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If you think outbound is dead, you’re either lying or you’re bad at it.
Quotas keep rising, your people are grinding, and the pipeline isn’t growing. It’s an equation that drives you mad. While everyone wants more opportunities, only a few know how to build an outbound culture that delivers.
I’m Todd Busler, former VP of Sales, now co-founder of Champify, and I’ve spent my career sharpening how to build a company pipeline that’s self-sufficient.
On this show, I’m talking to sales leaders who have cracked the outbound code. They’ve built an outbound culture beyond their SDRs and scaled repeatable systems that drive real pipeline without relying on hacks.
We’ll break down the winning plays, processes, and frameworks behind growing that outbound muscle to help you get results faster.
No fluff. No hacks. Real strategies from real people who have done it so you can stop guessing and start opening.
Kyle Asay (00:00):
I'm never as a leader going to have everybody on my team having a great day. I'm going to have days where I win deals, lose deals. I can't have this emotional whiplash. I have to show up consistent and steady for everybody. So that was a key moment.
Todd Busler (00:15):
Everyone wants to build stronger pipeline, but only a few know how to make it happen. If you're listening to this show, you know outbound is not dead. You just need a little help building a system that actually works. Well, you're in the right place. I'm Todd Busler and on this show we're breaking down the plays, processes and frameworks behind repeatable pipeline growth straight from the people who've built it. Let's get into it.
(00:43):
Hey everyone. You're going to love today's guest, Kyle Asay. You might've seen him writing about sales introverts and he has a big following on LinkedIn. Today, we didn't spend time on that. We spent time on what he learned during great runs at companies like Qualtrics and MongoDB and exactly how his first couple quarters have gone transitioning LaunchDarkly from a heavy inbound model to a very outbound-focused motion. He shared exactly how he increased outbound pipeline generation by 142% in the first three months at LaunchDarkly, and how we reduce the time of first sale from 65 down to 33 days. If you're an aspiring sales leader or a sales leader joining a new company, this episode is for you. Tactics, strategies, tips, failure points, et cetera. Also stick around about three quarters of the way in. He talks about how he evaluates opportunities, what are the most important things when looking at a new opportunity, and the advice he finds himself giving reps when they're thinking about a new opportunity. Enjoy.
(01:48):
Kyle, happy Friday. How are we doing?
Kyle Asay (01:50):
I'm doing well, Todd. How are you?
Todd Busler (01:52):
I'm great. I appreciate you doing this. You're one of the few people that puts out sales content that I find sharing with my team a lot just on frameworks. And you can tell someone that's like, all right, you're doing it. You've earned the right to say all the things you're saying, and I think your ability to put complicated concepts in short pithy frameworks is a real skill. So kudos to you and thank you for the value you delivered to me and my team.
Kyle Asay (02:16):
Thank you. Very appreciate the kind words.
Todd Busler (02:19):
Qualtrics, MongoDB, LaunchDarkly. You've built and rebuilt and scaled teams. What's been the common thread across these runs?
Kyle Asay (02:26):
The common thread. There's a few common threads? I think the things that I find super consistent are the traits that I look for in the AEs that I hire. The traits are the same, the skills might be different. Another common thread is going to do the emphasis on PG, which find why we're here today. I've always been in an environment where the expectation is the AEs own and source a good amount of their pipeline, and so building out systems that allow AEs to supplement marketing as J et cetera has been another major consistency.
Todd Busler (02:56):
Let's dive into one of them. LaunchDarkly. I saw a stat increased pipeline by north of 130, 140% in the first couple months. Doing that at a LaunchDarkly scale of company is not easy. There's so many moving pieces. There's politics, there's structure, there's commission. What could you equate, maybe are summarize the top two or three reasons or levers you pulled to make that happen?
Kyle Asay (03:20):
So the first thing we did is we recognized that we had three distinct types of accounts that we were not correctly approaching for PG. We had our net new business accounts, we had our enterprise tier customers and then we have our self serve PLG type motion customers. And so I realized the AEs were treating a lot of these accounts in generally similar ways, which wasn't optimized. So the first step was creating now a PG plan where we separated these three accounts, we taught here's how they're different, here's the different approaches you use against these three distinct categories, and then here's how you prioritize the urgency for how you select each of these accounts. Because before I came, account selection approach was literally just a random customer this week and then almost alphabetical order for new business accounts. And so teaching the distinct approach to three different kinds of accounts for PG and then nailing territory management so we could focus where we had the highest propensity and highest upside was the foundation to it. And then we got into all the aspects on understanding the personas, understanding good messaging on the customer side, understanding the framework of problems that we're currently solving problems we should be solving all those things layer on top of it. But honestly it began with, look, we need to actually narrow our scope to the top tier of these three distinct buckets and teach how to approach those in a layer on a bunch of plays off of that.
