Hiring Your First Sales Team with Andrew Boos

In 2026, B2B buyers are more insulated than ever. The explosion of AI-generated emails and automated cold calls has made it nearly impossible for startups to break through using traditional spray and pray tactics. On this episode of FiredUp!, we explore the fundamental shift in B2B buyer behavior and what it means for founders hiring their first sales team. We address the specific pain point of declining outbound conversion rates and discuss how to pivot toward a consultative selling model that prioritizes human credibility and in real life connection over raw volume. This week, episode 133 of the FiredUp! podcast is about hiring your first sales team! 

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In this episode of the FiredUp! podcast, Andrew Boos shares the importance of brand and credibility in closing deals, especially for startups without an established brand and actionable steps you can take right now to avoid common mistakes startups make when building their sales teams. 

Andrew Boos is the CEO and founder of Darwinian Ventures, a firm that specializes in building and running high-performance sales teams for tech startups. Andrew is a seasoned sales leader with a deep track record of taking early-stage companies from founder-led sales to a repeatable, scalable revenue engine.

Andrew and Morgan discuss:

• The Rise of the AI Researcher: Buyers are now using AI agents to vet vendors before ever speaking to a human. Your sales team must transition from providing basic product information to acting as high-level consultants who can navigate the specific, complex needs of an already-informed buyer.
• The "Death of the SDR" for Generic Outreach: High-volume, automated "spam" is a liability in 2026. Success now requires a "surgical" outbound approach—combining targeted, value-based outreach with strong brand credibility and strategic in-person networking.
• Hire for Curiosity, Not Just Quota: Your first sales hire shouldn't just be a "closer." Look for candidates with high emotional intelligence and deep industry curiosity. In an AI-saturated world, the ability to build a genuine, empathetic relationship is the ultimate competitive advantage.
• Leverage Brand Credibility as a Sales Tool: B2B buyers are increasingly looking for social proof before they engage. Using channels like Meta ads for targeted brand awareness and participating in "IRL" events are now primary levers for building the trust needed to fuel your sales pipeline.

Thank you for listening! Tune in to all the episodes for practical tips on crushing your startup marketing goals. Don’t forget to follow, rate, and review the podcast, and tell us your key takeaways!

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Firebrand is a startup marketing agency. We help tech startups secure outsized marketing outcomes on their path to growth.

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Transcript

Morgan McLintic: 0:00

AI is really changing buyer behavior, but what does that mean for your sales team and the skills and processes that they need to adopt? That's the topic we're going to unpack today. Hello everyone. Welcome to fired up the podcast for marketers working in early and late stage startups. Hello there, everyone. Welcome to fired up. My name is Morgan mcclintic, and today I am joined by Andrew boost who is the CEO and founder of Darwinian ventures. Andrew, welcome to fired up. How are you?

Andrew Boos: 0:35

Hey, I'm doing great. Thanks glad to

Morgan McLintic: 0:36

be here. It's great to have you here. Thanks for joining us. You run sales teams and build sales teams for tech startups. And so you're a great person to talk about this topic today hiring your first sales team, because I think buyer behavior, as I said, is just changing so much. And so let's just open up with that what you think is fundamentally different about the way B to B buyers buy today compared to two or three years ago? Yeah, well,

Andrew Boos: 1:06

there's kind of two angles to it. I think mechanically, it's different, like there's different ways to get a hold of people, and people are reacting to different things. That's definitely very real. But I think fundamentally, it's sort of this human journey that's the same, and it's been the same for a long time, and it will be the same for a long time. So people learn about something, they build trust with it, they start to envision the future with it, and then they go through roadblocks and take care of any logistical things, and they make a decision. The fundamental sort of psychological stuff is the same, but what we're seeing is just a whole new slew of ways to get in touch with people, ways to make it more relevant, ways to get data so that it's less annoying and more like the right thing at the right time, even if you're a salesperson, that's not annoying at all. That's a gift, you know? So there's actually a lot of improvements there, which I think make the experience on both sides of it a lot better. So that's kind of just a real highlight of what I'm seeing on both sides, right?

