How to Accelerate your Tech Sales Career in 54 Minutes (From a Top VP)

And I've learned that your career can't really grow faster than the company you work for. And so you may be wondering how on earth do I sell myself into a great company when I don't have president's club, I don't have massive quota attainment. And that's where I've seen reps even recently with profiles that I never would have reached out to because it's companies I'm not familiar with. There's no track record of success. But they cold called me, they cold called my leaders, they cold called my reps. And even though I initially brushed out their application, I've been coming back again saying, hey Kyle, I talked to this person in your org, I learned this. I talked to this leader in your organ. Learned this. Based on what I've learned, here's how I think I add value to launchdarkly. If they're going to approach this job the way they're approaching this interview process, I might just take a bet on them.

I'm Chris Bussing. Welcome to my channel. It's committed to helping more people create lives of freedom and impact through success in tech sales and the pursuit of self development. And it's brought to you by Tech sales accelerator. Launch your six figure tech sales career in the next 12 weeks. Man, do we have a great guest today. Kyle ac. He broke into tech sales as an SDR at Qualtrics, got promoted to account executive and he went to president's club five times as a seller and as a first and second line manager. Then he joined the sales organization at one of the greatest database companies in the world, MongoDB. And he led acquisition sales for commercial mid market and lower enterprise sales. Most recently he joined another incredible company, LaunchDarkly, leading global mid market sales. All the while he created salesintroverts.com where he helps 10,000 plus sellers use his frameworks to succeed at his level and as he says, exceed his own success. You guys are going to want to make sure you stay for the whole conversation and pay close attention. In fact, watch it a couple times, take notes and translate what you learn into action. We're going to talk about how to sell ourselves into the best tech sales opportunities and rise the tech sales ranks from SDR to AE and even the leadership if you so choose. Also finally, make sure to like this video and share it with more people who can benefit from the message. Kyle, thanks so much for being here. How's your day going so far?

Thanks Chris. Great to be here. Good day. Great start to the air so I'm looking forward to the conversation.

It's so great to have you. So let's dig right into it. On your LinkedIn profile, it says you begrudgingly got into sales and then you realized there was no way out. What is, what does that mean? What do you mean by begrudgingly? And that you realized there was no way out?

Yeah. So it starts with my first role in sales, which was door to door sales, which is miserable, especially for a highly introverted person. And so I had this, this concept of sales sucks because that's all that I knew for sales. Obviously, business to business is very different than direct sales. Very different in door to door. The other aspect for me is I am highly introverted. And so I had this perception that the best sellers were going to be these extroverted people always command the room, high energy. And I was like, I'm not, I'm not that guy. I don't want to be that guy. And so between my experience in sales, which was rough, and my perception of my personality being a disadvantage, those two combined to think sales isn't for me. When I was recruited to Qualtrics, I didn't even know what role it was. I got into the process, I knew it was a good company, so I was willing to learn more. I found out that Opportunity development was a fancy name for sdr. And I literally told the co founder in my final interview, I don't want to do sales. And he said, that's fine. We'll start you there and you can change anytime. You'll just make less money. And then I joke about no way out. But the reality is I love sales. I can't imagine doing anything different with my career. I do like to tell people I have a crippling fear of change, but that can't be true because I, I, I take change all the time in my, my current role in previous roles. But that's the compressed story of how I landed in sales. But I'm just, I, I can't imagine a different career path for me.

So you begrudgingly entered into sales, but quickly discovered you loved it. So what are the specific aspects of a career in sales that you love the most?

So going back to what I thought I wanted to do, I wanted, I thought I wanted to be a consultant working for a Bain or a McKinsey. I went to school for a specialist degree that led most people down that path because I love the idea of strategically analyzing a situation and providing recommendations for how to improve. Turns out that sales is really that you strategically analyze situations, you recommend a solution, but rather than a solution that is very theoretical, it's a solution tied back to your offering your product, your services. And I also ended up being a lot more, excuse me, lucrative than even consulting was. And so it was a win win. But I think that was the element that when it clicked, when I realized that I was doing a lot of what I wanted to do with my career, but in a more quantifiable way, in a more financially meaningful way, that's when I transitioned to being all in and realizing I wanted to get really good at this.

I had another great guest like yourself, Dan Pink, and he said B2B sales today is management consulting. And you just illustrated that. So I've noticed that you're choosy with the companies you go to. You're only going to the best of the best, like Qualtrics, MongoDB and LaunchDarkly. And I'll tell you, when I was with my CEO at a cloud services company at an AWS startup event in New York, and he's a former product guy, having worked at Siebel, he went to the LaunchDarkly booth and got a demo. And he said, as a product leader, I would have loved this stuff.

Love it.

You've been to great companies and maybe you got another launch darkly hype man on your hands, evangelizing you out in the market. But what are some of the common threads and characteristics between these different companies that drew you to them? Because I feel like you choose the best of the best.

