Justin Norris:
00:00:14
So let's face it, the sales leader has the hardest job in the company. Although I think the marketing leader is a pretty close second. And I'd argue this because success in sales is black and white. Like you've either hit your number or you haven't. The DocuSign has come in or it hasn't. There's no credit for influence revenue or brand or MQLs. And while sales is hard enough as an individual contributor, at least you have some semblance of control over your destiny, but when you're the sales leader, your fate depends on other people. It's whether you can motivate, enable, and support a team of sellers to all hit their numbers. And for those of us that work in RebOps, we know that's not always the easiest thing to get all those sellers marching in the same direction. So it's not surprising that when you look up the average tenure of a sales leader, you see some crazy figures, things like. 19 months and I'm really curious to understand what top performing sales leaders do Aside from asking their teams to update their forecast five times a day And so to help answer that question today, we are joined by Kyle AC He has spent over eight years in sales leadership at Qualtrics where he had years as number one corporate AE number one He's also one of the most prominent voices in sales leadership on LinkedIn. In his spare time, you'll find him as the founder of sales introverts, where he builds frameworks to help other sellers experience the same success. Kyle, so stoked to have you here today. Thanks for coming on the show.
Kyle Asay:
00:01:50
Thanks, Justin. Excited to be here.
Justin Norris:
00:01:52
maybe just to start off, we can focus on the current environment that we're experiencing. I'm a software buyer, rather than a seller, but I know that I am buying less software. the software that I am buying is scrutinized way more by, finance and legal and ops, uh, within my company. I am negotiating more. I am more price sensitive. Are you experiencing these things right now as a seller? And like, how have you adapted to this post reset world that we are in?
Kyle Asay:
00:02:20
Yeah, 100%. If anybody's not, shoot me a note and tell me what you're doing. What I'm seeing is where we used to win a lot of deals when we found a problem. Now we're only winning deals when we find the problem. And so when we're doing our discovery, it's not just understanding what is top of mind for you. It's what's top of mind for you that's also top of mind. For your boss and other leaders across the company. we're seeing a lot of problems that two years ago would have been solved immediately, but are now being pushed to the back burner because companies don't have the internal resources to solve it. They don't have the budget to solve it, or they're just more focused with limited headcount and capacity on a bigger priority problems. but yeah, we're seeing, uh, it's tougher to win. It's tougher to win big and it's lower to win. All, all those things are coming together.
Justin Norris:
00:03:10
I'm also finding strangely enough, and I don't know what it's like in your specific niche, but, the places where I'm participating as a buyer, usually it's actually even more crowded because I think it's, there's, you know, lower cost of entry to start building software. So there's way more vendors. The landscape is changing. How do you think about. Standing out versus your competitors or are you lucky enough that you have like a pretty narrow field where you're selling today?
Kyle Asay:
00:03:34
So it's very noisy. It's never been easier to create software to launch companies. that's part of why I was very selective when I chose another company to work for with LaunchDarkly. they're recognized as one of the top platforms in the space. So that helps. Like, I don't think I'm a good enough sales leader to sell a bad product. So that, that plays a role. But even when you have the best product, or you say you have the best product, because every sales leader says they have the best product, we still have to deal with the increased noise. I'm really big on, for my team, let's not just sell the best product, let's also execute the best. Because if you have a sales team that is quality enough to sell an inferior product, and you're lucky enough to sell a great product, those two things come together really, really well. So I'm all about, as a job seeker, I want to find a company where their product is great. As a sales leader, I want to drive sales excellence, so we can differentiate by how we sell. How we show up in discovery, how we show up in demos, how we show up in POVs, so that way the buyers aren't just thinking, okay, this product looks great, but they're also saying the experience with the sales team was better than what I usually see from other vendors in the space.
Justin Norris:
00:04:46
How do you do that at scale like I guess that's always the the challenge because you as an individual seller may understand how to drive that experience. is it a process thing? Is it like a coaching and an empathy thing with your team? Like how do you figure that out?
Kyle Asay:
00:05:00
You take one small bit at a time. And so this quarter, all we're focusing on is our continued improvements on messaging for our pipeline generation. That was our first focus in our PG outbound. How do we sound different? Then the competition, how do we not come across the same as everybody hiding behind, auto sequences and AI generated content? How do we come across different in that first touch? Now we're putting more emphasis on discovery from the very start of discovery, how do we show up and tell the buyer, I actually understand your business. I understand you as a person. I'm not going to spend your time for the next 30 minutes asking superficial questions. I'm going to get right into priorities. So now we're teaching that. We have a long way to go, because anything that has to be brought out across an entire org cannot be fixed overnight. We're very intentional around what is the most urgent thing to focus on first. For us, it was pipeline generation, and now discovery. And then what are tools that we can release through enablements, through marketing, to supplement the teaching that we're doing, and how do we go enforce it. So we rolled out this new way of discovery. We did enablement, now it's a scrutiny. Okay, reps, who's using it, who's not? I'm listening to calls, I'm doing call reviews. We're coaching, because it's not great yet. We're not differentiating yet by how we sell, but we're going to continue to make improvements. When we fix that part of the process, we'll figure out then how do we differentiate by how we demo. But how do we do POVs? And you keep going through the process. that's how you scale it. One, very small piece at a time until you get people in the right spot. Then you're on to the next.
Justin Norris:
00:06:37
I love what you're saying. and I'd actually like to even just go deeper because, you know, in RebOps, we're often a partner with the sales leader and helping design and roll these initiatives out. I faced these challenges firsthand. So maybe just starting from the beginning, like what you described, let's take discovery because we can all understand that one. You want to improve it. how do you think through like, the training or the framework that you're going to design up to the point of like releasing it and like trying to get this into the heads of all those people that you're working with.
Kyle Asay:
00:07:07
So you start with the outcome in mind. What are the takeaways that we as sellers selfishly want to have from the call? And then more importantly, what do we think that the buyer wants to get out of the call? And then you design from there. And so we worked closely actually with RevOps, we worked closely with marketing around, okay, what are the things that buyers most frequently want to understand after a first call with us? How can we bring them that context immediately in the conversation without falling into presentation mode, without going into a premature demo? Then what are the questions that we need to ask to understand their priorities? Their current states and how they're measuring the negative consequences of their current state to see if we even have a priority worth going further into. Then how do we marry those together? How do we bring together the information that we know the buyers want to get quickly? With the questions that we want answers to quickly and orchestrate it in a way we're in a 30 minute conversation. We leave. Do we have a priority worth solving? And is the buyer confident? That we're a likely enough solution to solve it that they want to invest more time with us. And then the umbrella behind all of that is the command of the message framework. I'm big on command of the message, never going to claim I invented anything to do with that, but we're really big on implementing that as part of discovery with the deck that we built as a mechanism to drive a conversation with context. So the buyer knows that we're educated. And discovery. So we go deeper into what matters.
Justin Norris:
00:08:36
So you've designed this, process. And let's say that like you as a great seller, you could go and take that process and run a great discovery to get your team up to that level. So first step, like, do you announce it? Do you have enablement, roll out a course? What's the next step to like get them on their way.
Kyle Asay:
00:08:55
Yep. So the enablement piece is all about the awareness. why are we implementing this? What are the gaps that we have so far that we feel like need to be addressed to improve assessment or moving forward? Cause you got to get buy in from the sellers to some extent. as much as sales leaders want to say, and I'm guilty of this too. Sometimes I get it. You have to do this. Go do this. If sellers don't have the buy in to understand the why. If they do implement it, it's not going to be implemented well, right? It's not supposed to be a check the box exercise. So the awareness of why, then teaching how to use it, then it's also embracing the idea that it's not perfect yet. We know it's not perfect. This is new. We need to go get data, review calls, figure out what's missing. But here's how we think it should be used. Go use it in this review together. So now we're in the process of reps using it. And some of us are coming back and saying, Hey, that went incredibly well. It was a great discovery. Others come back and say, Yeah, that really flopped. That went terribly. Let's go look at why. What did we do wrong? What's wrong with the tool? What's wrong with our process? And then we calibrate. that's the process. Why we had to do it. Why we did it the way that we did. Here's how to use it. Now, let's go use it, get feedback, coach, and get better.
Justin Norris:
00:10:05
I know when I am a buyer and I'm in a discovery call, I'm usually sitting there like to show me the product. I I think buyers in general feel this, like they just want to see product and there's good reasons to do discovery. And on the other side of the fence, we want to qualify, we want to extract information. you address that tension a little bit in your description of how you design the discovery process, but how do you like. Walk that line between like we need some information to make sure that we are heading in the right direction and that you know We know what your problem is you're trying to solve versus you don't want to sit there and play 20 questions as a buyer. You want to see the product quickly
Kyle Asay:
00:10:38
think it is how you set up the objective for the call. And I've been pretty passionate about this for the long time because the buyer is thinking, How can you help me? How are you different? And how can you prove it? The entire time. There's that skepticism. There's these fears of, you're gonna try to oversell me. You're gonna say you're the right fit. You don't know me, so I like to be very clear from the beginning. job today is to figure out if I'm right in my hypothesis of the problems that we can solve for you. And then we're going to leave the call with you having a pretty good understanding of how we would go about solving those problems, so you can decide if you want to continue the conversation. Now, before I can go show you specifically how we might solve those problems, I do need a little bit of context for how you're currently managing insert use case for us is how you're releasing software, right? I'm never going to be so bold as to say. We are the best solution for everybody. That'd be a disservice to you. And so while I think we might be a good fit, I'm not gonna tell you that we are until I better understand how you're currently doing it, what the gaps are, what you'd like it to look like. but I'm given the commitment upfront that we're not going to end the first call with. Okay, well, I just learned everything about you that I wanted to know. I know that you know nothing about me still, but let's schedule another hour. So then I can tell you how I might be able to help. Some of the buyers are like, nah, just send me a case study and I'll, I'll review it. Right. And so it's that balance of being upfront. I want to get to where you want to get to as quickly as possible. Here's what I have to understand before I can get you there accurately. Get the buy in, have that conversation. And then part of the deck that we have is to sprinkle in some of the context. Here are the outcomes we drive. Here's actually a little bit of the platform. Here's how it's constructed. Here's what it looks like. Here's how we're different. We're giving that context as we go, so it feels more like a give and take conversation than that 20 questions that you just mentioned, which is so common in discovery. I just barrage you with questions. Then at the end, I give you this 30 second, like, Vomit spiel of a demo, kind of, and then I beg you for another call.
