#149 How to Break Into Tech Sales: He Cold Called the Hiring Manager (Then Became One)

Speaker A: If you really want to stand out, here's a tip. Send them cookies after the interview because no one's done that before. I'm a big believer that first and foremost, pick up the phone. You should be cold calling every single person that you're interested in talking to at the company you're trying to get hired by. Because guess what? No one else is. I find that the reps that I end up hiring almost always have prospected into me versus just appeared on my calendar through a recruiter screening.

Speaker B: This surprised me a bit. But 76% of you who regularly watch the show haven't subscribed yet. And if you've been enjoying these episodes and feel so inclined, a free way to support what we're up to is to hit that subscribe button. I appreciate you and I'm going to keep bringing on the best guests and upping the quality for you. And if you're looking to uplevel in your career, my tech sales accelerator program is linked in the description of the video with that. Enjoy the episode. Joshua Gibbs, you broke into tech sales with no experience. You became a uh, top account executive at some of the best category leaders in tech sales like MongoDB. Then you went to LaunchDarkly and now you're managing a sales team. Let's talk about how to break into tech sales with no experience, how to become a mentally resilient seller and also talk about Omnichannel outbound, because prospecting is harder than ever before. But you've got the answers to the test. So Joshua, thank you so much for being here. Isn't it true that like you didn't even know what tech sales was at first?

Speaker A: Yeah. No. So the first time I ever heard about tech sales was uh, it was like 9 o' clock at night. I had just logged off of work at Deloitte.

Speaker B: I.

Speaker A: It was, you know, find it in tax season. It was going crazy. I was working 90 hours a week and I called my brother in law was like dude, I cannot do this any longer. There was no way I could mentally handling working another 90 hour, 90 hour work week while making 55k a year. It was miserable and I called him and I was just venting to someone that I consider a brother, right? And he just kind of turned around to me and was like dude, come, come be an sdr. It's like an SD what? Like what's an sdr? And he was like, oh yeah, like that's what I do. I, I do sales development. And at the time I was like Well, I thought you said you like cold called and stuff and like there, there's no way on earth I would ever cold call. There, there's absolutely no way. And um, there was a, there was a moment there. He was like, dude, you know you, you were telling me you only make like 55 a year. Like I made, I made over a hundred last year. Like are you sure you wouldn't be interested in like least checking it out? I was like, all right brother, if you send me your W2 and it says over 100k a year or uh, for, from your last fiscal, I will absolutely go and interview for whatever company like I'd be in. But I thought he was messing with me because he was a year out of college, he was new to the, you know, kind of professional realm as well as I was. And uh, a couple minutes later we got off the call, he said, all of a sudden I got a picture. It's like, what's this? I opened up my phone, there it was, it was like 107K. I was like, all right, well I guess I better get over this fear of cold calling because I want to make that type of money in my career.

Speaker B: So you went from 90 hours a week making 50k to a path where I've seen some people like when I was at Google Cloud, I think of Max, he, he worked 20 hours a week and made 400k, like unbelievable shift. And uh, cause that math doesn't add up. 90 hours a week, I can't even imagine making 50k. And so we gotta now unlock how you actually made it happen. But by the way, if you have other thoughts on why tech sales is amazing, we can flow there too. But I also, I wanna get tactical man on how you actually broke in.

Speaker A: Yeah, no, absolutely, uh, happy to go tactful first and then we can go into the kind of philosophy that I've adopted, why tech sales and why I think it's such an amazing career path.

Speaker B: Okay. Okay. So yeah, you're right. Let's get tactical next. So what was that first step? Did you network your way in and get like a warm foot in the door? Uh, and I guess you also have to figure out the right targets, the types of companies you wanted to work at. And so what was the first tactical step for you?

Speaker A: Yeah, so the first tactical step was I had the option to go all in with my brother in law. So whenever you look at SCR roles there there is a wide variety of opportunity in the SDR organization. There are a lot of companies that you Know you start out at 55k base and you can make up to 80k OTE and that that was great. But my brother in law just joined a company which had the most outrageous OT for an SDR that I'd ever heard of. Well since then been in tech for five years had ever heard of. Um, he was making a very significant amount of money as an sdr, um, over a six figure, you know, OT packages in sdr. I was like I don't want any of those other jobs, I want that job like I want an OT of a six figures coming up from 55. And so I'm a stumber guy. Um, I don't really believe in being spoon fed opportunities. Um, I definitely have the option to go and have my brother in law refer me in. But I actually decided to prove to myself that I could take an outbound approach to sales because that was my big question, right? It's like I'm an accountant, I'm a cpa, I know how to do Excel and like do I have the chops to be able to break into an organization? Um, and that's where I wanted to prove myself was like if I can break into this role and get the job then it shows that I belong in this category. So funny story, we told the hiring manager after I had been hired that we were related because we wanted to get my brother in law the referral bonus. But no wondering the entire process knew at all that we were related. They thought I was just some candidate coming in. I had no outside influence breaking into this particular role. Um, the first thing I did was I took an omnichannel approach to getting hired. So we spoke a little bit about how I approach um, omnichannel prospecting when I coach my reps very early on based on the great sales content all over LinkedIn, Josh Braun, Kyle AC, et cetera, I had an idea of what outbound was supposed to look like and I took the approach that I would rather show them I could do the job before I was actually in seat to make me the one that they wanted. Hire to hire versus the people that might have two or three years of SDR experience or some sales experience but are just going through the normal process. So I posted the other day on my LinkedIn but I actually sent the original email or LinkedIn DM that I sent to the hiring manager that ended up hiring me. He was the director of sales development at the company at the time. Um, but it started with any sort of omnichannel, right? I sent emails I LinkedIn DM'd, I cold called them, I did the whole thing. And so everything was unique because it all pointed to that LinkedIn DM to say, hey, this is who I am, this is why I'm trying to get into this career path and this is why I think you should give me a shot. And I did it across all four of the hiring managers that were there. So there were uh, three hiring managers and one director and I prospected in all four of them and I was able to book the meeting and get the opportunity.