Todd Busler (04:41):
How did you get there, Kyle? Because I'm sure there was other good sales talent and leadership that got LaunchDarkly to where they were before you got there, but how did you arrive on, oh wow, everyone's treating different accounts the same or how do you arrive on like, Hey, no, it's these three account types and this is how we have to kind of strategize accordingly?
Kyle Asay (05:00):
When I first joined, I just met with every single person in my org. If I didn't just talk to the managers that I led, I met with the SDRs, the AEs, international reps, and it was walk me through your workflow, show me how you pick an account, show me your territory. How do you think about PG planning? And so I was looking for patterns, where are the areas that are working and then where are their common mistakes? And the common mistake that I saw was everybody's territory had no structure. So it was show me your territories. Well, here's a list of accounts. Well which ones are your best accounts? I don't know. And so I see there's a thread and it's very different than when I joined Mongo because Mongo was at a very different maturity stage when I joined Mongo. They knew their best accounts, they had that tiering in, so we started a little bit further along that pipeline generation maturity funnel, but it LaunchDarkly, which is really fun for me, it was really back to the absolute basics. And since then we've significantly matured how we think about our account planning, PG planning, but man, it was just going in, how do you do it today? What are the few things working well that we can magnify? And then what is the lowest common denominator for a point of failure? And the lowest common denominator for point of failure is the average AE waking up every day was not going after the right accounts in their patch.
Todd Busler (06:18):
And do you think most of that was a lack of understanding on their end or just too much decisions and then therefore that you were losing productivity once you've been able to make that adjustment? Obviously it led to the big results, but was there some early wins there as well?
Kyle Asay (06:32):
So you get the right to stack on additional plays for PG by getting the early ones. So when I came in, there was a lot of the skepticism, oh, more leadership turnover, more leadership change. Who is this guy kind of a thing. The reality is the team had been built off of the very inbound heavy motion, great product, large market, lots of inbounds. They had been able to hit their number for a long time off of just inbounds Now that had dried up and gone away, which is why they bring in, they brought in people like me and some others to help rebuild the outbound standpoint. Once you get some of the early wins and they see, Hey, actually prioritizing my accounts, I found an explanation opportunity much faster, then you earn the right to layer on more and more and more. And so one of the things that I'm most excited about is through all the transformation we've done, we've actually had very low attrition from the reps that we wanted to buy in and stay because they saw some of the early ones, the skepticism began to go away and now they're like, yeah, we'll try anything because so far as it is a lot of money, so we're in to do more of this.
Todd Busler (07:32):
Funny, once it starts to work, you see everyone lean in on a lot of that skepticism side chatter going away. Can you dive in a little bit deeper on the, so okay, figure out these three different account types and then nail kind of the territory planning. How big of a change was the territory planning part? How did you approach it?
Kyle Asay (07:50):
It was a pretty significant change because reps had very large territories and there wasn't a lot of structure planning to it. And so getting their mindset away from trying to talk to all their accounts to just the top tier of accounts of each kind, that was a pivot. Understanding that we're not just going to reach out to two or three people per account. We're going to go a whole lot wider learning things like we're not just trying to set meetings at the VP level or CTO level. We're trying to go get a point of view by talking to below the line contacts to build up to the executive. All of those things were pretty significant changes in the operating rhythm and just huge kudos to the reps that were here when I joined because they did buy in. The trajectory was so much faster because so many of these reps took the coaching, gave feedback, helped us improve what I was suggesting, took ownership of it, and that helped us get where we are today a whole lot faster than if they would've been reluctant, not bought in and not been coachable.
Todd Busler (08:46):
Love that. One topic I've become a little bit obsessed with is you've seen what great looks like. MongoDB is a great sales organization. Some of those leaders have gone to do on really good things. I find that there's only so many parts of a previous playbook that transfer over, right? Different stage company, different buyers. What were things that were very different from other playbooks that you've seen well and you've seen it at Qualtrics and MongoDB, they're like on Mount Rushmore of sales execution. What didn't transfer over or what did you think maybe would've transferred? You're like, Hey, actually this is going to be very different here.
Kyle Asay (09:20):
A lot of the playbook is similar, but the order of operations has been very different. I rolled out just this quarter a year in something that I rolled out within a month of joining MongoDB just because of the maturity stage of the org that I was inheriting. But some of the pivots have been fun at LaunchDarkly because we have less constraints than we had at a much larger company like MongoDB. So for example, at MongoDB, territory management is very hard on the acquisition side because if there was an account that had spent 23 cents three months ago on an Atlas cluster, we couldn't work that account. And so trying to find the right accountants to call was much harder than it has been at LaunchDarkly. It's definitely some of the higher accountability things that I was able to implement sooner at Mongo because the culture was already partially there compared to at LaunchDarkly where I couldn't drive that right from the get go because it would've caused too much whiplash. The playbook at LaunchDarkly, it took me more time to earn the right than it did at Mongo because the LaunchDarkly was very rudimentary when it came to outbound.