Justin Norris:
00:12:39
and you've kind of alluded to that skepticism that uh a lot perhaps most buyers bring and I thought I found personally like the best relationships I've had with sellers. They have been able to like build some trust where I feel like my alliance almost shifts a little bit. Like obviously I'm always working in the best interest of my company, but more like I feel a partnership with the salesperson to try to get a deal done rather than like, we're on opposite sides of the fence. how do you think about building that trust, either as a seller or, things that you have your team do to build that trust?
Kyle Asay:
00:13:12
So trust and rapport, I think are two different things. Just call it that part of my philosophy. Cause I was never one for being great at small talk, right? So that's not how I went about building trust. I think trust is feeling like the seller. Legitimately wants to find a good outcome for you as a buyer, whether or not it's with their product. And this is really hard to do as a seller. When you're pressured to close deals, it's really difficult to actually go authentically disqualify buyers. But I found that when buyers give skepticism about something. Don't just disregard it. So yeah, that's valid skepticism. You should be worried about that. We actually have seen situations where it didn't work out. Here's why, but calling out reasons why you might not be a great fit for some people calling out reasons why they may not be ready for your solution, calling out the risks and how you plan to mitigate the risks are much better. Then, oh, we're so easy to implement. Everything always goes great. It's, hey, we get feedback that we're pretty easy to implement, but here are some things that we see go wrong that we want to get ahead of to make sure if you do move forward, you don't experience the bad outcomes. Little subtle tweaks like that, showing the buyer that we're not here to win at all costs, but we're here to actually help them make a great decision. And if we're not the right decision for them, end the conversation as soon as possible. So I can go back to where I should be spending my time. There's a long way to build that trust.
Justin Norris:
00:14:35
It's interesting that you differentiated trust and rapport, I hadn't thought of it that way before. is rapport still important from your point of view, or is it just, it's like a separate thing?
Kyle Asay:
00:14:45
I think it depends on who you're selling to, because there is the emotional element of sales, and think it's very difficult to work with somebody that you don't enjoy working with, but there are some people that great rapport is built because you understand their business, you understand the outcomes they care about. For other people, great rapport is built because you understand them personally. You understand what they like to do, what their weekend plans are. Uh, what I have found though, is most people on like the personality spectrum of, I want a lot of personality and rapport. They're all kind of medium, right? And so for me as a very introverted seller, there's only one deal that I can remember where I had to really elevate my sociability. Because the buyer I was working with was such an incredibly energetic, personable person, where if I had tried to get right down to business, they probably would have shied away. So I had to go way above my comfort zone on the rapport building aspect. But I found that most people are more in the middle of the spectrum. And so I default to look like rapport is great, but deals don't get closed in enterprise SaaS. Because they like you as a person deals get closed because you add value now You're going to get the chance to prove you can add value a lot more frequently if they like you So you can't just be a jerk and just go right to the business, right? Like if they don't like you they're not going to give you the chance to even go prove it But if I had it just one or the other I'm going with trust because people buy from people that they trust to actually deliver the outcomes that they claim they can.
Justin Norris:
00:16:17
100%. this is a tangent, but I'm curious, because you mentioned being an introverted seller, and I probably could have guessed that by the name of Um, and yet, very comfortable on camera, making videos, putting yourself out there all the time, trying to reconcile that a little bit. Like, is it, a conscious going against, the introversion that you, feel or, uh, how do you navigate that? I suppose.
Kyle Asay:
00:16:41
So I can do it. It just exhausts me. And so as an introvert, I get my energy from being alone, doing quiet things. But when I'm doing my job, like if I have to go give presentations to a large group, if I have to go lead all hands calls, if I have to go to an office and get people excited about what we're building together, I can go do that and people will think I'm an extrovert. What they don't see is when I'm at like a multi day training somewhere for our company, as soon as I finish my three hour presentation while everybody else goes to get snacks and mingle, I'm going straight back to my hotel room, falling onto my bed, and just like decompressing for that 30 minute break before going back to leave more presentations. So I can do the videos, I can do everything I need to do. It's just, it's not how I get energized, it's how I get drained. I also enjoy doing it, ironically. It just comes back down to where I get energy versus where I need to go, what I need to go recover from.
Justin Norris:
00:17:36
yeah, I'm the exact same way and I mean, I could ask myself the same question because there I am doing a podcast, but I go to like a conference or something. I'm back at the hotel room as soon as the trade floor closes and just sort of putting myself in that, vacuum, getting some space so I can relate completely to what you're saying. I want to dive bit more deeply again onto the sales management side. And I think this is a common truth across any role, but perhaps specifically in sales, there can be like a promote to failure thing where you have superstar. I see you say, great, let's make them a manager, become a manager. and they fail at it either because they're not prepared or maybe they don't actually enjoy that work. You've made that leap successfully. what did it involve for you?
Kyle Asay:
00:18:20
It involved a heavy reliance on documentation. And so what I found is, I generally knew what I was doing to have success, but until I really sat down and methodically wrote out what I was doing to have success, it was difficult to teach it. So I began to document all the stuff I was doing, the way I ran discovery, the way that I ran demos, the way I did territory management. As I wrote it out, it forced me to actually understand what, how, and why I acted the way that I did. Then as I was able to teach it in a more clear way, it was easier for people to adopt. And then I had to go through the transition of understanding that, well, okay, just so I can teach it clearly and it works for me, doesn't mean that everybody can apply it the exact same way that I have. So then it had to become more nuanced. How did I manage different people differently? And it all, grew from there, but it started with pressure in myself based on mentorship from one of my leaders, Kyle, you know how to sell, but you got a good figure on teach others how to sell. And documentation became one of the best things I have done for myself as I transitioned from an IC to a sales leader role.
Justin Norris:
00:19:30
Is that common with others? Because that's like a very rev up such answer like documentation and probably like that. I love to hear that. It isn't something I always see from other sales leaders that I've worked with in the past. Is it common in your experience? Or is that more of a you thing? So
Kyle Asay:
00:19:45
that I meet with that wants advice on career progression, whether they want to be an enterprise IC and a strategic accounts rep or a leader. Because people that are able to clearly articulate how they have success are more likely to be promoted than someone that has success, but can't define why, and some of them wants to go into leadership, having a documented process. I mean, talk about how easy my interviews are, when I go into new companies. So they ask me, what's your process for this? I just show them. How do you coach? Here's my framework. How do you do performance management? I wrote this. I just pull up everything that I do and it's very easy to articulate. And then when I'm asked to describe it, it sounds like it's so straightforward and clear, but it's just because I've written it out so many times So if you're not doing it today, do it because it'll pay off. No matter what your career path is, sales, rev ups, marketing, document what you do that works and doesn't work. Cause then when people ask you, how do you do it? And you give them a clear answer. If you're like me, you'll look smarter than you actually are, which has great benefits to a career.
Justin Norris:
00:20:46
taking it up for a second because I'm a big fan of first principles and I like define things. How do you think about? The job of a sales leader, like, aside from like hitting the number, like that's your job, obviously. But in terms of like what you need to focus on and do, how do you, what's your North star as a leader,
Kyle Asay:
00:21:02
one of the people leaders I had early in my career was big on this. So if he's listening, he'll be proud. Uh, your job as a manager, whether you're in sales or not is to drive an aligned result for sales, the support and aligned results is going to be revenue. The way you drive towards revenue is you're going to be recruiting and retaining great talent in order to recruit and retain great talents. You need to be able to develop people, motivate people and hold them accountable. But if I bucket out the job of a sales leader is charged with that foundational layer, recruit and retain great people. Which requires developing people, hold them accountable to hit their ceiling. If you do those things, revenue follows, and then the aligned results of quota attainment, high percentage reps sitting quota, highly engaged sales teams, high retention, all those things fall into place with those focus points.
Justin Norris:
00:21:51
you talk about recruit and retain, and, a lot of that can come back to who you are as a manager. And I know when we think about sales managers, you know, if you watch like corporate bros videos, sales managers don't come off super well, or even in some of your own videos, you kind of satirize yourself a little bit. Just sitting there, you know, asking people to update their dashboards. but it kind of does relate to a real thing. There are some toxic sales managers out there. There's some managers that people don't like to have. obviously you can't just be buddy buddy all the time, but being loved, not feared, and yet getting the result that you want, how do you figure that out?
Kyle Asay:
00:22:24
Part of it is recruiting the right people because the right people are going to be good with being challenged and held accountable to the right behaviors. If you, recruit and retain the wrong people. Then you're going to be forced to balance being the friend versus being the cheerleader, and it's very difficult to go have the hard conversations around accountability. So right people really is the foundational pillar there. Then from there, when you have the right people that want to be challenged, want to get better, I hold myself to as high of a standard for developing my people as I hold them accountable to the effort I need to be successful. And so I, love to go do call reviews with reps. I love to go diagnose their deals. I love to go help. I love to go help with pipeline generation. I'll send LinkedIn videos. I'll make cold calls. I'm not great at those things right now, but I'll still try. I want to do the work so that people know that I'm brought in. But what I've found. Is when you're all in on developing people when you're very clear on expectations and why they are expectations and why they matter and the reps buy in that they matter, but you combine great development focus and great accountability to the right metrics. Then you get reps that progress, begin to see wins, as they begin to see wins, they buy in more to what you're rolling out. That gives you the license to roll out more changes, more improvements, which leads to increased adoption, more winning. And then you do this right, and six to nine months after rebuilding the sales org, you're going to have a group of people that are thinking, okay. There is no company I can work for right now where I'm going to learn as much as I'm learning today. There's no company I can work for right now that's going to challenge me as much as I'm challenged today. And then why would they want to leave at that point?
Justin Norris:
00:24:10
You talk about the right people and coachability, obviously based on what you're saying is a very important part. What other criteria do you look at to identify the right people?
Kyle Asay:
00:24:21
So right people will vary based on the company that you sell for right now. What is consistent for me is the traits. So you're looking for coachability. You're looking for high EQ. You're looking for grit, work ethic. Like I never want to have reps that I need to remind to work hard. I don't want to prod people along. That's not a good use of my time or their time so that the traits are pretty consistent. Where it differs a little bit based on the company that I lead for are the skills because transferable skills do matter when you're looking at complex sales cycles and larger deal sizes. And so for me, I'm looking for proven understanding of sales process. It doesn't have to be my sales process, but it does need to be an understanding of how to methodically approach a deal. So I'm not starting from scratch with a seller. I need to have a proven ability to generate pipeline. They need to know how to cold call. Do good emails, use multi channel, and they need to have some level of technical acumen. We sell to developers. Developers do not inherently love talking to salespeople, and you quickly lose them if you have no grasp of their world. And so while I don't expect a seller to come in understanding our product from day one, I do need them to have some level of understanding of the technical landscape or the ability to quickly learn it. So when I'm hiring, I'm looking for all the traits I care about. Those are non negotiable. And then I'm looking for at least two of the three transferable skills, because if I hire somebody with all the right traits and none of the skills, they will ramp so slowly that they will likely get discouraged and give up before they have success. If I get somebody with the right traits and at least 3 skills, they'll ramp quickly enough to have that motivation, that desire to keep going, and will be set up for success within the org.
