Hiring an Early Stage CSM

November 3, 2023 | 48:56

Season 2, Episode 20

Why is the Customer Success function getting more attention in the market today? Is this translating into more hiring demand? And what skills does a “founding CSM” need to execute well in early-stage environments?

It was fun to discuss with our former colleague, John Gleeson, a former CS leader who is now running his own venture firm, SuccessVP.


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Transcript Text

Chuck: Hello and welcome to our latest talent GTM podcast. I am Chuck Brotman, the host for today’s episode, and I am very excited to have my former colleague, accomplished CS leader, and investor, John Gleeson on the podcast, John, thanks for joining us.

John Gleeson: Oh man, Chuck, it’s so good to be on the pod with you today. It’s nice to reconnect.

Chuck: Yeah, for sure. It’s great to reconnect. I know we’ve had a chance to meet a few times, since, since I left motive, but, great to have you as a guest on this show and really looking forward to talking customer success and SaaS with you. To share John’s bio with, with our, our listeners. John is a very respected customer success executive.

Chuck: He’s a seed investor and a thought leader in, in many things, SaaS and customer success, before starting his company success VP, which we’ll talk a little bit about. He was a VP of customer success at motive where he. Led the company’s post-sales efforts as it grew from a little north of 1 million to over 300 million in revenue and supporting the creation of almost $3 billion in enterprise value.

Chuck: John has recognized one of the top influential customer success leaders from 2017 to 2022, and he’s made a significant contribution to the industry, including appearances on other SaaS podcasts and being featured in the book, the Customer Success Economy, published by Wiley in 2020. When John is not, Talking customer success and SaaS.

Chuck: He has two young girls, age two and five, and likes to spend time outdoors with them at the beach, biking, mountain biking, et cetera. John, again, great to have you on the show. One thing I know and recall fondly about you, I think even when I first met you is, is how much of a, of an enthusiast you are for, for technology and SaaS.

Chuck: And I’m curious if you can tell our listeners a little bit about your own sort of interest. How you got, you know, how you got interested to begin with and maybe, you know, where that comes from and yeah, I’d love to kick things off there.

John Gleeson: Yeah, absolutely. Well, yeah, you hit I would say you like you hit it on on the head for sure. I’m and I’m absolute enthusiast about all things SaaS . You know, some people like follow sports and I feel like this is like what I geek out on. I’ve got so many, feeds and Updates and emails that I’m getting every day.

John Gleeson: And I just like, I really follow the movement of what’s happening in the, in the startup world. Like it’s a passion. I guess like, how did I find my way into it? You know, I’ve been a lifelong entrepreneur. I was like the kid who was selling stuff online before, even PayPal. You used to have to, you know, sell something on some forum somewhere and you do cash on delivery.

John Gleeson: So I always like knew that I was like in this world of building businesses. But we really like where it all came together as I joined a startup after my MBA. I was the first hire there. Really didn’t know like what I was getting into. But quickly knew there was so much. I didn’t know. I didn’t even know what what I didn’t know.

John Gleeson: And I just started to like, dive down the rabbit hole of, you know, reading things like what Jason Lemkin was posting at the time on Quora, and then it put me on to, you know, other bloggers and quickly, yeah, just fell in love with this whole, this whole world of SaaS . And at the time, you know, I was part of a startup in Halifax, Nova Scotia, Canada from Canada originally.

John Gleeson: And so this whole other world of what was happening in, in Silicon Valley actually felt like. So distant from where I was. So sometimes, like, when you just can’t, like, you know, Go see and touch that thing. You spend all your time like reading, reading up on it and following along. It’s almost like watching a movie.

John Gleeson: And so I just had like this, this massive fandom for it before I finally landed in Silicon Valley a few years later. And when, and when I got here, that’s actually, you know, when, when I met you. But now I feel like I get to kind of live parts of, almost like a fantasy around building companies.

Chuck: I, John, I was going to ask you about that being, being from Canada. You know, about the kind of the regional, dimension to this. I’m curious, do you, do you feel like if, you know, you were getting that MBA today or, or that initial job today, I mean, would, would that still, would you still have thought of this as, as a Silicon Valley thing and come out to the region and spend some time here?

Chuck: Or do you think times have changed now? We’re sort of the kind of innovation that excited you. You can find companies anywhere across the world or more distributed across North America, at least.

John Gleeson: Yeah, I think certainly like, you know, 15 years ago when I was getting into it, so much of the hub was, you know, certainly like Silicon Valley base. Like when I started to come out to the Bay Area all those years ago, like we used to have to actually go to Sand Hill Road. Like it was, it was kind of funny, like things hadn’t even moved up to San Francisco yet.

John Gleeson: And so I would certainly say that like, yeah, now great companies can be built. Anywhere in the world, there’s, you know, great startup ecosystems, you know, across the United States, across Canada. But I still think like there’s a gravitational pull towards, San Francisco, right. Or, or Bay Area in general, because of, because of like the longevity of that ecosystem, right.

John Gleeson: It takes a lot of different components for an ecosystem to develop. You need, You know, the schools, you need the funding. You need people who have been there and done that. And so all of these things take a long time. So I think for me, there still would have been that pull to come out and to see what it was like and want to test myself on maybe the biggest stage, In the world because that’s, you know, still what what it is in a lot of ways.

John Gleeson: So I would say like the path certainly would have led through, Bay Area, still, but I wouldn’t dissuade a great founder or great founding team from, from building wherever they are. I think every company is unique when it comes to the talent that they need to build their business, where their customers are, the customer base that they serve.