Todd Busler (10:28):
Doing what you're kind of glossing over is really hard getting some of the OG reps that have been there and they said, Hey, I've done well here. Who's this guy? Kyle, you mentioned going around learning what wasn't working, kind of summarizing that information, I'm sure you were thoughtful about how quickly you made certain changes. Was there anything else you have for maybe this up and coming VP of sales that's like, alright, how do we get buy-in from some of this existing team?
Kyle Asay (10:54):
I also heard from the team things that they really needed and I made them happen as quickly as possible. So some common feedback I got was we don't really understand career progression, we just have the corporate AE and then enterprise AE. There's really no way to get there. The territories are so different. And so one of my biggest initial projects was building out a whole leveling system. I promoted a large portion of the org after my first six months and I walked through how we were going to get there. And so when the AEC, hey, this guy is actually fighting to make the improvements that we said we need, maybe I'll give a shot at the improvements that he thinks we need.
Todd Busler (11:32):
We need, yeah.
Kyle Asay (11:32):
And then you have that magic mesh where the improvements that they need, we made happen, the improvements...
Todd Busler (11:38):
And you're delivering on them and you're delivering on them.
Kyle Asay (11:41):
And now we're both delivering for each other and now we have this culture where, look, we have each other's backs, we're going to go win together. But yeah, I think if you're the up and coming sales leader, you earn the right by one getting them the wins that are important to them, assuming that they're good wins. So you can't just go get everything done that every rep asked for. Then the other piece is I'm really thinking what can I roll out first that's going to make this team more money? Because if all of the first initiatives you roll out, the reps are not seeing an immediate impact to their commission check, you're not going to get the buy-ins. Like if you're an upcoming leader, you're going to hear a lot about the most important thing in sales leadership is to know the names of your reps, spouses and kids to know their hobbies, to know them personally. And I think that's all super important thing that I really do, but I honestly don't think is the most important. If you're a sales leader, most of your reps are working to make money and offer fun. As much fun as you all have in sales that we're all here to make a paycheck, implement things that show you, carry it by your reps earning money, getting better at the job, earning promotions as they see that happen, they're going to buy into you so much faster.
Todd Busler (12:48):
It's amazing advice. Kyle, another thing I really like about what you put out there is, look, you've had some really impressive runs and your career has escalated quickly, but you're also really open about sharing some missteps or mistakes or learnings. Was there any key inflection points where things started to click for you or a really big learning opportunity thinks were sharing that ultimately helped you get where you've gotten?
Kyle Asay (13:12):
I've gotten some really impactful feedback in my career that I consider to be inflection moments. There was one as an early leader where our rep told me that, Kyle, when you're stressed and when you're down, we all know it and it impacts all of us. So that was kind of a punch in the gut and a realization that I'm never as a leader going to have everybody on my team having a great day. I'm going to have days where I win deals, lose deals, I can't have this emotional whiplash. I have to show up consistent and steady for everybody. So that was a key moment. I've gotten feedback on how I tend to come to a decision. I can think it through and I can make a decision, but if I don't walk people through how I get to that decision, it can come across as being rushed and ill thought out. So I've learned to go explain my thought process in more depth to get more, especially man, the longer I'm in sales, the more I realize that I'm never going to be able to say this is what works, but more of here's what I think is most likely to work. We're going to try it cross our fingers to see what happens. And a lot of the time we're going to fail miserably, but we're going to bounce back anyway and try something different.
Todd Busler (14:17):
Two points. The last one you just meant. It's like I've been talking to a lot of great sales leaders through this podcast, I'm really enjoying it. But a common thread is what you just said. There's the more traditional, been there, done that, that's like, no, this is it. This is what works. And the common thread I see with people like yourself, I just talked to the DP of Sales at DBT who had an amazing run, same Ryan Heinig from ThoughtSpot. I don't know, this is what I think is best. Here's how we're going to try and measure it. You don't know. And every company's different and market's different and timing in the cycles is different. So it's a common theme. And then to your first point, I actually got that same exact feedback from a CRO and he said, Todd, hey, when we're doing great, your energy's incredible, but you're wearing your emotions on your sleeve and whether you like it or not, it's affecting people. So that was something I had to deal with as well and a good learning for me and very grateful for that feedback. Although it felt like a little bit of got punched at the moment. Where do you see most sales orgs go wrong? Right? So you just mentioned some really tactical and things that you've done. Where do you see people go wrong when it comes to outbound strategy rep productivity or rep accountability and making some of the changes that you mentioned?