So it's gonna, I'll be very honest, Qualtrics was lucky. I was in college. I had no idea what a great company looked like. They sold me on the vision. I believed the vision and it happened to be one of the companies that actually followed that vision, which was really fortunate. I was very intentional, though, about staying. When a lot of people left for short term pay raises, ote increases, I realized I was somewhere good because I saw the company progressing, I saw the company growing. And I've learned that your career can't really grow faster than the company you work for. And so where a lot of people got short term bumps in title and compensation, by staying at a great company, I ended up going a lot farther, a lot faster because the company grew. I reached a point where I realized I'd been there for eight and a half years. I had learned a lot of really incredible things. But until I expanded my horizon beyond the world of Qualtrics, I had a pretty heavy ceiling on my career. As a sales executive, MongoDB reached out to me and as I dug into it, I saw an opportunity for growth. I saw a more technical sale, which I wanted to get more on the DevOps side because it's a bit more challenging, a bit more complex than Qualtrics was. And I saw benefit to that for my, my career. But I was looking for phenomenal product, great leadership and a great team to build around with. LaunchDarkly, it was a very unique opportunity because they showed me some incredible metrics and then they explained to me how they got to those metrics and what I'm looking for at this stage in my career. And is Problem Kyle fit? And what I mean by that is I'm looking for problems that I am uniquely able to solve because that drives a lot of value for the company, it drives a lot of meaning for me. And so their recruiting pitch was, look at all the things. We're doing incredibly well, despite not doing well at all in the areas that you're really good at. So if you come in here and implement what you're good at, what can we do together? It was really intriguing to me, but from a fundamental layer. I'm always looking for great product because I'm not good enough at sales to not have a great product. I'm very picky about that. I want a product that customers love. I want to see great G2 scores, I want to talk to people and have them say, hey, I love you. I love LaunchDarkly, I love MongoDB. That's important to me. And I'm looking for massive market because if you have a great product, but it's a late stage company, it's past that growth curve and the, the there's not that much more addressable Tam. It's a lot less intriguing to me. So great product, massive market. Then on the people side, I'd say it's a little bit less important for me at my stage in my career because I can go build the right team, I can go get the right people. If I'm an ae, though, I add that people criteria in there. So great product, massive market, great people, and when you find that kind of company, get good, stick it out and you'll do a lot better than the ones that pop around quite a bit.

I talked to one of my buddies, Jay Johnston, who really admires you. I think he connected with you at one point in the past. And I said, jay, what would you ask Kyle about? And he said, kyle has this mindset that the best sellers sell themselves into the best opportunities. And if you're not getting the best opportunities, you're not selling yourself well. So you highlighted how to think about finding the best opportunities in your criteria. And I'm curious, can we start to unpack what it looks like to sell yourself into the best tech sales opportunities?

I'll give an example of. I'll give a couple different examples on this. Ways that you can sell yourself will start with what you've done so far in your career, which is not anything you can change in this moment, except for looking forward. But when I'm. When I see people that have done incredible work at prior companies, that's an easy, easy sell. Now, there's some people that will think, well, okay, that's all well and good, but I've been at three pretty crappy companies. There's no product market fit. I haven't sold much because I haven't had the opportunity to. Now, some of you thinking that maybe take more ownership, maybe it's more of your fault than you think it is, but some of you, you're completely spot on. It's valid. You haven't had success during the wrong environment. And so you may be wondering, how on earth do I sell myself into a great company when I don't have president's club? I don't have massive quota attainment. And that's where I've seen reps even recently with profiles that I never would have reached out to because there's companies I'm not familiar with. There's no track record of success. But they cold called me, they cold called my leaders, they cold called my reps. And even though I initially brushed out their application, now they're coming back again saying, hey, Kyle, I talked to this person in your org. I learned this. I talked to this leader in your organ learned this. Based on what I've learned, here's how I think I add value to launchdarkly. And that stands out because most reps don't do that in the interview process. And I'm thinking, okay, this person has a pretty bleak resume, but they're standing out by the way they approach. Then we get into the interview process and they're doing things like getting LaunchDarkly certified, they're sending me mock demos. They're doing all these things that other candidates don't. And now I start thinking, well, what if this candidate would have ended up at a great company for their first job? They probably would have been president's club. They probably would have a lot of promotions. It's not Their fault. They landed where they did initially. But. But if they're going to approach this job the way they're approaching this interview process, I might just take a bet on them. Even though they don't have the pedigree or the resume of other candidates, they differentiate in that way to stand out. So I would argue that regardless of where you're at in your career so far, with success, you can still replicate that second example. You can stand out in that way, pick up the phone, have conversations, build a point of view and show how badly you want it. Now, it doesn't mean it's guaranteed to work and I'll tell you that it's very discouraging to put in that level of effort and still not get the job. But if you don't have that great pedigree in this market and you don't differentiate by how you go about applying for jobs, you're never going to land at a great company and you're going to end up in this really painful revolving door of low product market fit, low quality startups. You're not going to learn, you're not going to earn, and you're probably going to hate sales.

That's so helpful to hear because someone recently booked time with me who is has mid market AE experience and was at some good companies in the cybersecurity space. But most recently now he was trying to stretch himself to an enterprise AE role, but he made it the final round and it's happened a few times, but they said you seem like a job Hopper. How do I know? Based on your resume, it looks like you're gonna leave in 15 months. And so you actually just gave a potential solution to maybe address that. But I wanted to bring this up in this specific situation because it seems like he did get to some final rounds and that was the objection. So do you. It's a unique opportunity to get your vantage point on can he do something to frame his narrative to proactively address this Job Hopper?

Objection. So job hopping is a tricky subject with a lot of strong opinions. So I'll tell you how I, how I view it. When I see a couple of short stints, especially at lower quality companies, I don't hold it against the replacement because I understand mistakes can be made. But if I see a pattern, if I see four or five, I had one recent, that was nine, nine jobs in a row with less than two years tenure, then I'm thinking, okay, one of two things has to be true. Either one, you're really not very good at Sales or two, you're a chronically bad decision maker and both of those are hard to overcome to wrote a great company. Right. So I think if you have that resume where you have moved around a little bit or a lot, be able to explain the why behind it, the intentionality behind it and why you believe this next role is the right role for you, why you think it's going to be a long term role. Another aspect to it where possible have really strong back channels and references to speak to your commitment. But the story really matters. It's a. It's the. I'll add one more thing. It's not uncommon for people to see progression early in their career when they do some job hopping SGR to ae.

