Episode 009 – Inclusive Learning and Leadership: Universal Lessons from Karsten Chearis


This week, I had the pleasure of speaking with Karsten Chearis, a Cybersecurity PreSales leader who currently leads a global team of SEs at Rapid7. Whether you're in the tech industry or thinking about joining, this insights-packed episode is a must-listen!

We delve into many lessons learned from Karsten's career and life journey such as: 

  • How to become a more effective communicator, leader, and life-long learner
  • Time management tips to level up your current process (at home and work)
  • DEI challenges within tech and PreSales
  • Strategies for overcoming such challenges through better relationships and more welcoming communities 
  • The dynamics and importance of mentorship, plus an amazing 3-part framework to improve your approach to fostering healthy mentor, mentee, and peer relationships

Hit play, then let us know which part of Karsten's journey and lessons resonate with you the most!

Resources Discussed

“Secrets to Success as a PreSales Leader” – Karsten's New Blog Post Series on PreSales Collective (a must read!)

PreSales Communities Mentioned


[00:00:00] Matt Madden: Hey everyone, this is Matt Madden and I'm so excited for today's episode. I'm here with Karsten.

Chearis. And we're gonna dive into his story and just his journey, where he's been, where he is at today, what's led to that moment, and there's just such a great conversation ahead. So just wanted to start by saying thanks for coming on the show, Karsten.

[00:00:18] Karsten Chearis: Hey, my pleasure. Thanks for, for having me. It's, uh, it's always nice if people want to talk to you, so, uh, as long as people want to, I'll keep talking.

[00:00:28] Matt Madden: Good deal. Well, I hope you're ready cuz there's a lot of areas I wanna dive into and I definitely want to talk to you and I'd love to just start by having you share a little bit about your current role, uh, and then we can zoom back out to where you got started within presales. Um, but I know you had a recent promotion.

I just wanted to start by saying congrats again, man, with where you're at at Rapid 7 today. So I'll let you tell your story there, but yeah, would you mind taking us on that journey and just giving us a high level overview and then we can dive in.

[00:01:00] Karsten Chearis: Yeah. So, um, yeah, so I'm, I I work at Rapid 7. For those of you who may not know, Rapid 7 is a, leading cyber security company. we have a global footprint, customers all over the world, and, we have a portfolio of products and services including cyber threat, intelligence, detection and response, managed detection and response orchestration, vulnerability management, AppSec, cloud, SEC pen testing.

It's, it's a, it's a bunch of things. Um, and again, just, a great company. I love the culture, I love the people. so that's Rapid 7 I, and I had to pull up my LinkedIn cuz I have a long title. Um, I am one of the global managers of Specialist Security Solutions Engineering. Uh, what, I lead a team of, Engineers across the globe, and our focus is specifically on Rapid 7s, external threat intelligence solution, also known as,cyber threat intelligence.

Um, so my, my team we're responsible for basically the presales and some postsales activities around our cyber threat intelligence, solution and how it works with the rest of our products in customer security ecosystem in general. So, I love it. Uh, it, it's been great. I've had, uh, a few promotions since I, I started at Rapid 7 and I'm, I'm enjoying every moment of it.

So that's kinda what I do now. Uh, I started on the customer side. Uh, so I was, you know, working in IT ops, starting at help desk, work my way up to engineering a lead level. Um, and. I was introduced to pre-sales. I didn't know it, but when I got to a point where I was more of a decision maker or had influence on what products and services my employers would use, I met sales engineers or pre-sales professionals.

I didn't know that's what they were, but I was talking to them and, you know, doing PLCs with them and all that. Um, and then, a recruiter reached out and offered me an opportunity to interview for a pre-sales, professional, role or sales engineer. And I had no idea what it meant. And he kinda explained, it's like, have, have you ever run a plc blah, blah?

Like, yeah, yeah, yeah. It's okay. So it's the smart people. So, um, see, I interviewed and, uh, I've, I've been in it I think five or six years now, I think. Um, and I don't think I wanna go back to the, uh, the operation side. I,

I love being on the pre-sale side. So, yeah, man, that's, that's kind a summary of, of where I am now and how I got here.

[00:03:34] Matt Madden: That's amazing. You made a comment that was quote unquote the smart people. I can see you on video, even though I know this isn't a video podcast. And sometimes a lot of times I've had to a, just throw that out there when you get on the call. And for me it always makes me a little comfortable cause I just feel like it's like, oh, come on man.

Like, I'm just curious your perspective. I mean, like, it's like on the one hand flattery, but it's also like, you know, let's, uh, let's not discredit what you're doing here on the call, you know,

[00:04:01] Karsten Chearis: No agree. I think being in sales in general is not an easy, profession, whether you are an account exec or you're a pre-sales professional. It's both of them involve sales. Both of them involve technical, aptitude. Both of them involves understanding your product and the landscape and competitors and all that.

So it's, you know, I'm a smart person on the call. My account exec colleague is a smart person. The customer is a smart person. I think the difference is, more often than not, the pre-sales professional is the smartest person in the room in regards to using, the company's products, right? So we, we've done the PLCs, the setups, the demos, all this stuff.

So we kinda know it in and out. We may not know everything about the field, but we know most things about this product and we can speak to it intelligently. So it's, it's one of those things you don't wanna get a big head, but you also don't wanna, you know, diminish or devalue what you bring to the table.

[00:05:06] Matt Madden: Yeah, no, that's such a great point. And it's so key, you know, regardless of where you sit on the technical spectrum, to be able to know that product that, or products that you are selling, representing on a very deep level, especially as the solutions consultant, solutions engineer, and so on. Uh, but be able to zoom out, you know, as needed to get focused around the value and the pain.

And that's, I, you know, it's always, it's been really interesting as I've had the opportunity in the podcast to speak with people that come from, say, more pure technical, role. Like, um, maybe either a software engineer or they came from operations, similar to your background and they were real hands on, maybe behind the computer, like doing that, and so on.

But then transitioned to being more customer facing and blending those skills, and putting their sales hat on in the pre-sales motion. And the dynamics of where you have to focus. being obviously different from somebody that's maybe coming from that non-technical background, it could be a totally different industry and they're very comfortable being in front of people, um, maybe even telling stories, leading the conversation.