Justin Norris:
00:26:05
I like the division between traits and skills. Skills obviously are things that are learned. Nobody, comes into the world with those skills. In terms of traits, do you think that people are kind of born with them or are those things as well, refined and, learned over time, in your opinion? In other words, are great sellers born or made?
Kyle Asay:
00:26:25
Great sellers are definitely made. I think there's some element of traits that's DNA related, but I think a lot of people, I have talked to people that have incredible grit. that have come from, very privileged backgrounds and very difficult backgrounds. I've seen people from all situations that exhibit incredible traits and a lot of it is from the circumstances that they fought through with things that they learned, right? And so I'm not a biologist, I'm not an expert in that area, but for the question, are great sellers born or made? I think they're made. Because a lot of the, traits are things that can be developed. And a lot of the skills are things that can be learned. And I have seen some reps that day one, when I met them, I was like, there's no way. And then a year later, they're crushing it because they wanted to work that hard and they wanted to get better. And they completely changed their skills. I recently had, a rep where the feedback to me was, Hey, that this person doesn't interview well. they've interviewed before and they're just really poor at it. And then they interviewed and they did great because they had worked, they gotten that feedback and they worked so hard to prove us wrong in that area. And it's a great example of someone that probably wasn't born to be a natural salesperson or natural interviewer, but now I'm betting on them to be a top performer in my org because of how gritty they were to go push through those areas and get better.
Justin Norris:
00:27:46
That's awesome. thinking about top performers. I don't know, but I imagine when you were in IC, there were maybe times where, you saw a shortcut, you know, in the process, or you saw a way of getting the result that you wanted that wasn't, standard operating procedure. And observed as a common trait of great sellers. Like they'll just, you know, we had a. I work with BDR's all the time. We had a BDR and she was showing us something she was doing and she's like, yeah, I just, you know, I delete the subject line. I use this because I find it doesn't work. Like they just instinctively will, correct for things that aren't working. And that's really valuable. At the same time, you want people to kind of follow a process. how do you, a, do you observe the same dynamic, I guess? And, and B, how do you sort of use the energies of those people appropriately that are kind of a little bit maverick, but often with a positive result?
Kyle Asay:
00:28:34
Yeah, I'm, uh, I'm really big on the philosophy of flexible process or frameworks of a process. It's really just words and how you define them technically. but the, prevailing philosophy on it is great reps will adapt process. To best meet customers where they are, to best meet a territory where it is, to best map to their, their current circumstance. As an IC myself, I had this turning moment when I was so focused on memorizing the sales process and being rigid with it and it not working, to paying attention to where did the buyer disengage in this process? Okay, how can I tweak the process based on where the buyer is today? Because not every buyer is at the same stage. And my career took off from that point. So when I'm teaching sellers today, a great example, again, is this new discovery deck we're using when reps like, Oh, these slides in an order, these questions, I got to be free. I got to be flexible. Like I agree. I want you to be free. I want you to be flexible. I want you to change the order of the slides. I want you to change the questions. But you can't make the process flexible until you have mastered the process. And so if I have reps that are skipping through the process because they don't understand it, that concerns me. Because they're probably finding shortcuts that are not going to consistently work. If I have sellers that understand the process so well that they're adapting it, Based on the campaign, based on the buyer, based on the deal, that to me is as close to sales perfection as you can get, because the foundation is good because the process is good, but we're recognizing that every deal has nuance. Every deal has changes, but reps, before you want to go try to have nuance. Get good at the foundation, understand the foundation. Otherwise, you're just making stuff up and that's not gonna work very well.
Justin Norris:
00:30:22
So once you know the rules, you can break the rules. In other words, is what I'm
Kyle Asay:
00:30:27
bend, I'm gonna go with bend.
Justin Norris:
00:30:29
You can flex, you can
Kyle Asay:
00:30:30
Yeah. you and, and you should, right? you should flex things because if you're in complex sales by nature of the job. Scripts don't work, Like in some transactional sales, sure, a script works. Go master the script, master the intonation, master the body language, but in complex sales, scripts don't work. But if you're just trying to wing it, and you don't have a strong foundation of outcomes to drive and how to drive them to work off of, You're really going to struggle creating sustainable, consistent success.
Justin Norris:
00:30:59
I alluded in the intro a little bit to the challenge and the pressure of being the sales leader and I truly believe that I'm in forecast pipe review meetings where there's good weeks There's bad weeks and the sales leaders got to step up and speak to it. That's a lot of pressure. Psychologically It's a kind of heavy weight maybe to carry all the time. How do you? Think about that. How do you deal with it? Is it just something you get used to?
Kyle Asay:
00:31:21
I don't know that you get used to it. I think you learn to adapt and, improve your mindset towards it. I've definitely had periods of pretty significant struggle with anxiety and stress from it. But, the book that I read that I'm sure many have read the subtle art of not giving enough. changed my perspective in a really positive way to good problems to have. And so when I start to feel this anxiety and stress about these numbers, I'm like, okay, Kyle, but look at the problems you get to solve today. And think about how many people would love to have the opportunity to solve these problems. And then I realized how lucky and fortunate I am to get a play business in this capacity and have a team that I enjoy working with, with a great company, with a great executive team. So yeah, there's lots of pressure. But for me personally, I would much rather have the problem of pressure and stress tied to hitting challenging targets than the pressure of not being challenged in a job or the the boredom of not being challenged in a job or people that right now are struggling to find work in a bad economy. That's stressful. That's way stressful, right? And so whenever I start to feel that overwhelmed feeling. I take a big step back, I look at it, and I put my stresses and problems into perspective. And when I zoom out, my problems and stresses are pretty minuscule compared to what many people are facing. And I consider myself very fortunate to have the problems that I do have to solve. And when that mindset flips, the mood flips, the anxiety slips away a little bit. And this is a constant remembrance of that. I also like to remind my team, like we talk about goals, we have accountability on goals, but at the end of the day, it's just a job. It's how we provide a living for our families. Uh, we like our jobs. We want to perform well, but the worst case scenario professionally is not necessarily a worst case scenario of life. We're going to succeed. We're going to fail at different times, but it's just a job. We're lucky at the problems that we have to solve and let's do the best we can together and try to have a little bit of fun along the way. And that mindset has served me quite well as I've moved into technically more stressful jobs in my career while still maintaining somewhat of an even keel.
Justin Norris:
00:33:30
That's a really healthy point of view. you put out a, uh, I thought it was really funny video, satire of a day in the life of a sales leader, but I'm, curious, maybe there's some similarities, maybe not, but what is, the real day in the life look like for you? Like, how do you organize your time and what are the things you, you focus on?
Kyle Asay:
00:33:46
Yeah, so a lot of meetings. If you want to be a leader in sales, especially the second line, third line level. It's a lot of meetings. So I'm meeting with my leadership team to understand the health of their team. We're talking about their people. We're talking about developments. We're talking about their quota coverage, talking about numbers. A lot of meetings with the cross functional leaders. So making sure we have alignment with marketing enablement with rev ops. So a lot of making sure that the goals that we're setting are complementary to each other and that we're rowing the same direction, not different directions, a lot of interviews. So I spent a lot of time interviewing candidates, a lot of time recruiting, but really most of my days are filled, With nearly back to back meetings across the day and then I do the rest of my work Uh when i'm not in meetings all day and that's just catching up on administrative stuff like making sure that territory assignments are getting done Making sure that compensation plans are all set correctly making sure that territories are allocated to the right There's all sorts of things that go into that above and beyond just the meetings but yeah a day in the life of a vps sales is uh, Probably not as glamorous as many people might think it looks like it's a lot of zoom
Justin Norris:
00:34:56
You manage both BDRs and AEs. there are full cycle AEs. There are ways of dividing up the role. How do you think about running a motion across both those types of sellers and how to work with them together in the most effective way?
Kyle Asay:
00:35:10
That is the right now big question because I'm new to this world. This is my first time leading an SDR org. So my first priority as I came into LaunchDarkly was to go hire somebody to help me build out that org. I found a great leader that has run global SDRs before that reports to me and is helping us help us structure that. it's interesting because the SDR to AE conflict is often AEs saying well the meetings I'm getting aren't good. So wasting my time with the SGR saying, accept my opportunity. I hit my numbers and I get to kind of sit in between the two. And I can have the mindset of, okay, well, the STRs, I don't, want an org where I'm going and telling the CFO, Oh, we generated 15 million a pipeline. And then he asks, well, how much closed? And I kind of whispered a really small number and then kind of duck away. I want to have an org that produces revenue. So part of that is a tight alignment for what good looks like, but it's also recognizing that when an STR is reaching out to an enterprise account, The first person we get a meeting with is probably not going to be the end decision maker for a purchase. Part of the job of the AE is to go hold those meetings and get a point of view for the account that we could then use to go get hired in the account. And so I'm really trying to find the right rhythm for that. How do we incentivize the right behavior where AEs and SGRs actually work together on accounts? Rather than an AE delegating accounts, they don't want to call themselves to the SDR. And then how do we make sure that we look at the initial STR set and the account as the start to a broader conversation, not a pass fail, is this the champion to drive forward a purchase of our software for a six or seven figures within the enterprise account? the other aspect to it, I think besides the revenue production piece is I really want the STR function to become the main place I hire talent out of for AEs. And so a big part of that is building out a sales readiness program where the SDR has come to my team, being the best at pipeline generation, the entire business, they've mastered that, but also being quite proficient with discovery. I don't need much more than that to begin with, but I do want to close the gap from them just being good at PG, not knowing discovery to day one, they can generate quality pipeline. And they can run quality discovery and then loop in ecosystem to help support them the rest of the way. So a lot to figure out as I move into this world. but, it's fun having the different perspectives of an AE leader as well as an SDR leader, as we think about targets, incentives, how we hire, how we retain, all those aspects.
Justin Norris:
00:37:47
think about very similar problems in my role, interestingly enough, and like finding that. Right place to put the dial where like, you don't want AEs wasting their time, but you also want to, one of my coworkers has a good example of like AEs who just want to like jump up and like hover above the rim of the basketball net and just wait for the ball to land there so they can, stuff it into the net and claim all the credit. how do you think about calibrating the qualification criteria of what makes it through that gate to an AE? So it's neither too stringent nor too loose.