Yes.

Commercial AE to mid market ae and you might expect the same as you continue to go. What you'll find is a stronger company will not usually promote somebody from a weaker company. And so if I'm interviewing somebody right now that's in a mid market role or upper mid market role and they sell a less technical product to a less complex buyer, even if they're crushing it, I'm not going to interview them for an enterprise role at my org. My job is harder. My role is harder.

Yes.

I might not even have them as a lateral move. They might need to take a step back to go learn a new Persona more difficult product. And so the willingness to show that you're all in on an opportunity and take a lateral move or in some cases even a downward move to get to where you want to be long term, that can also help overcome the job hoppiness, stigma and concern that can be hard for reps to do. But I'll tell you most of the time a lower level job at a better company will pay off a lot more for you midterm and long term than a higher level job at a worst company.

What a golden nugget. And I think you just presented the exact solution this individual is stretching for enterprise roles when he has mid market experience and a little bit of job hopping. Maybe humble yourself at least a comparable role or if anything be willing to take a maybe a lower level role on paper to get into the right opportunity vehicle as you said. And I'll never forget one of my peers, Tate, who started with me in sdr@oracle 10 years ago that got promoted to inside AE like myself. But then he humbled himself to go to AWS and took a DG demand generation or what their term for SDR role and greatest decision he ever made and he for Six years hit his numbers, made great money in equity. So really good lesson and I wanted to shift back to interviewing and specifically as we sell ourselves into great opportunities, what are the most important competency signals that you look for in candidates? As you are you or either people under you are assessing them in interviews.

So I bucket it into two areas. I'm looking for traits and I'm looking for transferable skills. Now a lot of sales leaders will only look at traits or they'll only look at skills or they'll just have a random process and good luck because they don't know how to hire or how to interview. It's a difficult thing to get right. When I'm looking at traits, it's not going to be different than most sales leaders. I'm looking for high iq, high eq, coachability, grit, motor, all those elements. But I'm also looking for transferable skills. Because if you give me the hardest working rep, the smartest rep, but they have no transferable skills, it's going to be too hard for them to ramp with a technical buyer and a complex product. Right? So when I'm looking at my candidates, I'm looking for three primary transferable skills. I'm looking for a proven PG operating rhythm. I'm asking people walk me through how you generate pipeline and I'm looking for specificity. If it's oh, I make calls and emails on LinkedIn. Okay, well give me more than that. What's your opener? What's your contact rate? What's your set rate? What's your conversion rate? I dig for details because every rep tells me I'm great at cold calling. I love to cold call and then sure enough, very few of them actually do it. So the PG is one skill that I have to have because that's a big part of the culture that I like to build. I'm also looking for the skill of complex sales management. Handing a complex sales cycle with multiple departments champion building, accessing a higher level EB and more complex deals and understanding how people progress that I don't necessarily need to have command of the message. I don't care if it's Sandler, I don't care what the methodology is. But I am looking for some of the understands complex sales process from start to finish. And then the third skill I'm looking for for the roles I'm hiring for at MongoDB and now at LaunchDarkly is technical acumen. I want them to understand the developer Persona, I want them to understand software development lifecycle and I Want them to have a proven aptitude to speak to some degree the language of the buyer. Now, candidly, I very rarely get a rep that is three for three and that's okay. I hire a lot of reps that are two for three on those primary skills. But I see in the interview process and to the vetting process, they have the acumen to quickly close the gap on whatever the third missing piece was.

Are there any aspects of interviewing that candidates need to focus on now? Heard that asking great research based questions is important. Having notes for the close like closing and following up. I'm just volunteering a few thoughts, but is there anything else you'd add in terms of how someone can really show up at their best in the overall interview process?

So I think there's elements of being succinct. And so when reps are able to convey how they do things quickly and concisely, that shows good communication. It's going to sound a little bit contradictory. But also giving depth of examples is big because reps will tell me like for example, 95% of us that have interviewed tell me they're hitting quota. Which when you think about how many actually hit quota in the industry right now, that's very unlikely. So I'm digging for the examples of specificity that tells me that what you're telling me is actually real. I think ways people can stand out the questions they ask are huge. When I open up time for questions for the rep I'm looking for, are you asking me questions that only I am able to answer? If you're asking me questions that you could have asked an AE on my team or a leader on my team, that tells me how you're going to approach a call with an executive at one of our accounts we're trying to sell to. I don't want you asking a CTO questions that you could have asked a developer. So I'm looking at that element. And then I'm also looking for people that try to close the call. Obviously don't come at me and say you're going to give me an offer. That's a committee decision. I do respect reps that will call out based on the interview. What concerns do you have with me? I'd like to be able to speak to them. When I'm asked that question, I always offer up some of my concerns and let people give their their feedback on it.

Are there any other aspects of the close, like is there anything more I can do to make myself a worthy candidate? Or what more can I do to Earn this opportunity. Now, I'll acknowledge you just said asking for objections seems to be fundamental, but I almost even want your feedback on what I just shared in terms of closing. Is that how does that come across to you? Like, what more can I do to earn this opportunity? And just showing the hunger to get going.

I prefer the seeking the negative more than affirming the positive. Which is why I like the what hesitations do you have with my candidacy? Because outside of me digging deeper into those concerns at the end of the interview with me, they're either moving on to the presentation round or they're not. And so if you ask that question, I'll tell you, if you go to a presentation, here are the things that I'm looking for. But a lot of the things that reps do to stand out in the, in the interview process are not things I give them. It's the reps that go get, for example, certified on LaunchDarkly or talk to reps to bring a point of view or do some of that deeper dig into customer stories to figure out how we fit in. That's what stands out more than asking me at the end of the interview, what else can I do to stand out? It's almost like at the end of a sales call asking the buyer, what else can I do to get you to sign a contract? It's like, well, part of sales is understanding how to do that with some initiative.

