How To Build Your First Go-to-Market Team with Swing Search

0:00Hey everybody, this is Ben Kesnoka, co-founder and partner at Village Global Global, a network-driven venture firm. And this is our podcast, where we go deep on all things business and technology with world-leading experts.

0:21Welcome to our masterclass on building your go-to-market team. I'm Lindsay, a partner at Village Global. I'm joined today by two absolute maestros, Magna Sundstrom, who's a senior partner at Swing Search, and Debbie Whistle, a president at Swing Search. For nearly 20 years, they've specialized in go-to-market roles at the director, head of, and VP levels, the hires that really matter the most to scaling companies like all of yours. They've worked with several village-level portfolio companies, including Multiverse, Growth Therapy, Mosaic Tech, Sora Schools, and they're currently partnering with MetaView and Alembic.

0:55Let's get this started. Magna, what's one mistake that you are 99 % sure founders will make with their go-to-market team? I'll start by saying mistakes will be made, right? You'll hear me say this again, and I'll hit this note a lot. Perfection is the enemy of progress. And so what we really want to focus on is progress. But the mistake that I see most founders make is when they're hiring those first go-to-market or early go-to-market members on their team, whether marketing sales, whatever the role is, they really default to going to senior. It makes a ton of sense, right? Because there's so much to get done.

1:30And oftentimes, you know, you're looking at mountains and you want to see somebody who can see over the mountain. But what I always like to say is like, let's look for somebody who can see around corners, not necessarily over the mountain. And so you want to bring that, that profile down to somebody who can do the tactical takeaway work that you need over the next 18 months. And so that's really where I see that mistake made is going to senior, too many reps under their belt. Yeah, that's generally what I see. And it makes sense, right? I think from a founder's perspective, you don't want to miss.

2:02And so you aim really high, assuming that this person has done all of this work before, they'll clearly get it done for me, but there's a disconnect there. Can you talk at all about what that disconnect looks like when you do hire the person who can see over the mountains? How do they overcorrect? What are some things you see? There's really two things that happen. You bring somebody in who's, let's say, a hands-on seller. Somebody's going to come in, just drive revenue, execute deals, run, go. You bring in a VP of sales instead. Somebody who's been there has seen the reps, has managed large teams.

2:38They're going to ask for two things. And so they're going to immediately ask for a team underneath them to do that tactical work. Early stage, cash is king. And so we want to make sure that we're driving revenue and not necessarily spending a whole bunch on headcount until that product market fit is built out. and you start seeing that revenue, you see that traction. The second thing is they're going to want to spend their time on the work of building the foundation. By that, I mean, they're going to come to you and be like, we don't have territories, we don't have verticals, we don't have all these things.

3:04You're like, we're throwing spaghetti against the wall right now. The work that they're doing is very much needed, but at just a slightly later stage, if you're really early hiring those hands-on tactical 18 months. And again, you want somebody, I would say, with a bit of maturity, a bit of seniority. It's always better to hire a little bit more of that up and comer because you can layer them down the line or you can bring in that executive presence as you need a little bit later. But you need somebody who's going to be doing the outbounding. You need somebody who's going to be doing the calling.

3:36You need somebody who's going to be chasing these deals, who's going to be really driving that forward. And a lot of times sales is past that in their career and they just don't want to spend the time doing that. I love the throwing spaghetti at the wall, right? Like so much of early startup, not just go to market teams, but really like on the product side, no one wants to admit that we're throwing spaghetti at the wall, but like, you're just hoping it'll stick, right? Yeah. While we were prepping for this, you also had an answer to that. What is one mistake you're 99 % sure a founder will make?

4:07This is something that I'm pretty adamant about because I've seen it a lot, but it's that they'll hire too early. they'll really try to solve a product market fit problem with a go-to-market hire. It's so painful because it ends up being like an oil and water problem, right? We put all this effort to bring on someone, a good go-to-market person with a specific set of skills that are almost orthogonal to what you need in terms of product, right? So much of product market fit, talking to customers, understanding what they want. It takes so much time and you really can't, I think, graft onto that assailing motion.

4:46So when my portfolio founders tell me they want to hire a go-to-market person immediately, I'm like, okay, let's take a step back because it's usually too soon. I have an interesting story. I know founders, there's so much that's going on and you're so heavily focused on the problem and building the product for the problem. And that's really where you want to spend your time. But the reality is you're never going to leave sales. I remember I was waiting for a client to join a call. The company was a hundred million plus in ARR and we were hiring for a go-to-market role, a CMO for them. And the client hopped on and was like, I'm so sorry, I'm late.

5:21I just got off a sales call that ran long. So this is a hundred million revenue company that the CEO founder was still attending sales calls. So it's just like, that is never going to go away. You're always going to be in go-to-market. You're always going to be in sales. And the instinct is to be like, oh, let me hand it over to an expert. But you are always going to be the best seller, even when you're late stage. Now, of course, your time is prioritized different when you're a hundred million dollar revenue, not jumping on the hundred K deal, but you're always going to be in those deals. I agree.