Kyle Asay (15:22):
I'll consider it the whiplash effect. It is when organizations, they swing the pendulum so heavily and then they'd make drastic changes when it doesn't work as expected. And so you're going from a heavy strategy over here and then almost completely reversing to another strategy when it's not working as expected. And so what I found with outbound strategy, with sales process strategy, you cannot make multiple big changes at once. You need to kind of pick your lane, test it, see what works, and then optimize and tweak as necessary. But I think a lot of orgs say, well that didn't work. Let's change three variables. Let's change account process. Let's change messaging, let's change our sequence strategy, let's change our dialer. And all of a sudden maybe one of those four or five changes is actually a good change, but how are you going to know? Because there's so many new variables in the mix. So I think that's probably the most common mistake.
Todd Busler (16:19):
How detailed are you, Kyle, in that? Super concretely, do you have almost like a kind of sprint cycle mentality, much like a product team that says, here's exactly what we're doing for the next 90 days and how we're going to measure it. And then second question is, how do you get a gut check on how much change is too much? Are you going to a CEO, some mentors in your network? How do you approach that? Because the balance is tricky.
Kyle Asay (16:44):
I do get a lot of feedback from my CRO on this. Am I thinking about this the right way? I try to follow a certain rule set. So first I keep the same outcome metrics constant. I have the same three things I measure and I always measure those. It's this quarter's revenue, this quarter's AE source pipeline and next quarter's pipeline coverage. Those are my three outcome metrics. Every rep in my org knows it, every leader knows it. Those are performance management, health of the business. I do not change those. Now the way that we drive to those can shift a little bit and that's based on these sprint cycles I guess you could say the priorities that I have to support those. But I have another rule for those. If I ever introduce a new focus area, I have to remove a current one. And so that way I'm never doing too much.
(17:31):
I'm not just putting on and on and on and on and making this very complicated pipe gen process. And it's so funny because I remember I presented my original pipe gen strategy to the CEO at LaunchDarkly and his first feedback was, this is so simple. I was like, yeah, that's the idea. So I think a lot of sales leaders want to go dress up these presentations make it seem super complex, but if you're trying to roll out anything organization wide and anybody in your org thinks it's complex, almost guaranteed it's not going to work. But that's my general thought process with the outcome metrics inputs, how frequently I can change them and how I think about simplicity versus complexity.
Todd Busler (18:09):
So you mentioned the three top things you looked at, right? Or you're always constant. Did they have that same level of focus on those three things beforehand? Was that new to the organization? Obviously they looked at it but it wasn't with the same rigor you were. Can you talk about that a little bit?
Kyle Asay (18:22):
No, they were really only looking at this quarter's revenue when I joined for my org, and so that's why there was allotted inconsistency. So the reason why I like those three metrics is one, they're highly controllable by the rep with revenue being the one that's least controllable, at least for this quarter. We have a longer sales cycle. I can't tell a rep halfway through that's forecasting the big miss figure this out. There's not as much in their control, but it's still obviously our most critical metric. But this quarter's AE source pipeline always controllable. Next quarter's pipeline coverage always controllable and if I have a rep that's struggling for revenue this quarter, but they're self sourcing pipeline to compliment marketing source and SDR sourced and they have front of pipeline coverage for next quarter, they're in great standing, they're going to go deliver a great quarter next quarter and that've got reps this quarter blowing through their number to help close the gap for this rep this quarter. And I found that very few sales orgs actually think about next quarter's pipeline as much as they probably should. I think it's commonly talked about, but it's not often a number that the rep has top of mind. But within my org, I make sure that when I do my end of quarter countdown, 15 days left, gap to forecast, I also have our gap to next quarter's pipeline goal and I count that down just as much as I do this quarter's revenue.
Todd Busler (19:43):
And to put some of this in context, Kyle, what's roughly, and I'm sure there's different segments and stuff, but what's roughly the cycle length for deal velocity?
Kyle Asay (19:52):
For our net new logo lands, usually four and a half to six months. Pretty typical for expansion of 45 days or so is pretty typical.
Todd Busler (20:01):
Makes sense. You also talked about reducing time to first sale pretty dramatically. I think 65 days to 33 days, that might only seem like high 20 number of days. That's dramatic, right? It almost cut in half. What changed in onboarding and broader enablement picture overall to make that happen?
Kyle Asay (20:21):
90% of that is territory. The sooner that the rep knows which accounts to focus on, the sooner they're going to have opportunities that can close. We talked a little bit at the beginning about the propensity aspect, accounts that are more likely to buy sooner. We get really good at quickly understanding, okay, rep, here's your accounts, let's go tier them together, teach you what good looks like. So within a week or two of you joining, you just don't have your account book, but you have your accounts tiered out, tier one, tier two, tier three, and now we're laser focused on tier one where I think historically they didn't have that kind of structure. It was more like randomly picking accounts to call. But when you're in your first few weeks and you're unable to call your top propensity accounts, you're much more likely to find a winnable opportunity faster.
