really learn what was under the cover at StackState, I saw a similar technical innovation that maps really well to the way customers are building and deploying applications today. The core innovation here is our time-traveling typology approach, which is powered under the covers by this versioned graph database that the company has created. And that ability to allow you to see what an application topology looks like over time, not just at a point in time, but historically, is the big innovation needed to help people who are deploying these really dynamic, complex, cloud-based applications succeed. 

Toffer: [15:49] There are so many services that are getting spun up and down, and containers that have a half-life measured in minutes sometimes, that unless you can understand what the dependencies and relationships are between all these components that make up your cloud environment, and then see how those are changing over time, and then use that, you have the change in order to understand what the root cause of performance problems are, you're toast. And that's what StackState uniquely does. 

Toffer: [16:20] There's plenty of other folks out there who will give you a view of your typology, maybe even a near real-time view of that topology, but the ability to time-travel across your typology and you see how changes that happened 10 minutes ago, or a day ago, trickle into performance problems as they impact downstream components, that's the magic here at StackState. And what I see is the big innovation upon which we can build a company that is Dynatrace like and scale today, a clear leader in a big market. And those are the stakes we're playing for. 

Anthony: [16:55] Yeah. So, my previous company, they were obviously in the AIOps space, and they didn't know whether to focus on AIOps or to continue focusing on the AI service management, which is like the chat bot side and how to automate the help desk. For me, that's not a very big industry because a help desk internally, maybe costs you anywhere between a hundred to 150 grands. And that means that if I invested in an AI tool, even if it takes over a hundred percent of those calls, the value is only 150 grand. That's it. That's all you bring to the table. 

Anthony: [17:37] Whereas with AIOps, you're dealing with the backend of the issue, the root of the reason why people would be calling that help desk or people would be calling that customer service desk. And that's usually for the availability or the lack of availability of say, a website, an application, or a service and whatnot. 

Anthony: [17:58] So, for me, AIOps was the more lucrative market. But to your point, it's incredibly busy, that everybody says, they're an AIOps tool. Everybody says now that they're an observability tool. You go to Splunk, you go to Datadog, you go to Dynatrace, you'll see the words, observability and AIOps, and all these other buzz words on their screens as they market those products. Why do we provide observability better when it aligns to that time travel that you were talking about? 

Toffer: [18:39] Yeah. I mean, I think having this technical innovation at our core, this version graph database, and using that to see how the dependencies between components change over time, I really think of that as like a prism by which other telemetry data can be viewed, right? Telemetry data at some level is kind of a commodity. People, there's lots of ways of doing tracing and a lot of ways of gathering logs and metrics. And sure, there's some complicated challenges around making that all searchable and useful. But the data itself is kind of a commodity. 

Toffer: [19:13] The innovation of being able to apply topology and changing typology is the prism through which all that telemetry data is filtered over time. And that's an important organizing paradigm that gives you this unique visibility into what ultimately the root causes of performance problems are. And even now the ability to find anomalies before they become performance problems to surface those to the people who are accountable for managing those environments, and to allowing them to troubleshoot them before they impact service quality and become visible to end users. That I think is a super important set of capabilities, and it's only possible when you've got this time series based view of typology. 

Anthony: [20:02] Yeah. I think this has become incredibly important now that we're dealing with more containerized technologies, right? If you think about 10 to 12 years ago, to your point around Dynatrace, right? The main problem you were solving was observability for physical and virtual infrastructure without a high overhead in terms of performance impacts. Right? So, getting that data real-time so I can see application through per, I can see where everything is communicating and to what ends. And that works very well. You can have a real time view. You don't really need to worry about time travel at that point, because there isn't so much change going on within the actual resources being used. Okay. Maybe a service will run and whatever, but it's operating systems at the end of the day. 

Anthony: [21:00] I find now with the containerized technologies that a lot of these, let's call them legacy ways of doing application performance management, really don't cater for the fact that the rate of change happens so frequently within a Kubernetes environment. You could say that, "Hey, I've got a real time view." But who's to say that container X, they get spun up at 9:09, gets spun down at 9:10, but then had a downstream impact, it may be obliterated and S3 bucket, or did something anywhere else within the environment. You won't be able to see that very clearly. 

Anthony: [21:45] And I think the way in which a lot of our prospects and our customers do it today without StackState is that they have to go through tons of logs in order to actually just get that view that, "Hey, this thing happens. That's the last thing that touched the bucket." The bucket is the reason why everything is dead. But then we need to figure out why the container did that in the first place. And without that time traveling topology, you really don't have that ability to see the play by play, that you get with StackState. 

Toffer: [22:16] Yeah. No, well said. 