Morgan McLintic: 1:55

Okay, we are seeing a shift much more towards buyers wanting to buy and self educate. I don't want to be sold to, not until the right time. And I think you hit on a great point there, and you've got this sort of whole dark funnel getting references and doing your research before they pop up and they're almost in the middle of their buying journey by the time they speak to you guys. Like, how does that really affect how sales teams are operating? Just walk us through that a little bit. Yeah, well, that's

Andrew Boos: 2:25

been that trend has been happening now for 10 years or so. This, like the pushy sales thing, doesn't work that much anymore, because everyone can self educate extremely well. So that's like a big shift that has been a long time in the making. So consultative selling is what they call it. Now. It's where you know you're not trying to push something down someone's throat. You're really more just this, like benevolent consultant, and you're an expert, and here's a great way to do the thing that you need done that is not going anywhere. And I'm just seeing that happen more and more. And we're also just seeing like across the board, nobody reacts well to any level of pushiness whatsoever. I think you're absolutely right. People would rather self educate. They'd rather learn things come to the conclusion themselves, and then the salesperson's role in that scenario is really more of guiding through the process, answering any questions, giving them insights, things like that.

Morgan McLintic: 3:13

And does that mean that like outbound and SDR motions, they still work? We're all being inundated by AI implemented emails. Is that sort of just salting the ground for the people who do it properly? What's working?

Andrew Boos: 3:28

Yeah, oddly enough, outbound has changed a lot, even just in the last six months. Not it's like changing in real time anything text oriented, so like emails, texts, anything written, even copy, like SEO, marketing materials, all that stuff. It's so easy to mass produce that now and personalize it and make it relevant that people are drowning in that. So email, we're finding that email across the board is not really working very well, like cold email, just doesn't really do that much. Now you could argue that it still works if you can get past all the new filters. So there's spam filters now that are just much more sophisticated, and there's all these sort of clever booby traps everywhere. So if you can find a way to get really relevant, you can still actually make it work. But it just in the heyday, like maybe five years ago, and it was like just a machine gun blasting so much cold email. And it would work, because even if one or 2% of people booked a thing, you could just do so much volume. So anyway, so anything text based is gotten a lot trickier. Oddly enough, I'm seeing two trends that are kind of interesting, that are real. One of them is or that are just showing where things are going. Phone calling is working better than ever. So cold calling, oddly enough, now there's some caveats to that. So calling is working, but I'm seeing a whole trend towards IRL. So like in real life, in fact, there's one company I know very well here that's really growing very quickly, and their entire strategy is IRL. They do dinners. So they have like, anywhere from one to two dinners in parallel every night, basically. So they're doing like 12 to 15 a week, and they invite 10 to 20 people, and they're all right in their ICP, and they have some cool speaker or some interesting restaurant or some whatever. It's a very expensive strategy. Energy, yeah, but it's IT people show up, and people love to be invited. They feel special. I think the big thing here is that even if they don't show up, they're way more likely to speak to you in some way. So the cold calling that I'm seeing do really well. It's the just, Hey, do you have time for a meeting, is actually doing better than you might think. I think because it's a real person doing it. So, like, at least it's not one of these AI spam emails, but the cold call in service of an invite is like,

Morgan McLintic: 5:24

doing great, yeah, okay, so I'm calling you to personally invite you to listen to this speaker or come to this dinner or this fancy restaurant. You're on the list, and I want to just

Andrew Boos: 5:35

give you the details. Now, maybe 10% of people would actually go to the thing, but at least you're talking. It's like, oh, thank you for thinking of me. Oh, great. Oh, cool. Hey. What do you guys do? So that's kind of an interesting trend. And then the other really crazy thing is meta ads. I don't know. I wouldn't have seen this one coming either, but we're getting great I don't know. Maybe you are too. You're in marketing, but like, at least for us, B to B, I would have never thought, you know, we're getting traction for high dollar amount technical B to B items on meta. And my only theory is that, because it matters, like Instagram, it's like cat pics. You know, everybody Doom scrolls, and the targeting is so good that somebody has the problem that you want probably looking at cat Pics or whatever it is, and if you nail them at the right time with the right message, you're just

Morgan McLintic: 6:13

catching them off. But to be clear, this isn't a brand awareness ad. This is a conversion oriented click the button and like, a book, a meeting, like I'm looking at my cat pictures, and then I'm like, hey, what I really want is an aisre. And in

Andrew Boos: 6:29

the back of my mind, they're like, my boss is on me about this. I gotta find something.