5:49It's the gold standard. And we'll talk more about this, I think today, but founders are always in selling mode, right? They're selling folks to come work with them. They're selling a product. They're selling investors, right? It's never ending. And I think that message bears repeating. I talk to very, very early stage founders about it all the time, that this is literally the job that you're signing up for is a sales job. So man, let's get good at it. And of course, bring on help. And that kind of leads to some of the questions that were submitted before this. One of the general themes was like, how do I define our founding go-to-market role?

6:24And how do I evaluate what should come first? Magna, I know that's a question that you hear often. Where do you start that conversation with founders? Yeah. So the conversation starts actually where we started, which is my first question is going to be, what's your product? Who's your buyer? How are you selling today? What's the motion that you're looking to build? And I think all of that matters into who is going to be the right person to help you build where you are from a stage perspective, but also where you are from a go-to-market perspective, just to simplify that. Let's take two very clear examples.

6:57B2B, you're going to start with a seller, most likely. B2C, you're going to start with a marketer, most likely, right? Because that's just the go-to-market motion that you have, that you've built. And that's how the company is going to be built. So when you start to think about who's in seat, who's going to come in, and then you go that layer lower where you're like, what's my go-to-market motion? Are we enterprise? Are we mid-market? Are we SMB? Do we have a PLG motion in our product? Are we B2B2C? Understanding all of those things will help you start to define and refine on who's going to be the right person in the seat.

7:28So anytime somebody says, who should I hire? I'm like, I've got 12 questions for you before I answer that. And then going into kind of product, product market fit, where are you from a revenue perspective? Like from a customer perspective, do you have two customers? Do you have a hundred customers? And so trying to understand a bit more about that. And to put you a bit on the spot here, how often do folks approach you for that conversation? And you actually say, you know what, it's not the right time. Go and figure this out. Do you see that? Yeah, we do see that. I would say because most of our partnerships that swing are through places like Village, that a lot of times that filtering by the time it comes to us as a search firm is done.

8:09But we do get a lot of referrals from our previous clients. And that's going to be my first question. So more often than not, I'm going to see that from a referral from a client where they're going to connect and I'm going to say, Hey, I don't think you're really ready for this right now. Or the role that you think you want is probably not the right role. When we talk to prospective clients, that's the first thing that we're trying to figure out is, are we the right solution for you? Because there's nothing worse than us getting into a partnership that's just not going to work for whatever reason.

8:40Sometimes I'll be completely honest. We had this happen one time with a client where the discovery happens in the process where product wasn't where it needed to be. In the process of the discovery, we felt like the product moved slightly farther along than it actually was. And then as you're getting feedback and you're digging more and learning more about the product, we're like, oh, there's a reason why this isn't working. And quite candidly, if you put somebody into this seat, they're going to cycle out in six months because this is not actually end up being the right person for you right now.

9:10you need to go back, focus on product, get to this, to a certain specific place, and then bring that forward and then bring a go-to-market person on. Difficult, but necessary conversations. What an experience in many ways, right? To have that opportunity to say, well, let's put on the brakes. Kind of related to this, where do you think folks get tripped up the most in terms of early stage founders? Where do they get stuck? Where do you notice the most disconnects in the conversations you have with them? I think it's where I see a lot of this sort of the get stuck is when founders are unsure or about making a decision about something.

9:51Again, I think that you're going to hear me say this a million times that leads back to perfection is the enemy of progress. And one of the things I was just reading a quote this morning, actually flipping through LinkedIn that came on, that was something along the lines of, look, as a founder, you're going to constantly be making decisions based off of incomplete information that is just going to be part of your job. And so you have to get good at that. And sometimes you're going to make mistakes and you have to get good at owning those mistakes, correcting them when you can, and as you can and moving quickly beyond that.

10:19That happens in hiring. It's going to happen on product decisions. It's going to happen on other strategic decisions because you just have incomplete information. And the fact of the matter is hiring is always incomplete information. You're always taking a little bit of a leap of faith. Even if you're looking at past experience and you're saying, hey, they were super successful here. they were super successful, similar buyer, similar motion, similar product, right? At similar stage of growth, 5 million to 10 million, one to 10, right? They've done all of this. It doesn't necessarily mean that it's going to end up being the right environment, the right place, the right time in their life.

10:52There's a million things that come into play there. It's asymmetry of information. It always happens. So you have to take the leap. I think that there's two areas of search, right? You talk about defining the role, focusing on what do we need? What do we need to hire. And it's startup, right? So it's a little malleable. You're like, hey, this is like a ball of clay and we've shaped it into a box and this is a box that we need, right? Maybe it's a little bit too tall. Maybe it's a little bit smaller, but like we'll adjust it, but it's generally going to be this box, right? So once you've gotten to that point, I think what I always remind people is like, we are moving candidates through as if we're going to say yes until we get to a no.