But, you know, there's certainly that requirement like you were speaking to. You need to be able to be that expert around the product in the room without, uh, letting it go to your head at the same time. so I'd love to learn from your perspective if this was the case for you, if there were certain things that.

you did or you found helpful along the way when you realized, hey, here's an opportunity for me to transition into this role. I hadn't heard of it, but I'm familiar with it having, crossed paths with folks that are in it. And here are things I, I am gonna intentionally focus on to really help me, land that role and then thrive.

Cuz you obviously have thrived, since you've landed within the role. you've, you've been doing very, very well, current day. So would you mind speaking to that?

[00:07:01] Karsten Chearis: Yeah, so for, for me, I have never touted myself as being like I. Super technical or, or, or smart, like I understand everything about MacBooks or networks. Like I've, I've never been that person. I, I, I, I knew myself, but I never felt that I was the smartest person on my team. and that's fine, but something I have always, just me personally, I've always enjoyed is communication.

Um, uh, I, I have, uh, at a previous job, I called myself a connoisseur of words because I, I love how words are the conveyor belt that transfers thoughts and ideas from my head and my heart to yours. And I think that's so important. So I've always liked to tell stories and, and talk to people. but oftentimes if you're in tech, You're behind the scenes, you're in the network closet plugging stuff up, or you're at your desk typing code.

You don't really get a chance to talk to decision makers and, and have influence and things like that. So the thing for me that really intrigued me about being in pre-sales was I can take on my technical knowledge, but I don't have to be hidden. I can actually talk to people, right? I don't have to always be behind the camera.

I can be in front of the camera, but not have the spotlight on me. uh, put the spotlight on the, on the prospect or customer, highlight their pains, and then talk about how my company's solution can fix it. So that's kinda like been the, the big driver for me. Now, other people they may.

Like the technical aspect more than the storytelling, but you have to have both. Like if you're going to be successful, if you're going to thrive, you have to have both. So, and we can talk about like, you know, how you can get better, but I would say, um, be good with your technical ability. But man, soft skills, communication skills, negotiation, active listening, all those things are so important.

And you're not going to go very far if you can't, master those.

[00:09:20] Matt Madden: Absolutely. And you said something that I love, just the connoisseur of words, how you referred to yourself in the past life and so on. And it made me think of the article, the series that you've started contributing to Pre-Sales Collective. And that's what stood out to me. Just the unique voice and the story you're telling and the way you're teaching the lesson was really compelling and engaging.

I definitely encourage people, I'm, I'm gonna link to it in the show notes, but you need to go read the article by that Karsten's put out already and, so I definitely want to get into, some of the work you've been doing, uh, this year, just contributing in many different ways, helping people, improve their skills, like you said, just, and, and certainly want to get into, maybe we could just talk about some of that right now and transition into skill building, some of the elements, uh, that you called out there and then others that you would add for.

At this stage, let's just say if you were speaking holistically about what, what contributes to being a excellent, solutions consultant, solutions engineer, sales engineer, and what are the things that, regardless of where you are in your experience, you can always get better at it. I mean, in addition to communication, which you spoke to.

[00:10:28] Karsten Chearis: Yeah. So, I'm a part of, as you mentioned, uh, pre-Sales Collective. I'm one of the ambassadors for 2023. For those of you who may not know, pre-Sales Collective is a community of aspiring pre-sales professionals, existing pre-sales professional, pre-sale professional leaders, and everyone, in between.

and when Pre-Sales Collective came up with this ambassador program, one of the goals was not for them just to have individuals that would help, the presales collective brand. But also people who were hungry to increase their own personal brand, because those two things work together.

And I think as a pre-sales professional, it, it's so important for you not just to be a good spokesman or spokesperson for your company's brand, but you have to speak for yourself too. You have to sell yourself. And so for me, again, I, I love communicating. I love, speaking verbally, but also like, communicating with my words, so I got a chance to write.

So the first post is an introduction to, uh, these five guiding principles, that I, have used to help me to get to where I am. I'm super excited for the second one. If you enjoyed the first. I think you're gonna really love the second, because I'm extremely transparent and I will actually tell you what happened when I didn't follow, uh, one of my principles and how badly I failed.

[00:11:57] Matt Madden: That's awesome. Can you tell us more?

[00:11:59] Karsten Chearis: yeah. Yeah. So the, the first guiding principle is, what I call take your time. And this is something that I have used for a while, but when I became a dad, I really found the, the way, the words to articulate it. And I, I tell my daughters, since this is your time, You need to learn how to take your time.

So if someone asks you a question, uh, my my oldest daughter, she's in karate. If, if she has to do one of her, uh, contests, so, so she can make it to the next, uh, bell to be in a tournament. Either way, someone asks my oldest daughter, Mikayla Mikayla, show me what you know, or tell me what you know. So that's your time.

And if it is your time, take your time. That doesn't just mean or doesn't mean be slow, but it means to exhaust and use the time you have been given. Um, you can't let people rush you. And the little bit of the carrot I'll give is, uh, when I was rushed, I failed. My team failed. The company failed. We failed the prospect.

It, it, it wasn't fun, but man, the things I learned from it.

[00:13:13] Matt Madden: It.

[00:13:14] Karsten Chearis: School of hard knocks. I I will never repeat that mistake again. Right. So that's kind of the, the little bit of the, of, of the, of the carrot. So the other part I think, again, is as you are working on learning things about your company and the products and the services, and you're learning, you know, the advantages your company, has over the competition, you have to do the same thing for you.

What advantages do I have or what are some of my disadvantages? How can I take those disadvantages and turn them into advantages for me? How can I, help elevate myself without pushing others down? And as I elevate myself, how can I elevate others? How can I take my circle and we, we can all eat, we can all sit at the table, we can all build our own tables.

So, um, yeah, that, that's kind of the mindset you have to have in order to be successful here.

[00:14:08] Matt Madden: one thing that you also shared in the article, I was gonna mention that phrase, cause I loved it so much that since this is my time, I'm gonna take my time and as a parent too, to think about that, that's something I'm gonna just ingrain in my brain because if my kid, or anybody can really keep that top of mind with what we're doing, it's relevant to every moment of our day.

