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S2E5 Transcript

Their Fingerprints are Everywhere - Matt Eberhart's Journey as a Cybersecurity CEO

 

0:01 - Todd Gagne 
Welcome to the podcast. Matt, we have you on today. And so I'm pretty excited. You're going to talk a little bit about your journey in cybersecurity, as well as kind of what you're doing at Query. So welcome, and thanks for taking the time.

0:12 - Matt Eberhart 
Yeah, thanks, Todd. Really excited to be here.

0:14 - Multiple Speakers 
Appreciate the invite.

0:15 - Todd Gagne 
Yeah, well, good. Well, why don't we just start with a little bit about your background. You've been with Query maybe 20, 24 months, somewhere in that ballpark. You've had kind of a long kind of career in kind of the cybersecurity space. So maybe just give me some kind of sense of like how you ended up here and maybe some of the highlights of your kind of past career.

0:36 - Matt Eberhart 
Yeah, for sure. So, you know, first and foremost, I think of myself as a cybersecurity operator. My whole career has been in cyber. I started off hands-on protecting organizations as a network security engineer back in the early 2000s. And, you know, really, I think a willingness to, like, raise my hand to solve problems kind of led me all kinds of places, some that were cybersecurity related and a few that weren't. I found myself at a startup after about 10 years of protecting organizations.

1:11 - Matt Eberhart 
That was SecureWorks in the Atlanta area. It grew to be one of the biggest and best MSSPs. I was there for over 12 years and went through this massive period of growth there that just created a ton of opportunity for so many, so many people. That's really where I transitioned from being more of a cybersecurity analyst and engineer and got a lot of go-to-market experience and that ultimately led me to four different startups where I was CRO and did a number of different things that we could go into a lot more detail on if you like,

1:48 - Todd Gagne 
So what was your background? Like, what did you go to college for? And so how did you, I mean, that's kind of going from a technical to more of the sales. And so maybe just talk a little bit about that transition. I mean, in a lot of cybersecurity, it is a technical sale in general. And so, you know, that's been helpful. But I'm just curious, like, where did you start? Like, you know, did you get some training before you got that kind of first job?

2:08 - Matt Eberhart 
Yeah, I, you know, I was just always good with computers and interested in it. And I didn't, I took like one programming class and I knew that I was not going to be a programmer. I liked, you know, kind of more of the technical side of computers. And so I kind of jumped right into working. I didn't finish college and on undergrad and just kind of jumped right in and later went back and got an MBA. Like I felt like I really needed to kind of have a stronger baseline, particularly on the finance and business side.

2:42 - Matt Eberhart 
And so, you know, who knew this, but you can actually get an MBA without getting an undergrad degree. I don't know that I recommend it, but yeah, it worked out for me. Well, good.

2:53 - Multiple Speakers 
Well, that's good.

2:54 - Todd Gagne 
So, you know, one of the things that we always see like when we talk to entrepreneurs, they either kind of start off as like their skill sets, either sales, product, or technical. And so I'm kind of curious on like, you seem to have a little bit of a lot of things, right? I mean, you had some kind of operational experience, you've done some product related stuff, you had some CRO and sales go to market. And so where would you say your strengths were? And then how do you balance some of that out?

3:18 - Matt Eberhart 
Yeah, I think it's a great question. Really, the one constant is I've always stayed in cybersecurity. I genuinely enjoy it. I'm curious about it. It's something that I've always found interesting. I found myself into go-to-market and sales because I was at SecureWorks and they were selling to a technical buyer and the CRO was like, you kind of represent the kind of people that we want to sell to and so I'll teach you. What the sales process looks like, And so I, you know, I learned like a traditional solution selling process and later MedPIC and, you know, the kind of the traditional enterprise sales tools.

3:59 - Matt Eberhart 
But I think I've always tried to understand the pains and the challenges that people have. It's like, all right, what is it that you're trying to accomplish? How are you trying to accomplish it today? Maybe what's working or what's not working there? And is this potentially a good fit? So I don't necessarily, never really thought of myself as selling something. I suppose I was, but I don't know that I would be good at selling cars or selling houses or selling airplanes, but cyber, I understood the challenges of the practitioner.

4:29 - Matt Eberhart 
And so after 10 years or so on the sales and sales leadership side, I did four years in product management. And that's really where I learned a ton. I think I had some good instincts that I had picked up from being an operator and kind of digging into the jobs to be done and the pains and the challenges, but really starting to understand the Silicon Valley product group strategy and pragmatic marketing and really starting to put some more frameworks and mental models around how do you truly build a great product.

5:05 - Matt Eberhart 
That was a great experience for me.

5:08 - Todd Gagne 
So a couple of things in that that I'd like to maybe talk a little bit about. And so maybe one is more a comment. I think when you talk about solution selling, it's really trying to sell a solution to the individual, to the problem that they have. And so it's really understanding the customer, which I think is a theme between both product and selling. I think in both cases, you need to know. Maybe the comment or the discussion would be interesting is I think you see people that get into these product roles and stuff and they get close to the customer, but maybe it's just telling the customer what they want that's right in front of them versus creating a vision about where a product needs to go.