Kyle Asay:
00:38:18
Right now we just have a sales accepted opportunities, which is pretty early in the stage. the benefit to that is it's more controllable for the STR function. I don't like having comp plans and targets with too much of it being left up to another org to execute. the downside to that is it can drive artificial behavior of just trying to land meetings that are just good enough to be qualified. And so really it requires a constant feedback loop from, Hey, we're hitting the targets. But for the stakeholders that might work to force, does our hitting targets lead to meaningful outcomes for you? If not, then we need to continue to qualify how we structure either the target or the definitions of the target. Or our approach all together maybe in a future podcast, I'll be able to roll out the answer to SDR compensation and modeling to align incentives. Perfectly. I don't have that answer today. I have some opinions on it. Like, I'm opposed to having a heavy compensation model tied to quota, closed because it's too lagging and too out of control for the SDR. I've also, though, seen downfalls to having it being too premature in the sales cycle because it leads to a lot of production, but not revenue. Because at the end of the day right now, every business is looking at these different functions, especially in revenue. And the question isn't, how much pipeline do they generate? Or how many SQOs do they generate? But it's, what's the payback period? What is the cost of the org compared to what is the production of the org? And so I really need to make sure that as we're building out the infrastructure, the team, the approach of the team is with revenue in mind and with development in mind, because if I can show the organization of business, we're bringing revenue to the table, at least enough to support the growth of the org and we're fostering the next generation of great sellers at launch darkly. I will feel fantastic about the SDR function.
Justin Norris:
00:40:14
when we think about the role of the A. E. In terms of having ownership of the full cycle, let's say alongside the BDR. There's kind of two points of view I've observed. Like I've had Brian Lamont on the podcast before he's a great AE and his point of view was, I always want to have control over my own destiny. So I'm always going to do, some level of, of outbound and pipe generation myself, there's an opposing point of view I've seen expressed where it's like, that is, you know, a waste of time of like a great ease. They should just be focused on closing. and so there's that duality. How do you think about this?
Kyle Asay:
00:40:45
I definitely align more with my friend Brian on that. great AEs, like the top 1%, will find a way to succeed against their number, with or without any support, from inbound, partner, CES, whatever. I, I don't know though that it's possible to build a decent sized sales org. In a complex environment where the AEs are solely responsible for their pipeline. And so I love a company where they recognize that, yeah, AEs need to generate pipeline, but we also need to support them. And so I love a mix. the ratios can vary. but I am generally, if you can tell me, hey, I can get your AEs 30 to 40 percent of the way to their quota between marketing, CS, partners, and SDR. And then we need AEs to go self source that remaining 40 to 60%. I'm pretty comfortable with that because what I found is AE source pipeline is generally higher quality than SDR source pipeline, which makes sense. They're more senior reps. They better understand the territory. They better understand the product. That's just the reality of experience in sales. So I already know that AE source pipeline is going to be stronger than some of the support. Then inbound. We don't always have control over that. There's seasonality to that. And if, inbound plummets, and your quota attainment plummets to the same degree, that's a problem on how you control your destiny. And so I love AEs that recognize that, yeah, I would love great support from inbound. I would love great support from CES and SDRs. But if I don't get it, I'll make up the difference. and that's a big topic right now at LaunchDarkly. It's like, here's the support we get. Here's the gap to close. And here's what we have to do as an AE org to get there. And a lot of the AEs are leaning into it and they're blowing out those numbers they need to go get to. And I can't wait to see the revenue results as we improve support from CS, as we improve support from SDR and they maintain that focus on the pipeline. Those are AEs that hit 200 percent of quota, not just a hundred percent.
Justin Norris:
00:42:47
It's a good place to be. I think I know your answer to this question probably, but, AI SDRs, you know, you're going to replace your whole, uh, SDR org with AI bots anytime soon. What are you thinking?
Kyle Asay:
00:42:58
I hope all of our competitors do. I hope they go all in on the AISDR in all seriousness, I think there are great tools being built. The problem is anything that can be scaled. Saturates and anything that saturates, even if it's really good is ignored. And so when I look at the channels that work for us right now in PG, our best channels are the things that can not be automated, can not be scaled. And so when I hear AI SDR. The goal is really personalized, really value driven emails and messages at scale. Well, when all of a sudden the buyer has hundreds of emails that are hyper personalized, very valuable, very relevant, all of a sudden, by default, none of them are personalized, none of them are valuable, and none of them are relevant. And so I've seen a lot of the data on it where people see a quick spike as they uncover some of the low hanging fruit, and then it decreases. For me and my org, there are no plans to replace SDRs with AI agents. I'm really big on AI in sales. I'm doing some work right now with Clay around territory management and my mind is blown at what I can uncover. But all of this is to accelerate what we do with sellers. Not to replace. So you'll hear me say often, I don't believe in shortcuts. I believe in accelerants. I want to use AI to accelerate my SDRs, accelerate my AEs, make us more efficient. But the idea of replacing, maybe I'll be burns, but I'm, I'm quite skeptical on that, at least for the foreseeable future.
Justin Norris:
00:44:37
No, I think you're right. And I think, as an accelerant, as an aid. As a way of automating, uh, work that is repetitive, that can be automated. as an assistant, I think that makes total sense, but yeah, the, the output that I've seen from evaluating these tools, to fully, have a, AI SDRs, I've not seen anything that I'd want to expose to my audience. let's think a little bit about the relationship with, sales ops or with rev ops. We've alluded to it a few times. I've had. Cody Guymon on the show before. I know you worked with him at Qualtrics. He actually introduced us a great revenue operator, really insightful guy. How have you, not necessarily with him, but just in general, how have you thought about an experience, this relationship with RebOps before? Sometimes there can be tension, RebOps and sales leadership. Sometimes it can be a great partnership. What's your experience been like overall?
Kyle Asay:
00:45:27
it's one of the reasons why I joined LongStar Arcly, because I interviewed with our RevOps leader and I love the guy. Like, cause I, I view RevOps as being a mission critical partner. I cannot make good decisions. without great data, or I can't form a good hypothesis, I should say, without good data. I cannot structure an org and scale an org through territory, through targets, without a great partnership. And so I view RevOps as being, the most critical partner for what I do, because they helped me work better with marketing. They helped me work better with enablement. They helped me work better with every function that partners with sales and without strong rev ops, all those things fall apart and we're no longer rowing in the right direction. I always joke that in a different universe, there's another Kyle that's just a little bit smarter than this version of Kyle. And he's our RevOps leader. He's not in the sales. He's in a RevOps. I love the stuff. And current, if you're listening to this, uh, you know that I love working with your team. Y'all are, y'all are a highlight for me.
Justin Norris:
00:46:26
So there's probably some rev ops folks listening to this right now that are thinking like, gosh, I wish that I could have that sort of relationship with my, sales leader. And, obviously there's, the sales leader themselves has a component part to play in that from the rev ops side, what would your advice be, like if you were designing your perfect rev ops partner, what would What are the things that they should do to provide maximum value to you as a sales leader?
Kyle Asay:
00:46:51
transparency is big. Like, especially when you come down to things like target setting. It's like, hey, when you share targets with me, give me the assumptions you're making. Help me understand the projections you're making. be human about it. Let's talk through things. Like, it's always nice when, uh, when you're talking about quotas and you're understanding. You're, you're balancing the needs of the business. You're balancing what morale will happen. With comp plan stuff, it's similar, because as a senior sales leader, you don't want to over index to sales, right? You do want to run a healthy sales work to support a growing company, but you also want to put out a plan where your people can have tons of success and make a lot of money. And so having that transparency aspect around target setting is huge. Uh, because oftentimes I've seen RebOps teams make decisions off of bad assumptions. And we didn't hear about the assumptions they made until it was already ruled out and a lot of damage was done. Had they shared assumptions up front that went into the model, we could have challenged it in that moment, and we could have come to a better conclusion. And so view it as a true partnership, not as like this little curtain between the two where we have to kind of guard things. Because not all sales leaders are just going to push for the lowest quota. Not all sales are going to go push for the highest possible comp rates. We understand the balance to the business, but if you're not transparent with everything going into the models, you're going to miss out on valuable insight from the sales side that if you understood would probably change those models and those projections. So that's the biggest piece. Be a partner, not a policymaker and an enforcer.
Justin Norris:
00:48:22
Good advice Maybe just in closing last question we have time for you've Built a really interesting side hustle with sales introverts. a huge audience for yourself. You have 65, 000 followers on LinkedIn. You know, I see you all the time there. You get lots of engagement in what you're doing. A lot of positive feedback. It looks like, just some lessons learned building a side hustle, doing it myself. I know it's hard. You also have a family, you have a lot of responsibility at your day job. How do you, figure that out?
Kyle Asay:
00:48:49
Yeah, my advice that also goes to sales leadership too. It's I, I focus on what I am uniquely able to do and I partner with others for the rest. And so with my, my business, I have a great partner that does website stuff, automations. Product design, all sorts of things. the only things that I have to worry about are content creation. And that's easy, because all I'm doing is taking what I'm doing every day at my job, and then repurposing it to be relevant to a larger audience, and not just a little universe. that I live in, uh, other lessons that I've learned is not all the feedback I get is always positive. It doesn't happen often, but sometimes I get very angry messages from strangers, uh, and I don't understand it, but it's just part of when you put yourself out there. And so I've had to learn to not worry about it. I'm trying to mature to the point where when somebody is a jerk like that, they just ignore and not feel the need to respond and I'm getting better. But my encouragement to people is, The benefits to sharing what you've learned far outweigh the negatives that might come from it. So yeah, I think those are really the main two things. I've had to learn what do I have to uniquely do, how do I get help for the rest so I can scale myself. And then, you're going to do things that get positive feedback, you're also going to get negative feedback. Don't sweat it. things with people that you get positive feedback from.
Justin Norris:
00:50:09
I'll have to say when I was researching this episode, I think I came across some Reddit thread where somebody was saying something, you know, mildly critical of you. And you actually jumped into that thread, responded to them. And they're like, Oh, wow. Like my point of view about you has changed as a result of this. So I think that was a masterclass of, hugging your haters and turning them into fans. I thought that was really well done.
Kyle Asay:
00:50:29
that guy was rational. A lot of
Justin Norris:
00:50:32
everybody is rational out there. I understand that too. really appreciate you being on the show. Super insightful, super useful. If people want to find you, they can look you up on LinkedIn or go to sales introverts. com tons of great resources there, but yeah, thank you so much for chatting with us today.
Kyle Asay:
00:50:50
a pleasure. Thank you for coming prepared with so many awesome questions. I really enjoyed the conversation.