I think that's a great point. And in terms of questions that someone could only ask you, you said don't ask questions that you could get answers from an AE on your team. Like, what might be an example of a question specifically for you and your role? That would be unique.

So my rule is a little bit unique because I run a few segments, Global sdr, Global Mid Market, and North America Enterprise Acquisition. And so questions that are very specific to my role might be, how are you changing your strategy for your new enterprise acquisition team compared to mid market? Right. It could be questions around how I develop people. So a great question I've been asked is, hey, I talked to your frontline leader. I understand how they coach, how they develop. I'd love to hear how you prioritize coaching with the larger org. How do you pick which ones to spend time with? How do you develop ICs from your perspective? Those are very, those aren't crazy, complex questions, but they're questions that I will have a unique point of view on compared to the rest of my leadership team, where if you ask me a question like, what do the best reps do in their first 30 days? Well, that's a great question to ask your future frontline leader. I can answer it, but they might have more detail for you because they're the ones that are managing new reps every single day for the first 30 days.

So asking questions that are tailored to the person you're speaking to, that is a really good nugget because you might have a good question, but it's not. It's better suited for a different person. And so one other question on interviewing, and then we could maybe shift to how you rose up from SDR to AE and beyond is when it comes to technically answering questions, you mentioned you got to be succinct. I'm assuming you want to see executive presence, yet you also said you want to be concrete, specific examples and some depth of examples. But what does succinct look like? Is it answers within 30 seconds to 3 minutes. I'd love to start to flesh this out with you.

I think it's less about how long it takes compared to how much information is conveyed in that short amount of time because there are stories that can be told. Very elongated, very repetitive. Versus here was my situation, here's how I approached it, here's the outcome. If you find yourself repeating a lot, you're probably not being succinct.

How do you feel about the Star framework? You know, obviously at aws, they have their whole loop and process. I'm sure you have your own very clearly defined process to launch darkly. But do you like the Star framework or do you want people to abide by that? Or you look. Or do you have a little more flexibility?

Flexibility, okay. I'm looking to understand the impact and the problem you were solving in a relatively quick way.

Okay. And one more question on interviewing. If we look at a specific question like walk me through your background, your resume, your experience, I might think to say, you know, happy to talk about my experience, but rather than tell you about everything, I'd like to focus on a few key aspects that are relevant to this specific role as a mid market at launchdarkly. And then you kind of go frame it that way and then go in. And based on your coaching that you've been given us so far, you might want to show some intentionality behind a move. The business impact you made, the results and kind of weave a little tapestry. But I just wanted to tee that up for you to give any other feedback on how to approach that, because that's a foundational question. Everyone's going to have to answer.

Yeah. I love the way that you just approached that. What I don't want to have happen is a walkthrough of every single thing on the resume that I actually, I already did read. I do read the resume. The resume.

Resume is important.

Okay. But if I'm hearing the rep. Talk me through, here is what I accomplished, here's what I learned, here's what I wanted to learn next, and why I made the move to this company. If I'm hearing from them, the highlights of what they accomplished and learned specific to the role that I'm interviewing for, that's going to stand out a lot more compared to very generic. Well, I spent three years here, and I spent two years here. Then I spent 18 months here. There's not much depth there beyond the resume.

So we sell ourselves into a great opportunity in tech sales, just like, I mean, you did with Qualtrics, although it seems like it kind of found you and you didn't know what you're getting into once you get in as an sdr, looking back, what were some of the keys that made you highly effective in that specific role that ultimately helped elevate you to the next level?

Yeah. So I'll be very honest. I wasn't very good at being an str. I was an STR for three months, part of part time. And then they promoted me, not because I was good, but because they were growing quickly and they needed an ae. And so I was thrown onto the sales floor with really no idea what I was doing.

Wow. Plot twist.

So that. That led to two years of missing quota. It led to two years of doubting if I could even be very good at sales. There was a good amount of time where I wasn't thinking about how do I get promoted? How do I make president's club? I was thinking, am I. Can I at least be average? I see the OTE of the AE Level 3. I'm an AE Level 1 right now. If I can be an average AE3, I can make a pretty good living for my family. But there was a. It wasn't. I didn't come in and start to click. I wasn't good. What. What changed is when I started to pay a lot more attention to the buyer and conversations. I. I saw patterns for where I ran discovery the way that I thought it should be running. And I saw the buyers check out. I saw lack of engagement. I saw demonstrations. I could see when the light would leave their eyes and begin to look off screen. They just weren't there anymore. Mentally. And I began thinking, well, if I keep repeating the same process, I'm going to keep struggling. And when I began to put the buyer first and thinking a lot less about how do I get them to the next stage in my sales process and thinking instead, what decision does the buyer need to make next? What information do I need to get them to help them make that decision? And how can I portray that information in the most interesting way to capture their attention? That's when things started to take off. And that was about two years into my AE career.

I once saw a post on LinkedIn where you put together a matrix based on Personas. And I mean it was so in depth, yet succinct. It was really cool. And I don't know if you remember this because you put out so much value between LinkedIn and salesiniverse.com so. But I wanted to get into that cause I feel like it probably informed the way you message. But do you know what I'm referring?