Todd Busler (21:06):
What's the next big milestone? I think the importance of the list and the ICP and your territory has even become way more important because we have to be more efficient. We have to swing at more strikes, right? I find myself talking about the list, the list, what is the next big milestone? So rep comes in the first 10 days, Hey, here's my territory, I have a kind of tiered planned, et cetera. What's next? What's the next thing you're looking for? You're like, okay, this person's going to be successful.
Kyle Asay (21:33):
I'm looking for evidence that they have the bias for action and they're willing to go fail. I see a pretty strong correlation between the reps that have conversations early versus the reps that want to study more and learn more and prep more before being customer facing. The reps that initiate the customer facing work faster usually do better. Short-term, midterm and long-term with a product like LaunchDarkly is fairly complex and the way that we sell to engineers are very dependent on how their architecture is set up, the integrations they're using. It's not something that you're going to master in your first even six to nine months. And so I think the next milestone is this rep willing to run and then we concurrently work on better understanding who we sell to. What are the problems they have usually how do they measure their success, how do they define that in their words?
(22:25):
Then layer on top of that, how does LaunchDarkly solve those problems? How do we solve it differently? All your typical command of the message type language that many sales leaders are familiar with, but I view that as less of a milestone that's just ongoing. Even my reps that are 2, 3, 4 years in share, they should still be learning more about the personas, learning more about the new products that we're acquiring and building. But that next milestone is though the... is this rep one that hit the ground running, having conversations is getting shut down on cold calls, is getting ripped apart by the senior architect. That blows 'em up for not knowing enough. I want to see that early failure because that mindset and that approach, that's really easy for me to go build on with knowledge over time.
Todd Busler (23:06):
And then with the team scaling, right? You have multiple managers under you or even managers and managers. How do you get a sense of how do you enable the frontline leaders to understand, okay, yes, they are failing, they are working. How do you do that across a big group of people?
Kyle Asay (23:23):
We have awesome analytics around territory penetration, conversations being had. We have ways to track meaningful activity that I've implemented around my Good Day Framework to get a lot of ideas around this, but we also have a very public PG Wins channel where when somebody has success with a cold call or a cold email conversion, they post how they got there, what happened, what the result was. It is fairly visible in that way too from a self-callout. And then there's some ongoing one-on-ones with the leaders talking about their ramping reps, whether they're seeing progress, whether they're seeing challenges, and then the other easy one is just the calendar check all periodically pull up reps, calendars, and when I see reps that have a lot of customer meetings, I'm excited when I see reps that have very few customer meetings, a lot of blank space. I'm a little bit nervous.
Todd Busler (24:06):
It's funny with all this tech, I find myself doing this all the time too. You can tell a lot just how many customer calls are we having, right? If you're having 10, 12 plus every week, usually good things are going to happen, right? It is as simple as that. You mentioned a Good Day Framework. I know what that is, but I'm assuming a lot of the people listening don't. What is that?
Kyle Asay (24:28):
So I found that one of the challenges of sales is it's very easy to fall into micromanagement as a leader and it's very easy to fall into activity for activity's sake behavior. Early on in my career, I would get frustrated when I was measured by number of calls made almost exclusively. I knew that there were some days where calls made were impactful, other days where it was a waste of time because I was just calling a stale list to get my dial numbers. So my Good Day Framework is an exercise where we work with the AEs and leaders to determine what are the activities that make you most successful, and there's usually things like adding net new prospects to your cadence to make sure that your pipeline is fresh for outreach. Having conversations on cold calls and learning more about an accounts booking meetings can broaden opportunities, but we determine together what makes a successful day.
(25:15):
Then we begin to track those things with the goal being that over time we know exactly how many inputs equate to quota attainment and so reps no longer need to worry or wonder what do I need to do today to be successful? It's very specifically, here's exactly the amount of activities I need to do across high impact activities to be confident I'll hit my number. If you go talk to most AEs and you say, Hey, what do you need to do every day this week to be on track to hit quota? A very low percentage of reps can actually tell you exactly what they might know, some of their general conversion rates like cold call conversion or discovery conversion, but very few know exactly how to time block their day down to a science to hit their number. The Good Day Framework is built to track what's most meaningful track, how it actually equates to revenue, and then over a three to six month period getting enough data to say, here is what rep A needs to do daily to be on track to hit X percentage of quota.
Todd Busler (26:15):
I love that. Kyle, I want to dig into some of the supporting cast because a lot of the things you're saying are not so easy in practice. How do you do this across multiple reps then? Before I do that, there's also been something really interesting happening at LaunchDarkly in a really positive way is that you mentioned really strong product, singular product, heavy inbound oriented to now much more of a broader product focus on expansion, new products, platform play. Can you talk about what went into the enablement for that shift?
Kyle Asay (26:45):
For the multiple products specifically?
