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EP 4: Corey Kossack, CEO at Aspireship

Podcast Transcript

James Mackey  0:12  

Hi, and welcome to scale by design! I am your host, James Mackey. And today we are joined by Corey Kossack. Corey, welcome to the show!


Corey Kossack  0:20  

Thanks so much for having me. James. Nice to be here.


James Mackey  0:22  

Yeah, we're pumped to have you on. And before we jump into it, could you just share a little bit about your background and what you're working on right now with the audience?


Corey Kossack  0:30  

Sure. So the short version is: I've been an entrepreneur for most of my life, been through starting, failing, succeeding, raising money, selling, starting up again, all of that kind of stuff, and currently founder and CEO of a company called Aspireship, say learning and talent platform for the SaaS industry or the tech industry. Broadly, we help people change careers pivoting into SaaS sales, and now, customer success, which is launching just now. 


So yeah, we work with companies all over the place, venture-backed companies dealing with all sorts of challenges. So I know the space well, and lots to talk about here.


James Mackey  1:14  

Love it. This is gonna be a fun conversation, both of us working within talent and talent acquisition, and also working with startups and growth stage companies. So there's a lot of overlap there and probably shared experiences. So this is going to be fun!


I know one of the things that you actually said is you started this company right before COVID. Which is kind of a weird time to start a company and talent acquisition and training, particularly within the startup and growth stage phase, which was pretty much completely shut off for a while. Can you talk to us a little bit about what that was like, and how you had to kind of shift your strategy to survive and navigate that environment?


Corey Kossack  1:51  

Yes, for sure. So first, I'm like, super fast context. I had started a company before Aspireship, which we acquired really early. And then grew the business inside a larger startup, and then eventually required by a publicly traded company, which was then taken private. And so I went through all of this stuff in like a really condensed period of time. And it was really interesting. 


And the genesis of this business was: people started coming to me left and right inside the company, from different departments, but most of them were non-technical people. And they all had some version of the same story and three years, five years, 10 years into my career, and I feel like I'm being typecast. So if I'm in customer support, and I want to go do sales, even if I've, knocked my metrics out of the ballpark, and everyone likes me, and I'm great at this and understand the product and whatever, I'm not even getting a shot internally, let alone externally for these roles. 


And the same thing was really true for people looking at industry swaps, right? So if you're in insurance, and you want to get into tech, it was like, oh, but you've never sold SaaS before, you've never done this, never done that, right? And at the same time, you know, being an acquired founder inside these larger companies, I got to go to all the exact meetings. And every time we would have a situation where we were short on revenue, or there was a threat of being short on revenue, it would come back to talent issues, you know, we're not hiring people fast enough. We're not ramping them fast enough, our attrition is terrible, and so on and so forth. 


And so basically tied these two things together and said, The reason for this, the reason that companies have such a hard time with hiring and with retention and productivity is that we as an entire workforce, we're hiring managers, we're hiring for the wrong reasons, right? We're hiring for a candidate's past jobs, how similar were they to the job that's being hired for, as opposed to what they are capable of. And there are a lot of reasons for that. 


So long story short, I decided to launch Aspireship. And the whole point of Aspireship was to build a platform that could educate people at a very large scale, on how to do a specific job in a specific industry, focused on SaaS and the tech industry, which is where my background has been. And then have them go through a process by which they could prove to themselves and to future hiring managers and to us as Aspireship, that they're capable of doing this job. 


And if they could do all of those things, then we could turn around to companies and say, "Hey, we actually have these, this great pool of candidates that you probably would have dismissed if they came right knocking on your doorstep". But you should hire them and you should pay us for the privilege of doing so. And so that's essentially what we built. 


And, now getting to the COVID part, so we launched the day before Halloween 2019. And with that launch, like any new business, in the first six months you're just trying to prove that it could actually work, right? So not only are we going out to market saying, Hey, we're gonna have we want you to hire out of our talent pool, we want you to hire people that you probably wouldn't have hired before. And we also want you to pay us extra money for the privilege to do that. Right? Pretty far, you know, far-reaching thing. And so we had just gotten February of 2020 was like, it works. We got our first couple hires, go in, they liked the people, you know, it's proven itself out. And then march 2020 hit and it was like..


James Mackey  5:42  

Everything was tight, the entire pipeline dead. Right?


Corey Kossack  5:45  

Yes. Like everything frozen in time. I remember sitting in my office. I don't think it was March, I think it was April, at this point. You know, looking out the window. There are no cars in the parking lot. So I'll stop there. But yes, what followed was quite interesting.