Speaker B: Wow. And this is real tactical and I can't believe that you decided I want to prove to myself I can do this. And you didn't take the warm intro and the silver platter. You didn't tell them until after. So, um, you know. And who was it again? What family member was it?

Speaker A: Uh, my brother in law. So my uh, okay, yeah, my wife is a twin and so her twin's husband was, was who was the sdr.

Speaker B: So just to tie about, you did still get him the referral bonus?

Speaker A: I did get him the referral.

Speaker B: That's cool. You were, you like orchestrated this thing incredibly. And the reality is most people aren't going to have a warm intro and a silver platter. So that's why this is so valuable. And you took a multi channel approach. You're emailing LinkedIn, cold calling and you alluded to reaching out to the um, decision makers, the sales leaders. And so tell us, I want to push a little more to get even more tactical on how you actually got in the door. Are you saying that you went to like three or four leaders and there was one that got back to you via LinkedIn specifically?

Speaker A: Yeah. Yep. So again, I'm a big believer in an omnichannel approach. So even this was back in 2020, so I believe this was like November of 2020. So even time automation was out of control. Right. There was so many LinkedIn automation tools, there were so many sales outreach tools. And so unbeknownst at the time, because I had no sales experience whatsoever, I actually stood above the noise during my, my recruitment process because I called them and left them a voicemail. I sent them an email and I pointed both the email and the cold call or cold call voicemail to that LinkedIn DM and that's what actually earned me the response was that multi channel approach.

Speaker B: Yes, uh, yes. And it's the same in actual prospecting. You use a voicemail. Voicemail, uh, one of the most underrated, underestimated things in outbound to actually point to the email or the LinkedIn. And so I'm going to keep pushing us to get more tactical, man, because this is gold. Right? It's like, what did the voicemail sound like? Can you remember?

Speaker A: At the time? It was horrible. Um, it's much different than now, where I've had four or five years of sales experience. At the time, it was, hey, this is Joshua Gibbs. I'm really excited about the SDR role. I sent you a LinkedIn DM. Um, right. Um, of course, that changes from what I would do today or what I would recommend someone to do today, which is do a ton of research on the company, take advantage of AI, make sure that you're getting good understanding of the problems that they solve, the ICP and the Personas that they deal with, and then come up with a hypothesis of why you would like to be at the company and why your skillset would help and make them successful. That's how I would do it today. Now, Joshua Gibbs, five years ago, who was a cpa, had no idea of any sales tactics whatsoever. And I just had a little bit of grit and a little bit of luck to get me there.

Speaker B: And what's so encouraging about this is don't wait to be perfect. Just do it scared and underprepared, but do it, like, leave the voicemail. And that earned you the opportunity. So that's the. The beauty of your story. I'm glad it wasn't perfect because it just shows. Guys, pick up the phone and make the call. And I did talk to, um, an SDR, uh, leader Orem. I was at Outreach's Unleash conference this past week, and she said, there's 225 candidates for one of my roles. Only one person called me. And so even I understand they didn't, like, pick up the voicemail point of the email. But don't you think there's just less competitions on the phones? Right.

Speaker A: I have a whole strategy whenever it comes to getting whatever tech job you want. Um, it is a very tactical strategy that, um, it is all about making sure that you stand above the noise and you're different from every single candidate that is applying to that same role. And I truly believe that it is the reason why that I have gotten the opportunities that I've gotten. So I'm a big believer that, first and foremost, pick up the phone. You should be cold calling every single person that you're interested in talking to at the company you're trying to get hired by, because guess what? No one else is. And if you do it, you set the bar up here, and everybody else can't meet that bar because they're not willing to make themselves uncomfortable enough to call a hiring manager.

Speaker B: Yeah, it reminds me of a Tim Ferriss quote, and I don't remember it exactly. Oh, I have it. Actually. Um, I have it because I have this paper I read to myself every day that inspires me. It's a little messy, but it says, um, the fishing is best where the fewest go. And the collective insecurity of the world makes it easy for people like Joshua Gibbs to hit home runs. While everyone else is aiming for base hits, you're aiming for base hits. You know, cold applying and getting ruled out by ATS or sending messages, which is still good when Joshua Gibbs is hitting home runs on the phone, baby.