I am very familiar with it. The Persona builder. Yeah, it's the idea that many reps go into conversations with buyers knowing very little about them. And so they're asking questions like tell me about your role. What do you care about? How are you measured? What's your day to day like? And buyers find that often to be a waste of time because they don't want to go educate you. And so I build out the Persona builder as a way to quickly inform AES. Here is how this Persona typically spends their time, here's how they're measured, here's the challenges they have, and then here's how our solution fits into that. Because everything should be very problem based. Understanding what problems are likely facing and how does our solution solve that problem better then the alternatives are likely using. The more clearly I'm able to convey that and the quicker I'm able to convey that, the more likely I am to have an actual real deal to pursue.

How important is disqualification versus, you know, qualifying? I'd love your take on that, especially as an account executive.

Absolutely critical. And it's one of the hardest things for reps to do, especially when it feels like it's so hard to get pipeline. You want to go scratch and claw and, and pursue anyone that's willing to talk to you. The problem is every call you take with somebody that is the wrong fit is a distraction from talking to people that might be the right fit. And so one of the things that we're really trying to get good at at launchdarkly is defining very clearly, these are the types of accounts that aren't a great fit for what we sell for this product line, even if they come inbound. It's an immediate red flag. Okay, here's why you probably aren't a great fit for us. I see RFPs sometimes that are very clearly written for a competitor. And I'm like, look, we could sink 30 hours into this and we're probably still gonna lose. Not a great use of time. But it's. I, I really try to teach this mentality of. I forget how I usually phrase it, but the, the mentality. There's all the, the abundant mindset. Right? The abundant mindset where I don't need to force my way into every opportunity because there's so few. I need to reject poor, fit conversations because there are so many potential high quality conversations I can pursue if I have the time and bandwidth to do so.

It really hits home with me because again, I'm 10 years into my career, but it wasn't until like a year or two ago that I really stepped into the power of disqualification and, and starting to say no to opportunities that I realized were not going to be profitable because I went through the pain of winning deals that not only were unprofitable, but I mean, I'm at a second founding seller to global startup, second founding the US business. And I've won deals that lost us money at a services company and that took a lot of effort and it actually felt horrible to close a deal like that. And so I've learned that lesson. I love what you're saying about respecting your own time and having an abundance mindset to be willing to say no to opportunities. And I've even seen that, by the way, in people in their job hunt where they got an offer from a startup that was being a little sketchy force, not forcing, but putting pressure to accept an offer when they had interviews with better companies. I've had individuals I've worked with actually walk away from those opportunities and it was the best decision ever. So, Kyle, another thing, another post that I loved is your post on winning your day gamifying your day with a point system as an ae. You said no AE that's played this game has ever missed their quota. And so I don't know if that's actually true. It probably is, but I've started using it. So thank you so much for putting that together. But can you walk us through how you gamify your point system for winning.

The day as an ae? Yeah, so I'll talk a little bit about the psychology behind it. So the premise is what you measure improves and what you measure and report on improves exponentially. I forget what famous person made that quote, but there was science behind it.

Yep.

So that's the foundational psychological element. The other aspect is if you ask the average AE or even pretty good AES, what is the most productive way to spend your time, it's not always a clear cut answer because there are so many good things that you can do in sales. There are, there are things you can do around account planning, pipe generation, deal qualification, deal progression. But I have found that a lot of AES will gravitate to the busy work. They'll do things that are busy because it feels productive. And then it's very easy to go a day, a week, sometimes longer, having been very busy, but not actually moving the needle on the most critical outcomes. And so the way the good day framework works is I give my initial recommendations for Here are what I think are the most impactful activities and outcomes you should be driving every single day. And here is the score that you should aspire to get to every single day using a combination of these inputs as inputs. Like how many conversations do you have? I don't measure calls because I've seen too many AES go make 60 dials to a stale list. They know no one's going to answer, they feel busy, but nothing got done. So I measure conversations, I measure meeting sets, I measure opportunities created. Then the important element is when I roll this out, I talk with the AES and the leaders on my team. Do you agree these are the right things to measure? If you actually do these things, are you having the best, most productive day for you? Because if it's not, it's the wrong thing to measure. Every single seller that has ever sold for more than six months has been asked to be held accountable to metrics they felt were worthless. They were asked to do things that they felt like were check the box. Not driving revenue. I can't have that happen with this framework. But once I have buy in that, yes, we're measuring the right things, yes, we're scoring those categories appropriately. And yes, I agree that if I attain that benchmark every day, it's a good day. Nobody that I want to work with is ever going to tell me I don't want to be held accountable to what I agree with makes me effective. Every top performer wants to be held accountable to what works. Top performers shy away from being held accountable to things they don't think works. But that's the premise of it.

Yep. I remember adding leads to the system, having conversations as you mentioned. Not just oh I made this many calls, but I actually connected with this many customers meetings that were set on the calendar discovery calls had. And I'm trying to think of what else. Is there anything else that is like a key activity that you would add?

Personal development. It changes and I'm rolling it out now at LaunchDarkly. It's going to look a little bit different than what you've seen. It's different than what I used it long ago because it's a different team. Right. But personal development I always include because it's important to use that time to get better as a seller. That time should be used to better understand sales process and sales methodology. It should also be used to better understand your buyers and what they care about. So a great use of time is to go spend 30 minutes to an hour reading the material that is popular for your buyers to be reading. Just like a Salesperson goes to LinkedIn maybe at this point to learn about sales hit or miss at this point I think engineers go to different blogs. They might have Reddit they subscribe they subscribe to. So I recommend find out what your buyers are reading and read that too is a great way to use that personal development slot.