Morgan McLintic: 6:34

Right? For a long time, we've thought about people are in a laid back and there's more open and you can reach them whilst there's not pressed for time, but it's interesting that you're finding that working. And I'm fascinated that the calling, like doing my agency, I used to do cold calling for my agency, you need to try and grind through. And I think there's a lot of value in just that's the front lines of sales right there, because that toughens you up and gets your pitch really quickly. But I quite like the nobody likes being called on this. We're all on cell phone. No one's in a desk phone now, so it's pretty invasive, right? You are calling someone, probably on their cell phone. They might be working but, yeah, it's a personal device, so you're softening that by saying, Hey, I'm not selling it. I look just you might be you're in this area, and so are we, and you might be interested in meeting other people building your network, like a

Andrew Boos: 7:23

group of experts, and you, your name came up. It's great. You really can just make stuff like, I shouldn't say, make stuff up, but we'll conjure things out of what might not trigger that. So if the CEO is going to New York for a meeting, yeah, all anyone who's a relevant potential customer in that area and say, hey, the CEOs here, do you want to grab coffee? And sometimes they'll take the coffee sometimes they don't, but it'll get us moving.

Morgan McLintic: 7:43

At least. It's a sort of soft,

Andrew Boos: 7:45

not a very AI answer, but it's working.

Morgan McLintic: 7:46

Wondering about it, because for a long time, on the cold email front, which is a bit of an art form, you had volume, or you had the kind of small but highly customized, niche thing, and to do it, well, you needed to come somewhere in the middle, right? It's at scale enough to be personal, but personalized enough to break through. And the people who were doing it well would have worked out a system to get in that middle, and then came AI and just made mass personalization at scale possible. And it just that went away then, and I suppose that filters got better. It is interesting. You gotta catch people at the right time there. Tell me a bit about marketing guys. Tell me about brand. You work with a lot of emerging companies and some later stage companies, for sure, but you're often hiring the first sales team building that sales engine. These are companies that no one has heard of, right? They may have not even heard of the type of Proposition, right? Because it's new. How important is brand and credibility in closing the deals, or getting the meetings and then closing the deals, compared to just raw, just go at it, sales execution there in that early stage?

Andrew Boos: 8:55

Yeah, it's huge. And that's the uphill battle that all startups face. Is that, like an established brand is a beautiful thing, and sales people at established brands usually don't recognize how wonderful it is that they have that behind them. So we've seen that so many times. In fact, one of our big kind of talking points at Darwinian is that most first sales hires actually aren't successful at companies. And one of the big reasons for that is that okay, if you're a new founder, you have this new thing. It starts to sell. Obviously you want to go hire someone who has experience bringing in a couple million a year in revenue. What you don't realize is that they had an established brand behind them in their previous company, and they had a work environment, they had CRM, they had aI help, or maybe they didn't, but they probably had lead gen, they had BDR teams, they had materials, they had daily coaching, they had leadership, all this stuff. And so when people bring a salesperson into their brand new company, and there's this complete void where all that happened, it's a real jarring thing. And a lot of times salespeople themselves, God bless them. They're wonderful, but they don't recognize it necessarily either. And so I've seen even folks that are very good at their jobs get brought into startups. And. It just doesn't work because they don't recognize they didn't realize that maybe, obviously they're good at their jobs, but also they had help, because there was an established brand there that people already knew. They knew what they sold, they knew the pricing, they knew that they were established. So startups really have their work cut out for them, getting that credibility and that trust. Now there's a little bit of an interesting thing going on now, just talking about AI, where there's a bit of a truce happening with buyers, because all this stuff is new. So there's a little bit of a thing now where it's understood that there are new brands that they haven't heard of. Obviously there are, because all this tech didn't exist a couple years ago. So there's a little bit of a suspension of doubt there, which is great for new companies. And you can play into that, and you can say, hey, look, we didn't even have the ability to do this a few years ago, so obviously, we're only a few years old, but our founders come from very great pedigrees, and we know what we're doing, and we've worked with big companies, you can dance around it a little bit. When you're selling into mid market enterprise, there is an aversion to the brand new company with no established brand. AI curiosity helps, and that we're seeing that if it's used properly, but there is still an uphill battle there, for sure.