Speaker A: And that's just the tip of the iceberg. Um, the way I got into MongoDB was a very interesting story as well, which I'm happy to go into or go into a different direction if you want to.

Speaker B: Ah. Oh, man. Dude, there's so much here that's so valuable because so many people, I hear, whether it's the channel or people that reach out to me, they struggle to get interviews. We will get to interviewing as well, but I do want to hear the Mongo story. Um, and the only other thing, man, I just. I'm getting so tactical with the voicemail now, right? It's. There's a. What Joshua Gibbs knows now to bring a relevant value hypothesis. Can you just. I'm putting you on the spot, but just an idea of what that might sound other. That versus the previous one of like, hey, I'm, um, Joshua Gibbs. I really want the opportunity, you know, like what it sounded like, like a high. Like a high level example.

Speaker A: So if. If I was going to launch Darkly today.

Speaker B: Yeah.

Speaker A: Uh, so I would leave a voicemail. Let's say I called Kyle Hayce or one of the other sales leaders the. The organization. I would, uh. So the. The unique thing about voicemail is it's guaranteed to be at least read, right?

Speaker B: Yes.

Speaker A: So the most important thing to think about is whenever no one. No one above a manager level is ever going to answer the phone. If they do, it's an accident. Um, I get cold called at least 10 times a day, and I'm a nobody. I'm a sales manager. I don't make decisions. I do not have budget. My VP does, but he's almost impossible to get on the phone. And so whenever you think about each touch point that you make. And this goes for interviewing and it also goes just for general prospecting. There are very few opportunities where you are guaranteed someone is going to actually read what you have to say. And one of the main opportunities is a voicemail. Because I read every single voicemail, I don't listen to it. I read every single voicemail to me because I want to know who's calling and if they leave me a voicemail, it's probably somewhat important. And so first and foremost I would keep it very simple and sharp. Right? I don't make this long, don't make it, don't rewrite the wheel because your relevant personalized email should already be the powerful thing that you've already put into their inbox. The thing about the voicemail, you want to do a brief hypothesis of why launchdarkly a brief hypothesis of why you would be a good fit and then a direct directioning to the inbox where the email is sitting for them, waiting for them. And then the LinkedIn DM where you sent a very similar message, slightly shorter as well. And so that, that what that does, that draws their attention to one of three, three places. For my boss, it would bring him to LinkedIn because he, he loves LinkedIn and he would look at the M message, take a look like, oh, okay, I'm interested in this candidate, maybe worth having a conversation with. Um, for other bosses that might be less LinkedIn heavy. Okay, like come on, this guy cold called me, he must be at least decent, right? I should at least read the email. You'll read the email. Well, let me tell you this. Well, what if the email has a 30, 60, 90 day plan about how you would join the company and crush the role? Well then I guarantee you you will have an interview.

Speaker B: If you're an SDR or account executive who's fresh in your role and you're trying to get off to a hot start or a seller who's trying to turn things around and you want to crush your metric and up level to your next promotion, then consider booking time with me at my calendly link linked in the description of this video because my tech sales accelerator coaching programs have been helping SDRs and account executives in big tech at Oracle, AWS Databricks and in the startup world crush their quota and up level in their career book some time and we'll map out a plan to hit your unique tech sales goals. All right, let's get back to the episode. You got me fired up. I got goosebumps. You just can't see it because. Absolutely right. Like throwing that 30, 60, 90, that just shows your commitment and your hunger. So, so basically the voicemail is going to be shorter. The email is a cornerstone. And so the email itself, and then we will get to, um, it's going to be fun to talk about MongoDB and then also get to the interview process. So, um, what does the, the, the email look like? That's where you have your hypothesis on, like, very specifically, why you want to bet your career and launch Darkly and why you're going to be a fit for the role. And it just. Can you flesh that out a little more?

Speaker A: Yeah, absolutely. And I think this is really important. So I've been blessed that I've had an opportunity to hire five people so far in my career. I've been a leader for six months and each one of my candidates stood out in some sort of way. Right. And I think that the candidates that I ended up hiring really differentiated themselves throughout the process. And so the way I would structure the email to stand out is that almost every single candidate I speak to is like, I love LaunchDarkly. I think it's the best thing. I'm like, so, like, do you know what we do? Like, like, do you know the Personas we sell for? Like, you have any. Have you actually ever done research on LaunchDarkly or is this just the same templated response that you send to every sales leader? So in the era of AI, you can do hours of research within five minutes, come up with a really, really strong hypothesis of why it's a great company? You can put that down and then you can, you know yourself better than anyone. You have to sell yourself. You have to tie your experience to what they're looking for. So look at the dot description. Are they looking for someone that knows outbound? Uh, are they looking for someone that can handle a hybrid book where growth is important, but also new business acquisition? And you have to make sure that you tailor your messaging to what the company is looking for, because each company is different. So if today I send that email to LaunchDarkly. If I was pging into Joshua Gibbs and I'm, uh, a new AE trying to break into LaunchDarkly. Hey, Joshua. Notice that LaunchDarkly is building, helping externally facing agents be built. One of the most critical parts of the agentic, uh, lifecycle right now is what LaunchDarkly is sitting in. I am a new business acquisition rep at XYZ company. I generate XYZ pipeline and I've closed XYZ deals. I believe I can take that success and bring it to LaunchDarkly. Here's my 30, 60, 90 day plan on how I would your team. I think that would earn a response every time.