00:00:14
So let's face it, the sales leader has the hardest job in the company. Although I think the marketing leader is a pretty close second. And I'd argue this because success in sales is black and white. Like you've either hit your number or you haven't. The DocuSign has come in or it hasn't. There's no credit for influence revenue or brand or MQLs. And while sales is hard enough as an individual contributor, at least you have some semblance of control over your destiny, but when you're the sales leader, your fate depends on other people. It's whether you can motivate, enable, and support a team of sellers to all hit their numbers. And for those of us that work in RebOps, we know that's not always the easiest thing to get all those sellers marching in the same direction. So it's not surprising that when you look up the average tenure of a sales leader, you see some crazy figures, things like. 19 months and I'm really curious to understand what top performing sales leaders do Aside from asking their teams to update their forecast five times a day And so to help answer that question today, we are joined by Kyle AC He has spent over eight years in sales leadership at Qualtrics where he had years as number one corporate AE number one He's also one of the most prominent voices in sales leadership on LinkedIn. In his spare time, you'll find him as the founder of sales introverts, where he builds frameworks to help other sellers experience the same success. Kyle, so stoked to have you here today. Thanks for coming on the show.
Kyle Asay:
00:01:50
Thanks, Justin. Excited to be here.
Justin Norris:
00:01:52
maybe just to start off, we can focus on the current environment that we're experiencing. I'm a software buyer, rather than a seller, but I know that I am buying less software. the software that I am buying is scrutinized way more by, finance and legal and ops, uh, within my company. I am negotiating more. I am more price sensitive. Are you experiencing these things right now as a seller? And like, how have you adapted to this post reset world that we are in?
Kyle Asay:
00:02:20
Yeah, 100%. If anybody's not, shoot me a note and tell me what you're doing. What I'm seeing is where we used to win a lot of deals when we found a problem. Now we're only winning deals when we find the problem. And so when we're doing our discovery, it's not just understanding what is top of mind for you. It's what's top of mind for you that's also top of mind. For your boss and other leaders across the company. we're seeing a lot of problems that two years ago would have been solved immediately, but are now being pushed to the back burner because companies don't have the internal resources to solve it. They don't have the budget to solve it, or they're just more focused with limited headcount and capacity on a bigger priority problems. but yeah, we're seeing, uh, it's tougher to win. It's tougher to win big and it's lower to win. All, all those things are coming together.
Justin Norris:
00:03:10
I'm also finding strangely enough, and I don't know what it's like in your specific niche, but, the places where I'm participating as a buyer, usually it's actually even more crowded because I think it's, there's, you know, lower cost of entry to start building software. So there's way more vendors. The landscape is changing. How do you think about. Standing out versus your competitors or are you lucky enough that you have like a pretty narrow field where you're selling today?
Kyle Asay:
00:03:34
So it's very noisy. It's never been easier to create software to launch companies. that's part of why I was very selective when I chose another company to work for with LaunchDarkly. they're recognized as one of the top platforms in the space. So that helps. Like, I don't think I'm a good enough sales leader to sell a bad product. So that, that plays a role. But even when you have the best product, or you say you have the best product, because every sales leader says they have the best product, we still have to deal with the increased noise. I'm really big on, for my team, let's not just sell the best product, let's also execute the best. Because if you have a sales team that is quality enough to sell an inferior product, and you're lucky enough to sell a great product, those two things come together really, really well. So I'm all about, as a job seeker, I want to find a company where their product is great. As a sales leader, I want to drive sales excellence, so we can differentiate by how we sell. How we show up in discovery, how we show up in demos, how we show up in POVs, so that way the buyers aren't just thinking, okay, this product looks great, but they're also saying the experience with the sales team was better than what I usually see from other vendors in the space.
Justin Norris:
00:04:46
How do you do that at scale like I guess that's always the the challenge because you as an individual seller may understand how to drive that experience. is it a process thing? Is it like a coaching and an empathy thing with your team? Like how do you figure that out?
Kyle Asay:
00:05:00
You take one small bit at a time. And so this quarter, all we're focusing on is our continued improvements on messaging for our pipeline generation. That was our first focus in our PG outbound. How do we sound different? Then the competition, how do we not come across the same as everybody hiding behind, auto sequences and AI generated content? How do we come across different in that first touch? Now we're putting more emphasis on discovery from the very start of discovery, how do we show up and tell the buyer, I actually understand your business. I understand you as a person. I'm not going to spend your time for the next 30 minutes asking superficial questions. I'm going to get right into priorities. So now we're teaching that. We have a long way to go, because anything that has to be brought out across an entire org cannot be fixed overnight. We're very intentional around what is the most urgent thing to focus on first. For us, it was pipeline generation, and now discovery. And then what are tools that we can release through enablements, through marketing, to supplement the teaching that we're doing, and how do we go enforce it. So we rolled out this new way of discovery. We did enablement, now it's a scrutiny. Okay, reps, who's using it, who's not? I'm listening to calls, I'm doing call reviews. We're coaching, because it's not great yet. We're not differentiating yet by how we sell, but we're going to continue to make improvements. When we fix that part of the process, we'll figure out then how do we differentiate by how we demo. But how do we do POVs? And you keep going through the process. that's how you scale it. One, very small piece at a time until you get people in the right spot. Then you're on to the next.
Justin Norris:
00:06:37
I love what you're saying. and I'd actually like to even just go deeper because, you know, in RebOps, we're often a partner with the sales leader and helping design and roll these initiatives out. I faced these challenges firsthand. So maybe just starting from the beginning, like what you described, let's take discovery because we can all understand that one. You want to improve it. how do you think through like, the training or the framework that you're going to design up to the point of like releasing it and like trying to get this into the heads of all those people that you're working with.
Kyle Asay:
00:07:07
So you start with the outcome in mind. What are the takeaways that we as sellers selfishly want to have from the call? And then more importantly, what do we think that the buyer wants to get out of the call? And then you design from there. And so we worked closely actually with RevOps, we worked closely with marketing around, okay, what are the things that buyers most frequently want to understand after a first call with us? How can we bring them that context immediately in the conversation without falling into presentation mode, without going into a premature demo? Then what are the questions that we need to ask to understand their priorities? Their current states and how they're measuring the negative consequences of their current state to see if we even have a priority worth going further into. Then how do we marry those together? How do we bring together the information that we know the buyers want to get quickly? With the questions that we want answers to quickly and orchestrate it in a way we're in a 30 minute conversation. We leave. Do we have a priority worth solving? And is the buyer confident? That we're a likely enough solution to solve it that they want to invest more time with us. And then the umbrella behind all of that is the command of the message framework. I'm big on command of the message, never going to claim I invented anything to do with that, but we're really big on implementing that as part of discovery with the deck that we built as a mechanism to drive a conversation with context. So the buyer knows that we're educated. And discovery. So we go deeper into what matters.
Justin Norris:
00:08:36
So you've designed this, process. And let's say that like you as a great seller, you could go and take that process and run a great discovery to get your team up to that level. So first step, like, do you announce it? Do you have enablement, roll out a course? What's the next step to like get them on their way.
Kyle Asay:
00:08:55
Yep. So the enablement piece is all about the awareness. why are we implementing this? What are the gaps that we have so far that we feel like need to be addressed to improve assessment or moving forward? Cause you got to get buy in from the sellers to some extent. as much as sales leaders want to say, and I'm guilty of this too. Sometimes I get it. You have to do this. Go do this. If sellers don't have the buy in to understand the why. If they do implement it, it's not going to be implemented well, right? It's not supposed to be a check the box exercise. So the awareness of why, then teaching how to use it, then it's also embracing the idea that it's not perfect yet. We know it's not perfect. This is new. We need to go get data, review calls, figure out what's missing. But here's how we think it should be used. Go use it in this review together. So now we're in the process of reps using it. And some of us are coming back and saying, Hey, that went incredibly well. It was a great discovery. Others come back and say, Yeah, that really flopped. That went terribly. Let's go look at why. What did we do wrong? What's wrong with the tool? What's wrong with our process? And then we calibrate. that's the process. Why we had to do it. Why we did it the way that we did. Here's how to use it. Now, let's go use it, get feedback, coach, and get better.
Justin Norris:
00:10:05
I know when I am a buyer and I'm in a discovery call, I'm usually sitting there like to show me the product. I I think buyers in general feel this, like they just want to see product and there's good reasons to do discovery. And on the other side of the fence, we want to qualify, we want to extract information. you address that tension a little bit in your description of how you design the discovery process, but how do you like. Walk that line between like we need some information to make sure that we are heading in the right direction and that you know We know what your problem is you're trying to solve versus you don't want to sit there and play 20 questions as a buyer. You want to see the product quickly
Kyle Asay:
00:10:38
think it is how you set up the objective for the call. And I've been pretty passionate about this for the long time because the buyer is thinking, How can you help me? How are you different? And how can you prove it? The entire time. There's that skepticism. There's these fears of, you're gonna try to oversell me. You're gonna say you're the right fit. You don't know me, so I like to be very clear from the beginning. job today is to figure out if I'm right in my hypothesis of the problems that we can solve for you. And then we're going to leave the call with you having a pretty good understanding of how we would go about solving those problems, so you can decide if you want to continue the conversation. Now, before I can go show you specifically how we might solve those problems, I do need a little bit of context for how you're currently managing insert use case for us is how you're releasing software, right? I'm never going to be so bold as to say. We are the best solution for everybody. That'd be a disservice to you. And so while I think we might be a good fit, I'm not gonna tell you that we are until I better understand how you're currently doing it, what the gaps are, what you'd like it to look like. but I'm given the commitment upfront that we're not going to end the first call with. Okay, well, I just learned everything about you that I wanted to know. I know that you know nothing about me still, but let's schedule another hour. So then I can tell you how I might be able to help. Some of the buyers are like, nah, just send me a case study and I'll, I'll review it. Right. And so it's that balance of being upfront. I want to get to where you want to get to as quickly as possible. Here's what I have to understand before I can get you there accurately. Get the buy in, have that conversation. And then part of the deck that we have is to sprinkle in some of the context. Here are the outcomes we drive. Here's actually a little bit of the platform. Here's how it's constructed. Here's what it looks like. Here's how we're different. We're giving that context as we go, so it feels more like a give and take conversation than that 20 questions that you just mentioned, which is so common in discovery. I just barrage you with questions. Then at the end, I give you this 30 second, like, Vomit spiel of a demo, kind of, and then I beg you for another call.