Anthony: [22:19] What would you say to people who are listening to us about our technology? What would you say would be a great call to action around how you can get involved with StackState and start seeing this time traveling topology in action? 

Toffer: [22:34] For sure. Well, I think one of the initiatives that we're just bringing to market is launching a playground version of StackState, so that for anybody, you can come into a StackState environment, see the central dashboards and user interface that have been already set up and are monitoring a demo application. But we will provide a guided tour through how do you use StackState to identify the root cause of performance problems, how to use automatic anomaly detection, so that you can prevent problems from impacting service level objectives, and really just really get a quick and easy taste of what the product is capable of doing. It's a great way for site reliability engineers to have that first initial experience and real hands-on experience with the product and what it can do. 

Toffer: [22:33] Of course, we'll have solution experts available along the way to help anybody with whatever questions or issues that they've got. But really being able to automate that entire experience from first touch of a prospect on the product, all the way through fulfillment and initial deployment, is the model that we are heading towards. And key part of that is being able to fulfill a demand for StackState through the AWS marketplace. That's been an initiative that I've been really keen on, and you've been instrumental in making happen over the last couple of months. 

Anthony: [24:09] We've talked a lot about StackState now. We spent about 20 minutes or so talking about, why StackState, what we're doing and whatnot. You mentioned you're up in Boston. Outside of work, what do you enjoy doing? What do you and the family like to do in your spare time? 

Toffer: [24:29] I'm a family guy first, right? So, I married my section mate from business school. We had our 20th anniversary last November. We've got two kids who are increasingly grown up. We just shipped my daughter off to college a week ago, and we are missing her presence around the home, but it's all part of a parent's job, getting kids ready for those kinds of experiences. 

Toffer: [24:57] In addition to my 18 year old daughter, I have an almost 16 year old son. And we love doing stuff together as a family, typically, active family vacations. Or something we love to do, we've got a handful of cycling trips, hiking trips together this June, just before I started at StackState, we all went to Moab and spent a week, hiking in the national parks there and paddling on the Colorado River. So, active stuff is key for me. 

Toffer: [25:26] When I'm not doing stuff with my family, I'm super enthusiastic about cycling. So, I do a lot of road cycling and a small amount of mountain biking and biking off road. But yeah, going off for short, sharp rides in the morning before work starts, or long, grinding rides on the weekend are part of the way I stay sane. 

Anthony: [25:52] Yeah. I don't get as that many opportunities to leave my house because I've got a three-year-old and one-year-old, and another one that's going to be one in December. So, if I if I turn on the TV, if I sit down or whatever, my wife gives me a look as if I'm swiping right on Tinder. It's the same thing. I have to make sure that I am there. 

Toffer: [26:20] You are in the very labor-intensive phase of parenting. And that I'm finding myself on the, just really out of that game right now. And now what you're trying to do is mostly be available for when they do choose to engage and just try to set the right time to have guard rails, so they don't go to far off the road and the right kind of expectations, so that they're pushing themselves to figure out what's going to make them tick in life. 

Anthony: [26:47] Yeah. I'm not going to lie, when you said you're shipping your daughter off, I was like, "Oh, I can't wait." So yeah. Is there anything else you want to kind of share, talk about? 

Toffer: [27:00] Yeah. I guess, I'd say I'm a big believer in the importance of organizational culture and culture in general, company culture. Yeah. There's that old saying attributed to Peter Drucker about, culture eats strategy for breakfast. And I'm not sure that's totally true. I think strategy is super important. But I do believe culture is equally, if not more important than strategy. And without a set of values that you live by every day and that you actively root out examples of behavior that run contrary to those values, you're not going to have an organizational culture that sustains both the organization and individuals through hard times, which any company is never really going to run through. 

Toffer: [27:50] So, being very deliberate about building a culture, about making sure that those values are modeled and celebrated, and rewarded is something that I care a lot about. As I said, every company is going to go through rough times. And I think one of the things that sustain people through those rough times is having a culture that is positive and differentiates it from other places they could go off and work at tomorrow. 

Toffer: [28:18] Building and enhancing a culture is something that is hard to do at the best of times. And it's really hard to do without being face-to-face and shoulder to shoulder with your coworkers. Yeah. I think Zoom and other things that have been able to remote work are super productive, and there's a lot of really promising upsides from them. I think they're probably fine for sustaining a culture, but I think it's really hard to build and change a culture without some of that in-person contact thrown into the mix. 

Toffer: [28:52] So, I just got back from a week over in the Netherlands with the team over there. It was great to be face-to-face in a conference room with the fully vaccinated management team, working on stuff. And I'm excited about us getting through this, what is hopefully a final surge and getting back to spending time face-to-face with our other coworkers, particularly as we start to build scale here in the US. 