We all have the same amount of time, 168 hours in a week, you know? And so with that, it's all about how you frame it and you think about it and how you value that. And a point you call out in your article, which I'm not gonna obviously speak to too much cause I want people to go read it. But I love how you mentioned that, if you're not careful then.

Your time is gonna be managed, or mishandled potentially by somebody else. Um, because, you know, if you're not planning that, you're not diligent about it, the clock is gonna keep ticking. And it also, I think there's this great parallel, or it, it not an even a parallel, it's directly relevant to anytime we get in front of the customer, at least in my experience, we're thinking about it.

Oftentimes it ends up being a meeting that's somewhere from 30 to 45 to 60 minutes, commonly from like maybe a first, discovery call that an AE wants to bring you in on. Could be 30 minutes, hopefully 45. We'll see. But, um, or it could be a demo and we've set up an hour where we can properly go through it, and so on.

And. We still have to be so careful about how we manage that time and partnership with everybody on the call, including the prospect because, they have meetings following this hour, just like we probably do. And, so Yeah. Would love to hear how you, if we zoom in for people that are wanting to break into the role and learn about that element, it's pretty specific zoom in, but how do you coach your team or teams you've worked with today?

When we think about just that time management regard, specific to your world at, at Rapid 7?

[00:16:05] Karsten Chearis: Yes. So if, if you are going to be in corporate America, um, you have to understand that again, if you don't have control over your time, other people and other things will, right? If the first thing I do in the morning is get my phone and look at emails and text messages, direct messages and all that stuff, I'm basically looking at life as what the other people need me to do. But if I wake up and I focus, uh, for me, I, I, I pray, I, I think about my day and all that. It's like, okay. What needs to be done? How can I make an impact? And as I'm pouring out into others, how can I make sure that I'm also being poured into so that I won't run out? Right? So, account executives, sales professionals, I don't think they always know what they're doing, but some, I I've, I've been on calls where the accountant exec will say, all right, hey, thanks so much.

Let me give you an overview of the company we were founded in this year, blah, blah, blah, blah. And now Karsten gonna walk you through how we solve for this problem and this problem, and this problem. He's gonna show you this, this, and I'm

[00:17:18] Matt Madden: And here you go. Karsten, have the mic.

[00:17:20] Karsten Chearis: Like, like stop. Like you, you can't tell me. I mean, where you can, I, you can verbally say it, but I don't have to follow that particular guideline because I may have heard something that the prospect or customer said, or the way they said, or a question, and that lets me know.

Uh, I know we do these 20 things, but specifically we need to focus on these two things, right? So in order to, to do that, one of the things you can do is if you're an existing pre-sales professional, have conversations with your account execs. Before you even talk to a prospect or customer, let them know that, Hey, I work best when I have this.

Please tell me how you work best. If I can do, fill in the blank, right?

[00:18:07] Matt Madden: Yep.

[00:18:08] Karsten Chearis: it's a relationship, right? So in, in, in my marriage, when I, my wife and I are talking, we, we say, Hey, you know, I don't, I don't like this, but I do love that same thing. Like, you have to tell your account, Hey, I, I don't like it if you telling me what to do?

And they may say, well, I don't like it if you demo for too long. Right? So you, you gotta work those things out. If you are trying to get into, presales and you're, trying to build your, portfolio or, or trying to update your resume to show, skills that you have. I would say if you are working in a retail store and you're folding clothes and selling t-shirts, yes, the customer wants stuff.

Yes, your manager wants stuff, but what do you want outta life? And how can you use this opportunity to get you to that next step in life, right? Maybe that means that, all right, I'm selling t-shirts, but I'm going to work on when a customer walks in for me to notice them, kind of study them a little bit, not being a stalker.

Cause that's, you know, I want you, but, okay, all right. If this, this person has kids, all right? So they probably need something that is gonna be stain resistant. All right? So let me talk about it like this. Or I see this person look to be physically fit. All right? So they probably want something that's lightweight, so they're, as they're moving, they can breathe, right?

And so they're not extra sweaty, right? So, so you think of things like that and then you tailor your pitch, you tailor your sales, method if you're a janitor, the same way. I know that from this time to. Uh, executives come in, that's when they use the bathroom. So I probably need to make sure this is done, but at this time, customers use the bathroom.

So I need to make sure, you know, you can start

to take

[00:19:58] Matt Madden: up on some extra paper towels. We're gonna have higher volume throughput.

[00:20:01] Karsten Chearis: Yeah. And then that's something that you have accomplished and achieved and then you have a story to tell. So yeah, it like taking your time is done all the time. It's not at that moment, but it's before the moment happens. It's as the moment is happening, it's after the moment has happened, what have I learned?

Cuz if I ever come through this again, I don't want it to take seven steps. So you just have to get in that mindset and, uh, it'll pay off. So, yeah.

[00:20:31] Matt Madden: That's right. You're not just getting through the time. You were thinking about the time and how do I make the most of it? At each stage of the journey, like you said, and understanding, you spoke to it in a couple different ways, which I loved that the dynamic. In any given situation, whether it's a relationship with somebody you work with, like your account executive, or it's the customer that's walking into the store, even if it's, you know, in your example around retail, which I love cuz you know, my, my wife worked in retail, uh, as a manager for, for years.

And I can just, I can think myself as a customer walking into her store and for me, I didn't get the same treatment like she did when she was serving. Like, you know, all, all the great people she did over the, over the years in doing that. But just to say, I mean, just gotta give a shout out on relationships, the dynamics of your colleagues, whether you want to get into pre-sales or not, but hopefully if you're listening to this, you are already are in pre-sales or you want to break into it, ideally, uh, you'll come to find, even if you're not in it, that, that picking up on.

the unique elements of how people like to operate is going to serve you so well. Um, and for me, I gotta give a shout out to Randy who connected you and I, uh, just said, Hey, Karsten is somebody you have to speak to, and she's somebody that, you know, operates in such an impressive way in terms of just her time management and accountability and working towards clear goals in that communication element.