Morgan McLintic: 11:04

That's interesting, because, okay, I'm not expecting you to have been around for five years, because this technology hasn't been around that long, and so you are going to be a small, emerging company, and that does buy you a bit of stop and look time. Okay, tell me, yeah, at the very least, I'm learning about the space and the vendors in the area, right? Does it cut both ways, though? Do they also stay in that sort of discovery stage for a long time? Because, honestly, a 90 day buy cycle, there's a new model that's come out, there's new capabilities. People are shipping features so, like, they just know, they never pull the trigger. Does it cut

Andrew Boos: 11:39

both ways? Yeah, well, that's always been the case. I mean, especially big companies just don't have just don't have a lot of urgency. They have so much inertia, like they're going to be around tomorrow and they're going to be around the next day, and they can just outweigh their vendors. But that also is going away a little bit, which is really interesting. So there's just these mandates across the board, from the board of directors down, to say, We got to get on this AI train, or we're cooked. And so the interesting thing is, I'm seeing that go away a little bit. So they'll, like, sit around a couple quarters and just wait, well, it used to be sit around a couple years, and we'll just wait till the price goes down. Like, who cares? We're still, you know, we'll be fine. Like these big companies are putting a million in the bank every day or two. We're seeing that all change. So there's mandates to bring an AI to do it quickly, make mistakes and learn. Sometimes it's related to headcount. Sometimes it's not. But we are seeing things like move a little bit quicker there sometimes. But then we're also seeing somewhere you're stuck in this like learning cycle forever. But I don't know if that's any different than SaaS like 510 years ago. I think that was the case then too. I don't know if that's actually fundamentally

Morgan McLintic: 12:36

different now, I would imagine, though, because it like the clock speed is so fast these days, and companies are shipping features so quickly, and your competitors can match your differentiator fairly quickly. And so you know, if you're trying to get someone to swap vendors, I just wait a bit, and my current established supplier is going to have that feature. So like, swapping is going to be hard, I'll just wait. They'll have it soon enough. So I guess that's really changing what's going through the buyer's mind. I don't want to pull the trigger up. I'm expecting this company to be small. I am happy to talk to them. I'm a bit cautious about pulling the trigger, because will my incumbent have this stuff soon enough, or will I bet on the wrong company and then someone else eclipses them, because there's a new model now, and they've got a different set of data to inform it, you know, but they've got to do something, these mandates, they've got to do something. So you can't just sit on the sidelines forever, and so it's just of doing that. It's an interesting time for the buyers, too. Let's talk about building your the first sales team, because you often do this, right? So you're coming into a company founder led growth. That's the motion at the beginning, the founder, the CEO, often has a good Rolodex, established experience in this space, gets the first few landmark customers in there, builds what they think is the sales process. To your earlier comment about other people coming in, but at what point should they stop leading sales? And what are the signals for that transition? Yeah, you know.

Andrew Boos: 14:07

So in the typical scenario, yeah, the founder gets the first bit of sales. That's just how it works. So the founder gets the first, call it a couple 100k, maybe even up to a million, if they're really prolific, and they could keep going linearly, like they could still close another, like, some amount every quarter, and just keep it going. I think typically what happens is they kind of run out of tricks. So usually there's a lot of, like, low hanging fruit in the early days. So they have all these buddies. They can call everyone they went to grad school with other former boss, you know, their rich uncle who works at Microsoft, like whatever, like, they're going to use all those. And they come to an end where that doesn't work anymore, and then they really just have to grind and find referrals and find maybe do some cold prospecting, or what have you. That's usually where we start to get involved. So we know that it's sellable, and there's a good range of different customers that are paying. And the founders run out of they really need to go faster, and they run out of moves that they can. Deploy. So that's usually when they would start to hire folks. And we've just seen so many times those first hires are a disaster. It's particularly acute with technical and product founders, again, God bless them. They're really good at what they do, but managing and running a sales team is just it's a very weird and different, especially to an engineer. It's like a squishy, intangible thing. And so that's where, usually our big observation I sort of alluded to this is that you'll bring in a seller who has a great track record selling at an established company, and you drop them into this new environment. Now there's two things that happen that usually throw people off, and these are, like, very frequently made mistakes. They they'll say, okay, all right, new salesperson, you're you come from an environment where you're making one or 2 million of revenue happen a year. That's great. Even if you do half that, we're going to be in a great spot Ready go. And usually they'll tell them things like, Hey, we're building this environment from scratch, and you'll need, we'll need your input and help. And, hey, we got to set up this and this, and the seller, they want to work there. So like, yeah, we'll do it. We'll do it. I'm good at this. I've used these tools all that sellers are actually they're not that well equipped. Usually, I'm just speaking in general, sort of, yeah, but engineers are good at engineering, right? Sales, sales, people are good at selling, but they're not always the best at building intricate systems with details and things like that. In fact, the best sellers I've ever known struggle to open up a PowerPoint and edit it like they're really good at personal relationships, building trust, pushing a deal forward, audience management, knowing when to ask for the deal, like, all these things, but when it comes to sitting at their computer and, like, building an intricate thing, it's just really not how they're wired. And these new sellers will come into a company, and they don't have all these things that they're used to, and they're just not really that well equipped to go and build them themselves. And the founders are usually busy with other like, they don't really know what to do either. So they're not doing the daily like going on call reviews and like checking in on how we're framing things and all that stuff. What you end up with is just this kind of disconnected, disoriented person who isn't really equipped to build their own environment. And I've seen so many companies waste 612, months, yes, and it's just miserable for everyone. That's why we exist. We come in and build the work environment first, we build all the tools. We put in somebody who can do the strategy and sort of the daily check ins and coaching and all that. And then we embed and staff a seller, but that seller has all of the work environment built around them, so they have the tools and the systems and the daily coaching and all that. And then if the client likes them, they can hire them and keep it. You can do it without us. I think that's the other big point I want to make. Is that if you have a sales founder and you've managed sales teams before, maybe some of this stuff is instinctive. We just have found that there's a huge subset of companies where it isn't, and that's where we can make a big difference.