John Gleeson: You know, those unique needs are different for everybody. And so I think it’s really important to, to adjust accordingly. But knowing that, you know, there still is a lot of money and a lot of know how in in the Bay Area that can accelerate a journey. and you know, when we sign up to go on this, let’s say venture backed high growth technology startup journey, you know, sometimes just being close to that can be pretty helpful.

Chuck: Yeah. No, I definitely agree. Someone who’s been in this area a long time. I think there’s, there’s a lot of value to it and it still is a hub, for a lot of innovation and networking opportunities. I wanted to, to segue a bit from your interest in technology to your interest in, in, in customer success, because I similarly remember when we first met that you had, I thought a real passion for that as well in terms of the importance of thinking about CS in a certain way, you know, early in a business’s life cycle to set a good foundation.

Chuck: And I’m curious if you can talk a little bit about that. I, you know, my own career, I. You know, I was in customer facing roles before there was a function called customer success and predating sort of the maturity of SAS. So I remember the pre CSM days, but I’m curious for you as someone who, you know, at least when you joined Motive, sort of in the heyday of SAS, if you will, what, why customer success?

Chuck: What got you so interested in that as part of your interest in entrepreneurism in general?

John Gleeson: Yeah. So I actually went into customer begrudgingly. It was, yeah, it was, it was not love at first sight.

Chuck: Before Motive, we’re talking now,

John Gleeson: before, yeah, before motive. So like I said, I joined this startup post MBA. I was the first hire. It was pre product market fit. I ended up actually moving down to New York city with this company.

John Gleeson: And my first job was to do customer discovery. My first job was to just like, you know, get the doors opened up for us and go talk to. Our potential customers. We were selling into the ad tech space and there’s agencies and brands in New York City. So I went down to New York City to kind of just like unlock customer discovery.

John Gleeson: So then we, you know, we started to meet people and customers and we started to have a product that we could sell. So then my job was actually to to sell. So I was our, Really our first salesperson. And because I was in New York City, the founders are back in Canada. I was the person in the room basically doing the first And so I did the first million dollars, in sales alongside the, the founder.

John Gleeson: I was in sales and then we had something that, you know, I could sell on my own without any help from the founder. So my job became to sell and we did that and then we, you know. It was clear we had some product market fit and we needed to scale the sales team. So I started to build out our first sales team.

John Gleeson: Well then we had all these customers and, we were a subscription business. So we needed to renew them. And, one of the co founders basically came to me one day and said, Hey, listen, you know, I’ve been reading up on this thing called customer success. We’re a recurring revenue business. You know, we, we need your help.

John Gleeson: You’re the figure it out guy. Go figure out this thing called customer success. And I was so bummed because, you know, like, you know, you’ve had a great career in sales, you know, the high of closing a deal, you know, what the commission paycheck can start to look like as you start to like really unlock. You know, how you go about selling something and the velocity accelerates.

John Gleeson: And so I was like, dang, like customer success. This is a silly name. Like, geez, this is, this is going to be career suicide. This is not good.

Chuck: Right.

John Gleeson: So I begrudgingly did it because I was the figure it out guy, but it turned out it was actually like the. Best thing that could have ever happened to me. You know, this was not quite 10 years ago.

John Gleeson: But Gainsight. So Gainsight was just coming of age. Nick Meta, had just become the CEO of that company. They were doing a ton of work on category creation and they were really just like defining, the motion for customer success. So here I was, I had this like canvas and this growing company.

John Gleeson: where I, you know, was the figure it out guy. So I could really like, you know, go and explore a lot of different things. And I had gain site that was coming of age, creating this category. And so it didn’t matter that I was, you know, only a handful of years into my career, you know, nobody was an expert at this.

John Gleeson: Everybody was learning customer success. And so I quickly got to become, An expert in, in this space. So like the timing just couldn’t have been, more perfect. and so,

Chuck: Did you deploy

John Gleeson: we did. Yeah. Yeah. We use game site. That was, you know, a long time ago now that was my evenings and weekends. project.

John Gleeson: There was one summer, where, you know, we didn’t have a biz ops department to help me. And that was basically became my evening and weekend job that that whole summer was to get it Gainside up and up and running. Yeah.

Chuck: gainsight? That’s awesome. So in a way you, I mean, you as the figured out guy tasked to do something initially begrudgingly, but as you dug in, I mean, was it kind of a, I mean, did you have a light bulb moment where you realize like. You know, getting this right is really key to building a healthy SaaS company.

Chuck: Is, is that a fair way to put it? I mean, is that, was that your epiphany about how this all connects with SaaS and your interest in entrepreneurism?

John Gleeson: Oh yeah. Totally. Like that, like, you know, like, yeah, at my core, I think I am a, a sales leader still at my core. And so when I started to just like unpack the math of how a SaaS business. actually works. That was when I was like, actually, this is really cool. I’m going to get to own the biggest number in the entire company at some point if I do this well, right?

John Gleeson: You know, all of us in, in SaaS are searching for that proverbial hockey stick curve, right? And when you like break out that curve, in SAS, you, you basically have three ways to, to make it. Do its thing, right? You can sell more new customers. You can sell more to your existing customers, or you can do a better job of keeping your existing customers.