Cuz another thing you spoke to was, we gotta be clear in how we communicate. We're not all mind readers, you know, so, and, and she's very great at that. So that, thanks again, Randy. just a quick shout out for you and, Karsten, I know you, you and her crossed paths as

[00:22:12] Karsten Chearis: Yeah. Yeah, yeah, yeah. I'll, I'll echo that. What's up, Randy? Thank you so much for, being a part of my network of my life. she's, uh, she's just good people. It's, it's nice to be surrounded by good people. my, uh, one of my first mentors had a phrase. He said, People don't have to be nice.

And if they are being nice, they don't have to be nice to you. Uh, so if they are being nice, appreciate it. So Randy, we appreciate you. We, we, we thank you for, for being nice and being one of the, the good peeps. So yeah,

[00:22:42] Matt Madden: absolutely. And don't kill me, Randy, for giving you a block of this episode, but it's well deserved, so

[00:22:49] Karsten Chearis: Agreed.

[00:22:50] Matt Madden: Awesome. Well, let's dive in. I loved what we just touched on. One of the things, uh, that I know going into today, I was really hoping we can dig into and I think now would be a great time, is when we think about our style when it comes to learning and how, for you, if you have something new you need to tackle, you're in a space that is, So dynamic right now within cybersecurity, the threat landscape is evolving constantly.

There are tools, I'm sure, outside of your, product suite and services at Rapid 7 that are important for you to stay on top of, as well as that landscape shifts. So could you just speak to me about what habits or approaches have served you well? Um, we can get into, are there resources you turn to on a regular basis for maybe somebody that wants to break into pre-sales from a cybersecurity perspective?

Um, just, you know, wherever you want to go with it, but I'd, I'd love to get your perspective there.

[00:23:50] Karsten Chearis: Yeah, so the the saying is, um, experience is the best teacher. I strongly disagree with that. I would say other people's experience, is the best teacher. So like if I'm learning something, I understand that I am going to make mistakes cuz I'm not perfect. But just because I know I'm going to mistake, going to make mistakes doesn't mean that I should just purposely go out and just try to trip up.

Like if, if I'm trying to figure out how to get from my house to a new restaurant, why would I sit here? Well, let me walk it out first and just try to like, no, I can literally use Google Maps because the cool thing about Google Maps is, it just doesn't know the fastest way from point A to point B, but it also has taken into account traffic.

How many people are there? How many smartphones are there? So traffic is probably backed up. So why would I try to figure this out all on my own? Learn from the experience and mistakes and successes that other people have made. So that's the ethereal, that's the, the theory. How do you get into the application?

So for, for me, I try to, um, I, I'll, I'll go back to my previous employee. I worked in email security and we had about, Five main, I think we're around five main products that we sold. And for me, I said, all right, I know we have a portfolio of five, but that's, that's too much. Let me focus on this one. I know that this one will also bleed into number two and all that, but I will get to that later.

Let me learn about this one. Right? And so when I got comfortable with that, I, I read up on it. I watched, demos or heard demos, and I, I asked questions, and then I got to the point, okay, let me demo this to one of my pre-sales, uh, peers. And I did that. I got the feedback once I, I don't wanna say mastered it, but once I said, okay, I feel good with this.

Now I'll move on to number two. And then the same thing. And as I'm learning number two, how does number one bleed into number two? How does it make number two better? And then number three, and so on and so forth. So I have learned that it is very easy. Well, I, I suffer from, high anxiety. And, uh, when the pandemic happened, I suffered from depression, uh, which was not fun.

and it's, once you overcome that, there are always little roots, a little seeds where anxiety and depression can sprout again. So you, you have to do what you can to not be overwhelmed and just constantly remind you. So, all right. Look, I, I wanna get into cybersecurity. All right? Let me first start learning operations, because if I don't understand operations, I'm not gonna understand how to secure operations and what are some of the vulnerabilities in operating in this way.

All right, then let me move into vulnerability management, then. Let me move into, application security or whatever, right? So you have to take the whole buffet and break it down one bite at a time. Take your time right, uh, throughout the whole thing and you'll, you'll be successful.

[00:27:07] Matt Madden: That's amazing advice. It's something that I too have struggled with anxiety off and on, and been certainly one to kinda have a shiny object syndrome when it comes to what should I learn and focus on. And it's easy to get into that trap, but like you said, it can be so overwhelming. So if you don't just say, you know what, I'm gonna focus on this.

I'm gonna try to just really get it under, under my brain, so to speak, for what I'm learning and. Like, I love the example you mentioned with the five products that ultimately you had to learn and know well, but you started with one. And then as you progressed and felt good about that, you started to see connections strengthen from one to the next.

When you think about just how, you know, here are the parallels, here's something that's maybe a little unique about this product, but we know there are elements, uh, from, you know, the first thing you learned about that are still relevant. And it reminded me of, one of my former managers, PRITE Patel, he was on, a couple episodes back on the show and, uh, I would encourage others to go and listen to it, but that was exactly how he encouraged me to learn our product at Central, which is the closest thing to working in cybersecurity that I've done so far professionally.

Um, but there's a. Function within the product focused, within cybersecurity due diligence. And so getting familiar with just some of the frameworks that are very common there, the process for due diligence within, engagements and so on. We, working with consultants was really informative and eye-opening, great learning experience.

So, um, yeah, I love that. but it was so key. If I had not, if he said, go learn everything, I would've been drowning in information and anxiety through the roof on that pressure there. So, you know, if there are leaders out there that aren't maybe taking as a stepped approach where appropriate for certain learning tasks.

Um, I, I mean, I'm not in a leadership position today, but I would love if I were their employee that they, they gave me that opportunity to, to ramp up. And I'm sure they do. I mean, that seems pretty

[00:29:10] Karsten Chearis: Yeah. Yeah. I'll, I'll tell you, I'll actually, first, I'll challenge what you just said because, and I, I know, I know what you meant. leadership is not a, a title or a role. I have worked, for plenty of managers that were not leaders. My first manager, I don't wanna slander anyone, but let's just say he, he was not good.

Um, right. And I, I learned basically how to be a good leader by just doing the exact opposite of what he did, right? I'm like, this, this dude makes me mad and frustrated and this, so if I just, I don't have to learn anything, but if I just do the exact opposite of what he did, then I think people will like me.