5:43 - Todd Gagne 
And I think we always talk about get closer to the customer, get closer to the customer. Well, a lot of times the customer doesn't know where the product needs to go. And so maybe talk a little bit about that from both a sales standpoint, which is thought leadership, and then from a product perspective, which is literally product strategy.

5:59 - Matt Eberhart 
Yeah, let's start on the product side because I think you're right and I think the approaches are a little bit different. So on the product side, it's like trying to really understand what problems that you want to solve and really digging into the world that your users are living in and what are the real problems that they have and getting deep enough to understand if you are able to deliver your vision for your products to this particular user, how does it change their world and their environment?

6:31 - Matt Eberhart 
Does it really solve their problem or does it just create some new problem that they hadn't experienced before? And so I think being able to dig into that and to have the empathy for the person that you're talking to and deeply understand, because a lot of products, only solve one part of the problem. And so you need to kind of understand really a little bit more holistically. And so I think spending the time on that and being willing to listen and take the feedback, but you don't necessarily need to.

7:02 - Matt Eberhart 
I think sometimes people think you need to pivot hard left or right. I mean, you're trying to build a frame of reference. And to your point, the user's probably not going to give you the answer. Like, I think that's sometimes I see product people earlier in their careers, like, well, you just go do 20 discovery meetings and the users are going to tell you what product to build. That's actually not how it works. There's hints and signal, and it's a puzzle to put together along the way.

7:29 - Matt Eberhart 
But you have to keep actioning your thesis, if you will, and keep actioning the learnings along the way. On the sales side, I think it's a little bit different that you're trying to, You almost want the person that you're talking to to realize through interacting with you that whatever it is you're selling is the solution to their problem. You do that through discovery as well and asking a lot of questions and getting to know them and getting to know the challenges that they have. If you're selling something that's a new approach, you may challenge their way of thinking a little bit and have some good back and forth about, well, you know, you may be focused on solving the problem here, but what if I could solve it three steps backwards for you?

8:14 - Matt Eberhart 
And what would that change look like, And so, you know, I think solution selling does a good job of, you know, a lot of detail we could go into on that, but it does a good job of giving you a frame of reference to, you know, kind of understand the pain, understand the world people live in and then help co-create a solution to solve that.

8:34 - Todd Gagne 
What do you think about like just the thought leadership piece? I mean, you kind of mentioned it a little bit, even in challenger sale type model, where you're kind of challenging the assumptions and maybe talking about where things are going to go. I think a lot of companies don't necessarily just want to partner with you for the point source solution that you're thinking about today. They want to basically be with a partner that's basically evolving in a direction that they agree on and hopefully innovating in that space to like anticipate what's coming.

8:58 - Matt Eberhart 
Yeah, I think that's right. I think the type of thought leadership that needs to be produced is very different depending on the stage of the company. And so if you're at a startup and you're going into, you're offering a different disruptive solution, something that's a little bit different, you want to be very specific and you really need to have an opinion about why the way you're solving the problem is better. And you want to really get into as much detail as possible. I find the type of thought leadership pieces that perform the best in that space are actually very long.

9:37 - Matt Eberhart 
They're 20 25 pages sometimes. They clearly articulate the challenges and they really paint a clear vision of what the future looks like, So I think sometimes there's this desire with thought leadership. I see this on LinkedIn all the time to be very surface level, you know, very like, just talk to the outcome and the value of the outcome in a sentence or two. Look, I mean, that might capture someone's attention, but they want more meat on the bone. They want to really understand, you know, why do you believe what you believe?

10:09 - Matt Eberhart 
And how, why should I believe you? And maybe what have you learned along the way?

10:13 - Unidentified Speaker 
Yeah.

10:14 - Todd Gagne 
Yeah, that's good. That's good. So when you think about like all the jobs and stuff you had, maybe, is there some common themes about either skill sets or things that you've kind of gravitated towards that you basically have a kind of a playbook that you kind of go back to?

10:29 - Matt Eberhart 
Yeah, you know, I think in the early days it started as just like, I like hard problems and challenges and I kind of get bored easily, so I would often raise my hand for new assignments or things and that kind of got me a reputation for fixing problems and led me in some interesting directions. And then I think from there, in more recent times, I've gone into a number of different companies as an executive and seen a team kind of looking toward me for the vision. Like, okay, where are we going next?

11:03 - Matt Eberhart 
And so I've created kind of a model for that where I do a lot of listening. I think I'd say in the last 10 years, I've really tried to do a lot more listening. Really to be able to ask good questions, to be able to understand where people are in the journey, what are the challenges, what do they see, and then ultimately bring the team together to co-create the vision for where the company is going. And I think that that is an important skill to have when you come into a new company. But actually, in a startup world, your ability to learn very quickly and to put the learning to action is often the difference between success and failure.

11:49 - Matt Eberhart 
And so I think you're actually doing that kind of co-creating of the vision and all along through the process, right? And as you see things, you can't action everything either, right? So you have to really understand, is this something that we need to take action on now? And that usually, for me anyway, involves asking a lot of questions and having a lot of discussion with the team around me.