John Gleeson: And so in customer success, you come to own. Those latter to sell more to your [00:13:20] existing customers, do a better job of keeping your existing customers. And really like the only way that that curve right be due to like the compounding nature of recurring revenue businesses. The only way that curve ever happens is,

John Gleeson: if you expand you renew your customers really well. And so once I started to like connect the dots on on that, I was like, okay, here’s here’s where the real power lies. Let’s let’s do this. This is cool. So yeah, for sure.

Chuck: Do you, do you think in a way, I mean, it, what you’re sharing, I feel like this has become, it’s spot on by the way, an excellent way to frame it, I feel like it’s. It’s not controversial today and there’s just, you know, quickly growing recognition of the importance of the second and third categories. and I mean, do you feel like in a way, like we’re companies sort of, you know, almost irrational and clinging a bit too much to like the importance of like AR growth at the expense of expansion and retention and sort of, you know, have they been kind of forced to make a healthy course correction that was almost overdue based on kind of our changing Economic climate today and the fact that companies have less money to spend, like, is this an, I guess, is the sort of focus now in the market, if you agree that there’s like a lot more focus now on the importance of expansion and retention, is this an overdue change that sort of, you know, that you kind of anticipated or, is it, you know, maybe just something that’s, you know, that’s, it’s based on, on our error today, just people not having that sort of the extra dollars to invest in, in AR growth.

John Gleeson: U I would say like everything like, you know, you know, runs its runs its course. You know, I never got frustrated. You know, when I was on the CS side, and, you maybe saw more emphasis happening on the new logo side, as opposed to what happens after the fact, like. You know, I think that’s like reasonable to expect, right?

John Gleeson: If you’re not, you know, if you’re not getting new logos at a great clip, well, you’re not going to have customers to renew and expand. So like,

Chuck: at the time that we were both working at Moda when it was really a greenfield market and getting those logos to begin with was imperative, right?

John Gleeson: yeah. And I think like, that’s so important. It’s, you know, you should never discount just how hard it is to really get. That machine up and running, right? It’s it’s not trivial to take something that the founders, you know, had to learn how to sell and then, you know, get 10 people to figure out how to sell it for themselves and then take those 10 people and turn them into 30 people who can all, you know, spit out quarter after quarter predictable.

John Gleeson: New logo acquisition like that is the hardest thing.

Chuck: right,

John Gleeson: right. I think, though, like what I’m seeing now in market is that people are starting to spend more time on what happens after the sale because they have to, right? You know, the market has changed so much from, you know, zero interest rate. Market where cash is flowing to, Hey, you may never be able to raise another round.

John Gleeson: So take everything that you have, polish it up. And I think that, that’s really, really important right now. That’s probably like the big reason why I started, you know, success VP, my venture fund, I was, you know, just hearing from upstream investors, how much their companies, were struggling with either renewing or expanding their existing install base.

John Gleeson: And there just wasn’t like a clear, Unpack on on how to fix that problem. But I would I would say all things run their course. I think right now, customer success may be having a moment where people like really need to care about it. But that’s not without, you know, some some ways. And so much of this is is tied to macro and is unique to each company as well.

Chuck: I want to ask you about that moment because, you know, I, you know, certainly I’m seeing as we’re discussing here, there is definitely a, a paradigm change and recognition from you know, all pockets of, of SaaS that retention matters, expansion matters, and our matters, et cetera. So I, so no doubt there’s, there’s been a shift there and it would seem to mean this is the moment for, for CS, you know, in, in our recruiting business, I don’t feel like we’ve seen this translate into increasing demand for customer success.

Chuck: Personnel. Now, I’m mindful that, you know, obviously in this, you know, economy, there have been a lot of people, you know, put back on the market due to rifts and downsizing in general, which, you know, unfortunately has created, you know, an imbalance of talent, at least from the perspective of job seekers, unfortunate, right, that there’s more talent out there.

Chuck: But I don’t feel like I’m seeing sort of the surge in demand for customer success personnel that one would expect given this paradigm shift. Now, I don’t have numbers to back this. A lot of this is, you know, it’s anecdotal based my business. So I’m curious what you’re saying, you know, is are there indications whether from data sources you have or just your own observations like is demand for customer success picking up?

Chuck: Is it picking up in certain segments over others? Or, you know, is it more that Yeah. You know, this is getting more focused, but people are expecting, you know, more for less, so to speak, right? and then it’s less about hiring more CSMs and more about just, you know, investing more in process and tech to ensure that the CS team you have now is, you know, accountable and executing at a high level,

John Gleeson: that’s a great question. Actually, I don’t disagree, with like the, the output of it. Like I haven’t seen an uptick in, in hiring. Here’s what I’ve observed, kind of happening. I think like the focus. Is super high, but the way in which it’s coming out in companies is probably a little bit different than maybe we expect.

John Gleeson: I’ll explain it to you and maybe like or share what I’ve seen in in two waves. So think about like the last couple years. Like we had 2021 everybody. could raise cash. They did. They built these great big sales teams, right? And they probably did that ahead of when they should have. You’ve probably seen this as well.

John Gleeson: They weren’t quite there on product market fit. It was pretty loose, but You know, cash in hand. Let’s scale the team. What you started to see then as 2022 shook out and funding starting to change is you had incredible growth. You know, you know, and I know a great salesperson can sell. You know, an okay product and make it work.

John Gleeson: So then what we started to see is we started to see actually like churn really spike in a lot of companies through 2022. A lot of poor fit customers, a lot of like stretched value. Our roadmap is just not there yet and we never got to the roadmap or we didn’t have that ICP story dialed down yet.