James Mackey  6:07  

Yes. I mean, I suppose the other challenge, too, it's like, even when the market was coming back initially, there was so much highly relevant, qualified talent available on the market, that one of your I'm assuming, like one of your core value propositions is the tight labor market. 


And this is a way to get people in, that are motivated to succeed, that you've trained up. Maybe, there are even some benefits from a cost perspective in terms of salary that you can bring in. And maybe one of the value adds, right, if they have the ability to hire all of these highly qualified SaaS individuals because it was a loser labor market. I could see that potentially. Also being interesting to navigate.


Was that one of the challenges in the early obviously, not now. But in the early days of COVID? Was that also an issue?


Corey Kossack  6:59  

Yes, for sure. I mean, so I think, number one, you know, we from the start, we're pushing a paradigm shift, right? 


When you talk about highly qualified people, we think of it as like, okay, if I'm hiring for SaaS sales, find me, someone that's hired that spent, you know, X number of years doing this at a company similar to mine with a sales cycle similar to mine. And if I have that person, and I have somebody else who hasn't done that job before, or hasn't done it in this industry, or this buyer persona, this one is the right one,  this is the qualified one. 


And so our trick, of course, over time, is to show that this one over here actually has a higher probability of outperforming the other one, right? And so nobody would really believe that until we start proving it. And so, at this point in time, you know, going back 2020, you know, we had no data to show we had no, no historicals, no momentum, all of that stuff. 


But I think the biggest challenge was, you know, we talk a lot about market conditions. We were riffing on this before the show officially started. There are a lot of parallels to today. And that is basically that in 2020, essentially, what happened, especially for all these venture-backed companies was, they have boards they have people to answer to, they have people that have lived through other cycles that are giving advice. Some of it's really good, some of it's not. And also, like, no one knew what was going to happen. Right, you think back to what you thought about COVID when it started, and what the impact was gonna be, you know, you didn't know it was just a bunch of fear. 


And so basically, the advice was, cut deep, do heavy layoffs. And there I was pitching to investors for like, our seed funding, you know, factoring this time. And they're like, Yeah, but I mean, it can be 24 months before anybody hires anyone again. And I was like, well, here's what I think is gonna happen. And I remember saying this stuff, basically, companies are going to cut so deep and be paralyzed for a quarter or two or three, and then you're gonna get to the end of 2020 or early 2021. And they're gonna go, how in the world are we going to hit our numbers for next year? Like, let alone the fact that this year was a nightmare, but everyone kind of wrote it off? Like, yeah, it's gonna be a nightmare. It's COVID and the whole thing you know, 2020 is this epic year that we've never, you know, experienced before at least not in our lifetime. 


And so, that is what played out. So basically in 2020, we had next to no revenue, and we did a little over 100 grand for the entire year and that was our first year in business. And, we had to decide, okay, are we going to stick to our guns on this?  Is it going to come back, and we're just going to build for that moment and be okay with the revenue loss or are we gonna freak out and you know, do something else.?


And so we stuck to our guns. And we just built a lot of value for the candidate community and started really building a grassroots name for ourselves during that time. 

And as soon as hiring started to tick up, it was like this little baby increase. And then all of a sudden was like, right, because demand went off the charts. And everybody in their brother was trying to hire. And not only could they not find people, but you were shifting from local to remote and all of this stuff. And so we're really well positioned to start getting people to take a chance on us. And as that happened, we built great relationships and have a lot of, you know, people where the proof is in the pudding, they hire somebody, and they're like, Oh, they're great. I want more, right, let's just keep doing this.


James Mackey  10:56  

Well, you know, it's actually interesting now that I'm thinking about it. As hard as it probably was in  2020, 2021 was probably one of the best years of all time to prove your model. Because companies had to hire so badly that I feel like they're a lot more open to just saying, Yeah, sure. Let's just try it. Let's see if it works, right? And that opens up so many doors. 


We had a lot of clients. So what we do is basically, tech companies borrow recruiters from us, right? That's, that's the model. It's not contingent based. It's not retained. Exactly. It's kind of like a subscription thing where people borrow recruiters from us. 


And there were a lot of companies in the startup and growth stage, a part of the business that they've really not done before. That model was more so historically done in enterprise companies, right? And so we were kind of bringing that to startups and to the growth stage. And so a lot of them, they really hadn't done it before. But 2021 was a great year to get in there and say, Hey, let's try something new. Right, what you have right now isn't working. Right? So maybe you don't just totally abandon that. But why don't you augment those efforts and try our solution? 


And that was a huge driver of business, just willingness to experiment and try new things that I think was just already kind of breaking down because people were already changing employment packages and opening up remote, and they were already trying all this new stuff. So I think people were also more open to just trying new things and 2021 as a result of just the insane growth that we were all experiencing, right?