Todd Busler (26:47):
Yeah, multiple products and more of a platform-oriented sale, way heavier percentage coming from outbound.
Kyle Asay (26:52):
Yeah, so on the platform piece, it's really trying to fight the urge to go make it all about the product and it just becomes even more important to understand the bigger picture problems. And so if you look back at old LaunchDarkly with feature management feature flag, and that can solve pretty transactional problems at a transactional price point, you're never going to sell a platform with transactional problems. And so understanding that we need to go uncover with our deals, what is the most important problem facing the entire engineering org? Chances are that problem is bigger than simple feature management can solve, but there's also a good chance that the platform play can solve that problem. Then from a PG standpoint, it's just understanding. It gives us so many more ways into an account where a year ago now, maybe AI wasn't, well, it's still pretty popular even a year ago, but a year ago we would've had a hard time setting meetings with a VP of AI or AI architecture or AI product.
(27:54):
Now we have a product specifically for developing on AI. It's a lot easier talk effect now to go earn a seat at the table to begin a conversation, and so learning how to tweak your initial pitch to across different value drivers, then tying to the product is valuable. And I'll add that last piece is really critical. We did a whole refresh of our value framework and value drivers. I never want our reps calling into companies going through list by list of the new products. I want us doing discovery around the different value drivers and then discovering which of those is most important. Then we can go in with a bit more of the product centric approach.
Todd Busler (28:31):
Kyle, for people that maybe aren't familiar, you said value driver a couple of times here, what exactly is that?
Kyle Asay (28:37):
A value driver is something that generally exists in an account with or without your company, so it's important to them and it can kind of stand alone, but then it should tie back something that you do very, very well. Usually value drivers are going to tie back to either making money, saving money or mitigating risk. Can different companies have different ways of phrasing that because the way that your company helps the company make money is going to be different than how we do. If you have value drivers that don't tie back to one of those three things, then you need to probably find a different company to sell for.
Todd Busler (29:06):
Yeah, it's getting called to some of the team building scaling parts. So you took an org, I believe from eight ramped reps, scaled it up to 40 while improving productivity. You talked a lot about some of the inputs there. What were some of the supporting cast or other roles that you had to bring in and how do you kind of sequence that? For instance, I know you have Laura who focused specifically on pipeline programs, which I think is really smart and I'm surprised not more popular. I'd love to hear how that happened and some of the other supporting casts.
Kyle Asay (29:39):
So the eight to 40 was a Mongo and it was a very different supporting structure than I have at LaunchDarkly, and I think Launch actually does a lot a better job with it, where Mongo had phenomenal support around leadership development and enablement, really good sales enablement resources. There wasn't as much on the system side, and I found that when it comes to great PG programs, great sales programs, having the right approach and framework, the right systems and then the right enablement of the systems has been critical. And so Laura as a great example where we can be in our one-on-one, she's the one that takes my angry ranting and rambling and hypotheticals and grandiose ideas then and takes it and actually makes it happen with our tooling and systems to build it out. And so that has been a phenomenally important resource. Then I also, when I think about resources, a big part of it is within my own org with the AEs and the leaders, and so a big reason for our recent success has been the fact that a lot of my most tenured AEs are mentoring and helping new reps with the historic knowledge they have of how to sell LaunchDarkly, our territories, our older tools.
(30:51):
I've always been very fortunate to have incredible AEs in my org that are willing to be a resource, and that's basically supersized enablement in a lot of ways. And then the frontline leaders play a massive role too, to go drive adoption. The processes drive accountability of processes, but if you give me Laura, the great reps that I've got and the great leaders that I have, it's going to be hard for me to screw it up.
Todd Busler (31:16):
Was it as simple, Kyle, as some of the reps that have been there for a while have had some success at tenure? You mentioned how you kind of earned the right, you delivered some quick wins for them and had some great details around that. Do you do anything else formally or informally to encourage some of that knowledge sharing or like you said, kind of getting enablement at scale?
Kyle Asay (31:36):
It's something that I can't really take credit for, right? Because from day one I've said, Hey, I want our culture to be one of wind sharing and teaching, but everybody knows that what the VP puts in their culture slide isn't the culture, it's a goal, it's aspirational, but I think what I've done an okay job of is just recognizing it. Like at our last QBR, when I was recognizing top performers, I had a whole, so it was my most important slide for me at least, and I just walked through all the reps. Some had missed last quarter, some had hit. I was like, these are the reps that are setting the standard for culture because they're willing to share, they're willing to mentor, they're willing to encourage, and I just made it incredibly clear to everybody how valuable that is. And then I do everything within my power to reward that financially as well through how we think about a lot of different areas. But man, part of that, I can do a really good job as a sales leader, but if you don't have the kind of high integrity, incredible people that I'm lucky to work with, it all falls flat. And so if anything, this is just a shout out to these reps at LaunchDarkly that if it weren't for them buying in and being the incredible people that they are, we would not have nearly as much success as quickly. And that's something that a leader can't take credit for. That's just having high integrity people on your team.