John Gleeson: So we sold to a lot of customers that eventually churned now. What I think a lot of founders actually, there’s probably two ways that a lot of founders took this, and this is getting into 2023. So 2022 we saw happening was a lot of founders went back to that. And the first question they said is, man, did we get customer success?

John Gleeson: all wrong. Like, why is it that they’re turning? Did I get the wrong CS leader? Did what? Did I fail to hire for this role? Well, do I not have enough people there? And I think what a lot of founders actually realized in process was, Ooh, actually, I didn’t have as good a product market fit at it as they had initially anticipated.

John Gleeson: And so what happened was that actually translated into their sales. Hiring instead of customer success, they kind of paused where they were on customer success. They curbed their sales hiring on. They started to go back to actually like what is our real value to our customers? How do we go to market here?

John Gleeson: And they pause on that side. So there was a little bit of a a pause there. So you didn’t see it come out on the customer success side because actually I think what a lot of founders realized was there was actually more foundational elements that they needed to address first. I think some companies in, in that wave, you’re still seeing this shakeout where they said, Hey, look, we’ve got, you know, cash in hand.

John Gleeson: We’re going to keep the sales machine going. We’re going to. over hire on customer success. And customer success is almost going to, solve for our lack of product market fit. Then Byrne went on, they maybe took credit for the thing that customer success was stitching together for them in that.

John Gleeson: You know, CS was there kind of with the band aids and duct tape, helping all these customers along when the product really wasn’t doing a lot of lifting. They got deeper in their burn and they knew that maybe that other funding ground wasn’t coming around. And then all of a sudden they make cuts or the CS team got.

John Gleeson: Just over leverage, right? Account loads went beyond what is maybe reasonable, and then their churn, started to come around to, but it led them back to that same decision where, oh, man, we’ve got to actually go back to the drawing board on, on product market fit, you know, you can think of, you know, just in the last week alone or two weeks alone, go through some of the big layoff stories, and in talking with CS leaders or sales folks on the side, that’s exactly the story that happened.

John Gleeson: Played out, but maybe not the story that plays out in, in the news, but it’s really a, a pull back to finding better product market fit. So I still, I still don’t think like we’re there on the hiring side on customer success, but I think the appreciation for the fundamentals of actually how a subscription business work are probably more appreciated now than they were, two and a half years ago, three years ago.

Chuck: yeah, it’s a, it’s a, it’s a, it’s a really compelling theory that actually kind of helps to explain perhaps why many early stage companies that, you know, have sort of, if there is such a thing as, you know, partial product market fit or some uncertainties and still cash in hand, you know, maybe thinking about. You know, kind of retaining or, or hiring like a, you know, founding account executive who can help them like essentially, you know, maybe close more deals, run more experiments and kind of lead that charge perhaps to then sort of figure out where they need to be and then what the success or it should look like to follow.

Chuck: Perhaps that’s a little bit of what we’ve seen as well. I’m a curious part because definitely I do. I do feel like, you know, demand for. Mid market enterprise sales talent. It has held up. We’ve seen more of it. At least now I recognize that, you know, given, you know, my team’s shared background in sales.

Chuck: Sometimes we tend to see more of that than demand for customer success. But I think you offer another way to look at this. Maybe shifting gears a bit. John, I’m curious to just kind of get your perspective on. You know, the notion of hiring and maybe sticking with, you know, the market today, maybe the world we all believe should, you know, we should stay in right of, you know, efficient growth, where, you know, growth at all costs is not, getting in the way of figuring out how to, how to, to build and scale a business that can be successful in the longterm, even when, you know, hopefully interest rates do come back down.

Chuck: But, in this world, You know, what’s your point of view on, you know, when companies should think about, you know, hiring like a founding, you know, customer success manager, do you think there’s an opportunity in the market today to maybe look more towards, you know, individual contributors who can, you know, be these first CS hires, prior to hiring, like an actual CS, you know, VP or director, or do you feel like, you know, companies, you know, ought to sort of, You know, you know, be more cautious about even making those first CS hires until they’ve done X, Y, and Z, like, what’s your point of view on the notion of like a founding CS role when you’re building an early, an early stage business?

John Gleeson: Yeah. So I very much go back to like, you know, we talked about product market fit and I really think that’s like absolute key to making a good hire in your customer success role. And I definitely advocate for that founding CSM. Person certainly well before that, that head of customer success hire. The analog that I like to use, like, you know, think [00:26:40] about like how these things get going, right?

John Gleeson: Founders like the, the common wisdom is founders will sell on their own. Founder led sales to let’s say a million in air or even 2 million in air. Sometimes they can stretch it. If they have that one or two founding sellers alongside them, that’s not a head of sales. These are just. Extra capacity, extra people to sell, right?

John Gleeson: So you just like, think about this motion. Okay, so you get to 2 million in AR. That’s probably when you bring in your first head of sales, right? Now your motion is, cloning that whole founder led thing. Packaging it up so that you can go out and hire, let’s say 6, 7, 7 reps to repeat that process. Okay. So think about like the ramp time on that for a second.

John Gleeson: Now you’ve got this new vintage of founding AEs or like early stage AEs. They’re all on this, their own journey of like. Let’s say product market fit, learning how to sell, sell this thing. So now they start to close. Let’s say they ramp really fast. Three months in, they’re starting to close, right? You got to think these, this first wave of customers, they look and feel a little bit different.