Yep. You're selling to retail. Read on the latest retail trends and I'm sure like some of the analysts like Gartner might have some info or McKinsey consultancy is talking about say I'm in cloud infrastructure, the top trends in retail and cloud computing. And then you have subsets of data and AI and security, et cetera. Sales process like you said. I'm assuming you want to learn how to be efficient in your sales process terms to reduce sales cycle times and also just take more control of the conversation. Is improving on the sales process. Is that like maybe there's internal documentation that you have at launchdarkly, but is it also just a matter of reflection or talking to top performers? What does it look like in terms of or is it like reading a book with a certain methodology?

How do you Some of it is. Some of it is reading the book like Sell with by Nate Nasrallah. Great book to read. That's a great book to read. Part of it is finding people that are posting content that works today around outbound and discovery and bring that in. Don't try to apply everything you read. You need to pick people that you actually see have had success in your space or similar space at LaunchDarkly. Right now I really try my best to align to what we teach at the global level and then I go teach my teams a deeper dive on that. So as an example, we just rolled out our first meeting deck to help us have more thorough discoveries enablement. Did a great job rolling out. Here's what it is, here's how to use it. But now I want to go salesify it and make it really clear here's how I'd be using this. So I have a separate session scheduled to go deeper into that. But then a lot of the best enablement are reps taking the initiative. I had a rep reach out just today. Hey, I've got a big discovery call today. Can I have 20 minutes with you to prepare for it? Make sure I have the right questions, plan the right point of view and have a game plan. Love that. That's a great example of taking initiative, asking somebody to run a lot of discovery conversations to weigh in on your approach and getting that real time coaching. There's a lot of ways you can sharpen your sword as an ae.

I like that they had the guts to reach out to you as the leader and they took initiative and they're saying, I'm coming with a perspective. I actually put in work within a project approach and I'd like your blessing on it and feedback rather than like, oh, can you help me shape it and like come bring nothing to the table. So by the way, I noticed that that was a nice little thing they did right there now. So I love that you're highlighting the importance of learning and development and it makes me think of seven habits of highly effective people and sharpening the saw. My mind is just dancing to the topic of habits and whether they are habits that are just high performance habits or health habits that you have to show up at your best or sales specific health habits. What are some of the most important habits that have served you and served the people on your teams?

So habits. Because I look at habits as being, like you mentioned, both professional, also personal. So I'm at my best when I exercise in the morning, get a good start to the day. That's big for me. I'm at my best when I eat healthy and track what I'm eating. That's a big habit for me. I'm at my best when I consistently track the same metrics and I hold myself, my teams accountable to those metrics. That's a very important habit for me. And then another really important habit for me is developing. I am trying to think every single day, every single week. Who in my org can I be developing? What feedback and coaching can I deliver to get them to the next step in their career? And delivering on that habit repeatedly has been a big part of my professional success as a leader because when you develop people, they buy in to what you're trying to build.

So at Mongo you are leading acquisition teams. You know you're, you're the growth engine. And is that the same at launchdarkly when you head up global mid market sales, is it hunting roles or is it a combination of farming and hunting?

Yeah, so my, my mid market roles and commercial roles are both. They're hybrid. We go after new logos and we go after our, we, we expand our customer base. And then I also have North America Enterprise Acquisition which is a new logo only team new to this year to help us go focus on the upper aspect of the market for acquisition as a strategic bet for us.

So I asked that because you must have some good ideas on Outbound and I know you said you struggled early as an SDR but somehow even though you didn't do well, you went to AE and then figured things out. But you must have some great ideas on Outbound. So just high level question is, are there particular channels that you've seen most effective in outbound? Obviously with the first phone email, LinkedIn, I might have guessed that you're going to say multi thread but I just want to hit a little bit high level on, on outbounding and what you're seeing work.

I am heavily de emphasizing email. Okay. Emphasizing phone. We see our best success through phone. Right now our primary approach is building point of view across the bottom of the account. Try to have as many conversations, as many conversations as possible to go pull out code names, project names, specific goals that we then use to call the top of the account. So my enterprise acquisition team, I have the AE and the STR joint account plan. Let's go figure out because I can go in and tell the CTO hey, we help you release faster. That's very generic. That's not going to stand out. But if I say hey, we spoke to Angelica and Steve learned you're trying to go from four launches a month to eight while also improving your MTTR by X amount that captures attention and the only way to get that specificity is having conversations. And we are seeing most conversations where we get those nuggets through the phone and through LinkedIn.

That's a golden nugget. That's even enough for Outbound is talk to the lower level folks using the technology to get specificity on the business outcomes you can produce and then take that to leadership. And you said mtt, which sounds like mean time to repair and releases like how fast can you release new software? And if they can release more features for the product, I'm assuming the product might be tied to the revenue stream. You're tying into the growth of the business and meantime to repair. If we flesh it out a little more concretely, why does, why does that matter?

It matters because the longer it takes, the more customers can hurt when things go wrong. So when we look at companies having outages and downtime and the impact it has on their customer base, bad customer experience leads to customer churn. There's a lot of. There's even compliance issues in some of our industries. And so what we do a lot at launchdarkly as a plug is we're helping people release software faster and safer. Because if you don't go fast, you fall behind on product. If you don't go safe, it doesn't matter. You lose customers.

I love that we dug into it. This is an example of the specificity with which you need to go to executives to illustrate how a solution impacts again like business outcomes and the consequence of problems that if they're unaddressed. So I love that we hit on an outbound and I'm managing the time we have. We have a little bit more. I'd say we got about 15 minutes to make sure we end on time. You've managed teams and still do across commercial, mid market, even the enterprise level. And so especially for the folks that are newer to tech, sales are just breaking in, just getting started. Can you walk through the trajectory of like the. In some distinctions between the different roles, like what's it look like when you're selling commercial, what types of accounts, how much could you maybe make? Mid market enterprise.