Todd Busler (32:51):
Love it. Kyle, we were talking about this a little bit before a hit go and record, you build a sizable brand around Sales Introverts. Why do you think the sales world needs that message or what have you been out to accomplish with that?
Kyle Asay (33:04):
It started because early in my career, I generally felt like I had a ceiling on my success because I was so different than the perceived top performers in sales. In what way? All the top performers were the ones that loved the client dinners and golf trips, and they were very loud and very outgoing, very charismatic, and very seemingly extroverted. Now, by the way, charismatic sometimes loud does not mean that you're an extrovert. There's a lot more to it than that, but the perception of sales is extroverts have the advantage. I still see this all the time, especially on Twitter and LinkedIn. People say, oh yeah, introverts just can't sell as well. I think part of it was just wanting to break that perception because introverts are just as capable as selling really well and being great sales leaders as extroverts. That was the main premise of it. I just wanted to be an example that, look, you can hate events but still be good at them. You can not like social activities, but still be good at them and you can be drained by a lot of calls in a day, but still be a great salesperson. You can have all the introvert tendencies being solely created sales, and it's resonated with a good amount of people, which I'm grateful for.
Todd Busler (34:15):
Amazing, and I told you this I think before we hit record, but I get a lot of value for it. I think your ability to approach problems that everyone's dealing with on the sales side and give frameworks is the top out there, and I know it takes a lot of time to do that. So thank you on behalf of the broader sales community.
Kyle Asay (34:32):
Thank you.
Todd Busler (34:33):
Kyle, I saw something you wrote about average reps in great org often outperform great reps in average org. I agree with you here, but I would imagine with your track record and B, just the way you critically think, I would imagine a lot of people that have worked with you for you come to you for career advice. What advice do you find yourself giving when people are working through different opportunities?
Kyle Asay (34:58):
Man, so I'll start with the environment being most critical. I just got this question just yesterday. I think it was like rank these things in order like rep skillset, market climate, product market fit. I said, well, first product market fit, because you can be the best rep in the world, but if you're not a product market fit, you're going to struggle and the environment matters. And now a lot of reps, I don't want to get controversial here, A lot of reps will say, well, I can't really control my environment, but I think often you can when reps say, well, I'm not having success because the companies I work for suck. There's ways that you can battle and try to find a way to hire quality companies over time, and I urge people to do that from a career standpoint because your career is not often going to grow faster than your company is able to grow and support.
(35:44):
There are incredibly phenomenally talented sales leaders and sales reps that are not making very much money because they're at the wrong company, at the wrong time, at the wrong face, either too early or too late. And so my first advice is assess your environment. If you put everything into it, if you get as good as you can, if you do everything within your control to succeed, do you have a high ceiling or are there real constraints around the product quality, company quality, holding you back? If there are, then you need to fix the environment first and foremost. Then I'll give you one more. So the environment matters. If you look at the companies I've worked for and you go look at how we're rated by our customers, go look at the most recent G2 crowd for LaunchDarkly, like I've never seen that big of a gap.
(36:33):
I'm smart enough to know that I'm not good enough at sales to sell a bad product. I don't accidentally find myself come as a great product. That's very intentional. But then the second piece is the sooner that you master the internal locus of control, the better off you're going to be. I think a lot of people that struggle in their career are always finding another reason why they can't have success. My sales leader doesn't develop me. My territory isn't good enough. I haven't gotten lucky inbound. There's always another reason for why they're not as good as they think they should be, and it's never ever their fault. Now, I'm not saying that there aren't things outside of sellers control that influence us. I just talk to how important the environment is, but the best reps and leaders I've always worked with have always had the internal locus of control. They feel like their success or failure is largely up to them and how well they take advantage of their circumstances. Some other piece of career advice, find the best environment you can and then take complete ownership of your success and failure because as long as you think you're dependent on other people for your success, you're probably right and nobody is going to care more about your progression in your career than you do. That's a really bad combination.
Todd Busler (37:45):
How did you learn that last part? Did someone teach you that? Did you come to it over time? What I mean is the locus of control part.
Kyle Asay (37:51):
Oh, yeah. Oh yeah. I was early in my career and I was not having success and it was in my mind because I didn't have as good a customers. He just got that great inbound. Of course, he's going to hit quota. I'm not going to hit quota. I wasn't having success. I was not willing to, one, put everything I had into success, so I was concerned. I was scared that if I do everything I can and I still fail, then I have to actually accept that I'm a failure, which that's hard if you're not trying as hard as you can. You always have the mental out of, well, I'm not as good as I could be because I'm not trying. I could be that good if I tried harder. It's a mental hedge and then the comparison piece, and so my second line media at the time sat me down and was like, Kyle, you got to run in your own lane.