12:14 - Todd Gagne 
I think that takes some discipline and some maturity because I think when you come in and you're, you know, in a leadership position, people look to you. And so you don't want to say the wrong things early on and you don't want to say anything early on. And so I think sometimes we're like, you know, innately you want to just say stuff that you think is smart and people will lead. But in a lot of cases, what you need to do is just what you said. You need to listen. You need to synthesize. You need to take your opinions and their opinions and then come up with a hypothesis that actually makes sense.

12:41 - Todd Gagne 
And I don't think that's always easy.

12:44 - Matt Eberhart 
Yeah, no, it's not. And listen, I think I would say that there were times years ago where I frankly wasn't very good at that. Where you see something needs to change and people are looking to you for an answer. It's like, okay, let's just go. I'm going to make this decision and go. Look, you want to be decisive, and when decisions need to be made, they need to be made. But I think being able to ask a lot of questions, and I've found that when I have a great team around me, I don't feel like I'm giving them the answers.

13:20 - Matt Eberhart 
Engaging them in a dialogue. I'm asking them questions and we're kind of coming up with maybe the answers together. And then understanding, is this my decision to make or is it their decision to make? And I think being clear with the team on that. And I worked for a great leader years ago that would say, don't strap me into the co-pilot seat. It's okay to have a I have a conversation about it, and if you're asking me for my opinion, but if this is in your area and your decision to make, you've been experiencing this and thinking about this for weeks or months or whatever.

13:55 - Matt Eberhart 
I'm having a five-minute conversation with you.

13:59 - Todd Gagne 
Maybe digging a little bit on that one. I think that there's a trap a little bit I think a lot of us fall into, or at least me personally, is from a problem-solving. I made my career doing that as well, and I was good at doing it, but I think as I got older and maybe a little bit more experience, I spent way more time on problem identification to really understand it versus running to solutions. And not only does that mean me, but I mean that teens spending more time in meetings with smart people to help facilitate that.

14:26 - Todd Gagne 
And so I'm kind of curious, does that resonate with you? Do you think, do you think that, um, that spending more time and really understanding the problem from a multiple level, not just the superficial that we see in our front of us versus just quickly solving the problem that you put the bandaid back on?

14:42 - Matt Eberhart 
Yeah, right. Totally resonates with me. There's an Einstein quote that I won't try to butcher, but it's something like, if you have an hour, spend 55 minutes on figuring out what the proper questions to ask and what you're really trying to solve, and then spend the last five minutes solving the problem. I think that there's a lot of truth in that and I think I certainly would say I feel like I put a lot of effort into maturing how I do that over the years and really understanding what problems should be solved.

15:13 - Matt Eberhart 
I mean, in startups in particular, I think this is in business and life, but in startups in particular, There's so much that comes at you. You can't solve everything. I talk with my teams a lot about giving them and giving their folks permission to let fires burn. If you're pushing a change in the product, you're like, look, I know this isn't perfect, but this is what I'm trying to solve. You've got to understand what it is that you're ultimately trying to do. I totally agree with what you're saying.

15:48 - Matt Eberhart 
I think it can be hard to do in practice. I know for me, and I think a lot of great leaders that I've worked around, they want to help people. They want to solve a problem if it's right there in front of them, but you don't want to just go from problem to problem, fire to fire, right? It needs to be a little bit more strategic.

16:08 - Todd Gagne 
And so I'm curious on like how this all kind of fits into, we've talked about like problem solving, we've talked about a willingness to learn. How does that fit into like a culture that you've basically taken from company to company or, you know, even like some of the companies that got acquired? I mean, that's difficult sometimes. And then, you know, you're coming in last, you know, 20, 24 months. Into an existing culture, and how do you kind of build into that? So there's a whole bunch of things around culture, and I think we maybe don't talk about that enough in startups, but I do think, at least in my experience at Concur, if we didn't have the culture that we did and reinforce it, I don't think we would have scaled and had the success we did.

16:43 - Matt Eberhart 
Yeah, I mean, I think you're right, and you highlight something that I think I've seen before, where it's like, looking back, you can see that there was this great culture and that there were these threads that ultimately carried you through. And I've seen that in my career, right? And it's like, As I came into Query, knowing that I've been here for the 24 company has been around for four years, and so when I met the founder, Dhiraj Charan, I was really drawn to how kind he is. He has this great kind of kindness, and it was clear to me that he cared deeply for the people at Query.

17:21 - Matt Eberhart 
I'm like, okay, I don't want to lose that. And when you do a leadership transition, Duraj is now our chief scientist. And when you do a leadership transition, things can change. People start to pick up on everything that you're doing, basically, as the leader. And so I spent a lot of time asking questions from the team about what they wanted to be known for. And we created this vision of where we were going with the company very quickly around federated search. Who we were going to be targeting with large enterprise customers and things like that.

17:56 - Matt Eberhart 
But then it was like, okay, let's spend some time on what we want to be known for. Picture success. And we had some clearly defined success metrics. So it's like, let's picture that. Get that picture of success in your mind 12, 24, 36 months from now. Look back mentally and like, what were the things that we had to be great at that got us there? And so We came up with, we wanted to be constant learners. We knew we're kind of charging new ground. We're pioneering this startup. Like we're truly willing this into existence.