Corey Kossack  12:24  

Yeah, that was totally true. And I love how you phrased it, right? It wasn't just like, " Hey, anybody could do well, in this market where, you know, companies are dying for talent". It was more about having enough scale to prove the concept. 


And so we were able to do that, you know, in spades had a huge growth here, in 2021. Both in supply and demand. You know, we went from, you know, very little on both sides to hundreds of companies hiring through us and 10s of 1000s of candidates going through on the learning side. 


And, so it was a very, very interesting time. And now, we're back to I don't really think it's like COVID. But, for anybody paying attention, there's this, like, new thing going on, right around inflation and interest rates, and how that's impacting company valuations, and therefore the funding environment, therefore, they're spending and therefore they're hiring. And it's all happening really quickly. Because the advice is coming from a consolidated number of places and being pushed, you know, out. 

And so it's just a very, very, very interesting time. But I think there's going to be a lot of parallels to what we saw in COVID, it's a little bit different. But we're gonna see this, you know, there's back to this pent-up demand strategy happening again,


James Mackey  14:01  

Right, in terms of specifically for, I don't know, for tech, we're not technically in the same industry, but we're both, you know, essentially helping customers with talent acquisition, right, in our own different ways, right? 


But it's just interesting, that cycle specifically for us to where it's like, okay, at the beginning of a contraction, right, or perceived contraction. I mean, I think a lot of companies in the SaaS space were cutting even before they had any, you know, could even see if there was going to be demand issues, right? 


So what typically happens is they're going to look at, okay, what vendors do we have because they want to try to avoid layoffs if they can, right? So they're going to look at vendors, they're going to try to see okay, are there any cuts that we should make there? Right, and then from there, they're going to cut deeper due to their VC advice, right? Again, who knows, maybe revenue is even affected, but they're still gonna do that, go through that motion. They're gonna cut their internal team. 


And then ultimately, when they're coming out of that thing, they're gonna go like, Oh, we need to go hire recruiters. But then everybody's hiring recruiters, so they can't, so then they start looking for vendors again. And then we start to see that upswing and really coming out of it. A lot of times, players in a similar space to what we're in, end up growing a fair amount, because a lot of these companies, they've kind of cut all their internal resources. And they need to leverage this even more than before, right? 


So it's just very interesting to see that I mean, a lot of companies look at recruiting and talent acquisition as like a transactional notion, That they can just kind of flip on and off. 

And so to some extent, if you can be a vendor that helps facilitate some of that demand fluctuations, that can be really valuable, too. But it's just been interesting for sure to see the different market conditions, it's a really interesting time to be in talent acquisition. I think the companies that have the right strategy and approach to overcome them. And there are still a lot of great opportunities. I'm very bullish on external talent acquisition providers, whether it be services or platforms, or marketplaces right now because I think companies ultimately are going to want more flexibility than ever before, just due to a lot of the volatility in the market. And I think companies similar to ours are going to be the ones that benefit from that, personally. 


Corey Kossack  16:14  

Yeah, so, a couple of interesting things. 


So one is, what you said is true about the vendors, and third party talent, stuff, and all of that, and internal recruiting and all that stuff, too. The other thing that happens, even if layoffs don't happen, is that companies pause.


So there's one thing that is like a huge contraction, I'm gonna lay people off, whatever, but just the act of pausing. Especially when all of these companies we're talking about, right their growth companies. So even though they're being told, and this has valued, this advice has value to it, they're being told, "Hey, we'll be willing to sacrifice some growth for the sake of better unit economics, better short-term profitability or path to profitability runway extension, because that's what the economic conditions, you know, are saying, that doesn't mean no growth. And it doesn't mean slow growth, right? Because slow growth will do much worse to the overall valuation of the company than some of these other things. 


And so just the mere act of pausing creates pent-up demand for the moment in which people say, "Okay, we actually have some understanding of what the future is. We don't think the Federal Reserve's gonna go insane over the next three years, like most of it's understood, like, what's going to happen, and then there will be a reset. There also will be a bunch of other things. Like, I can't tell you the number of PE firms and stuff like that, that are inbounding, and if they're inbounding, to me, they're inbounding to a lot of companies, right? Because they're like, Hey, this is our moment.


James Mackey  18:01  

Try to take advantage, they're hoping that you need cash.


Corey Kossack  18:04  

Is our moment like, we're gonna displace the VCs? Right? So all those things are true. And interesting, and it will create demand cycles for later.