John Gleeson: Like the first 2 million in customers. It’s one thing to buy from a founder. It’s another thing to buy from. AE number six, right? And so I really think like you have to keep that in mind when you go to make your first customer success hires. You actually need, you almost like you’re in a stage behind where the sales team is at.

John Gleeson: You have to hire people who are a little bit more, let’s call them like athletes. They’re a little bit more nimble. They can adjust. We know that we’re going to get, you know, a different profile of customer coming through the door. We know that we, you haven’t learned all that we. Can learn about how to make them successful.

John Gleeson: So you really need to optimize for, just like a dynamic player. It’s not so much like a cookie cutter. Let’s rinse and repeat. It’s all about process. It’s a little bit more like there’s got to be that flexibility there to accommodate this next batch of customers. and to learn. I also think that you really need this first wave of CSM to almost be like an extension of the founder.

John Gleeson: I tend to like lean more towards like product oriented, almost like, like engineering background type people. Because if you think about like that fit finding on. Founder led sales up until two million in AR, there’s a lot more fit funding that happens after that customer closes, right? What does it actually take for them to become successful?

John Gleeson: And so again, the way in which a founder is going to create capacity is like, if they have these product like CSMs that are an extension of them, I think that’s a really healthy dynamic. If you can have the first two, three CSMs be in that profile, And then it’s generally around like 3 million, almost pushing 4 million in ARR, where that institutional knowledge really lives in the founder’s head.

John Gleeson: They start to have this good package about, you know, how to, how to bring it to market, but also how to serve it once they are a customer. You start to have some really good data points on, early retention. Rates. A lot of times, like we we fool ourselves into thinking we have good retention rates because people just haven’t come up on renewal yet.

John Gleeson: And so our retention is artificially high. So I like to wait a minute before hiring that first head of head of customer success. And then now you’ve got something that can be renewed, can be sold, and it really comes time to, to optimize more for process. and I think the timing of that is, is super applicable to, let’s say you’re a venture backed company.

John Gleeson: You get to 2 million in ARR, your goal now, okay. The VCs are saying, okay, you got it 2 million in ARR. Now you’re going on this triple, triple, triple, maybe double, double journey. Right? So now that curve is starting to go like this. And that’s when you have to create scale and efficiency out of. Out of what you’re doing.

John Gleeson: And that’s where I think, you know, the more mature senior CS leader can really, really help. But I think early on, like to just summarize, optimize for flexibility. Customer success tends to support not only your customers, but actually the whole go to market motion.

Chuck: Where, where do you, where do you think that that founding CSM should report based on what you’ve shared? I mean, there’s an argument that maybe, maybe that person should roll up directly into the founder or CEO versus, you know, the VPS sales if there is one or like the initial founding AE. Like, how do you think about reporting structure in the context of structuring the business way you described?

John Gleeson: I would definitely report it in to the CEO for as long as possible. Yeah, without a doubt, because if you think about like what you’re optimizing for, it’s really like understanding of the customer post sales and, um It it’s, it’s almost like if phase one is founder led sales phase two is founder led customer success.

John Gleeson: And so I think founders need to go on that journey and I think you break a feedback loop if you plug it into your, your first head of sales. I think it’s too, it’s like, it’s outside of probably the scope of what a great. first head of sales is, is, is maybe going to have like a deep skill set in. And plus that, that first head of sales job, like is one of the hardest jobs in all of startups.

John Gleeson: And there’s so much figuring out to do on just like getting a new logo. I think you, you want to set that individual up for success. And it’s probably better suited for the founders to take on that responsibility.

Chuck: You know, it’s, it’s interesting because I, Candidly, I don’t feel like I’ve, I’ve seen the, that found beautiful description of and I totally agree with everything that you’re saying the way you’re thinking about the kinds of skills and behaviors to look for. You know, I haven’t seen as many CSMs like you describe as they have like founding AEs.

Chuck: And, you know, as you were kind of going through that, I was thinking about, yeah. You know, for companies that make these hires and do these the right way. I mean, how valuable this is not only for, you know, helping to firm up product market fit and retain the great early adopters, but also you think about how vital it is for early stage companies to like, you know, get their customer stories, right.

Chuck: Understand the problems and challenges. The current state issues are helping their customers solve on what successful outcomes look like. I mean, don’t great founding CSMs really set maybe an underappreciated foundation for great marketing in these companies as well, maybe even more so than the work that the AEs are doing because the CSM is in a position to sort of see through those successful outcomes and the value achieved that then becomes the foundation for basically all future marketing as well.

John Gleeson: Oh, I like dude, you are, you are singing from my song sheet, but I, yeah, I generally believe that like customer success can, you know, really ignite your go to market motion, right? If you think about like, you, you know, this journey where it’s like, okay, you have 20 customers. Now you want to turn those 20 customers into your next hundred customers.

John Gleeson: Well, at this stage of the game, like you don’t have a brand. You’re a startup, one of hundreds of, of startups, so it’s really hard to cut through the noise. How do you sell that next wave of customers? It’s through your existing customers, it’s case studies, it’s references, it’s them getting on a phone call and saying, Hey, listen, startup X, Y, Z is great.

John Gleeson: They’re not going to let you down. They’re going to be there for you. Like that’s. and so when you have that extension of the founder, that’s what you can ignite, right? You get, that early advocacy. It’s really a flywheel. But I think like even like if I maybe like take a counter opinion to what’s out there in the customer success world is like you have a lot of CS people who have maybe been in a big company.