So, but what, a leader is, is, is someone worth following, right? So you may not have a team reporting to you, but people are looking at you whether you know it or not, and they're learning by what you're doing, right? And so, uh, you're leading people and you may not even realize it. But with that being said, yes, managers, directors, everyone above and between and all that.

Please make sure that you're not overwhelming your team. And if you're not a manager, if, if you know the mistakes you've made, you know what has worked for you and what hasn't worked, you know that this new hire that's gonna work, with you alongside you, they probably need to learn these things.

So take the initiative and reach out like, Hey, let me, let me kind of tell you what worked for me. I said, it's gonna work for you, but this is how I learn and this is how it work for me. and that's, that's what's gonna give you good experience with, one day being a, a manager or director or whatever in the first place.


[00:30:52] Matt Madden: I love that. And certainly, yeah, for me, I'm always trying to just improve how I think about leadership and what makes a good leader. I really appreciate you sharing that. Cause I'm sure even for people that are wanting to break into the role naturally, if they're not coming from a, a management background or leadership leadership position, they're looking at an individual contributor, role as a first step in their path, I should say.

But, you know, we all have ambitions to grow within our career and that vision might look very different, often looks different from one to the next, but a lot of people view, uh, natural. Kind of milestone, if you will, is moving into a title that is more of a leadership role. You're man managing others and so on, whatever the title may be.

but it doesn't have to be that way too, which is great. I love about, as I've learned more about different paths within pre-sales, not to be corny with our name here, but I, I've seen some great posts just calling out, Hey, the end all doesn't have to be that you become, a very senior, leader within the pre-sales function of that organization.

But yeah, it's absolutely a great goal to drive towards as well. And for me, that's, you know, I would love to kind of move towards that path cuz I get a lot of energy out of helping, educate and see other people succeed and so on. I would venture to guess that's, that's why you love it as well, Karsten.

so I definitely love your perspective on that. And, just wanna, send it back to you on that. Just get to your take on, for folks on, on the different paths within, uh, whether that's, aiming for leadership or, or elsewise

[00:32:26] Karsten Chearis: Yeah. So, so let's, let's look at, let's take this a few ways. Let's look at pre-sales and maybe talk about the possible career choices. I don't know, uh, for, for me, when I was a kid, my favorite series of books was, uh, this book series called Choose Your Own Adventure. And, if you haven't read, like there, there were so good.

Uh, I remember one of them. Was you, your character is in space in a rocket ship and there's a vampire on the rocket ship, uh, with you and you have to survive. And so you're reading like from page one to four, and then it says on page four, you hear a knock, at the capsule door.

If you open it, turn to page 18. If you, walk away, turn to page 32. And it was just so, so, I, I loved it. I loved those books so much. It helped me think differently. But anyway, so with that being said, choose your honor intervention with pre-sales. You can have, an associate or junior. And just for the sake of discussion, I'm just gonna say sales engineer.

We know the titles can be solution to consultant and all that, but just for simplicity, let's say sales engineer, so associate or junior sales engineer, sales engineer, senior sales engineer. you can then get into maybe, team lead of sales engineers, uh, principal sales engineer. Yes. At that point, maybe then you can go to management director, blah, blah, blah.

Or you may go into what's known as a field CTO or field cso, which is basically someone who may not be necessarily quota caring, where they have to close X number of opportunities in their region. But there are. Their quota is being a thought leader and talking to leadership at the, different prospect, companies and all that, and helping influence their decision, right?

So there, there's multiple ways you can, you can go about it either way. Being a leader is important every step of the way. And if you do have aspirations to get into management or you do have aspirations of being a principal or a senior, just look at processes. Look for things that are broken.

If there's nothing broken about the process, try to break it and then make it better. And as you're making it better, document it. Like, this is why this doesn't work, this is why this does work. And then figure out ways how you can articulate that to someone else. All right. So when I explained this to Matt, like I had to tell him like six different times.

Doesn't mean something's wrong with Matt. It's probably something wrong with the way I'm articulating this. So lemme change it, lemme change my approach. That skill. I use it every day as a manager. I, I still talk to prospects and customers. I use that every day talking to prospects and customers. I use that every day.

Talking to my immediate manager and his manager. Uh, I use that every day talking to the account exec. I use that talking to my wife and my kids, you know? Um, so it, it's, I I think that's, that's super, super important. the other advice I would give is being a leader isn't bragging rights. It's, it's servanthood.

Like being a, I'm a leader. To my daughters. That doesn't mean I, Hey, you go to bed at this time, but it's when they run into a problem, I'm approachable where they feel safe coming to me and saying, Hey dad, I need help with this. Or, I messed up. Help me get out of this. Right? If, if it's a bragging right, if I'm putting myself up on a pedestal, I'm just building a wall around me and it's gonna be harder for people to come talk to me and they just don't wanna do it anymore.

And eventually no one's gonna talk to me at all. So, um, you don't want that being in pre-sales.

[00:36:30] Matt Madden: That's a great perspective and so true. it reminds me of what we were talking about earlier a bit where we were talking about picking up on other people's dynamic and within the team, you were speaking to how you use that every day. You have to read and be enough to step back and say, you know what?

It was maybe me, likely me. That was the reason that so-and-so didn't quite connect the dots on the feedback I gave them. And let me go back to the drawing board because. As a parent, I know you have the choice and it's easy to make the wrong choice to, you know, you communicate something, you think it's very clear, but somebody's at a different stage in their journey of learning and you gotta quickly, take a step back and recognize that and, and just realize you have an option.

Yes, I can get frustrated myself and feel like I'm, talking to a wall here with what I just said, or I can say, you know what, that didn't connect. It was on me and I need to look for ways to better communicate. And, you know, that's just part of the process. Uh, I mean in, in parenting or working with colleagues and, and

it, it's on me to help work through that as well and and the other person, you know, is, is, is gonna be building that trust with you in the same way, you know, through how, they manage that situation. And so, you know, one thing in that, that I'm curious how you've seen. People within your team support others as well as how you've supported folks. If you see somebody is struggling and they're maybe not able to articulate that, but you know, it could be something like anxiety, you know, something outside of work even that could be really stressful, which I, I imagine as a manager, I mean, I know for me if something happens, the first person I'm gonna go to is who I, I report into.