Justin Norris:
00:12:39
and you've kind of alluded to that skepticism that uh a lot perhaps most buyers bring and I thought I found personally like the best relationships I've had with sellers. They have been able to like build some trust where I feel like my alliance almost shifts a little bit. Like obviously I'm always working in the best interest of my company, but more like I feel a partnership with the salesperson to try to get a deal done rather than like, we're on opposite sides of the fence. how do you think about building that trust, either as a seller or, things that you have your team do to build that trust?
Kyle Asay:
00:13:12
So trust and rapport, I think are two different things. Just call it that part of my philosophy. Cause I was never one for being great at small talk, right? So that's not how I went about building trust. I think trust is feeling like the seller. Legitimately wants to find a good outcome for you as a buyer, whether or not it's with their product. And this is really hard to do as a seller. When you're pressured to close deals, it's really difficult to actually go authentically disqualify buyers. But I found that when buyers give skepticism about something. Don't just disregard it. So yeah, that's valid skepticism. You should be worried about that. We actually have seen situations where it didn't work out. Here's why, but calling out reasons why you might not be a great fit for some people calling out reasons why they may not be ready for your solution, calling out the risks and how you plan to mitigate the risks are much better. Then, oh, we're so easy to implement. Everything always goes great. It's, hey, we get feedback that we're pretty easy to implement, but here are some things that we see go wrong that we want to get ahead of to make sure if you do move forward, you don't experience the bad outcomes. Little subtle tweaks like that, showing the buyer that we're not here to win at all costs, but we're here to actually help them make a great decision. And if we're not the right decision for them, end the conversation as soon as possible. So I can go back to where I should be spending my time. There's a long way to build that trust.
Justin Norris:
00:14:35
It's interesting that you differentiated trust and rapport, I hadn't thought of it that way before. is rapport still important from your point of view, or is it just, it's like a separate thing?
Kyle Asay:
00:14:45
I think it depends on who you're selling to, because there is the emotional element of sales, and think it's very difficult to work with somebody that you don't enjoy working with, but there are some people that great rapport is built because you understand their business, you understand the outcomes they care about. For other people, great rapport is built because you understand them personally. You understand what they like to do, what their weekend plans are. Uh, what I have found though, is most people on like the personality spectrum of, I want a lot of personality and rapport. They're all kind of medium, right? And so for me as a very introverted seller, there's only one deal that I can remember where I had to really elevate my sociability. Because the buyer I was working with was such an incredibly energetic, personable person, where if I had tried to get right down to business, they probably would have shied away. So I had to go way above my comfort zone on the rapport building aspect. But I found that most people are more in the middle of the spectrum. And so I default to look like rapport is great, but deals don't get closed in enterprise SaaS. Because they like you as a person deals get closed because you add value now You're going to get the chance to prove you can add value a lot more frequently if they like you So you can't just be a jerk and just go right to the business, right? Like if they don't like you they're not going to give you the chance to even go prove it But if I had it just one or the other I'm going with trust because people buy from people that they trust to actually deliver the outcomes that they claim they can.
Justin Norris:
00:16:17
100%. this is a tangent, but I'm curious, because you mentioned being an introverted seller, and I probably could have guessed that by the name of Um, and yet, very comfortable on camera, making videos, putting yourself out there all the time, trying to reconcile that a little bit. Like, is it, a conscious going against, the introversion that you, feel or, uh, how do you navigate that? I suppose.
Kyle Asay:
00:16:41
So I can do it. It just exhausts me. And so as an introvert, I get my energy from being alone, doing quiet things. But when I'm doing my job, like if I have to go give presentations to a large group, if I have to go lead all hands calls, if I have to go to an office and get people excited about what we're building together, I can go do that and people will think I'm an extrovert. What they don't see is when I'm at like a multi day training somewhere for our company, as soon as I finish my three hour presentation while everybody else goes to get snacks and mingle, I'm going straight back to my hotel room, falling onto my bed, and just like decompressing for that 30 minute break before going back to leave more presentations. So I can do the videos, I can do everything I need to do. It's just, it's not how I get energized, it's how I get drained. I also enjoy doing it, ironically. It just comes back down to where I get energy versus where I need to go, what I need to go recover from.
Justin Norris:
00:17:36
yeah, I'm the exact same way and I mean, I could ask myself the same question because there I am doing a podcast, but I go to like a conference or something. I'm back at the hotel room as soon as the trade floor closes and just sort of putting myself in that, vacuum, getting some space so I can relate completely to what you're saying. I want to dive bit more deeply again onto the sales management side. And I think this is a common truth across any role, but perhaps specifically in sales, there can be like a promote to failure thing where you have superstar. I see you say, great, let's make them a manager, become a manager. and they fail at it either because they're not prepared or maybe they don't actually enjoy that work. You've made that leap successfully. what did it involve for you?
Kyle Asay:
00:18:20
It involved a heavy reliance on documentation. And so what I found is, I generally knew what I was doing to have success, but until I really sat down and methodically wrote out what I was doing to have success, it was difficult to teach it. So I began to document all the stuff I was doing, the way I ran discovery, the way that I ran demos, the way I did territory management. As I wrote it out, it forced me to actually understand what, how, and why I acted the way that I did. Then as I was able to teach it in a more clear way, it was easier for people to adopt. And then I had to go through the transition of understanding that, well, okay, just so I can teach it clearly and it works for me, doesn't mean that everybody can apply it the exact same way that I have. So then it had to become more nuanced. How did I manage different people differently? And it all, grew from there, but it started with pressure in myself based on mentorship from one of my leaders, Kyle, you know how to sell, but you got a good figure on teach others how to sell. And documentation became one of the best things I have done for myself as I transitioned from an IC to a sales leader role.
Justin Norris:
00:19:30
Is that common with others? Because that's like a very rev up such answer like documentation and probably like that. I love to hear that. It isn't something I always see from other sales leaders that I've worked with in the past. Is it common in your experience? Or is that more of a you thing? So
Kyle Asay:
00:19:45
that I meet with that wants advice on career progression, whether they want to be an enterprise IC and a strategic accounts rep or a leader. Because people that are able to clearly articulate how they have success are more likely to be promoted than someone that has success, but can't define why, and some of them wants to go into leadership, having a documented process. I mean, talk about how easy my interviews are, when I go into new companies. So they ask me, what's your process for this? I just show them. How do you coach? Here's my framework. How do you do performance management? I wrote this. I just pull up everything that I do and it's very easy to articulate. And then when I'm asked to describe it, it sounds like it's so straightforward and clear, but it's just because I've written it out so many times So if you're not doing it today, do it because it'll pay off. No matter what your career path is, sales, rev ups, marketing, document what you do that works and doesn't work. Cause then when people ask you, how do you do it? And you give them a clear answer. If you're like me, you'll look smarter than you actually are, which has great benefits to a career.
Justin Norris:
00:20:46
taking it up for a second because I'm a big fan of first principles and I like define things. How do you think about? The job of a sales leader, like, aside from like hitting the number, like that's your job, obviously. But in terms of like what you need to focus on and do, how do you, what's your North star as a leader,
Kyle Asay:
00:21:02
one of the people leaders I had early in my career was big on this. So if he's listening, he'll be proud. Uh, your job as a manager, whether you're in sales or not is to drive an aligned result for sales, the support and aligned results is going to be revenue. The way you drive towards revenue is you're going to be recruiting and retaining great talent in order to recruit and retain great talents. You need to be able to develop people, motivate people and hold them accountable. But if I bucket out the job of a sales leader is charged with that foundational layer, recruit and retain great people. Which requires developing people, hold them accountable to hit their ceiling. If you do those things, revenue follows, and then the aligned results of quota attainment, high percentage reps sitting quota, highly engaged sales teams, high retention, all those things fall into place with those focus points.
Justin Norris:
00:21:51
you talk about recruit and retain, and, a lot of that can come back to who you are as a manager. And I know when we think about sales managers, you know, if you watch like corporate bros videos, sales managers don't come off super well, or even in some of your own videos, you kind of satirize yourself a little bit. Just sitting there, you know, asking people to update their dashboards. but it kind of does relate to a real thing. There are some toxic sales managers out there. There's some managers that people don't like to have. obviously you can't just be buddy buddy all the time, but being loved, not feared, and yet getting the result that you want, how do you figure that out?
Kyle Asay:
00:22:24
Part of it is recruiting the right people because the right people are going to be good with being challenged and held accountable to the right behaviors. If you, recruit and retain the wrong people. Then you're going to be forced to balance being the friend versus being the cheerleader, and it's very difficult to go have the hard conversations around accountability. So right people really is the foundational pillar there. Then from there, when you have the right people that want to be challenged, want to get better, I hold myself to as high of a standard for developing my people as I hold them accountable to the effort I need to be successful. And so I, love to go do call reviews with reps. I love to go diagnose their deals. I love to go help. I love to go help with pipeline generation. I'll send LinkedIn videos. I'll make cold calls. I'm not great at those things right now, but I'll still try. I want to do the work so that people know that I'm brought in. But what I've found. Is when you're all in on developing people when you're very clear on expectations and why they are expectations and why they matter and the reps buy in that they matter, but you combine great development focus and great accountability to the right metrics. Then you get reps that progress, begin to see wins, as they begin to see wins, they buy in more to what you're rolling out. That gives you the license to roll out more changes, more improvements, which leads to increased adoption, more winning. And then you do this right, and six to nine months after rebuilding the sales org, you're going to have a group of people that are thinking, okay. There is no company I can work for right now where I'm going to learn as much as I'm learning today. There's no company I can work for right now that's going to challenge me as much as I'm challenged today. And then why would they want to leave at that point?
Justin Norris:
00:24:10
You talk about the right people and coachability, obviously based on what you're saying is a very important part. What other criteria do you look at to identify the right people?
Kyle Asay:
00:24:21
So right people will vary based on the company that you sell for right now. What is consistent for me is the traits. So you're looking for coachability. You're looking for high EQ. You're looking for grit, work ethic. Like I never want to have reps that I need to remind to work hard. I don't want to prod people along. That's not a good use of my time or their time so that the traits are pretty consistent. Where it differs a little bit based on the company that I lead for are the skills because transferable skills do matter when you're looking at complex sales cycles and larger deal sizes. And so for me, I'm looking for proven understanding of sales process. It doesn't have to be my sales process, but it does need to be an understanding of how to methodically approach a deal. So I'm not starting from scratch with a seller. I need to have a proven ability to generate pipeline. They need to know how to cold call. Do good emails, use multi channel, and they need to have some level of technical acumen. We sell to developers. Developers do not inherently love talking to salespeople, and you quickly lose them if you have no grasp of their world. And so while I don't expect a seller to come in understanding our product from day one, I do need them to have some level of understanding of the technical landscape or the ability to quickly learn it. So when I'm hiring, I'm looking for all the traits I care about. Those are non negotiable. And then I'm looking for at least two of the three transferable skills, because if I hire somebody with all the right traits and none of the skills, they will ramp so slowly that they will likely get discouraged and give up before they have success. If I get somebody with the right traits and at least 3 skills, they'll ramp quickly enough to have that motivation, that desire to keep going, and will be set up for success within the org.