John Gleeson: They’ve had a ton of success there. They’re advocating for customer success. Right. Right. As a function earlier and earlier and earlier, but they missed the mark on maybe of like what truly is happening as a company transitions from, you know, just getting started scaling their early sales motion, scaling their early customers to what it looks like at maybe a company that’s doing 20 million and in air, it’s, it’s a little bit different and I think CS just evolved so much more and Yeah, there’s so much that CS does to support the entire go to market motion, not just your customers.

Chuck: Well, let, let’s talk about that because I think it’s one of the, the things about your career that’s, so impressive, you know, is, you know, the fact that you, you, you’ve personally, you know, you’ve been successful in all these different stages and, you know, have you in a unique position where you achieved a lot of that success as part of, you know, a single high growth company in motive.

Chuck: What, based on your own experiences and your learnings there, What is some guidance that you would have for, you know, founding and, or just early stage CSMs who join organizations where they’re doing a lot of great work. They’re athletes that are adaptable. They’re aligned with the founders, the sales team, and they’re driving growth.

Chuck: And you’re getting to 10 and 20 million and beyond, right? Like, how do those people, how should they think for those for whom maybe this is their, you know, you know, second or third role in a SaaS company, right? How do they balance? Continuing to do the great work they’re doing with kind of thinking about, you know, career padding for themselves and what are some of the options they should be thinking about?

Chuck: Like what, what’s some of your guidance there for, you know, early, you know, CSMs coming in that individual contributor role and seeing that kind of success.

John Gleeson: Yeah, so I think like first things first is like you really have to take your career into into your hands. If you join a company early on like there is. no career path for you. Like nobody’s going to set that out for you. Nobody’s going to spoon feed that to you. And I think like you also have to be like super honest with yourself as well.

John Gleeson: You know, some people really thrive in that early stage of of company building. That’s where they fit in. They know that about themselves. That’s what they want to do. And I think that’s great. Like, that’s a really fun stage. And, um,

Chuck: How, how, sorry, how do people, what are some things, maybe some people don’t know that about themselves. What are some things to ask yourself to help figure out if you’re an early stage person out of curiosity? Okay. Thank you.

John Gleeson: I would say like you really have to tune in to like where your source of energy comes from and what you’re hoping to get out of your, your employment experience, I would say, or like your, your journey here. And so, you know, like you see people where it’s like they don’t want maybe a defined role per se.

John Gleeson: You know, they, they want to do many different things. They want to be really close, let’s say with the founders. You know, you start to hear things that maybe are only available to you, in an early stage company. And as things get to be a hundred people, a thousand people, it’s just inevitable that that won’t be the same experience.

John Gleeson: I would say like for folks who like want to go on that journey though, of. Like, you know, this, you’ve seen this play out so many times, the, the leader who might be a fit for 2 million in AR might be able to get to 10 million in AR, but they’re not the person from 10 million to let’s say 50 and the person from 50 may not be the person from 50 to, you know, 200. They’re really different motions. And it’s pretty rare that like people can scale through all of these stages. It’s just like, it’s hard to grow maybe as fast as a high growth company is, is growing. And so I’d say like, if you find yourself in that situation, would, I would encourage you to just, You know, treat treat your job.

John Gleeson: you’re almost preparing for the next job. And so, you know, and there’s times in your life when this you can do this. There’s times in your life. Maybe when you you can’t a lot of this is timing and also. You know, where your energy is at and what you want to do. But I guess like speaking from my own self, like I always have motive, like once things were humming along, I knew kind of the rarity of how fast this company was growing.

John Gleeson: I knew that, I may never find myself in a situation like this again. I’d listened and read enough on venture that I knew that the odds of this happening, it [00:40:00] wasn’t an everyday thing. What I said to myself was, okay, at every time, you know, every funding round, they’re probably gonna like, try and top the role.

John Gleeson: They’re probably gonna, know, go out and up level the organization. Like, this is just the facts of life in a high growth startup. And I said, okay, like, make sure that you’re learning everything that you can and you’re doing everything, that when they go and they lift their head up and say, okay, we’re going to, we’re going to go hire for that acts function.

John Gleeson: When they look around and market, they can’t find anybody better than you. And so do all of that extra learning. Make sure you’re doing all the extracurricular activities. Make sure that you’re building the relationships with the parts of your organization that are going to be important at the next stage of growth.

John Gleeson: And just see how long you can hang on. And if you make it through one iteration of that, man, hat, feather in your cap. This is great. If you make it through two, great. And just hang on as long as you possibly can. And if you do, well, it’s You know, that’s that’s gonna make you a unique story on the other side, and maybe you can find that next opportunity a little bit or your odds of finding that next opportunity will be higher because you’ll be able to say, you know, 1 to 10 or 1 to 50 or 1 to 100.

Chuck: Really great way to put it. So, I mean, I think, you know, for, for our listeners here, I mean, you’ve certainly sketched out a, a plan and playbook for getting exposure to, to opportunities in, in mid and late rounds and sort of recognizing the unique circumstances that you’re facing. But also going in with the understanding that.

Chuck: You know that you could be topped at any time and that larger organizations are going to continue to be looking for scale and process to support those next stages of growth, which often look very different than what you helped to drive in the early stages. But what I also hear you saying is that for those who You know, maybe have a passion for, you know, solving, solving multiple problems and working closely with founders like that’s okay too.