If it's something that is non-work related that I, I have to perhaps take a day off all of a sudden now, um, as a parent, you probably find yourself in those situations more often. Like, this illness is tearing its way through the school now. And okay, here we are, let's, let's figure out a game plan. But like, so as a manager, I'd imagine you hear a lot more of what's going on and, and it's not like something you're gonna go and necessarily for certain situations share with the whole team.

But if somebody's really struggling with mental health, I mean, it's, we're almost outta May, but it's mental health awareness month. So I just think, it's important to kind of talk about how. life bleeds into work and I know, I'd love to hear your perspective there. but, um, yeah.

Would you mind giving your thoughts?

[00:38:55] Karsten Chearis: yeah. So, uh, you probably heard the phrase, um, you know, I don't, I don't see color. I don't, I don't see Ray. And that's, I, I dislike the phrase, and I'll, I'll, let me give you a little bit of, of story then I'll tell you why I, I said this. Um, it's when I, when I'm talking to someone, while I may not be looking at them to say, all right, we're different in this way, and because I'm a male, I feel like I'm better than this person because they're a female, or because I am this rate.

Like, it's, it's not saying that, but I have to understand that where the person is, uh, to whom I'm talking, right? Um, I had a coworker, I'm a, I'm a black man. They had a coworker, uh, who was a white man, and this was all related to pre-sales, but he just basically was saying, but look, man, I don't care. Like if I, if if we're hearing this and I ask you to do this and you just need to do it, I'm like, I don't, I don't think you are trying to sound racist, but the dynamics is giving off a lot of racism with the way you're articulating that.

Right. And so, um, I, I, I say that to say that it's so important to understand that you don't understand everything about this person. Um, if, if someone is coming to me and they're, let, let's just say there's two different people on my, on my team and they have the exact same problem or, circumstance in their personal life, I have to understand, okay, this person is married.

With kids. And so them going through this means fill in a blank for them. This person is single, no kids, younger, earlier in their career. So if they go through this, it may mean that, right? So you, you have to understand context. You have to be aware of situations, you have to take what you have learned.

And then again, like I said, you have to remember that you don't know everything about the situation. And they may not be telling you everything because it's none your business. Maybe it doesn't matter. Well, it's just too embarrassing. So when I, when I, when I say that, um, my, the application would be is to understand that man, we're all human, that we're all dealing with our own stuff and we're also dealing with the same stuff.

Um, for me, with my depression, it was when Covid first happened, and, uh, my kids, you know, school was closed, everything was closed. So my kids were here, but I worked from home. So while I'm working and demoing and POCing, I got two girls flipping and fighting and chasing dogs and all this stuff. And then there was a lot of, uh, uh, social and political, unrest and, uh, a lot of people that looked like me were being murdered at the hands, of, of police brutality.

And it was just a very depressing time, right? And so I would want my leaders to understand that without me having to say it. I'm not asking for them to give me a, a pass, but I just need you to be mindful and understanding of that, right? And so that's the same thing with, with you, right? You, you, what I know about you is that, uh, you have a wife, you have kids, uh, you have younger kids, you have a podcast, you have a day job.

I should be able to understand that that means that you may be wrestling with this and you may have aspirations to do that. So I should be careful with my words because I don't wanna, you know, dissuade you or, or depress you. I wanna always try to help you and encourage you, so,

[00:42:53] Matt Madden: No, I love that. Thanks Karsten. I appreciate you sharing that story. Uh, the personal stories and what we struggle with within work dynamics, within what's happening around us. I mean, just the, injustices Andthankfully, I mean you mentioned pre-Sales Collective earlier today. they've just held a great summit around, diversity, equity, inclusion within our industry specifically. And, um, I'm gonna link to just resources that they have there for folks that want to go.

And if you're not involved in Pre-Sales Collective today, I know that you can sign up and hopefully can access those webinars, that they had, cuz you know, just happened. So that'd be amazing. but yeah, on that note, For people that are looking to break into the role, that, are coming from a background, such as yourself.

maybe they've experienced challenges in the workplace, um, they're not a white, male person working in the industry. like myself and like so many within tech still today. That's, that's the imbalance , you know, the reality. Um, what would you just say to them to help encourage 'em if they feel like, you know, they're just encountering things that, is, it's a different situation in that scenario potentially for them.

I, I just want you to speak to that and, uh, just I'd love, love for you to, um, share any additional nuggets of wisdom like you've been throughout the whole episode. Honestly, man,

[00:44:08] Karsten Chearis: Yeah, I, I, I would say, um, seek community, right? Let, let me, if I may, let me give a account of something. I think everyone, uh, well, most people know, even if they, they don't believe, but in, in, according to the Bible, Adam and Eve were created. The first man, the first woman. they were told that they can eat of any, fruit except for this one.

Uh, a snake walks up and says, Hey, you, you should eat this one. Right? And so they did, but when they did, they didn't talk to each other. They, they didn't say, Hey, should we be doing this? Right? And then once they did, then they ran and, and, and hid my point in saying that was one of the first big problems in humanity was separation.

[00:45:08] Matt Madden: Mm.

[00:45:09] Karsten Chearis: And then you look at that as we continue, there are, uh, a lot of homophobic people. There are a lot of racist people and, and, and bigotry. It's, it's a big thing. um, People have lost friends and family over, who they voted for, in presidential elections, right? There's so many things to separate us, but when we try to do things on our own, that's when we fail, and that's when we don't have a support system and like, ah, I don't need anybody.

Yes, you do. You do need somebody, right? So I would say seek community for me and pre-sales, pre-sales collective is great. There's another, group called, uh, forgive me if I, misquote the name. National Association of Sales Engineer. It's, it's N A A S E and I'm, sorry that I can't remember the name, right now, but that's another one.

There are various groups, and I can email this to you and you can add in the show notes if you

[00:46:04] Matt Madden: yep. Will do. Yep.

[00:46:06] Karsten Chearis: Yeah, you know, there are are different, organizations for women in tech or women. One, again, in tech, African Americans who wanna get in, tech, people of Mexican, heritage and culture.

They want to get into tech. You know, like you, you have all these communities. So Google them, look for them. Use your social network. Say, Hey, listen, I am in this dynamic and I really want to learn how to do this. What advice do you have for me social media network? And people, they, they will reply, they will respond.