11:28Because every state, we're going to pull back a layer on that candidate and we're going to do a little bit of discovery and you're going to learn something. So hopefully we've defined early in the process, right? Go to your network, talk to people sitting in seat, understand what the role is, get as deep as you can. Once you have that, you feel confident about that, then make move candidates forward and get to that point of making the decision. And at the end, you're always going to be making a leap of faith. But by the way, it's also on the candidate side. Like you're asking them to come early.

11:58You're asking them to come to like, Hey, we're early product market fit. Maybe we're pre-product market fit. Maybe we're starting to see some scale, but like they are also taking a lead buffet. So ultimately you guys have to like clasp hands and jump together. Yeah. So well said. There's so much to dig into there. Two things I want to pull out. One is conviction, right? As you're talking through this, it just reminds me of the investment process, right? We're doing the same thing as we meet founders early on in the journey, right? You're getting to know them. You're talking to your network. You're talking to their network.

12:28It's all about building conviction. I think that is something that's in short supply. The hardest investments are the ones where you can see an investor kind of wavering on their conviction, right? Because everyone wants to get behind something. It's harder to be like, let's get into the messy stuff. Super appreciate that point, right? As a founder, you've got to be convicted. On the other side of that, we chatted about this a bit yesterday, vibes, right? So we've got vibe coding, maybe vibe investing, vibe hiring. Is there such a thing as vibe hiring? And if so, what is it that has to be vibed, right?

13:06Is it just conviction? Like, curious there. Great question. Vibe hiring, you're starting to see it a lot. It makes sense, right? It's the word of the year, I would say. Vibe hiring is like a rebrand of what I would say in 2015 was the culture interview, right? You come in and what you're really looking for is you're saying, hey, is this person going to be my person? It's so easy in the hiring process. It's part of the reason why, and I'm going to take us a little tangent here, but it's part of the reason why we also really enforce process in the course of hiring, like defining what is the scorecard?

13:39What are the things that we need this person to do? Being super clear about what the tactical takeaways are. We have all of our clients run through a process called it's MOC, it's missions, outcomes, and competencies. And I think it was originally an A16Z thing, but it's like, what is the mission of the role? What are the outcomes we want to see? and what are the competencies that relate to those outcomes that will give us those outcomes that we need to be hiring for. And if you even just get that down, you have a good sense of who's going to be successful in the role for the tactical takeaway.

14:07I think on the flip side of that is who's going to be right for me as a founder, who's going to be right for me as part of the early stage team too, as well. If you hire somebody, I do think it's important because if you hire somebody who doesn't vibe or like kind of clashes with the team and you're sub 10, fewer than 10 people at the company, it is felt, it is felt every day in every communication, in every Slack message that you get. And that can be draining, right? So I think there's a sense of you do need to have conviction that this is the person that's going to be there when you're like in the times, right?

14:48Conviction is the word. So a really tactical question here. I work a lot with technical founders. I'm a former technical founder myself. There are playbooks for hiring technical talent in terms of getting them to work with your team ahead of time, right? You can bring folks on for three to five day contracts, right? They can be committing code. Is there a version like that for go-to-market hires where you see them coming into an org and like literally working with people, ideally to avoid some of these things that you're suggesting. Where we see, and now in the return to office days, we are being able to go back to this, which is the full day in office and doing some type of working session.

15:23So it's not quite the same way where you're coding together and in that deep level, the way it does in a technical interview. But generally what you'll do is you'll have some type of project, some type of pre-work that the candidate comes with, and then you're going to do a working session. So challenge ideas, assumptions, see how you work together, see how things happen. When I was internal, before I was external, we used to elect somebody to be the naysayer and to be like the challenger and to challenge an idea and to see how that person works in that environment. Because especially for the candidates that are like breezing through really quickly and they're saying all the right things, that yes moment, we also want to make sure we're doing our diligence too as well in the process.

16:03And so be that challenger. One of the things that I do caution on in an interview process, and especially if you're hiring those like founding AEs, first in seat sellers, is in such high demand right now that we want to make sure that interview process is like is clean, crisp, clear and engaging the candidate through that. So spending a day working with a team or three days in office, because we're often talking to passive candidates, so they already have a job. So we're trying to balance. But that working session, I think, pulls out a lot of that. How do we communicate? How do we talk together?

16:40And candidates really like it, by the way, because they see how the team talks to each other. And they see how the team works. It's always a two way. It's always bidirectional. You've got to be aware of that. The hiring exercise should never be a tool for perfection. Because again, if it's counterproductive to progress, then it's too much, especially in this candidate market for sales and marketing. For sure. So there's another thing to dig in there in terms of what you just said, which is some of these candidates breeze through, they've done this job multiple times. It's their gig as they come early stage and they stay for a couple of years maybe, but they keep doing these roles.