Chuck: Right. And if you want to pursue those opportunities, you know, if, if you pick a unique winner, you may, you may find yourself in a position where at some point down the road, you might be looking for another early stage company to go, to go join. Right.

John Gleeson: I think that’s okay. I think like the definition of what success looks like is so broad that like there’s a lot of different ways that you, you can be great at what you do. And, you know, it’s, it’s kind of like sports, you know, there’s, there’s some players that can play multiple positions or some who, you know, want to fit into different roles and throughout their career, they evolve as a, as a player.

John Gleeson: I think the same is, is true. And, know, don’t get bbummed when, when you’re in one of those evolution periods.

Chuck: that’s a good analogy. Good way to put it in. In closing, John, I, love everything you’ve shared. You’ve shared here for our listeners who are maybe a little bit less tapped into the goings on in the world of SAS. You mentioned Jason Lemkin and, you know, and his work. Either, like a short list of podcasts, readings, books that you would recommend for our listeners who are interested in just, you know, learning more about SaaS and customer success and, just in general that you think are worthy listens.

John Gleeson: Oh, man. Okay. Where do you even start? Okay. So I would say like one of the best resources on just like all of the metrics in customer success is a website called for entrepreneurs. David Scott is is the guy who puts out that website. I think that’s fantastic. A guy named Tomas tongues. If you go to his blog, there’s a really good click through on customer success and his learnings over the years.

John Gleeson: Thank you. I think that’s that’s a really good resource. Certainly like Sastr, Jason Lemkins. I think that’s, that’s really powerful. I always like the content that Gainsight does on customer success specifically. My favorite book on the topic, you’ve probably read this, is the Sales Acceleration Formula, right?

John Gleeson: That’s, that’s not necessarily on customer success, but I just think everything that you learn in that book about hiring, testing, AB testing, all of that translates perfectly to, to customer success. I always go back to a predictable revenue by Aaron Ross. That’s an old classic. I often read the hard thing about hard things again and again, because it’s just like it, It’s an honest take on like what you sign up for when you go and work for a startup, right?

John Gleeson: It’s not all beanbag chairs and, Eminem machines. It’s it’s the hard thing about hard things. And then, actually, probably your history. PhD, right? Okay, so my favorite, my favorite book is, is Leadership in Turbulent Times. It’s a Doris Kearns

Chuck: Okay.

John Gleeson: but I love this one right here. Just because when you’re in those situations where you’re maybe scaling through multiple stages of growth, you know, you’re not the only person.

John Gleeson: In history, who’s ever had to scale through something hard. And so it’s just a re recount of kind of the setbacks and the evolution of three different presidents and, kind of what it looked like and how it wasn’t a straight line that maybe history. Let’s you believe it really highlights their stepping back from it.

John Gleeson: Their setbacks, their moments of defeat. And so I think that’s a, that’s a great one to read as well. If you’re somebody who maybe signs up for that. Hey, let’s see if we can scale through multiple stages of growth. But I always think like, yeah, just be doing your homework at all times. Always, know, you don’t know what’s around the corner, so prepare yourself for every possible outcome.

Chuck: Yep. Good guidance. Do you spend a lot of time on, on LinkedIn? What’s your, what’s your perspective on consuming content there these days?

John Gleeson: Ah, Ah I am not good at social media. I don’t like it. Um,

Chuck: It can be a distraction, can’t it? Yeah.

John Gleeson: I think it can be a distraction, and I think, like, you just, you know, I always think of content as, as your diet. Right. And what you’re putting in your brain is ultimately like what’s going to come out the, the other side. So I tend to try and like focus on a little bit longer term, or like, you know, longer form content, things that like I have to engage with.

John Gleeson: With the content more and use what I’m going through as like more of the reflection piece to it. I really struggle with like, you know, the chat GPT generated content that we see five things that every CS leader should do. I think like this misses the mark and probably causes more heartburn than than good. I get it. Everybody has to promote their What they’re, what they’re doing and, staying top of mind and relevant is, is so important in this world.

Chuck: No, I think that’s great guidance. I think, I mean, there’s a ton of great content on LinkedIn and a lot of what you’ve shared. I mean, I often find that, you know, through through LinkedIn, but it can be such a slippery slope to distractions and, sometimes, You know, reading things that aren’t necessarily, you know, helpful for your own, your own growth and mental state too, because there is a lot of braggadocio and very derivative content and it’s hard to know the credentials of any given individual who, you know, is sharing and posting a lot and finding inspiration from others who say, you know, post daily, post daily, post daily.

Chuck: So I think you’ve given a lot of great reading recommendations. I’m going to add these to, to our podcast description for those who want to, Make sure they capture all of this. I need to check out that George Kirin’s Goodwin book. Appreciate the history plug there at the end. And John, thanks for joining.

Chuck: This is an excellent podcast. You’ve got my wheel spinning on a number of different topics. I really appreciate you coming on and sharing with me and with our audience.

John Gleeson: Oh, well, it’s, it’s always a pleasure to hang out with you, Chuck. I miss you a lot. And can’t wait to see you next time we’re in the same place.

Chuck: Yeah. Sounds good, John. Take care.

John Gleeson: All right. Take care, sir.

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Frequently Asked Questions

Hiring Companies

How do you charge for your services?

We offer multiple services, depending on the needs of our clients. Please reach out to us for more information, and see our GTM recruiting services page for more details.