18:29 - Matt Eberhart 
And so we knew we needed to be constant learners. We knew we wanted to be, we wanted everybody to have a voice. We didn't want just the loudest person in the room or someone that tends to speak up or not speak up to get left out. So we make sure that we do a lot of sharing of information and writing things down. So we spent a lot of time purposefully coming up with that. And it wasn't just me. I mean, I did have some things that were important to me, but I found it all came out in the group. When we actually got together at our first in-person company meeting, we spent the majority of our time going through those values and the different attributes that we wanted.

19:13 - Matt Eberhart 
That was 18 months ago, and we still talk about that all the time.

19:19 - Todd Gagne 
Well, that's good. And I guess what I draw from it is it's a combination of looking at the people that you have around you and kind of what they value, as well as maybe talking about some of your leadership influences from a culture perspective and really merging it. And then it becomes a foundation that basically you can build and bring more people in. And I think it's a really good lens for like hiring, right? Like you want these types of people because you've articulated what it is, and then you can reward that behavior internally.

19:43 - Todd Gagne 
And then basically talk about when there's bad behavior, you know, closed doors, you can basically reinforce that as well.

19:48 - Matt Eberhart 
Yeah, yeah, that's right.

19:49 - Unidentified Speaker 
Absolutely.

19:50 - Multiple Speakers 
Absolutely.

19:51 - Todd Gagne 
So maybe like taking this a step further, you have kind of a disparate team. So maybe talk a little bit about you kind of have, you know, you're based in Atlanta. I think you got people in San Francisco, you got people in Miami, you got people in India, you probably have some other folks elsewhere. And so again, this cultural piece is really important because that's kind of what binds you. But then how, how, how does communication, how does, like, how does that work in that environment?

20:14 - Todd Gagne 
We've been kind of going waffling back and forth and is, is kind of an industry, right? Where it's like, we were all in the office or some hybrid, then we went remote with COVID and then we're trying to find this next new kind of balance. And so I'm kind of curious how you kind of make that work across kind of a wide range of people in different time zones.

20:32 - Matt Eberhart 
Yeah, we have a very large engineering pocket in Kansas City. The company is all remote. Our CTO, Jeremy Fisher, has a lot of network in Kansas City, so we have a pocket of engineers there. That's been great. We don't have an office there, but they do get together from time to time. I think prioritizing some face time one way or another is important. We get the entire company together once a year, and then we have the different teams get together kind of as needed. We do a lot of our communications via Slack.

21:10 - Matt Eberhart 
So we're very active Slack users, maybe almost too active sometimes, because I can't ever find anything. I'm like, what channel is that in? But we also do a company huddle. Every single week where we tend to each month or each quarter have what we call a most important thing. So we talk about the most important thing and how we're making progress around that and then all the things that connect to it. We go back and forth between go-to-market updates and R&D product updates.

21:42 - Matt Eberhart 
Sometimes we'll do both. Sometimes we'll deep dive into one or the other. One of the things that I love that we do is we show the products that we're building in almost every company meeting. It's like, I mean, look, we're a SaaS company, we're building software. I get really excited when I see these new capabilities. Then we talk about how users are going to use them and how that's going to change ultimately the outcomes that they can achieve. I've been in companies before that were software companies where, you know, you don't ever see the product at a company meeting.

22:15 - Matt Eberhart 
And I think that having everybody be bought into what we're building and why is, I think it's good, not only for early stage pioneering startups, but I think it's good all the way through. Now, of course, as you, if you get a huge suite of products that gets more difficult, but I still think that there's ways to do it.

22:37 - Todd Gagne 
Well, that's good. I mean, um, and so I think that's really awesome. And I think just finding the, um, the Communication mechanisms that work and then creating some consistency with it. Um, do you find that like, basically you have to write things down more and think through it, like there's less verbal, you know, through kind of, you know, uh, zoom and that sort of stuff and more kind of written communication. I mean, you kind of inferred that with Slack.

22:59 - Matt Eberhart 
Yeah, we do a little bit of both. I'm very transparent, so when we share the board deck and the strategy that we're going toward with the company, we do have a strong written element to our culture, so we're thinking about the problem that we're solving in the product or a new direction that we're going with the product. We spend a lot of time building out the product documents, requirements, what is it that we're trying to solve, giving people the opportunity to contribute to that.

23:31 - Matt Eberhart 
And then talking about it in the company huddles as well. Sometimes we'll get direct feedback, but I actually often have people reach out to me and be like, hey, will you talk about X, Y, or Z in the company meeting? Always try to make a note and make sure that we do that and we engage in conversations about that. And I think spending a good bit of time on the why, like why is it that we believe that we're doing this? And we have customers come to our huddles and our meetings. We talk about the feedback that we're getting, both good and bad.

24:10 - Matt Eberhart 
And it's like, what did we learn from a deal that we won versus what did we learn from a deal that we lost? And just really trying to make sure that we're actioning all of that.

24:18 - Todd Gagne 
So maybe this kind of goes back to just the culture piece of it. How do you create a culture of accountability in all this? I think you hear a lot of founders that basically, I'm just the guy that's going to do a lot of it. I'm going to make it happen. And then I'm almost inferring everybody else has got the same level of passion and commitment as I do. And I think you see this as they start adding people that necessarily doesn't happen. And so I think there's one thing you said before that I thought was important is you don't have five number one priorities.