Speaker B: Hey, what a masterclass on getting in the door. Um, across just multi channel. We gave examples of the call and the voice, uh, mail, the you know, LinkedIn message. And this email message actually is a cornerstone. And you could see the audience get a feel too, like little nuggets of this will find their way across the channels. And so I say now we talk about uh, you know, getting into Mongo. That's an amazing company. What an elite sales organization. I know Kyle, um, your boss was there too and he doesn't pick them wrong and clearly you've followed suit. So um, you know what, what drew you to Mongo? And then what are some of the lessons you learned from getting in there?

Speaker A: So it's, it's interesting. Whenever I was looking at organizations I was at a, uh, an accounting technology company that was a great fit for me from a understanding perspective. I, I'm a cpa, I'm an expert in accounting technology. I felt at the time that there was a skill set that I was missing which was truly being able to be a full cycle ae. Right. So I was in this situation where I was doing well. I was running very nice, uh, size deals but it was a lot more of a, hey, you manage the deal throughout the process and less of my SDR roots. Right. Like there was a lot of, you know, kind of this more deal management aspect and I felt like if I really wanted to make it within my sales career, I should be able to own the process from prospecting all the way till closure and be able to do it in a repeatable format. And so when I was looking at companies I candidly, I was training someone else that had just been promoted from SCR to AE at my previous my company before Mongo. And, and He's a huge LinkedIn guy, loves following all the influencers. And I actually scrolled onto Kyle's post like, wow, that guy actually sounds like he's somewhat intelligent. Like I'm going to follow him. And then uh, over a course of a couple of weeks I just kept seeing this guy pop up and I was like, man, he really is a smart guy. Um, seems really nice, really, uh, like his content. I, you know, all that. And then all of a sudden he posted a job opportunity. And so at the time I wasn't really looking but he had made me curious enough about the role just from his, his Persona, how he kind of presented himself out into the world that I wanted to work for him or at least have a conversation with him to see if it was something that would be worth me making a bet on. And so I like, kind of similar with, you know, what I just stated. I sent out a LinkedIn DM to him. I was gonna call him. Uh, but before I could call him, he responded to me and sent me to his hiring manager. Um, and then that kind of became the process of me joining MongoDB. Um, I had an amazing interview process over there. Had, um, a great leader, um, at the manager level. Uh, so Kyle was the second line. I, uh, had a manager, the first line that I really appreciated and did a lot for my career. And, um, the interview process was great up until the point I withdrew from it. Um, yeah. And so I, uh, actually was to the point where I was going to the final round of the interview, and I kind of was looking at my pipeline, at my current role. I was like, dude, I don't think I can walk away from this. And so I withdrew my candidacy. And what I'll tell you is the way that Kyle responded to that is one of the reasons why I work for him today. Um, he. He messaged me privately, like, just, you know, this. Of course, I'd mainly been interacting with the hiring manager at the point. At this point, because Kyle's the second line. Um, he messaged me privately and said, hey, man, I really, really appreciate that you, you know, didn't. That you were honest with us about where you were at, how you felt about the process before. We committed all the time to bringing you through the final round, and we're excited about getting you on boarded. I understanding timing is not right now, but please reach out when timing is right. And guess what? Three months later, timing was right. And so we picked up right where we left off. And I felt like I had found a leader that truly respected where I was in my career and wanted the best for me versus a, uh, leader that was willing to get me at any cost.

Speaker B: Wow. Do you think that setting aside, you know, product market fit and the total addressable market, which, honestly are great things to think about, and when I had Kyle on my podcast, he talked about that with Mongo and LaunchDarkly, and you want to ride that wave, but do you think that having the right leader is actually more important than anything else?

Speaker A: I don't think it's more important than anything else, but I do think that you would Be foolish not to find a shepherd in your career.

Speaker B: Mhm.

Speaker A: Now, the right combination that I found so far and Kyle, my kid, you know me and I look, I love Kyle, but man, you know, I probably get on the guy's nerves ever once in a while because I'm a, I'm a go getter. Right. Um, but I found a combination of a leader who is not only thoughtful and intelligent, so he's found a company that has a great product market fit. But I've also built enough of a relationship where he has become a shepherd for me. He's. I've come from Bongo to launch Darkly. Um, he's promoted me into leadership. And so I've had a really unique relationship where I've had someone shepherd my career in a very meaningful, intentful and intentful way. And I think that is incredibly important that you find someone that is intelligent, that you can follow, that will make the right choices. Whenever they're making their career pivots, right, like they're going to go to a company that has the right product market fit and then if they're truly a shepherd of you, they'll bring you along for the ride. Right. And that's what I think is really, really valuable is whenever you get an intelligent leader that can make the right calls on the market and also willing to mentor you and develop you and grow you and bring you along for their journey as well, I think that's a very special relationship.