So, so join, communities, uh, that I, I will say that will probably be the, the biggest thing. And then the second thing is to don't separate your experiences. And what I mean is, is as, as people listen to this, this broadcast, they have heard, you and I talk about our jobs, but also our families and things that happened with our families made us better at our jobs and things that we learned at our jobs from, okay, I don't need to do that to my family.

Like, don't, don't necessarily try to put a wall between your personal life and your work life because what you learn in one will help you with the other. Right? It, it, it goes both ways. So, be open-minded and don't feel like anything you go through in life is just happenstance and it's wasted. There's, there's a reason behind it.

If you kind of sit and think about it, you may not know it now, but maybe you will in six years from now, and those things will, will build upon themselves. So,

[00:47:40] Matt Madden: Absolutely, man. And what you said, you sit and think about it is a key piece of it. Taking the time to reflect. I think I've heard you mention that multiple times when you're talking about a scenario and just having the awareness, the emotional intelligence to make time for that. Cuz it's, I'm so guilty of not making time to reflect on, how did the week go or how did the day go?

Even on a more granular level and say, you know, what is the things that I want to keep doing? What's the things I need to ensure I don't repeat? And just even, journaling personal journal where you also are logging your activities for your workday and that, and you know, you're being mindful of that, how you account for your time blocks that you have dedicated to what you're doing within your current role.

And then when you think about the mornings in the afternoons, like if you're not working in pre-sales for me, When I was looking to first break into my first tech role, which I spoke to before, but wanted to be a, front end engineer, was kind of what I was focused on, and then I got focused on data analysis and it led me eventually to a role within a data analytics company as a sales engineer, but, I was probably most on top of my time before and after my, my day job at that point.

Like I'm, I'm getting back into that rhythm now because, you know, to do this podcast, I have to be very specific about, evening hours when I do that, or on the weekend without sacrificing the commitments to my family, obviously to my current employer and everything that is, first priority for me, within this, but still wanting to get this project going.

And so like, I'm, I'm working hard to try to make more time to reflect on, even at the end of my workday, like, what, what went well and how does, how does that influence or shape what I'm gonna do tomorrow? And I'm curious about how you think about just time blocking and, and time management, when it comes to reflecting, and then structuring your day or what comes next based on that reflection.

[00:49:36] Karsten Chearis: Yeah, so, um, I too have a, a shiny thing syndrome. Um, and every time there was a new productivity app, I'm like, oh, I gotta sign up, you know, and I have gone from all these note taking apps and to do, uh, apps. I have, uh,

[00:49:54] Matt Madden: what do you use now?

[00:49:56] Karsten Chearis: Say again.

[00:49:57] Matt Madden: What's your favorite right now?

[00:50:00] Karsten Chearis: That's a hard question. I, I'll answer it this way. The one that I am trying to use the most right now is notion,

[00:50:08] Matt Madden: Ah, yeah. I love Notion.

[00:50:09] Karsten Chearis: because it's, it's very flexible and you can make it what you want it to be. But another one I've used, uh, has been, mim ai.

I really love the calendar integration because for every meeting, uh, or every entry on your calendar with the click of a button, you can make notes on it.

And then you can use tags and connect all the different things. I've tried obsidian. It's

[00:50:36] Matt Madden: Oh wow.

[00:50:36] Karsten Chearis: again, I I've tried,

[00:50:37] Matt Madden: Sorry to derail your train of thought where, where you're going with that but I wanted to get that out there. It's probably helpful for people.

[00:50:43] Karsten Chearis: no, no. It's,I think it's, it's merited. But, for, for me, I, I have to block my calendar because if it's in my mind, I'm gonna forget it. If it's in my to-do list, I'll remember it. But if it's in my calendar, I'll do it. Right. So if I don't block my calendar from eight to nine when I was an individual contributor, alright, you've gotta build this PLC environment and check up on my current PLCs and send emails, right?

I need to block time. All I know that I got two demos and a p c check-in call at this time. So that's fine. I need to block time for lunch. I need to block time to pick up my kids, right? Not that I'll forget to pick up my kids, but hey, don't expect that I'm gonna be able to demo and talk to you while I'm picking up my kids.

Unless you wanna hear, I want McDonald's, I want Wendy's. You know, that's,

[00:51:40] Matt Madden: Yeah, I, I know that time block well, yeah.

[00:51:43] Karsten Chearis: yeah. Yeah. So you, you, you have to block those things, but not just for work before your personal life, too, right? Um, if you have aspirations to get a certification or learn coding or get better with spreadsheets, put it in your calendar, and then get in the habit of one. The first things you do in the morning is look at your calendar so you have a reminder of what needs to be done.

Get in the habit of having time in the morning for you to be strategic. Have time in the evening for you to be strategic. All right? I, I accomplished this. This is gonna be pushed here tomorrow. I actually realize this is actually stupid. I don't need to do that, so I'm gonna completely cross it out. Right?

Um, so, so yes, please, please, please block your calendar. The other, uh, little piece that I'll add to that is find three people in your life. Find someone that's a few years ahead of you that can mentor you. Find someone where you are kinda neck and neck. You're in the same stage of this part of life. So you have a, a peer, someone you can talk to and they can talk to you and then find someone, uh, that you can speak into.

So someone who is aspiring to be where you are. If you do that, you shouldn't run dry because you have someone pouring into you. You have someone that you can bounce ideas off, and then you have someone to take what you're learning and give it to someone else. That's benefiting them because they're learning, but it's also benefiting you because the best way to show that you've learned something is to teach it to somebody else.

That's when you know if you've really mastered it, because they're gonna ask questions. And if you're like, I don't know, lemme back. You know what I'm saying? Like, you, you, you're going gonna get better. So block your, your, your calendar definitely. But also look for those three people in, in life.

[00:53:46] Matt Madden: man, that's awesome. I'm gonna spend some time really reflecting on that cuz I can think you know about some folks that I would consider to be kinda at those three stages that you mentioned that I know I've connected with. But my follow up question immediately that I wanted to get your quick perspective on was what's a cadence that you think where you would recommend works well for, you know, connecting with those people?