Do you recruit outside of the US and Canada?
Our focus is currently North America, but we’ve also worked with tremendous people in APAC, LATAM, and EMEA. If you have needs in these regions (whether you are based in North America or elsewhere), we want to hear from you!
What roles do you recruit?
Our team superbly recruits for any roles within go-to-market (GTM) functions, including:

  • Customer Success: Standard, Senior, and Principal Customer Success Managers, Onboarding Specialists, Implementation Managers, Community, Customer Support, & Solutions Architects
  • Marketing: Growth & Demand Generation Marketing, ABM, Events, and Content / SEO Marketing
  • Sales: Sales Development, SMB, Commercial, Mid-Market, Enterprise, and Strategic Account Executives
  • Account Management
  • Revenue Operations and Enablement: Marketing, CS, and Sales Operations
  • Solutions Engineering and Post-Sales Solutions Architects
  • GTM Leadership: Front-line, second-line, VP, and SVP / C Level placements (CRO, CMO, COO)
I've worked with so many headhunters and recruiting firms. What makes you different?

Put simply, we aspire to be as proficient in articulating your business value prop as your internal employees. Exceptional talent does not want to speak with “head-hunters;” instead, they want to connect with educated ambassadors of your business and your brand about meaningful career opportunities.

We go deep on your business and into talent markets to foster connections that other recruiting firms tend to miss. And we work with our hiring clients to ensure excellence in their hiring process. Please reach out to us for more information!

Is SaaS experience important when hiring?

Hmm, what does this mean anyhow?! We recommend defining the skills and behaviors sought before running a search rather than using buzzwords or phrases from other people’s job descriptions. We help employees go beyond acronyms to ensure they develop robust job descriptions that tie to specific candidate profiles for targeting in the market. Need help? Let us know!

Job Seekers

I don’t see any roles for me. What Should I do?

Blueprint runs a monthly Transferable Skills Workshop to help early talent and career switchers find opportunity in the market and prepare to interview. It’s currently offered at no cost. Interested? Please reach out to us.

How do I negotiate fair compensation ?

The Blueprint team always shares compensation range information with candidates before initial screening calls. Beyond this, we encourage you to consult with review sites and other data sources to educate on the market for the roles you’ve held. Want to discuss? Reach out to us.

Is it still important to send 'Thank You' notes?

Interviewing should always be treated as a two-way street, and a candidate should never feel obligated to show gratitude and follow up first.

That said, if you believe a given opportunity aligns to your role and company interests, we recommend sending interviewers a follow-up email after every step in the process. This gives you a chance to recap your learnings & enthusiasms briefly and authentically. It also helps you stay top of mind with interviewing companies.

Check out the roundtable discussion our leadership team recently held on the topic of post-interview thank-you notes.

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Make sure you prep before every interview, particularly by reviewing the company website, recent new articles, and the LinkedIn profiles of relevant interviewers and company leaders.

Consider business casual attire - ask your recruiter for any additional guidance. Try to make sure that you are able to sit front and center facing your camera - test it with friends prior to running an interview. If you need to take a call by phone, it’s best to let your recruiter or the hiring manager know in advance, and offer them an option to reschedule if they prefer.

Lastly, prepare some questions in advance based on your research, but do everything you can to stay in the conversation. The more you can listen and be in the moment, the better you’ll execute and be able to vet the opportunity for yourself.

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Despite so much innovation in HR tech and recruiting, hiring remains broken. As former operators with decades of experience hiring GTM talent, we wanted to start our own business dedicated to helping B2B tech companies across a range of industries do a better job at attracting and sourcing tremendous (and diverse) talent.

How do you charge for your services?

We have multiple services packages, depending on the needs of our clients. Please reach out to us for more information, and see our sales recruitment services page for a breakdown of our packages.

Do you recruit outside of the US and Canada?
Our focus is currently North America, but we’ve also worked with tremendous people in APAC, LATAM, and EMEA. If you have needs in these regions (whether you are based in North America or elsewhere), we want to hear from you!
What roles do you recruit?
Our team superbly recruits for any roles within go-to-market (GTM) functions, including:

  • Customer Success: Standard, Senior, and Principal Customer Success Managers, Onboarding Specialists, Implementation Managers, Community, Customer Support, & Solutions Architects
  • Marketing: Growth & Demand Generation Marketing, ABM, Events, and Content / SEO Marketing
  • Sales: Sales Development, SMB, Commercial, Mid-Market, Enterprise, and Strategic Account Executives
  • Account Management
  • Revenue Operations and Enablement: Marketing, CS, and Sales Operations
  • Solutions Engineering and Post-Sales Solutions Architects
  • GTM Leadership: Front-line, second-line, VP, and SVP / C Level placements (CRO, CMO, COO)
I've worked with so many headhunters and recruiting firms. What makes you different?

Put simply, we aspire to be as proficient in articulating your business value prop as your internal employees. Exceptional talent does not want to speak with “head-hunters;” instead, they want to connect with educated ambassadors of your business and your brand about meaningful career opportunities.

We go deep on your business and into talent markets to foster connections that other recruiting firms tend to miss. And we work with our hiring clients to ensure excellence in their hiring process. Please reach out to us for more information!

Is SaaS experience important when hiring?

Hmm, what does this mean anyhow?! We recommend defining the skills and behaviors sought before running a search rather than using buzzwords or phrases from other people’s job descriptions. We help employees go beyond acronyms to ensure they develop robust job descriptions that tie to specific candidate profiles for targeting in the market. Need help? Let us know!