17:16One fear that folks have, and I think this came up in the questions, is how do you check to make sure you're not being sold by a seller, right? Like what do you do there? So my clear takeaway when I'm on a call with a seller or a marketer is if they don't know their metrics, they're probably not the strongest candidate. And I'm talking like detailed metrics. There is a difference between somebody saying I had a hundred percent quota attainment between, I had 112.2 % quota attainment. And had I gotten that last deal in under the line, under the wire, I would have had 122%. And I'm super bummed that I didn't hit that.

17:53Like that is the difference there. When you're hiring first sellers, the question that I always ask, which it's not just attainment, but then it's also, where did you rank against other sellers? Were you in the top three, the number one, because maybe that most of that team, maybe 70 % of that team was above a hundred percent and they sound great, but they're in the bottom quartile or the bottom half percent of everybody else. So it's not only just like, what did they attain, but how did they rank against their peers that were also selling? So I'm curious to hear from both of you, Magna and Debbie, around what's your speculation as to why that makes a difference That 112.2 versus I was really good.

18:32It's a fascinating observation. And you guys, you've both been in this business for a while. So what do you think makes that difference? I think it's two things. Look, sellers are competitive by nature. They know where they rank. They know where they sit. They know where they are against. They know what their goals are. Like you want a seller who's coin operated, right? And that person should be like VP of sales to like an AE to a BDR. Like you want them to be coin operate because that's their job, right? To drive revenue. And so they know where they rank. So they know exactly where those numbers are because they're personally motivated to hit those numbers.

19:06So I think there's a bit of an action or drive that comes with that. But then I think there's a component of like intellectual rigor and discipline that comes with knowing the number so detailed. If somebody is like, I know I got above a hundred percent, but I'm not like really a hundred percent. I'm not sure what that number is. I'm like, where's the discipline and the rigor around that? I think it's the two things that I look for because sales is 80 % process repetition, like going after those deals, being that gritty going through. And especially for those sellers, like getting to that, you know, that, that DNA.

19:40So you want somebody who's got discipline and ambition. Magna, I think a follow-up question to that is like, when I hear your overview of that, I'm like, yes, that is exactly what I want for my second through nth seller. But for the founding AE, which I know many people on this call want to hire, there's a little also more communication needed for that founding AE. They have to report back to the CEO. They have to partner. They have to partner with the product team. Would you still say that metric number is as important for the founding AE? Yeah. Because I would say it for a CRO knows their team, like a CRO of a$200 million, like a strong CRO is going to know how they're hitting against the quota, how the company's doing, right?

20:19Like what they're doing from a revenue perspective. So I don't think that ever goes away. So I still think that's like a good litmus test to understand if somebody's like selling you in the interview process or actually very good at their job, going back to that original question of like, how do I determine? So I think it's still a good litmus test. But what I would say is that, yes, with that founding AE, what comes into play here a bit is really, I think that maturity and that ability to come in and understand and have strong enough business acumen to understand that the conversations that they're having with customers, they need to feed that back to product.

20:58To have enough years and repetition that you can put them in front of a seasoned buyer or like a CRO or CFO, regardless of whoever your buyer is, right? That they can sit in front of that call and they can do that first initial discovery call and they're not going to say anything crazy. I think there's a bit of that too as well. But I think that I honestly, I don't think you ever lose ambition and I don't think you ever lose the discipline. And I don't think you ever lose the coin operated aspect. I think people who are good at those three things are the ones who rise through ranks. I want to dig in a little bit to something you said around 80 % of the job is like process and right.

21:39They're like things to do 20 % question mark for me, but I want to fill in that question mark a little bit with tools, right? What are the tools that you see teams using now that really like bridge gaps and accelerate particularly early hires? Yeah. It's a great time to be in go-to-market right now. If you're curious, AI, it's, I think going to impact go-to-market tooling and we've already I've seen it in a significant way and in a variety of different ways. So there's a lot of things out there right now. So if we just take top of funnel from a prospecting perspective, there's companies like Common Room, Pocus, like Clay that are out there that are making prospecting easier.

22:20I've always had this concept of a 10X engineer, right? The engineer who can do 10X the amount of work, right? Now what these tooling are doing is they're creating like the 10X BDR, the 10X AE. And so I think that there's a lot of tools out there and that curiosity and that ability to try different things, look at different tooling. And then one of the things that Debbie and I have chatted about before is that idea of your first 10 hires are really important. Also are your first 10 software selections of tools. Totally agree. Yeah. Because what ends up happening is as a company scales and grows, like you're going to replatform multiple times for whatever it is.