James Mackey  18:17  

Yes for sure. And I think, just to kind of echo what we were talking about earlier with the VC firms in the advisement. Obviously, yes, like raising interest rates, like the macroeconomic conditions inflation. Now, there are a lot of things to be concerned about. I just feel, though, that a lot of founders, and CEOs are not putting enough trust in their own evaluation of their companies. And they're prematurely kind of shooting themselves in the foot by cutting budgets, even when demand is holding strong, which, particularly if you're cutting, demand budget, revenue budget, that that can really very quickly become a self-fulfilling prophecy. Right? Where you shoot yourself in the foot and you actually start to miss out on growth. 


And so I just one of the things that I've been talking a lot with founders and CEOs about is just "Look like yes, you take into consideration all this advice, but also do an evaluation of your own business and your own evaluation and understanding of your own industry, meet with finance, obviously, make sure that revenues and whatever, you know, your is your typical operating procedure. Everything looks good there. But to the extent possible, we should be maintaining an aggressive posture, right, like we should be investing in demand. 


That's one thing at SecureVision is, when all this volatility uncertainty was kicking in and Q1, we started doubling down on demand. We basically didn't ask the question, how are we going to survive? If there's a recession, we ask the question, how are we going to thrive? Right? How can we have our demand gen efforts accelerate faster than a marquee contraction so we can continue high growth? 


That's a high-quality question. That's the question you want your executive team trying to solve not " Hey, how are we going to get by? I understand we have to survive in order to thrive, right? I just think that when you set the goal of, "Hey, we're going to get super conservative and, and just really just accept the fact that there's we can't really do anything better than surviving. I think that's a mistake. 


And the last thing I'll say on it is, particularly in my industry, a lot of companies did get really conservative in Q1 and Q2, they started to cut back. And now they're going through a lot of layoffs, quite honestly. Meanwhile, my company had our best lead gen month, in June, and we just surpassed 5 million ARR. We are growing and hiring. And again, I'm not saying that I have all the answers, I'm just saying that we maintain an aggressive posture. 


We didn't, we didn't stop investing in demand. And that's, instead, we invested more, we invested more, because we're like, you know, we should do it now. And we have the margin, it's a lot harder to make that decision when you're in a recession, and, you know, profitability starts to slip away, it's a lot harder to make the decision to invest more, you know, so I mean, that was our strategy, and thus far knock on wood. It seems to be working out for us. So we'll see.


Corey Kossack  21:11  

Yeah, for sure. I mean, so So some things to think about for founders, right is, number one, I always say it's a really big world. And we live in a bubble, so to speak, where we're hearing things, and whatever we hear, we think like, that's everybody, everybody everywhere, okay, hiring is going to come, you know, screeching to a halt, right? Or whatever spending is going to come screeching to a halt. 


Even with the signs that we see that these things are happening, right? It doesn't mean that everybody in the world is not going to hire anybody, they're not going to purchase anything. And so just your tactics have to change a little bit, you know, for the time being, but also, if you think about, like, your position, my position to any startup at whatever level of revenue, number of customers, whatever, thinking about your place in the overall picture, you're like a little ant, right? 


And so like, can you get enough to feed that little ant during this time period? And the answer is, of course, you can, right? Of course, you can. We're not all market-dominant leaders who now like as the market shifts, it's going to hammer everything. And so there's just a lot of bobbing and weaving to do. And I feel like, for us, we're just, we're almost used to it at this point, because it's like, went through COVID Great resignation, greatly shuffling. Now this market panic and inflation, and it's just like, this incredible roller coaster seesaw situation going on. And you just have to navigate your way through it.


James Mackey  22:57  

Yeah, you just really got to stay focused. I mean, focus on what you can catch as simple as that sounds, that it's obviously something that everybody's heard a million times, it really is the truth, we just have to focus on, how do we ensure that delivery is strong, we're producing great outcomes for our clients, we're retaining our clients as much as possible. Right? 


And then how do we accelerate our sales and revenue efforts? What channels are working? How can we tenax that? How can we open up new channels? What do we need to do to optimize there? Where do we need advisors? Right? Like to help us accelerate results there? 


I think one of the things that have really helped us too, is that we don't get stingy with advisers like I will pay somebody over $1,000 an hour. I don't care as long as they can help me produce a result. I think a lot of people look at that, like, Oh, my God, that's a lot of money. But the way I look at it is like, " look if there's somebody amazing, and I can leverage their 30 years of experience for a really compact, just hour, a few hours of advisement, that's cheap. That's a great return on investment. 


So I think companies have to be focused on that, like, how can we optimize demand delivery, open up more channels and just go all in? I mean, that's what it's about. But the more we're just starting to, like, think conservatively, we get our eyes off, you know, attacking and growing. It's just to me, I just think it's just a big mistake a lot of companies are making right now.