24:45 - Todd Gagne 
You have one top priority, and you're all working and pulling the oars to that direction. So there is some kind of accountability to what we're trying to do, and we're not diffusing some of that. But maybe talk to me a little bit about just creating a culture of accountability, especially in a disparate organization. Sometimes that can be difficult.

25:01 - Matt Eberhart 
Yeah, I think to me it starts with making sure that you have a culture that's deeply centered around learning and taking action on the learning. When we're doing something new, it's like, okay, what is it that we're ultimately targeting? When are we going to ship it or what is it going to be? Having some clear goals around that. But depending on the situation, you may come up short, you may learn something along the way that causes you to want to course correct. So just making sure that you reward that, the learning, the taking of action.

25:40 - Matt Eberhart 
I think that's really important early on. I've experienced and I've talked with people that will say, hey, I'm in this big company now and it feels like we can't get anything done. It's easy to see that maybe across big companies, but I actually think that the seeds of that get planted when the companies are small. One of the things I've found, and I've had to adjust some of my tools on this, is you you have to be willing to let people fail and struggle a little bit and learn and ultimately apply those learnings.

26:15 - Matt Eberhart 
And if that feedback loop can get pretty fast, you're probably going to be able to weather a lot of storms and ultimately solve a lot of hard problems. Whereas if failure is something that's really beaten down on quickly or then it just kind of teaches people different behaviors around how to navigate that. I don't know, what have you seen in that Todd?

26:40 - Todd Gagne 
No, I agree with you. And I think maybe I classified it slightly different. I always thought of it as a culture of continuous learning. And so I think you say learning, but it's like we're just constantly getting better. So something didn't work, but we're going to learn from that and we're going to apply it. But it is always a treadmill and we're always trying to get better regardless of what we're doing. And I think if you have a safe culture like that, where as long as people try and they work hard, and they're learning something from that mistake, then we're going to be fine.

27:07 - Todd Gagne 
And I think, and we're all pulling the oars in the same direction. I think that's a big part of it where we're not siloed and it's me versus them. And so, because that happens quite a bit too, or can.

27:17 - Matt Eberhart 
It does. Yeah, absolutely. Right. I mean, even if you can just get 1% better every day, those compounds, you're on your way quickly.

27:26 - Todd Gagne 
Yeah, that's good. Well, good. Maybe talking a little bit, maybe zooming out a little bit on just thinking about like the journey you've been on, it's got some scale to a lot of the jobs that you've done. And the difference between, you know, finding your first customer and getting to a million dollars is different than, you know, being at 10 million and trying to go to 20 million. And so as you've kind of gone through that, maybe kind of articulate some of the inflection points and like, where do things break?

27:52 - Todd Gagne 
Where do entrepreneurs really need to invest? Because I think a lot of people just struggle with it, right? And I think what you find with great founders is they have this continuous learning and they're always trying to figure out like, where's the next break going to be?

28:03 - Multiple Speakers 
And then how do I stay ahead of it?

28:04 - Todd Gagne 
And I think where companies, where the founders stay with it, that's great. But I think you also find some opportunities where they're just like, they flat out and they're just like, this is where I'm good at, right? And I'm not making the pivot to like the next level. And so I'm kind of curious, you've gone through a number of these where these milestones are difficult and you've had to change your personal leadership to basically reflect where you are in the process.

28:28 - Matt Eberhart 
Yeah, no, it's a great question. I think we'll use maybe some loose revenue brackets, but I've found it can be a little bit different to the situation. And they call it zero to a million, or sometimes even zero to two or three million. You're truly pioneering. Everyone there is trying to will it into existence. Getting up every day, focusing on that. And to me, you know, often the most important things there are like, what problems are we ultimately solving? How are, how are we going to solve those problems?

28:58 - Matt Eberhart 
How are we, how is that really going to be differentiated and better? And then it's about acquiring users and customers, right? And really like willing that into, into existence. And I believe that in those early stages, the founders and the executives on the, the, either the CEO or the head of product and R and D like, they really need to be the ones that are selling the product. I've seen a trend recently where some companies will raise a seed round and be almost pre-product, pre-revenue, and they're hiring a CRO.

29:32 - Matt Eberhart 
If one of your founders happens to have been a CRO, high five, that's awesome. But you don't need a CRO. You need to be able to constantly learn, as you said, and action those as quickly as possible. And then call it somewhere typically around 5 to 20 customers, depending on how big they are and how complex and your product mix. You start to look back and you're like, okay, of these 20 customers, I've kind of figured out now that eight or nine of these fit into a particular kind of mold, and we want to repeat that, that we're truly solving their problem, we have removed the friction in the sales process, we know how to identify them, we feel confident that they're going to stay with us for a long time, they're making references to theirs.

30:21 - Todd Gagne 
Messaging's working. The messaging's kind of resonating with them.

30:25 - Matt Eberhart 
All of those things. And then you'll probably find that a couple of them don't fit at all, right? Because as you were pioneering, you had a few along the way in the early days that just don't really fit with now what you've figured out. And so that inflection point called a million or two million to five to ten. Is when you need to start getting repeatable on some of those things. So that's when I actually think that at that stage, having a great frontline seller or sales leader, like someone that can really roll up their sleeves and is out there closing the deals and works with the founders, but is able to kind of repeat it.