Speaker B: So having a leader that's inspiring and a shepherd is very important. It's not the most important thing though, and that's a good insight. At least that's your perspective. So as people look to find the companies to bet their careers on, what would you say is actually maybe the top factor or two to look at? And obviously you really hope you have a great leader as well. What are those factors?

Speaker A: Yeah, so you could have the best leader in the world, but if the product sucks, you're not going to do well. Um, I have a beautiful family that my job is to provide for them and I'm very lucky to do so. My number one commitment to my family is to make sure that we have a nice house, plenty of food, clothes, um, and it's my job to figure out how to do that. Right. And so for me, the most important thing when I'm looking at SaaS organizations or tech companies, not really SaaS organizations anymore, but tech companies, is making sure that the product is actually needed by the market. And I think AES make huge mistakes because they get excited Especially if it's someone that, that's coming from an underperforming organization, they'll choose anything else. They won't be selective, they won't be targeted and thoughtful about where they're trying to go. And if you just blindly make decisions based off of who's going to hire you next or the biggest ot, you're going to land in probably a worse spot than where you're coming from. So I think understanding the product market fit is so important for you whenever you're making your decision.

Speaker B: And let's think practically about some of the signals that that's there. And so I'm just going to throw out some stuff like I mean in terms of stages of growth of a company, it seems like seed stages to figure out the product market fit. Series A is maybe build out the maturity of the product and like B and beyond, you know, you start to really get like that's when you're scaling. But so it's like yeah, you want to get to a company with a certain level of maturity and you could look at funding as a signal, but you've also got like the analysts like Gartner and Forrester and then Gartner is their magic quadrant and up into the right is a leader. And there's different things you can look at, you know, um, maybe the customer base on enterprise customers on the website. But I'm throwing out some ideas like how maybe it's just so obvious because Mongo and LaunchDarkly are just unbelievable companies. But how do you think about assessing product market fit?

Speaker A: So my answer today is very different from what it was whenever I joined LaunchDarkly, mainly because of the role that agents and AI play in the market today. Um, so I look at three things or I look at, I compartmentalize companies in three different ways. I compartmentalize them as an AI first company. So a company that is on the leading edge of AI. I then see companies that are supporting the enablement of AI development as a second category and then I think of a SaaS company as a third category. And so there's three different categories. So when I look at the SaaS category, the first thing I think is, is that can this be vibe coded within a weekend and easily replaced as a solution? And if the answer to that question is yes, then it's probably not a company I personally would want to make a bet on for the long term impact of my career. Right. So that's, that's kind of the first category. And then whenever I think about the Other two, uh, SAS or AI development support. That's a really interesting category because let's look at anthropic, let's look at OpenAI, let's look at cursor, all of those teams. Like, it's not like you've missed the wave if you're joining those guys, because you're not. You're going to have a great career and you're going to earn great money, but the equity packages are probably pretty already distributed, top heavy. Right. So you're not going to make that massive upside that you really want to make. And so I really think that second category of AI supportive, like coding supportive companies are where you want to be. Who's helping these people build AI? And that's what excites me because it's like the amount of development that people are doing today is 100xing what they did six months ago. And so if you are at a company that is enabling that in a way that is helpful, the upside is limitless and the potential of the company is limitless.

Speaker B: So LaunchDarkly is one of those, right?

Speaker A: Yes.

Speaker B: Okay. And so here's what I want to do. I'll throw out some, uh, I could throw out some other examples of companies like that. But I also want to hear it like, it's fun to plug a little bit like how LaunchDarkly is enabling it, because I'm actually curious. But it's like, let's look at a few other things. Nibius, like my former Google Cloud sales leader went to Nibius, and they're like a cloud infrastructure for AI. And I've heard of Core Weave, they're kind of like a cloud for AI. So these are alternatives, of course, like Google Cloud, where I sold, uh, aws, Azure Power infrastructure that supports AI. But now there's these niche cloud providers. And then of course there's Nvidia, there's my buddies at Vast Data, the fastest data infrastructure company ever to 100 million. But now they're like way beyond it and they're like an AI operating system. So I guess that's kind of what we're talking about is like maybe developer tools, infrastructure and data platforms that power AI.

Speaker A: Yes, sir.

Speaker B: Would databricks. Databricks, man. They support unstructured and structured data. That actually would be an example. Right.

Speaker A: I think databricks is a great place to be right now.

Speaker B: Yeah. Okay. So it's funny because we're making it tactical and some of our audience members might see like, okay, these are cool places, but let's hype up, man. LaunchDarkly, uh, and how it empowers AI. And like, why you're so excited about it, because there might be some future LaunchDarkly sellers in this audience. And I know certain current reps will see this too, but go ahead.