Corey Kossack  24:24  

Yeah, you know, you mentioned the whiplash, I don't know if it was during the podcast, or before you determine the whip, the concept of whiplash with this. 


And it's really true. It's difficult to thrive through all of this stuff. And not just the actual results that follow but psychologically, right, as a founder or revenue leader, or any of these things, you're like, ah, like, seriously, can I stop getting curveballs here, you know, like, I just have this all figured out, right? And that's just not the time we're living in. 


But if you think about the history of a lot of this stuff. The advice comes down and it may be sound advice, or it may be serving somebody else's agenda, right? And so you have to take all of that stuff with a grain of salt and say, "Alright, what are the things that I can do to avoid the whiplash and try and smooth things out?"

Because as you pointed out, what happens is the pullback happens, and maybe companies are prematurely laying off, or they're doing other things like that. Or they're slowing certain efforts. And they're going into the wait-and-see mode, which is a lot of what I see right now. And then the end of the quarter comes, and it's just awful. 


And then the board's like, yep, cut 75%. Seeing it happen. You're seeing much less than that percentage basis, things announced, but I'm seeing this kind of stuff happen. Because when you're already thinking, hey, I may need to do this. And then you start slowing, and then the results are that self-fulfilling prophecy that we're talking about, then it just gets worse. 

And it's like, okay, so now we've made those moves. Like, how long are we going to hibernate for? Like when is time for offense? Because the only way it's going the other direction is with some offense?


James Mackey  26:18  

I think so, and honestly, you want when you're coming out of whatever correction, you want to maximize the entire wave that entire recovery. I mean, you just got to be as aggressive as you can, I mean, obviously don't want to be stupid, and you have to look at your runway and cash flows. But to the extent that you want to, right, whoever is going to be in the best position coming out of this is the one that's going to thrive the most, right? 


So to the extent, you can keep your team in place and your revenue strategy in place and not make huge, significant cuts, you're going to be able to rebound a lot faster. Right. So, that happened to us.


Before COVID, we had a different business model. So we really did a complete overhaul, essentially, it's been a new company since 2020. But I will say the most significant growth we had was coming out of COVID. Really starting in Q4, for us of 2020, it was pretty much nonstop from there. 

And I was just running because after living through COVID, I just did not slow down, right? I was like, I don't know how much longer this market is gonna last. I want to get as far as I possibly can before the next correction. So we're in the strongest position possible. 


And that was always the mindset of just like this could end two quarters from now, right? It could end. And that was just kind of where I lived. And so it's like, right, when we would hit certain revenue milestones, it's like, alright, VP of Marketing, let's go, right? Get the Head of Delivery in place, VP of Operations, I would just move so fast, to ensure that we can build out the process infrastructure strategies, so that going into whatever this is, we can be as well positioned as possible. 


It's been a crazy couple of years. Definitely. I've learned a tonne. I feel like I've learned a lot at least. 


Corey Kossack  28:10  

Yeah, I certainly have. And the one thing I'll say and you know, this will hit people differently depending on who it is that's listening to this, is there will be ebbs and flows, there will be pullbacks, there will be things like that. We're going to feel it. We're already feeling it. But we're gonna feel it, especially in the tech market. But this industry is going to grow like gangbusters. It has and it will, this is not stopping. 


And so there's just an interesting moment right now. Got to figure out your way through that moment. But make no mistake, this is not going to be some five-year slide and tack. That is not possible. And that is not happening. Even evaluations come down to any of those things. The industry, the innovation, it all exists for a reason. Is it because people need it, right? People need what we're delivering, companies need what we're delivering. And you know, the pursuit of growth is never going to stop. It's just going to pause for a little, little tiny bit.


James Mackey  29:24  

Yeah, well, I'm really excited to see how y'all continue to grow. And it sounds like things are going really, really well. And I'm excited to see what you're doing in the future as you guys continue to scale.


Corey Kossack  29:33  

Thanks, man. Yeah, appreciate it! 


James Mackey  29:37  

For sure! Thanks for joining us today. We're coming up on time here. But I had a lot of fun speaking with you. And if you're up for it, I would love to get episodes on a regular rotation, maybe meet up a couple of times a year to do another show like this. This was great!


Corey Kossack  29:50  

Yeah, I'd love to, I mean, seems like we'll get along great and have a lot of common things to share. So happy to be here anytime.


James Mackey  29:57  

Yes, let's do it. And for everybody tuning in. Thank you for your Joining us and we'll see you next time!

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