Anthony: [29:20] Yeah. I'm about ready to get out of my basement and do a bit more traveling. I enjoyed the old business trip anyway, even if it's to random cities. I've been in the US now almost eight years. I actually haven't left the US in almost seven years. But it's actually been nice because before living here, I had only visited California, Texas, Florida, and New York. But having lived here now, there's just so much diversity in this entire country. You could go to Denver. You can go to Portland, both in Oregon, wherever. Right? And there's a lot to see and discover, I find just in this one country. 

Toffer: [30:11] Yeah. No, it's an amazing country to live in. And so many great things about it. Some unusual and crazy, and deeply dysfunctional things in this day and age too. 

Toffer: [30:23] Yeah. Well, for people who are interested in both startups and culture, maybe we can take it out with a couple of book recommendations here. I recently read Ben Horowitz's, The Hard Thing about Hard Things, and thought that was fantastic. A great firsthand account about what it's like to be a CEO and living through multiple, near-death experiences as you build a startup. And I was so compelled by that, that I read another of his books. I think the title was, What You Do is Who You Are, a really an organized book about culture, and for people who are interested both in startup life, and then understanding the importance of the culture in a company, how to actively build the one that you want for your organization. Those are two great books that are well worth the read or listen, if that's your way of consuming books. 

Anthony: [31:21] Let's see what we'll do. We'll put links to that in the transcripts, which will be posted on stackstate.com. So, if you guys are interested in reading or grabbing the audible version of those books, I'm more than happy to do it. I actually started reading a different one. This one is more for my kids at my stage, but it's called The Family Firm by Emily Oster. Basically, it's a data-driven guide to better decision-making in the early school years. It's basically an economist running their family like a business through the early years of school. So, I just thought it was interesting to read that. 

Toffer: [32:06] I'll tell you about it. So, for closing out with like a parenting frameworks here, one of the most insightful things I saw, and I wish I could remember exactly who the author was, but I went to a lecture by an author of kids' psychology books. And the framework that he put up has always stuck with me, that there are parenting styles, if you plot them out on two dimension. There is that one dimension, think of it as the expectations that you have for your kids, are they high expectations or low expectations? And then there's a degree of control that you try and exert over your kids, high or low. 

Toffer: [32:44] And his assertion presumably backed up by data, although I can't cite what it was now, his assertion was is that the parents who have high expectations, but relatively low control over their kids are the ones who end up having kids who find for themselves in life, what it is that they're really excited about, and avoid a lot of the pitfalls that many kids get sucked into as they're growing up. The low expectations and high control or the high expectations and high control, had a bunch of toxic byproducts associated with them. But the high expectations and low to moderate control as far as parenting style goes, it seemed like it was the winning formula. 

Anthony: [33:30] You should come talk to my wife. I'm always telling her to let go. 

Toffer: [33:35] I'll let you share that framework with her. How about that? 

Anthony: [33:40] Okay. Okay. I might be out of work for the next couple of weeks. 

Toffer: [33:45] It's been great working with you, Anthony. 

Anthony: [33:47] Yeah. No, thanks. Thanks again. And thanks for the recommendations. And thanks for the parenting framework thought at the end there. Yeah. 

Anthony: [33:56] If anybody wants any information around Toffer, feel free to reach out on LinkedIn. Or if you guys want to contact us for more information, you can always go to stackstate.com. I'm more than happy to share any kind of insights. And obviously, we'll have more people that we'll be interviewing, both inside and outside of StackState in the coming weeks. 

Toffer: [34:22] Terrific. 

Anthony: [34:24] Awesome. Thanks, Toffer. Enjoy the rest of your day. 

Toffer: [34:26] Thanks, Anthony. Take care. 

Annerieke: [23:03] Thank you so much for listening, we hope you enjoyed it. If you’d like more information about StackState you can visit stackstate.com, and you can also find a written transcript of this episode on our website. So if you prefer to read through what they’ve said, definitely head over there and also, make sure to subscribe so that you will receive a notification whenever we launch a new episode. Until next time. 

Subscribe to the StackPod on Spotify or Apple Podcasts.

About StackState

StackState’s observability platform is built for the fast changing container-based world. It is built on top of a one-of-a-kind “time-traveling topology” capability that tracks all dependencies, component lifecycles, and configuration changes in your environments over time. Our powerful 4T data model connects Topology with Telemetry and Traces across Time. If something happens, you can "rewind the movie” of your environment to see exactly what changed in your stack and what effects it has on downstream components. 

Curious to learn more? Play in our sandbox environment or sign up for a free, 14-day trial to try out StackState with your own data.

35 min listen