Speaker A: No, I hope so. So it's crazy. We are. There are two problems that I'm talking to VP of Engineering and CTOs every single day. It is a repetitive problem that everybody is facing. I was at a customer on site in Seattle a couple of weeks ago, and the one thing that, that our, uh, the VP of engineering there said was I was in a room with 20 other CTOs and VPs of engineering having a conversation about the exact problem that LaunchDarkly solves. And we had no idea to solve that problem. And so where we're sitting is that there are two pain points that are just hurting people whenever it comes to building out, building AI. Uh, building with AI or building AI. So they're two separate, distinct problems whenever it comes to building with AI. So using Claude Cursor, um, you know, whatever, whatever tool that you're using to accelerate your code development, there is candidly, so much code being going into production, it's either allowing more bugs to enter production, which is causing downtime issues, which has massive business impact, or it's the flip side because there's so much code, people are terrified to release it because we have no idea what's in it. And so development and, or, uh, sorry, releases actually slow down. And so that's one problem we're solving. And that's a massive problem because everybody's experiencing it. The other problem is no one knows how to build AI agents. Um, everybody's figuring it out. It is complete green space. And it is one of the most exciting points in my career because I've never. I was too late to the party for the cloud boom. It was just like, by the time I got into tech, it was. It had already passed. Um, but I'm assuming m, this is what it felt like to sell in the cloud boom, where everybody was learning every single day. Like, no, no one is. It wasn't. Is an expert in agentic AI. Everybody has no idea. There are true very, uh, intelligent engineering leaders and CTOs and thought leaders in the space that we can influence as sellers at LaunchDarkly, because we have such a strong opinion on how LaunchDarkly can fit into building AI agents. And guess what? It's working. And that's what's so exciting. Is that what the problems we are solving are the problems that directly correlate to what the leaders on our prospect or customer sides are experiencing. I've never seen such synergy between a company and our customers. It is absolutely amazing to be part of LaunchDarkly right now. I'm so grateful to be here.

Speaker B: Wow, you got me fired up, man. You're riding a wave. You're solving very meaningful business problems on that wave. And uh, if I was a W2 seller again, I mean, I'd want to work for a company like LaunchDarkly. And you gave us a nice little show verse tell about how to frame value to prospects even in a cold call or a discovery call. I love too like the social proof or that least alluding to. You know, I talk to CTOs and VPs of engineering all the time. And in fact I was in a room of a hundred. Like this is like storytelling. But also, hey, I talk to people like you every day and they're running into a couple challenges and you actually built up like suspense in my mind too. And. And then you're talking about problems that impact downtime, which costs company revenue and I just can't even imagine sometimes cost companies millions of dollars depending on their scale and slow time to release of software because they're afraid making a mistake which could like erode their competitive advantage and have them fall behind in their market. So. And then not being able to even build, uh, AI agents and ride the wave. Like, dude, that was powerful the way you framed it and clearly a very precise control of how you frame ultimately what prospects care about which is relevant challenges that are impacting them. And so is there anything you would add though on kind of meta, on what you just did there? You also were just speaking passionately from the heart, but anything else you'd add,

Speaker A: so, you know, it's something, uh, I'm going to piggyback off of something that Kyle has been teaching us as leaders, which is we are in a really unique spot where AI is allowing sellers to gain technical acumen at a rapid rate. So one thing that I've done differently than a lot of my peers, not necessarily at LaunchDarkly, we've, we're locked in at LaunchDarkly with AI. But what I've seen in, in different, um, groups that I'm in and different convers. Conversations I've had with people across the industry is that we use AI to understand our product at a more technical level than we could six months ago. So us as sellers, even though we're not SEs we have our SE counterpart who are the technical resource. We have a better understanding of the challenges, our prospects, our uh, prospects and customers are dealing with because we sit there and we leverage AI to understand what they're building, understand how they're building it, understand why it's a business impact. And whenever you go that second and third layer deeper and then understand the core problems that these Personas are facing, well, you have a winning combination there.

Speaker B: So I want to manage our time because we could fill multiple podcasts, but this has been unbelievable, man. So tactical and a lot of showing, verse telling, which is huge. So just high level look at the interview process and just extract a nugget or two of like if we had to 80, 20 the interview process, like what's the 20% of things you might have done or you see top candidates do that moves the needle to get the job.

Speaker A: Yeah.

Speaker B: What are those? Few things to stand out.

Speaker A: Yeah. So first and foremost, the most important thing is to realize that as the seller, you are the talent and you are in the front seat. If you are top tier talent, let's change the attitude. You are uh, you are an asset to this organization. So you should be interviewing them just as much if not more than how they're interviewing you. And so I see a lot of reps come in and they're very timid and uh, they're scared to ask questions or they'll thoughtlessly like write one question to ask at the end. No, the candidates I get excited for come in are like, why should I work for you? Like, you, uh, know, I had one candidate that I hired recently, she's phenomenal and I, I planned to interview her and I got on the call and it was discovery on me. And I was like, oh my gosh, like this was amazing discovery. You asked second level questions, you asked third level questions. Like so, so shifting that mindset to you're interviewing the company as much as they're interviewing you, like this is a mutually, mutually beneficial relationship. This is not a one way street where they hold all the power. You, you as the rep are the talent and hold a lot of power. So that's one thing I see. The next thing I see is the prospect into the organization. I find that the reps that I end up hiring almost always have prospected into me versus just appeared on my calendar through a recruiter screening. I very rarely hire people just naturally that appear on my calendar. Um, I hired a guy recently, um, had experience selling elevators. Not my target ICP Persona. I would never like look for him on LinkedIn. Uh, the way that man prospected into me was phenomenal. The LinkedIn message, the emails, the, the. And, and candidly, on my first interview, I told him I wasn't interested in hiring him. And guess what? He proved me wrong. Now he's one of my top performing reps whenever it comes to AI understanding