31:02 - Matt Eberhart 
And over time you see less and less founder engagement and those opportunities. And then when you get to a point where as a executive or the CEO, you're in a meeting and like a deal that you'd kind of heard of, but you really don't know anything about is now closed. And that customer is referenceable. That's probably when you need to hire a CRO. I'm kind of joking, but that's usually to the point where you're like, okay, we've clearly figured things out and now it's truly time to scale up.

31:40 - Todd Gagne 
And when you talk about scale, I mean, there's a lot of machinery. Maybe just even putting some words in your mouth. In the beginning, it's a little bit guerrilla, right? Where it's like you're basically leading the charge, and you're trying to figure it out. And you're like, that didn't work, but this did. And you're creating gates, and you're trying to see repeatability. Then you start getting some repeatability, but it's not really scalable quite yet. And then you start to like, think about, okay, I'm going to put the systems in place because now it's a machine and I got a lot of people and I got a lot of tools and the messaging is working and I can go to this country.

32:08 - Todd Gagne 
I could do these other things. Um, and so it's just like the operational cadence and complexity gets just much more, um, interesting and can be more complex.

32:17 - Matt Eberhart 
Yeah, and I think when you go through an experience like that, and it's highly successful, and you scale past five, past 10, past 25, past 50, and you look back, you see these inflection points where it's like, okay, we leaned in, we kind of kept narrowing down our messaging, and we got better and better at it. And then I think the flip side of that too, if it doesn't go well, it's often because you didn't really deeply understand what was it that was really driving the success? And so I guess if I'm giving tips from looking back at my times of having done that well and where I've struggled, you deeply understand and challenge why you think something is working.

33:01 - Matt Eberhart 
And I love once an opportunity, once a prospect becomes a customer and you kind of go through like, build a relationship and go back and talk to them a little bit about those early days. Get the story and try to triangulate that because if you can really understand why someone is choosing you and how you really stand out and then lean into that, if you're right, that can be a real superpower. But sometimes people think they're right on that and they're actually totally, totally wrong.

33:37 - Todd Gagne 
So maybe I'll abstract this a little bit. As you talk about the scale and stuff, I think one of the things that I always felt kind of fortunate at Concur is, you know, we started, I think I started with them when they were, you know, 7 million bucks and we went to like 1.7 billion. And I think what I had was some good managers that basically invested in me to help me understand those inflection points and help me change In some of those years, I had to throw away 50% what I did last year and learn something new.

34:03 - Todd Gagne 
Sometimes you just didn't know which 50%. My question for you is, as a leader, developing and nurturing talent that you want to continue to grow through these inflection points is part of your job. How do you do that? How do you think about setting expectations with people? Because you're trying to get them to execute in what's in front of them, but you're also trying to prepare them for what's tomorrow.

34:22 - Matt Eberhart 
Yeah, I think having a lot of clarity about what, particularly in an early stage startup, about what short-term success looks like and having a lot of discussions around that. I'll tell my leadership team all the time, I love to engage with you. You know, conversations and like, let's talk about the things that are challenging. And, you know, I try to really be disciplined about like, not taking their decision-making power away in that. Like, let's have a conversation about this.

34:54 - Matt Eberhart 
And I, you know, I could think of a situation recently where someone was asking me about a particular hire and I'm like, you know, this is your call. Like, let's talk through, you know, and we were kind of trying to balance out what the job we think to do now is versus what the job is going to be six to 12 months from now. I think it's having enough trust to engage in those types of conversations and also being open yourself as the leader to feedback on that. What are you seeing? Are you seeing something different?

35:27 - Matt Eberhart 
You're closer to it in the field or with the teams and really being able to make sure that you're talking about the right things and you're having those conversations. So I don't know that there's any one specific piece there other than trust is a factor that, as I've looked back in successful situations, I can't think of a company where I've been part of where we've grown and been able to solve hard problems where we didn't have trust.

35:57 - Todd Gagne 
I think that's a good one. I also think from a leadership perspective, it's this balance between investing in the tactical here and now, because we have to go solve it, and then basically trying to set them up for success and saying, here's where I think you're going to have to grow if you want to continue to grow. And we know some people basically say, I'm totally fine at this point, and I'm fine with it. And then there's other people that are like, I want my career to grow with the company.

36:19 - Todd Gagne 
And you're like, OK, if you do, then these are the investments that you need to make and you need to understand. And somebody from a leadership perspective needs to help you get there, or at least help you identify that. Because sometimes you're just blind.

36:29 - Multiple Speakers 
You just don't know.

36:31 - Matt Eberhart 
Yeah, and I think people being exposed to different leadership styles and being open to having these kind of conversations we're talking about that they'll trust, they'll often come to you and say, hey, I'd like to get to this level, or I'm trying to figure out what the next step is. And if you have that trust, then you can kind of tailor that to the situation. Look, I think a lot of my career, I really think has, I've been fortunate to get a little bit lucky as far as picking companies that have gone through these periods of hyper growth that just create a ton of opportunity for people.