(38:33):
You are so worried about everybody else is doing that. You can't get out of your own way. You have your territory. You have your job. Go focus on your jock and do the best you can there and see what happens. I was like, all right, let's try that. And then ever since then I've tried my best. Here's my lane. I'm going to sprint in that lane as hard as I can, but I'm not going to worry so much about the things that I can't control. And over time, especially in sales, if you do that over a long enough time horizon, the cream will rise to the crop. I've seen reps get lucky, have great years. I have never seen a rep luck their way into a decade of success.
Todd Busler (39:12):
I started my career at SAP, and there's one rep that has been there and he had seven years in a row of high earning years, and where all the people we started together the first year or two, you're like, this has to be luck, right? No one does it for seven years consistently, right? There's something there. So I agree with that. Last two questions I have for you, Kyle. This has been amazing. So we talked a little about kind of choosing the right opportunity and how you approach that from the pure leader perspective, not the rep perspective. How much do you think about phase dependent of a company, like exactly the right revenue bands, et cetera? How much does that go into your equation?
Kyle Asay (39:47):
I've learned a lot the last few years on that. It's extremely important, but there's also not one right phase for everybody. You kind of got to know the problems that you like to solve, and so I'll add to that on the environment piece for leaders specifically. And so when I was looking at LaunchDarkly, it had my non-negotiables, great product, large market. Then it also had massive opportunity because their biggest problems were things that I am pretty good at solving. And so when you're a leader, you're looking for product market fit and then problem you fit. Because if you go to a company where the problems are ones that you're not good at solving, you're going to be pretty frustrated a lot of the time. But if there are problems that you're good at solving and you get to be the person that goes in and solves the big problems for the company that's really good for your career and the problems the company is facing is directly correlated usually with the phase that the company is at and their trajectory.
(40:44):
And so for me, I love this late stage startup phase because there's definitely product market fit. There's underlying systems and processes. I have resources call me lazy, but I like to have resources, support a lot of the things that we're trying to do, but it's also early enough where when I want to go make a change, I don't need to go write a memo and have it circulated amongst 73 people. It's going to take me 13 months to get approval to add a Salesforce object. That's not a good phase for me. That's not my happy place. But yeah, man, the problem-leader fits. I think it's something that more leaders should think about when they think about career progression. Career journey.
Todd Busler (41:22):
I love that. I remember my previous company was like zero to 25 million brought in as COO, and it was clear he was going to become the CEO, and I said, what'd you see about this? Right? You have millions of opportunities said, I love this stage. It has the big hard things that are hard to solve for a good product, big market, and it's the right level of messed up and the things where they're bad I'm very good at. And I was like, wow, that makes a lot of sense. Last question for you, Kyle, as we wrap here is, I don't know if this is true or not. Maybe it's partially because sales introvert or how you carry yourself, but you seem a lot less stressed and a lot less overwhelmed than a lot of other sales leaders at a high growth company. How do you do that? How do you go about that? What have you learned on how to deal with that and approach it?
Kyle Asay (42:06):
Yeah, it's been a journey for sure because early in my career I was very stressed, but my perspective has shifted. I look at it as I am very fortunate to have the problems that I have. I'm very fortunate to have the stress that I have. Being in sales leadership, we get paid an awful lot of money to do things that at the end of the day just really aren't that big of a deal. And so I tell my own team this all the time, this is just a job. We want to be good at it. We want to provide a good life for our families. We want to be competitive. We want to be the best at what we do, but at the end of the day, it's not worth being highly stressed over because it's just a job. It's a means to the end and my identity, my life's purpose, the things I want to be known for, the legacy I want to leave, none of those things are going to be tied to my job.
(42:56):
And so that perspective has helped a lot because that means I can go do the best I can and whatever outcome, if I do so badly that LaunchDarkly does a public post on LinkedIn about how terrible Kyle Asay is as a sales leader, I can live with that. If I do a great job and I help the organization grow on a scale of a lot of success, that's cool. That's a lot better of an outcome, but it's not going to make my life by any means, my happiness, my joy, everything that's most important to me, it is tied completely at this point to faith and family. My job supports those things, but it's not my identity.
Todd Busler (43:28):
Kyle, there's some gold in here. I really appreciate you taking the time. Share some of your learnings, frameworks, hard earned right learnings, and I love the way you approach it on all front, so I appreciate you taking some time.
Kyle Asay (43:39):
Of course, great conversation. I appreciate the preparation for.
Todd Busler (43:43):
Alright, take care, Kyle. Thanks for listening to Cracking Outbound. If this was helpful, let us know by messaging me, Todd Busler, on LinkedIn and share this episode with a friend that you think will be interested. If you want more resources about building and scaling all things outbound, you can sign up for our newsletter at champify.io/blog.