Yeah. So commercial is traditionally going to be somewhere in the very SMB space. Up to usually 500 to 1000 employees. On the high end, you can expect to earn. OTEs are going to probably be in the 130 to 160 range. Is pretty typical for a commercial role in tech. Again, I live in my tech bubble, so this is wildly wrong for other industries. I acknowledge my bubble.

That's our bubble here.

All right, that's the bubble. From a mid market standpoint, you're looking at accounts in the 800 to 2000 employee range, depending on the company size. For some companies, a thousand plus is enterprise. Others is a much higher bar. But generally speaking, you're in that that range from an OTE standpoint, you're usually going to be in the 170 to probably 210 range in the high end for mid market and then for enterprise I've seen a thousand plus employees. I've seen it based on revenue, usually around a billion. I also see enterprise at larger companies being Fortune 500. It can vary pretty widely and so be careful on rules when you're looking at it because what is enterprise at one company is mid market at another. And the otes can vary and the experience varies. When you think about the trajectory, what really is changing the most is how many stakeholders get involved to make a decision. The larger the company often means more stakeholders and then how hard it is to get to the economic buyer level. When you're working commercial accounts, SMB type accounts, you're usually never more than one layer away from the economic buyer. And so it's relatively easy to understand their perspective, their point of view and build a business case that appeals to them in the mid market space. Now all of a sudden you're often working two to three levels below the economic buyer. In enterprise you may never talk to anybody that's closer than three to four levels away. The economic buyer. And so being able to sell effectively when you're not in the room with the buyer, building business cases that resonate when you can't talk through it and translating technical value to business value at the IC level, leader level and executive level become key key skills needed to progress from an SMB to mid market to enterprise role.

And like you said, Nate Nassarella's book selling with would be really useful when at the enterprise level, when you're a handful of levels rem from the C levels, the decision makers to empower the champion to sell internally when you're not in the room. Now I heard it said that maybe I don't know if it was you, it could have been Brian Lamanna who I recently had on the pod as well that mid market enterprise is actually a great space and I've even seen it back when I was at Google Cloud that there were some enterprise sellers. It was feast or famine. You'd have bad accounts and not do well. And some wanted to go to our corp segment which was kind of like a mid market enterprise but for digital native companies. Right. Running on the cloud. Do you think the mid market enterprise is like one of the best segments where you know, you maybe get more at bats but still good deal sizes? Again, I'm kind of projecting but I want to get your take on mid market enterprise. Is that the place to be?

I'm going to give a cop out and say it depends. Right? Because when I see like the seven figure deals being done, when I see reps earning a million dollars or more a year, doesn't often, doesn't often happen in the mid market space. Now to be fair, you can be wildly successful, make a lot of money and not make seven figures. That is not the requirement to be successful in sales. The benefits of mid market and lower enterprise is you do get more at bats. It's not as feast or famine but the there, there is a level of a ceiling on your earnings. You're probably not going to go close a $10 million deal within a mid market account. Whereas a strategic rep, if you have the right account base, you have the right product and you swarm an account, you're able to go focus in on a small number of accounts and build up this refined business case that does justify that 5 million, 10 million, $20 million purchase and that's life changing money for that rep. So reps, reps do get caught up chasing that. But there's a lot of power in being a rep that consistently hits 150% to 300% equal to in the mid market space because there you're probably making between 400 and 600 thousand dollars a year. And that's pretty good.

That's pretty great. But hey, the fact that you could make a million dollars a year seven figures in tech sales is pretty special. And a guy who's done that, that's come on the podcast. Brandon Fluharty, he made seven figures a handful of years. He was a live person selling customer facing AI technology to I think it might have been JetBlue or some big airlines. And I bring him up because I read his like seven steps of seven figures. He had like a little ebook or something and he finally realized that his introversion was a superpower. And you're an introvert as well if you can't tell. I'm an extreme extrovert but I. So we probably compliment each other well, but I remember Tate, the guy I alluded to, a guy that humbled himself to go to aws, going from inside sales to demand gen and SDR at AWS and he's just crushed it. I remember he was a top performer and he was the opposite of me and very introverted. So as we round out the conversation, let's talk about how being introverted is really a superpower in sales.

Yeah, I think there's a so one of the misconceptions of introverts and people, I've been even challenged before. So I'll go to a company event, I'll go to sko and I'm out there, I'm energetic, I'm talking to people, I'm excited. And they're like, there's no way you're an introvert. I'm like, that's what people get wrong is I can seem extroverted, I can be confident, I can be. I can be a lot of things. But it's what they don't see is as soon as I finish my speech or whatever I'm doing, while they all go to lunch, I go to my room and collapse on the bed to recharge quietly. Right. So I think that that's one piece to acknowledge is just like an extrovert can be quiet, an introvert can be extroverted. We just, it just drains us and we get tired.

Yeah, Kyle, real quick. It's like I'm so extroverted and so energetic that back in the day, say it was in the Google office if I wasn't high energy. People are like, what's wrong?

What's wrong?

Flip side, people think something's wrong with me because I'm usually so high energy. So it's kind of funny.