Speaker B: and oh my gosh, from elevators to selling cutting edge technology, empowering the AI revolution, like that is ridiculous, man. And so one, he sold his way into you. Um, and he probably messaged you. I'm just going to assume in a way that you messaged. But is there anything you would add? Like was there anything. Just real quick before we get to what he did in the interview process, was there anything in particular that stood out on how he messaged you or was it kind of what you described already?

Speaker A: It was kind of what I described already, which is what made me pay attention to it. Yeah, I, I get a lot of messages and like I said, I'm a first line leader that's been a leader for six months. I'm nobody special. But if I get prospected into and I get bombarded with messages, if. Imagine that at a VP's level. Right. And so you really do have to stand out in each process. And so whenever candidates do stand out like that, I take notice. Um, and he was one of those candidates that stood out. Um, another thing that sounds really silly and I will. It is nitpicky. I never notice when someone sends me a thank you note, but I always notice when they don't send one because it's like, it's such a reflex. Like people always send thank you notes, um, but whenever they don't, it's always a yellow flag. That's just like, it's just, just like what? Like. But if you really want to stand out, here's a tip. Send them cookies after the interview because no one's done that before except for me.

Speaker B: I've done, uh, so you, you sent cookies after an interview?

Speaker A: That's how I got before my final interview at Mongo, after I went back and rejoined the process, I sent all the interviewers cookies beforehand. And ah, I love that.

Speaker B: And you know what? That's actually, I've never seen that before. I've never done that before. And I've done over 200 plus podcasts with a ton of leaders and also real world sellers and people who freshly broke in. I never heard it. Now when I was, um, going for Google and I did get it, Jen, my recruiter, I did Figure out her favorite coffee and got her blue bottle coffee. And I did wonder. I'm like, am I allowed to do this if it doesn't matter? So similar type of thing. Um, okay, so. So as we start to round out, I. I have to go back to this guy who sold elevators. He must have given you a good elevator pitch. Man on getting into work. Uh, for you, pun intended. Uh, I'm a dad jokes guy. But hey, what made you change your mind when you. You did say, like, I actually don't plan to hire you. Something like, you said something like that, I bet. I don't know. What did you say? And how did he change your mind?

Speaker A: I can tell you the exact moment that he changed my mind. Um, because it's whenever I called my. My director. So, uh, my second line leader. Because Kyle's now a third line leader now. Yes. Tons of promotions. Um, I m called my second line leader. I was like, dude, I don't care what you say, and look at his resume. You need to interview this guy. Um, so we were talking about how, like, his sales process with the. With the elevators and how, um, you know, that the problem that they were experiencing was that whenever. Whenever you're supposed to purchase the elevator or kind of make the decision about the elevator is during the architectural process. You don't just build the building and then put the elevator in. You have to design the building around the elevator. And he was like, well, I started to notice that. And so I started to take the architectural guys out to lunch and have conversations with the architectural guys, and I convinced them to design around our elevators. So whenever they came around to purchase elevators, six months later, they only had us as an option. And I thought that was brilliant.

Speaker B: Uh, and it shows. Hey, maybe there's a little more nuance and complexity selling elevators than I realize. So I've heard it said that, um, you know, John, uh, McMahon, who's a good leader in our space, he's advised a lot of CROs. He just talks about looking for things like coachability, grit, emotional intelligence, and foundational things. And, uh, clearly you found someone with those qualities and with, uh, you're able to assess as a leader? You did a great job with this. Those transferable skill sets and the transferable mindset. So that is so cool. And how encouraging is it, um, to see someone go from elevator sales to tech sales? I've seen mail men get into tech sales. Like, it's just unreal. So, all right, I want to round out with this. There's so much more I want to ask you about, but we'll save it for another conversation. Um, you were so terrified of cold calling. You told me, um, and I'm not going to steal your thunder and put in perspective how terrified you were. I'd love to hear the story from you, but you transformed it. Became a top cold caller, a top rep, um, and leader. And now look at you on a podcast here, just sharing, like, dropping gems, man. So it's like, what. Where were you at originally with cold calling? Put that in perspective. And how did you build the mental resilience to get to where you are now?