Justin Norris:
00:26:05
I like the division between traits and skills. Skills obviously are things that are learned. Nobody, comes into the world with those skills. In terms of traits, do you think that people are kind of born with them or are those things as well, refined and, learned over time, in your opinion? In other words, are great sellers born or made?
Kyle Asay:
00:26:25
Great sellers are definitely made. I think there's some element of traits that's DNA related, but I think a lot of people, I have talked to people that have incredible grit. that have come from, very privileged backgrounds and very difficult backgrounds. I've seen people from all situations that exhibit incredible traits and a lot of it is from the circumstances that they fought through with things that they learned, right? And so I'm not a biologist, I'm not an expert in that area, but for the question, are great sellers born or made? I think they're made. Because a lot of the, traits are things that can be developed. And a lot of the skills are things that can be learned. And I have seen some reps that day one, when I met them, I was like, there's no way. And then a year later, they're crushing it because they wanted to work that hard and they wanted to get better. And they completely changed their skills. I recently had, a rep where the feedback to me was, Hey, that this person doesn't interview well. they've interviewed before and they're just really poor at it. And then they interviewed and they did great because they had worked, they gotten that feedback and they worked so hard to prove us wrong in that area. And it's a great example of someone that probably wasn't born to be a natural salesperson or natural interviewer, but now I'm betting on them to be a top performer in my org because of how gritty they were to go push through those areas and get better.
Justin Norris:
00:27:46
That's awesome. thinking about top performers. I don't know, but I imagine when you were in IC, there were maybe times where, you saw a shortcut, you know, in the process, or you saw a way of getting the result that you wanted that wasn't, standard operating procedure. And observed as a common trait of great sellers. Like they'll just, you know, we had a. I work with BDR's all the time. We had a BDR and she was showing us something she was doing and she's like, yeah, I just, you know, I delete the subject line. I use this because I find it doesn't work. Like they just instinctively will, correct for things that aren't working. And that's really valuable. At the same time, you want people to kind of follow a process. how do you, a, do you observe the same dynamic, I guess? And, and B, how do you sort of use the energies of those people appropriately that are kind of a little bit maverick, but often with a positive result?
Kyle Asay:
00:28:34
Yeah, I'm, uh, I'm really big on the philosophy of flexible process or frameworks of a process. It's really just words and how you define them technically. but the, prevailing philosophy on it is great reps will adapt process. To best meet customers where they are, to best meet a territory where it is, to best map to their, their current circumstance. As an IC myself, I had this turning moment when I was so focused on memorizing the sales process and being rigid with it and it not working, to paying attention to where did the buyer disengage in this process? Okay, how can I tweak the process based on where the buyer is today? Because not every buyer is at the same stage. And my career took off from that point. So when I'm teaching sellers today, a great example, again, is this new discovery deck we're using when reps like, Oh, these slides in an order, these questions, I got to be free. I got to be flexible. Like I agree. I want you to be free. I want you to be flexible. I want you to change the order of the slides. I want you to change the questions. But you can't make the process flexible until you have mastered the process. And so if I have reps that are skipping through the process because they don't understand it, that concerns me. Because they're probably finding shortcuts that are not going to consistently work. If I have sellers that understand the process so well that they're adapting it, Based on the campaign, based on the buyer, based on the deal, that to me is as close to sales perfection as you can get, because the foundation is good because the process is good, but we're recognizing that every deal has nuance. Every deal has changes, but reps, before you want to go try to have nuance. Get good at the foundation, understand the foundation. Otherwise, you're just making stuff up and that's not gonna work very well.
Justin Norris:
00:30:22
So once you know the rules, you can break the rules. In other words, is what I'm
Kyle Asay:
00:30:27
bend, I'm gonna go with bend.
Justin Norris:
00:30:29
You can flex, you can
Kyle Asay:
00:30:30
Yeah. you and, and you should, right? you should flex things because if you're in complex sales by nature of the job. Scripts don't work, Like in some transactional sales, sure, a script works. Go master the script, master the intonation, master the body language, but in complex sales, scripts don't work. But if you're just trying to wing it, and you don't have a strong foundation of outcomes to drive and how to drive them to work off of, You're really going to struggle creating sustainable, consistent success.
Justin Norris:
00:30:59
I alluded in the intro a little bit to the challenge and the pressure of being the sales leader and I truly believe that I'm in forecast pipe review meetings where there's good weeks There's bad weeks and the sales leaders got to step up and speak to it. That's a lot of pressure. Psychologically It's a kind of heavy weight maybe to carry all the time. How do you? Think about that. How do you deal with it? Is it just something you get used to?
Kyle Asay:
00:31:21
I don't know that you get used to it. I think you learn to adapt and, improve your mindset towards it. I've definitely had periods of pretty significant struggle with anxiety and stress from it. But, the book that I read that I'm sure many have read the subtle art of not giving enough. changed my perspective in a really positive way to good problems to have. And so when I start to feel this anxiety and stress about these numbers, I'm like, okay, Kyle, but look at the problems you get to solve today. And think about how many people would love to have the opportunity to solve these problems. And then I realized how lucky and fortunate I am to get a play business in this capacity and have a team that I enjoy working with, with a great company, with a great executive team. So yeah, there's lots of pressure. But for me personally, I would much rather have the problem of pressure and stress tied to hitting challenging targets than the pressure of not being challenged in a job or the the boredom of not being challenged in a job or people that right now are struggling to find work in a bad economy. That's stressful. That's way stressful, right? And so whenever I start to feel that overwhelmed feeling. I take a big step back, I look at it, and I put my stresses and problems into perspective. And when I zoom out, my problems and stresses are pretty minuscule compared to what many people are facing. And I consider myself very fortunate to have the problems that I do have to solve. And when that mindset flips, the mood flips, the anxiety slips away a little bit. And this is a constant remembrance of that. I also like to remind my team, like we talk about goals, we have accountability on goals, but at the end of the day, it's just a job. It's how we provide a living for our families. Uh, we like our jobs. We want to perform well, but the worst case scenario professionally is not necessarily a worst case scenario of life. We're going to succeed. We're going to fail at different times, but it's just a job. We're lucky at the problems that we have to solve and let's do the best we can together and try to have a little bit of fun along the way. And that mindset has served me quite well as I've moved into technically more stressful jobs in my career while still maintaining somewhat of an even keel.
Justin Norris:
00:33:30
That's a really healthy point of view. you put out a, uh, I thought it was really funny video, satire of a day in the life of a sales leader, but I'm, curious, maybe there's some similarities, maybe not, but what is, the real day in the life look like for you? Like, how do you organize your time and what are the things you, you focus on?
Kyle Asay:
00:33:46
Yeah, so a lot of meetings. If you want to be a leader in sales, especially the second line, third line level. It's a lot of meetings. So I'm meeting with my leadership team to understand the health of their team. We're talking about their people. We're talking about developments. We're talking about their quota coverage, talking about numbers. A lot of meetings with the cross functional leaders. So making sure we have alignment with marketing enablement with rev ops. So a lot of making sure that the goals that we're setting are complementary to each other and that we're rowing the same direction, not different directions, a lot of interviews. So I spent a lot of time interviewing candidates, a lot of time recruiting, but really most of my days are filled, With nearly back to back meetings across the day and then I do the rest of my work Uh when i'm not in meetings all day and that's just catching up on administrative stuff like making sure that territory assignments are getting done Making sure that compensation plans are all set correctly making sure that territories are allocated to the right There's all sorts of things that go into that above and beyond just the meetings but yeah a day in the life of a vps sales is uh, Probably not as glamorous as many people might think it looks like it's a lot of zoom
Justin Norris:
00:34:56
You manage both BDRs and AEs. there are full cycle AEs. There are ways of dividing up the role. How do you think about running a motion across both those types of sellers and how to work with them together in the most effective way?
Kyle Asay:
00:35:10
That is the right now big question because I'm new to this world. This is my first time leading an SDR org. So my first priority as I came into LaunchDarkly was to go hire somebody to help me build out that org. I found a great leader that has run global SDRs before that reports to me and is helping us help us structure that. it's interesting because the SDR to AE conflict is often AEs saying well the meetings I'm getting aren't good. So wasting my time with the SGR saying, accept my opportunity. I hit my numbers and I get to kind of sit in between the two. And I can have the mindset of, okay, well, the STRs, I don't, want an org where I'm going and telling the CFO, Oh, we generated 15 million a pipeline. And then he asks, well, how much closed? And I kind of whispered a really small number and then kind of duck away. I want to have an org that produces revenue. So part of that is a tight alignment for what good looks like, but it's also recognizing that when an STR is reaching out to an enterprise account, The first person we get a meeting with is probably not going to be the end decision maker for a purchase. Part of the job of the AE is to go hold those meetings and get a point of view for the account that we could then use to go get hired in the account. And so I'm really trying to find the right rhythm for that. How do we incentivize the right behavior where AEs and SGRs actually work together on accounts? Rather than an AE delegating accounts, they don't want to call themselves to the SDR. And then how do we make sure that we look at the initial STR set and the account as the start to a broader conversation, not a pass fail, is this the champion to drive forward a purchase of our software for a six or seven figures within the enterprise account? the other aspect to it, I think besides the revenue production piece is I really want the STR function to become the main place I hire talent out of for AEs. And so a big part of that is building out a sales readiness program where the SDR has come to my team, being the best at pipeline generation, the entire business, they've mastered that, but also being quite proficient with discovery. I don't need much more than that to begin with, but I do want to close the gap from them just being good at PG, not knowing discovery to day one, they can generate quality pipeline. And they can run quality discovery and then loop in ecosystem to help support them the rest of the way. So a lot to figure out as I move into this world. but, it's fun having the different perspectives of an AE leader as well as an SDR leader, as we think about targets, incentives, how we hire, how we retain, all those aspects.
Justin Norris:
00:37:47
think about very similar problems in my role, interestingly enough, and like finding that. Right place to put the dial where like, you don't want AEs wasting their time, but you also want to, one of my coworkers has a good example of like AEs who just want to like jump up and like hover above the rim of the basketball net and just wait for the ball to land there so they can, stuff it into the net and claim all the credit. how do you think about calibrating the qualification criteria of what makes it through that gate to an AE? So it's neither too stringent nor too loose.