Yeah, yeah. Where introverts have superpowers is we are genetically dispositioned to go towards deeper, more thoughtful conversations. As much as we hate small talk, we love deep conversations. So when you think about working with an executive that really wants to be understood and drive a business transformation, they don't want to spend 30 minutes talking about golf and the weather. They want to understand, they want to talk about meaningful impact to their business and how we can help. Introverts also can come across as not being a traditional salesperson. And when you think about buyers, buyers have a bias against salespeople. So whenever a salesperson comes across as being similar to or the same as other salespeople, the buyer goes, okay, here we go again. Where the introvert, they come across a little bit different. The buyer might not have those same biases against that personality. Introverts also are usually fairly good at deep questions and understanding. So we have strengths there. But what's really important is anybody can learn these skills. That's why people always say, what's better, introvert or extrovert? I'm like, the rep that gets good is better. Extroverts can go learn the skills that are more natural to introverts, and introverts can go Learn the skills that are more natural to extroverts. So regardless of your personality, go figure out the skill gap, get good at those things and you're on your way.

Amen. And one of the greatest gifts of this path, looking back, is that it has demanded I become a better version of myself. So hey, I'm extrovert. And early on as SDR at Oracle, my time at Google and now my current company sales has shone a light on opportunities to become more well rounded. Address I don't want to call weaknesses, but imperfections that can be managed and expand who I am and my ability to communicate. So like you said, an introvert might have things to work on to become more well rounded and extroverted as well. And the key is just to get better to your point. So I wanted to ask you about sales introverts, like what led you to create that in the first place? Because you've been just crushing it on the real world and yet clearly something pulled you and compelled you to make this. It must be very meaningful. So why did you end up creating it?

There were two factors. The first factor was I was annoyed at how much bad advice advice there was on LinkedIn from people that had never been successful in sales. And so my thought process, well, if somebody that has never had success can go apparently drive some kind of impact, I don't know if it's a good impact. Maybe somebody that has done well in sales can drive positive impact. Then the other element and where I thought of the name sales introverts was kind of the, the mission of I want to be an example to people that might feel like they have a disadvantage in sales to understand they don't have a disadvantage. In a lot of ways they do have an advantage. And it's been cool getting quite a few notes the last few years around people expressing, hey, I had a lot of doubts that I could be in sales because my personality and now I realize that I can. And so as cheesy as it sounds, having some kind of an example of an introvert in sales doing okay has been a big part of the mission.

So this audience is mostly 20 to 30 somethings based on the data of aspiring tech sellers, current tech sellers, they try and break in. Maybe they're SDRs, maybe they're AES, maybe there's some leaders who follow this too. And how can they think about sales introverts? Because from what I've seen, you've got frameworks to help people succeed at many different levels. So what can they expect when they Check it out. And by the way, guys, it's linked in the description of this video.

So I. One of the things I'm most proud of is I share what I see work. I've been fortunate to win awards as an ic, as a leader, as a second land leader, as a global vp. I've been fortunate to promote now well over a hundred AES and leaders in my career. So I build out frameworks that are just what I teach my teams when I build out how to do discovery. I'm teaching the same thing to my teams at LaunchDarkly to help us improve discovery. My goal is to go expand the impact of what I'm learning well beyond the small sphere that I get to operate in as a sales leader. And you can also expect that I'm always improving it. And so I'm on my second rendition of the AE frameworks. I'm working on a big update for the third. Like as a sales changes, I want to make sure to evolve. But my, my commitment to people are. This is what. What I've actually seen work. It's not hypothetical. This is what I've used over the past years. It's what I use today. And the results would show that it's at least fairly effective.

This has been an amazing conversation, and we could fill hours and hours of podcast time with your insights. So I see we've got four minutes, so maybe I'll ask you two more questions that we'd fit in to get this done on time. One, you've risen the ranks from STR to AE and leadership, and we probably can't deep dive, we can't into leadership today, but are there common themes or a principle or two that has led to you to rise up? Have there been any common patterns?

So on the leadership side, it's pretty simple. The better I develop my team, the more I progress. Because as my leadership team gets stronger, our scope gets bigger, as my reps get stronger, we get more resources. It builds on itself. But I've always focused on developing, developing people, and my success has followed. As an ae, it was just a relentless desire to get better every single week. What were the best reps doing? What can I replicate? What can I improve on? What did my buyers need more of me? What did my buyers need more of for me? How do I deliver that? And that that obsession over always improving led to my success there.

And the final question is, it's so broad, but it's, you know, just wherever you want to take it. Any final words of encouragement and inspiration for this audience of 2030 something tech sellers, it could be career related or it could be around like what actually matters in life. But any final words of encouragement before we sign off?

I'll give a couple I'll say one there's going to be a lot of reasons why you could be pretty negative right now about careers and sales, about the economy, about AI don't like the the more you focus on what's wrong, the less time you have to go win. And the best people I've worked with think very little about what's going wrong and they think about all things going right and maximizing it. And so I'll just say that the future is bright and it's going to be even brighter for people to figure out how to make it make it that way. And then the second piece is almost contradictory, but I remind my leaders, myself, my reps whenever they're stressed about sales because Trials is a stressful job. But I'll just say it's just a job. There has never been a deal that has been worth losing sleepover. The deals that I've lost sleep over three months later didn't matter. There's never been promotions that made or broke my career. Everything continues in life and the moments of real life when they hit. And you forget all about work, whether it's sickness, family, challenges, whatever it might be, remember that perspective. And when you do get super stressed, please, please just remember it's just a job. Do the best you can, make a good living, but don't put too much pressure on yourself.

Kyle, I am so grateful we finally got to have this conversation after over a year of prospecting you you came onto the stage and delivered. This was so inspiring. I can't wait for people to enjoy this message and guys, make sure to share it with more people and make sure to connect with Kyle and follow him on LinkedIn. He has some great actionable posts and check out sales introverts.com linked in the description of this video for his framework. So you can just fast track your success and reach the highest levels that you want to reach. So Kyle, thank you for your time and to the audience, to your success in tech, sales and in life, happy selling and happy living and we'll see you in the next one. Thanks Kyle.