Speaker A: No. So my. My history with cold calling is. Is a hard one. Um, it, to me, it wasn't a do I go into sales. And like, I love. From the day I joined a sales org, I loved it. I was like, this is what I'm meant to do. This is what I want to do with my career. And then it was like, Then the cold. As I had to start cold calling, it was. It was torture for me. It was because I'm, um. There was a lot of, uh, anxiety involved with not being able to control outcomes. Right. And so it's something that, you know, whenever, as someone who is. I'm very intentional with how I present myself, what I do, um, you know, and I like to control things. And whenever I was then reliant on someone else's response, and I had no control over that. And then the response was, most of the time, nine out of 10 times, rejection. It really started to impact my mental health in a pretty massive way. Um, to the point where I'd lost weight. I, um, was really reconsidering my career path. I was like, I don't know if I can do this long term. Like, this is mentally draining. I'm, like, sick. I'm losing weight. Um, and really what it came down to, to get over it. There's a few things. Um, first and foremost, um, I'm the biggest believer that we should get rid of every slimy sales tactic imaginable, because we are not salespeople, have a negative aura around them, I guess, whenever it comes to, like, how people categorize our career. Um, and I was looking into that aura. Like, I was like, I'm double, double dialing these people so they pick up and I'm doing, like, weird sales tactics where I'm sending them a $50 gift card for them to take a meeting. And that didn't resonate with what I felt like I was bringing to them. Right. Like, I was bringing a solution to A problem that they might have. And these sales tactics that were, you know, at the time very popular in the 2020, early 2000s, uh, during COVID just didn't resonate with me as a person. Um, and so I had to shift from that to a very open and honest, transparent approach to sales. Um, especially within cold calling. Um, I know permission based openers are one of the most heated, debated topics, um, ever. You know, some people say they suck, some people say they're awesome. I find there is no greater power than a permission based opener. And the reason behind it is there's a little psychology attached to it. Whenever you get a cold call and you pick up the phone, you're on the defensive, someone is breaking through your day, you have no power and you feel like you have to be the jerk to hang up, right? I think there is so much power in giving the person that's receiving the call power to be able to say, no, thank you. Because not only are you giving them the psycho psychological aspect of like, okay, I can control when I end this call. And like, okay, I'm, I'm willing. This guy was nice and transparent about the situation. I'll hear him out. That was a huge shift for me whenever I took the psychological burden off of myself, um, and turned it over to like, look, if you don't want to hear me out, I'm not going to force it down your throat. That was a huge change for my mentality and my, my psyche. Um, and then really the third thing was, I hate to say it, you just suck it up and do it. Um, that's not very tactful or tactical. Um, but at the end of the day I really love, loved my job. Like as an scr, as an ae, um, now as a sales leader, I, I truly enjoy what I do. I'm not a person that would do this if I didn't have a blast doing it. And I wasn't going to let one small part of my job if I wasn't going to let 20% of my day ruin the other 80% of my day, that I was doing something I really, really enjoyed. And so whenever I made that decision, there was a lot of, um, a lot of internal maturity that came through the last three or four years that got to the point where I was able to do it with confidence and then I had a strategy around it. I have my, my permission based opener, I have my hypothesis how we can help and I, or excuse me, a pain point understanding, uh, of the pain points that they're Experiencing and a hypothesis about how we can help. And whenever you have all three of those things, you are empowered to make the cold call. And you're also giving them the respect they deserve to be able to decline the time if they want to to.

Speaker B: Joshua gives everyone what a conversation. And I want to encourage you all to follow Joshua on LinkedIn like I do. I love his posts, I'm learning a lot from it. Um, and make sure to reach out to him and, and share some love, you know. Share what? Like a nugget that stood out from the conversation, that's helping you in your job hunt or even on the phones. Um, Joshua, any other ways to engage with you? I thought LinkedIn might be the main one, but is there any other ways?

Speaker A: Yeah, LinkedIn is the main way. Um, always responsive to anybody that reaches out to me. I'm, I'm here to help and help people further, further their careers. Um, LinkedIn is an amazing community that's helped me tremendously. So I would love to return to favor the favor to some of you guys.

Speaker B: Don't hate me. But one final thing to crescendo in the conversation, we said we would say why tech sales is amazing. And even if it's just a brief thing, take us home with. Now, looking back, you've been at top companies and our manager. Why did this prove to be such an amazing path?

Speaker A: Yeah, so there's very few jobs where your inputs lead to very significant outputs. And so what I found in my career is if you control the inputs you put over put in day over day. So the amount of dials you make, the amount of prep you do before each call, the amount of, uh, partnership and collaboration with your solution engineer. You control all of this, but what you don't control is your outcomes. But what I've noticed that makes me love tech sales is as long as I control those inputs, and I'm fanatical about those inputs, the outputs will usually come and if they don't, I have done every single thing I could possibly do to control what I can control. And the rest is up to luck, a higher power. Um, but it's not on me because I've done what I'm supposed to do. And that's what makes it amazing because at the end of the day, if you do what you're supposed to do, you're going to get an amazing upside.

Speaker B: I love this path, my friend, and I'm glad it brought us together. Thank you for your time and sharing, your passion, your insight. I know it's going to serve, um, this audience. And to the audience, thank you for tuning in, and I respect you for being someone who's investing in your personal and professional development and wishing you all the success in the world in tech sales and in life, happy selling and happy living, and we'll see you in the next one.