37:07 - Matt Eberhart 
And that's one of the things that I like personally about startups is like, you get to see people and put people in these challenging situations and then see them kind of grow. And sometimes I've experienced to the flip side of that, where you put somebody into a position and they come back to you and they're like, hey, this really isn't for me, or it's too much. And you've got to be willing to do that and course correct there as well. But yeah, I love that part of building startup teams.

37:38 - Todd Gagne 
I do too. And I would say in my career, that's probably one of the favorite things is seeing people succeed, right? And just basically whatever talent you got, you've maximized it. And they're excited about that growth. I mean, I think that is a superpower.

37:48 - Multiple Speakers 
I really do.

37:49 - Matt Eberhart 
Yeah, it's awesome. And at Query, it's not just me, it's the whole team. But we've really tried to reference hire wherever we can. So we've got a lot of people here. Almost everybody has worked with someone before. And And some of us here have worked together two or three times before. And I really think that that helps to take some of the risk out of building a company. There's certainly a period of time that it takes for people to come together and get to know everyone and really start getting to that level of high performance, and it can short-circuit some of that when you've got people that have worked together.

38:25 - Matt Eberhart 
It's also good to inject some new talent in there as well, but I really like reference hiring and startups whenever I possibly can.

38:35 - Multiple Speakers 
Well, it's kind of funny.

38:36 - Todd Gagne 
We're about 35 minutes in, and I really haven't brought in your current gig. And so I know you've been there. We've been talking a little bit about more themes and stuff, but maybe this is a good opportunity to talk a little bit. You've been with Query about two years or something, a little bit less. So maybe why don't you tell me a little bit about the story and then kind of just basically the journey? Because I think a lot of what we talked about is an overlay to kind of how you think about growing Query.

39:02 - Matt Eberhart 
Yeah, for sure. So I got the chance to, as I said earlier, to kind of get to know the founder of Dirage before I came in. And it was clear to me that the federated search capabilities that we have were what was special here. And so when I came in, I very purposefully co-created like a new vision for where we were going to take the company with the team. And we did that In the first 30 days with a lot of meetings with customers, with prospects, board members, in the first 90 days we met with like 75 security teams to kind of run them through this vision and get a lot of feedback.

39:44 - Matt Eberhart 
I found that that was just like really brought the team together. You know, it was as I'm not a founder, I came in as the CEO. And so I think, you know, people were looking to me kind of like, okay, what, you know, what's he gonna change? What changes are gonna happen? And so there was a book that I found to be really helpful called the New Leaders 100 Day Action Plan. I've actually used some version of that book for a couple of my transitions, and it has some really good tips and models for that.

40:19 - Matt Eberhart 
And so as we kind of co-created that vision, then it became about execution, and that's where we put the new operating system for the company in place. How frequently you're gonna meet and what's expected and what is our planning process look like and how are we gonna come up with company goals together and so I did all that very transparently so that it and and it wasn't just me like everybody kind of had their fingerprints on it and so like by the the first board meeting after I came on was about 60 days in and we had you know complete new strategic plan, metrics for the next 12 months, like what our OKRs were going to look like, you know, what we were learning in the field.

41:02 - Matt Eberhart 
And it just, it felt like we were just, you know, running off to the races, if you will. Very quickly, like by day 60, it kind of felt like I had been there for years. And I think I've experienced transitions that didn't feel like that, where you're 60 or 90 or 120 days in. You're still kind of like, oh, this doesn't quite feel like home yet. And for me, after some reflection, I think that that can come from, and you said this earlier, it's like you don't want to do too much too soon, you don't want to change too much too soon, you want to involve people.

41:42 - Matt Eberhart 
But at the same time, when it's time to change, it's time to change. And I think it's getting everybody together so that they feel comfortable, that they're like, oh, well now I know If something's going to change, I know what's going to happen. It's going to be talked about in a company meeting, and there's probably going to be a document that spells out why we're doing it, and we're going to have metrics around it. I think once people get comfortable with that, change is actually a good thing.

42:09 - Matt Eberhart 
I would say particularly in a startup, the ability to change is often what ultimately leads to your success.

42:17 - Todd Gagne 
Well, I think you're saying a bunch of things in that. I think like, you know, transparency and trust, right? Like, I mean, I think like change is scary if there's not trust, right? And so I think you've brought trust up multiple times and things. And so I think if people believe in the leadership and they believe in the transparency they're giving them, then that's good. And I think at the end of the day, all they're looking for is like, am I set up for success, right? And so in a lot of times, This is about if our priorities have changed, then I got rid of the old priorities and there's this priority and I'm going to work on it and I'm going to execute on it.

42:45 - Todd Gagne 
And that's safe, right? Because I just know it. And I think the best startups that I've seen is that always happens, right? Like there's a handful of priorities and they're clear focus and there's clear ownership on them. And so the accountability is there, the transparency is there, the trust is there. And if you get an organization that continues to execute, even if it's not like perfect and you need to keep iterating a little bit, people are excited about it because you feel like you're making progress.

43:09 - Matt Eberhart 
Yeah, and I think for me too, I think those are great points, and it spurs the thought of, for me, I need to be super passionate about the mission. To me, it's a recipe of, I want to work with great people, I want to be driving toward a mission that I feel very passionate about, and I want to feel like we can win. And if there's all three of those things, it's like, I'll, you know, I'll run through a wall. And as I, as I've gotten older, like, and I, I had, this is my first CEO job. And I've actually looked at a number of CEO jobs years ago and had stayed on the CRO COO route.