Does it is, do you aim for the same cadence for each stage, each of the three stages? Or is it different depending on the stage?

[00:54:16] Karsten Chearis: It's. It's gonna be different depending on the stage, but it's also going to be different depending upon where you are right now in life. Um, so for me, a lot of people wanna wanna talk to me. A lot of people send me LinkedIn messages and emails. I ain't Karsten out, man. I, I, I think what you're doing is great and I want to get into that, or I read this, or I heard you say this.

I would love to dive into it. I get invitations to podcasts and, and things like that, and all of that is great, but I have to be very careful with my time, right? So what, what a lot of people don't know is that you and I have been connected for a few months now, but we've found this time that it worked good for both of us, right?

So, uh, you, you, you have to know that, hey, if I, where I am in life and what I'm doing, if I'm going to help someone else, I can't meet with them weekly, but I can commit to once a month, right? For me to. Get guidance from other people. I know that, hey, this person that's one of my mentors, that's a senior director, and they also mayor and they have this, this, and this going on.

All right? So they may only be able to talk to me once a month or twice a month, right? So I gotta work with them. Typically, your peers, you can talk quote unquote all the time. You can always shoot a text, slack, you know, email, you know what I'm saying? So that, that's different. But the people to whom you're looking up and the people to whom you're helping, that's when you probably have to be a little bit more, uh, strategic.

So I will say that for me, I need to work on spending more time with people who are pouring into me. Uh, I talk to them, but not in the way that I need to. So that's something, my homework after this is to make sure I, I have time blocked for them.

[00:56:07] Matt Madden: I hear you man. Well, I've got a lot of homework coming off this because you've shared so much awesome advice and tips throughout this conversation. And I wanna be respectful of your time because you've been very generous with it. Uh, not only today, but like you said, leading up to today. And I think a key thing that I reflect on when it comes to this session happening is we had to be a little fluid.

There were things that came up on your end, things that came up on my end, and such as life with parents, but just life in general or life with kids, I should say. Not life with parents. Um, so yeah, that's just key and being flexible and not being, um, Offended if something doesn't work out at Exactly The timing that you are hoping for is something that I try to take into everything cuz we run into it all the time and work dynamics, like we're really hoping, looking forward to this follow up sales conversation.

And maybe it's key for where we're at in the quarter and we're, we're really kind of banging on this cause we feel like it's a great opportunity. It could, you know, just one example, bringing it back to the role and it doesn't work out. Something comes up on their end or our end and so on. We gotta reschedule.

But you know what it's all about how do we manage the, the communication, the dynamics in between, uh, you know, being mindful of the other people. A lot of the things we've talked about today. So, um, yeah, I love that. Well, I wanna just ask you one final question, before we hit stop on the recording. Is there anything I didn't ask you today, Karsten, that you think it would be good for people to know, uh, who are looking to break into the role?

Just any shoutouts or things to look forward to that you're working on as well?

[00:57:42] Karsten Chearis: One. Shout out. Shout out to my mom. Uh, my mom has always, been my, my biggest, uh, supporter. My first supporter. And, uh, I would not be where I am if it was not for my mom. So, I love you, ma. Um, the second thing I would say is, um, People like incentives. So you just gave a good example of, hey, you know, you work really hard and you, you're banking on this opportunity closing and something happens.

[00:58:18] Matt Madden: Mm-hmm.

[00:58:19] Karsten Chearis: All may not be lost. What's the incentive? Hey, you know, Mr. Miss Prospect understand this came up, but you told me right, that this is a problem for you and you're kind of bleeding money because of this, this issue. What would be the risk if we postpone this for another month? Or, or what, what can we do to help you make this a, a priority or reprioritize this, right?

You can do that with your prospects. And then you do that with the, the person to whom you're, uh, you're mentoring. So, hey, look, I'm, I'm doing this for you, right? What I, what I need for you to do is, can you, can you help me by doing that? Right there, there, there's an incentive both ways. The person who is mentoring you, they're pouring into you.

But like, Hey, listen, since you're pouring into me, let me give you an incentive. Um, can I take notes for you in this meeting? Yeah, I don't, whatever, you know, depends upon the dynamic, but I always try to look at the incentive that, uh, that you're receiving and that you can give others, cuz that'll, that'll help communication going just in general.


[00:59:24] Matt Madden: I love that there's a saying. I heard one of my online mentors, not a direct mentor, but he's somebody that I learn a lot from, uh, especially when it came to learning this podcast. He often wears a shirt. It says, serve first. And I think it's just such a great mantra going into everything. Um, and so, you know, uh, his name's Pat Flynn, but, um, a lot of you, you know Pat Flynn.

Yeah. Heck yeah, man. Yeah, just,

[00:59:51] Karsten Chearis: Watch his

[00:59:52] Matt Madden: yeah, he's on YouTube. he is got such amazing free content out there. So just, across the spectrum and just serving others in the digital capacity, which, you know, at the end of the day, if we really step back,

that's what we're looking to do. I mean, we gotta keep that, that serve first mentality in place.

[01:00:07] Karsten Chearis: agreed, agreed.

[01:00:09] Matt Madden: Awesome. Well, Karsten, it's been an honor and a pleasure having you on the show and uh, I look forward to just hearing everybody's feedback. If people want to follow up with you, what's the best way for them to do that?

If you're open to that?

[01:00:20] Karsten Chearis: Yeah, yeah. Uh, LinkedIn will probably be the best way. Feel free to gimme a connection, request, follow, whatever. Feel free to slide in my dms. Please don't be offended if I don't immediately get back to you. Um, uh, I'm not all that, but, uh, I do have some things going on, but I am always willing and able to, uh, extend my network and help you extend yours.

[01:00:43] Matt Madden: Love that. And I would encourage everybody, if you want to just shoot a question across that you're hoping to hear answered on a future episode or even a reconnect that I could do with Karsten or others that you've heard on the show, send me an email to matt@pathtopresales.com and I'll get right back to or message me on LinkedIn so you know all the, all the ways you can get in touch.

Uh, try to make it easy. And uh, yeah. Karsten, thanks again man. I hope you have a great evening.

[01:01:10] Karsten Chearis: You too, man. Thanks everyone.

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