Kyle Asay:
00:38:18
Right now we just have a sales accepted opportunities, which is pretty early in the stage. the benefit to that is it's more controllable for the STR function. I don't like having comp plans and targets with too much of it being left up to another org to execute. the downside to that is it can drive artificial behavior of just trying to land meetings that are just good enough to be qualified. And so really it requires a constant feedback loop from, Hey, we're hitting the targets. But for the stakeholders that might work to force, does our hitting targets lead to meaningful outcomes for you? If not, then we need to continue to qualify how we structure either the target or the definitions of the target. Or our approach all together maybe in a future podcast, I'll be able to roll out the answer to SDR compensation and modeling to align incentives. Perfectly. I don't have that answer today. I have some opinions on it. Like, I'm opposed to having a heavy compensation model tied to quota, closed because it's too lagging and too out of control for the SDR. I've also, though, seen downfalls to having it being too premature in the sales cycle because it leads to a lot of production, but not revenue. Because at the end of the day right now, every business is looking at these different functions, especially in revenue. And the question isn't, how much pipeline do they generate? Or how many SQOs do they generate? But it's, what's the payback period? What is the cost of the org compared to what is the production of the org? And so I really need to make sure that as we're building out the infrastructure, the team, the approach of the team is with revenue in mind and with development in mind, because if I can show the organization of business, we're bringing revenue to the table, at least enough to support the growth of the org and we're fostering the next generation of great sellers at launch darkly. I will feel fantastic about the SDR function.
Justin Norris:
00:40:14
when we think about the role of the A. E. In terms of having ownership of the full cycle, let's say alongside the BDR. There's kind of two points of view I've observed. Like I've had Brian Lamont on the podcast before he's a great AE and his point of view was, I always want to have control over my own destiny. So I'm always going to do, some level of, of outbound and pipe generation myself, there's an opposing point of view I've seen expressed where it's like, that is, you know, a waste of time of like a great ease. They should just be focused on closing. and so there's that duality. How do you think about this?
Kyle Asay:
00:40:45
I definitely align more with my friend Brian on that. great AEs, like the top 1%, will find a way to succeed against their number, with or without any support, from inbound, partner, CES, whatever. I, I don't know though that it's possible to build a decent sized sales org. In a complex environment where the AEs are solely responsible for their pipeline. And so I love a company where they recognize that, yeah, AEs need to generate pipeline, but we also need to support them. And so I love a mix. the ratios can vary. but I am generally, if you can tell me, hey, I can get your AEs 30 to 40 percent of the way to their quota between marketing, CS, partners, and SDR. And then we need AEs to go self source that remaining 40 to 60%. I'm pretty comfortable with that because what I found is AE source pipeline is generally higher quality than SDR source pipeline, which makes sense. They're more senior reps. They better understand the territory. They better understand the product. That's just the reality of experience in sales. So I already know that AE source pipeline is going to be stronger than some of the support. Then inbound. We don't always have control over that. There's seasonality to that. And if, inbound plummets, and your quota attainment plummets to the same degree, that's a problem on how you control your destiny. And so I love AEs that recognize that, yeah, I would love great support from inbound. I would love great support from CES and SDRs. But if I don't get it, I'll make up the difference. and that's a big topic right now at LaunchDarkly. It's like, here's the support we get. Here's the gap to close. And here's what we have to do as an AE org to get there. And a lot of the AEs are leaning into it and they're blowing out those numbers they need to go get to. And I can't wait to see the revenue results as we improve support from CS, as we improve support from SDR and they maintain that focus on the pipeline. Those are AEs that hit 200 percent of quota, not just a hundred percent.
Justin Norris:
00:42:47
It's a good place to be. I think I know your answer to this question probably, but, AI SDRs, you know, you're going to replace your whole, uh, SDR org with AI bots anytime soon. What are you thinking?
Kyle Asay:
00:42:58
I hope all of our competitors do. I hope they go all in on the AISDR in all seriousness, I think there are great tools being built. The problem is anything that can be scaled. Saturates and anything that saturates, even if it's really good is ignored. And so when I look at the channels that work for us right now in PG, our best channels are the things that can not be automated, can not be scaled. And so when I hear AI SDR. The goal is really personalized, really value driven emails and messages at scale. Well, when all of a sudden the buyer has hundreds of emails that are hyper personalized, very valuable, very relevant, all of a sudden, by default, none of them are personalized, none of them are valuable, and none of them are relevant. And so I've seen a lot of the data on it where people see a quick spike as they uncover some of the low hanging fruit, and then it decreases. For me and my org, there are no plans to replace SDRs with AI agents. I'm really big on AI in sales. I'm doing some work right now with Clay around territory management and my mind is blown at what I can uncover. But all of this is to accelerate what we do with sellers. Not to replace. So you'll hear me say often, I don't believe in shortcuts. I believe in accelerants. I want to use AI to accelerate my SDRs, accelerate my AEs, make us more efficient. But the idea of replacing, maybe I'll be burns, but I'm, I'm quite skeptical on that, at least for the foreseeable future.
Justin Norris:
00:44:37
No, I think you're right. And I think, as an accelerant, as an aid. As a way of automating, uh, work that is repetitive, that can be automated. as an assistant, I think that makes total sense, but yeah, the, the output that I've seen from evaluating these tools, to fully, have a, AI SDRs, I've not seen anything that I'd want to expose to my audience. let's think a little bit about the relationship with, sales ops or with rev ops. We've alluded to it a few times. I've had. Cody Guymon on the show before. I know you worked with him at Qualtrics. He actually introduced us a great revenue operator, really insightful guy. How have you, not necessarily with him, but just in general, how have you thought about an experience, this relationship with RebOps before? Sometimes there can be tension, RebOps and sales leadership. Sometimes it can be a great partnership. What's your experience been like overall?
Kyle Asay:
00:45:27
it's one of the reasons why I joined LongStar Arcly, because I interviewed with our RevOps leader and I love the guy. Like, cause I, I view RevOps as being a mission critical partner. I cannot make good decisions. without great data, or I can't form a good hypothesis, I should say, without good data. I cannot structure an org and scale an org through territory, through targets, without a great partnership. And so I view RevOps as being, the most critical partner for what I do, because they helped me work better with marketing. They helped me work better with enablement. They helped me work better with every function that partners with sales and without strong rev ops, all those things fall apart and we're no longer rowing in the right direction. I always joke that in a different universe, there's another Kyle that's just a little bit smarter than this version of Kyle. And he's our RevOps leader. He's not in the sales. He's in a RevOps. I love the stuff. And current, if you're listening to this, uh, you know that I love working with your team. Y'all are, y'all are a highlight for me.
Justin Norris:
00:46:26
So there's probably some rev ops folks listening to this right now that are thinking like, gosh, I wish that I could have that sort of relationship with my, sales leader. And, obviously there's, the sales leader themselves has a component part to play in that from the rev ops side, what would your advice be, like if you were designing your perfect rev ops partner, what would What are the things that they should do to provide maximum value to you as a sales leader?
Kyle Asay:
00:46:51
transparency is big. Like, especially when you come down to things like target setting. It's like, hey, when you share targets with me, give me the assumptions you're making. Help me understand the projections you're making. be human about it. Let's talk through things. Like, it's always nice when, uh, when you're talking about quotas and you're understanding. You're, you're balancing the needs of the business. You're balancing what morale will happen. With comp plan stuff, it's similar, because as a senior sales leader, you don't want to over index to sales, right? You do want to run a healthy sales work to support a growing company, but you also want to put out a plan where your people can have tons of success and make a lot of money. And so having that transparency aspect around target setting is huge. Uh, because oftentimes I've seen RebOps teams make decisions off of bad assumptions. And we didn't hear about the assumptions they made until it was already ruled out and a lot of damage was done. Had they shared assumptions up front that went into the model, we could have challenged it in that moment, and we could have come to a better conclusion. And so view it as a true partnership, not as like this little curtain between the two where we have to kind of guard things. Because not all sales leaders are just going to push for the lowest quota. Not all sales are going to go push for the highest possible comp rates. We understand the balance to the business, but if you're not transparent with everything going into the models, you're going to miss out on valuable insight from the sales side that if you understood would probably change those models and those projections. So that's the biggest piece. Be a partner, not a policymaker and an enforcer.
Justin Norris:
00:48:22
Good advice Maybe just in closing last question we have time for you've Built a really interesting side hustle with sales introverts. a huge audience for yourself. You have 65, 000 followers on LinkedIn. You know, I see you all the time there. You get lots of engagement in what you're doing. A lot of positive feedback. It looks like, just some lessons learned building a side hustle, doing it myself. I know it's hard. You also have a family, you have a lot of responsibility at your day job. How do you, figure that out?
Kyle Asay:
00:48:49
Yeah, my advice that also goes to sales leadership too. It's I, I focus on what I am uniquely able to do and I partner with others for the rest. And so with my, my business, I have a great partner that does website stuff, automations. Product design, all sorts of things. the only things that I have to worry about are content creation. And that's easy, because all I'm doing is taking what I'm doing every day at my job, and then repurposing it to be relevant to a larger audience, and not just a little universe. that I live in, uh, other lessons that I've learned is not all the feedback I get is always positive. It doesn't happen often, but sometimes I get very angry messages from strangers, uh, and I don't understand it, but it's just part of when you put yourself out there. And so I've had to learn to not worry about it. I'm trying to mature to the point where when somebody is a jerk like that, they just ignore and not feel the need to respond and I'm getting better. But my encouragement to people is, The benefits to sharing what you've learned far outweigh the negatives that might come from it. So yeah, I think those are really the main two things. I've had to learn what do I have to uniquely do, how do I get help for the rest so I can scale myself. And then, you're going to do things that get positive feedback, you're also going to get negative feedback. Don't sweat it. things with people that you get positive feedback from.
Justin Norris:
00:50:09
I'll have to say when I was researching this episode, I think I came across some Reddit thread where somebody was saying something, you know, mildly critical of you. And you actually jumped into that thread, responded to them. And they're like, Oh, wow. Like my point of view about you has changed as a result of this. So I think that was a masterclass of, hugging your haters and turning them into fans. I thought that was really well done.
Kyle Asay:
00:50:29
that guy was rational. A lot of
Justin Norris:
00:50:32
everybody is rational out there. I understand that too. really appreciate you being on the show. Super insightful, super useful. If people want to find you, they can look you up on LinkedIn or go to sales introverts. com tons of great resources there, but yeah, thank you so much for chatting with us today.
Kyle Asay:
00:50:50
a pleasure. Thank you for coming prepared with so many awesome questions. I really enjoyed the conversation.