43:49 - Matt Eberhart 
Because I'm like, I really want it to be something that I'm super passionate about. And then when Query came along, and while I'm not a founder, I've worked in this problem space of security operations. And we help teams access, search, and understand the security data that's all around them and their enterprise environment. And we're very different from the traditional approaches to doing that. And I've worked in that problem space for 25 years now. And so I'm like, ah, this is something that I get up every single day.

44:19 - Matt Eberhart 
I'm like, we have the opportunity to change the world. Yes, it's a small niche of the world with security teams and enterprise companies, but truly, I mean, I think To me, the picture of success is five or ten years from now, people are like, oh, Query was the company that changed the markets where you don't have to centralize all your data anymore and you're able to access and understand it and really protect the environment using all the data that's all around you. I mean, that's the picture of success I'm driving toward.

44:49 - Multiple Speakers 
Well, that's good.

44:50 - Todd Gagne 
I mean, I think passion is a big part of this, right? I mean, it's like if you want to bring the heat every day and you've got some skills, and I'm like you, I think when I get bored and when there's not this kind of high growth rate in businesses and stuff, and you're kind of getting to like the fine tuning of the last 10%, I'm not your guy. I'm just not. And so it's knowing who you are and then putting yourself in a position because when you do, there's usually good results.

45:14 - Matt Eberhart 
Yeah, it was like the hard thing about hard things, fuck, like, hey, peacetime or wartime, CEO, like, yeah.

45:22 - Multiple Speakers 
There's a lot of clarity when it's wartime.

45:24 - Matt Eberhart 
There is, I agree. In a startup, it's always wartime.

45:29 - Todd Gagne 
Yep, exactly. So kind of wrapping this thing up, like maybe talk a little bit about maybe some advice for entrepreneurs, right? So that's kind of what this podcast is kind of geared towards is entrepreneurs, either people that are on a startup journey or thinking about doing it. So are there a handful of kind of words of wisdom or themes that you would kind of pull from that that you think would be good to really kind of reinforce?

45:53 - Matt Eberhart 
Yeah, I mean, so I'll say for particularly for those startups that are maybe first time CEOs or thinking about being a CEO or even in any kind of leadership position, I think there's a couple of things. Like I've certainly for me, I think the number one skill I've been trying to cultivate these last few years is being great at asking questions. Like just really being able to listen. I know for me, for my own kind of tuning fork, when I start to get a little anxious to like rushing to the decision, I've kind of trained myself to be like, this is actually a time where I need to ask some more questions.

46:29 - Matt Eberhart 
And that completely changes the dynamic with people. And I think I If you can get your leaders doing that as well, it kind of spreads around.

46:39 - Multiple Speakers 
So I think that's probably one thing.

46:40 - Todd Gagne 
How did you get better at that? Was there anything that you did to like, is it more just a conscious thing? Did you read something? I mean, it's one thing to ask questions. It's harder to ask good questions.

46:51 - Matt Eberhart 
Yeah, I think what was really most helpful for me is I experienced it. I worked for a great leader, his name's Kevin Haynes, and he's probably the best person I've ever seen at asking the right questions. I would have something that I've been chewing on for a week or two, and I'd give him the five minutes of it, and he'd ask a question, and I'd be like, now I know the answer. All he did was ask a question, and I'm like, man like it's just it's it's pretty it's pretty magical and so I think um you know and for me that kind of it usually drives around when I'm trying to ask those questions it really is like trying to I'm trying to genuinely understand like what problem you're trying to solve and who you're trying to solve it for and why.

47:35 - Matt Eberhart 
And when you take somebody through that type of a process and they've been like chewing on a hard problem, they usually have some sort of insight that gets thrown on the table. And then I think the second thing for folks working in startups and really are coming into anything is just that idea of like co-creating a vision. As the leader, you're often looked at as the person that needs to have the answers and is going to ultimately set the drumbeat for what's happening. But that doesn't mean that you can't co-create that with a lot of input from people.

48:16 - Matt Eberhart 
Getting people's fingerprints on it and getting their advice of a number of folks. I think that you're still ultimately maybe responsible for the decisions, but you still need to do that co-creation. And that's something that I've seen from some of the business books and things that get talked about and podcast. I think you could maybe walk away like, oh, I just need to go in there and start making decisions and kind of that, maybe, but probably not.

48:45 - Multiple Speakers 
Probably not.

48:46 - Todd Gagne 
Yeah, I think it's good. Well, Matt, this has been really a great conversation. I really appreciate your just transparency, your honesty, the way you kind of talk about things. And I think there's a lot of just kind of nuggets and kind of wisdom that people can take from this. So I really appreciate you taking the time and doing this with us today.

49:02 - Matt Eberhart 
Yeah, thanks for having me on and letting me ramble about startups and leadership and building great companies. It's just being able to kind of see what the next right thing to do is, right? Just keep progressing and willing it into existence. But it was a lot of fun today.

49:18 - Multiple Speakers 
Thanks very much.

49:19 - Todd Gagne 
Well, thank you.


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