Morgan McLintic: 17:32

Yeah, I see this gap too, right? And I've seen startups fail because they lost the six months advantage they had right floundering around with bringing in the new salesperson, and their competitors have eclipsed them. It's tempting to say, Okay, I'm a seed stage company. I'm going to hire this person who's the Sales Lead at a B round, C round company in my space. They have the Rolodex. We're set. They know they've got some domain knowledge about it. The ramp up time is going to be and they're obviously very, yeah, they're charming, a good, good they're good people, and they're good, they've got the numbers, but yeah, you're you're right. But selling with a big brand, with the processes all built out the playbooks, we've we've got answers to these questions, etc, and then they get dropped into a small company where the founders intimately knowledgeable about the product and but there's nothing written down or documented, or how do we overcome these objections, or what is the product roadmap? And a founder can say in the meeting, yes, we will add this feature to close the deal. But the new sales guy's like, I can't say that, and they can easily fail. Plus they are used to having, as you said, a BDR team, like, they're used to having some leads coming through that they can work with, and people have heard of them, and you're building on something. So it's not impossible, but it is a very different skill set to build a process rather than be in the process.

Andrew Boos: 18:54

Yeah, and I see this actually in leadership too. This is a tangent, but, like, I've worked with some incredibly good CROs, like, a billion dollar annual revenue teams. And I've met a whole bunch at all sorts of different levels. It's really fascinating thing, because in a sales career path, oftentimes the best sellers are making more than their boss, and that's just kind of normal. So if you're a really good salesperson, you don't necessarily need to climb the ladder. In fact, you might not want to at all. It's burdensome and annoying and weird, because now you have to go back into this like system building tinkery mode, where you're like, do we have enough lead flow? And is the load balancing happening between BDRs and lead operation, creation, like all this stuff, it's a way different headspace. And so I see all these people who are great salespeople that will think, Okay, now I'm going to be a sales manager, and they're really not great at it, even though they were wonderful salespeople, and then vice versa. I'll see some people that are mediocre salespeople, but they're really good at leading and managing the one combo. And this is again, inspiration for how we deploy. Is like the best CROs I've ever worked with. Have a really good right hand person, like a sales ops rev ops person, and they're the, like, factory builder. They're. Are the they're like the drill sergeant. Mechanical trains run on time. Integrations are clean. Everything's set up. Roles are defined, commission structures are defined, daily expectations are defined. All that stuff that combo scales to billions, literally billions, of annual revenue and but it's almost always very that one person's maybe the spokesperson, but that duo is really what makes it all work. So that's our deployment. So it's like a fractional leader, fractional tooling, factory, kind of data integrations, person, and then a seller. It's like the tiniest bite size of what we've seen work.

Morgan McLintic: 20:32

Yeah, I think that's that makes perfect sense to me. Because you might even see at the top of a company, you know, it was often this sort of visionary, and then an integrator, like the person who's sort of right. I don't know how we get there. We're going to get here. And that's energizes people, and that might be your CR and then the robots person, like the person who's going to make it happen, right? And your rev ops person might not want to be in front of a prospect selling. They're not going to pick up the phone. This isn't a thing that they enjoy doing. They enjoy building processes with the factory? Yeah, they're the factory people, right? And you need both, and some people can do some people can be both. You get people who are a visionary and an integrator, but they're pretty rare, right? So I like this. And so we decided, okay, it'd be tempting to look at a later stage company in my space and cherry pick one of the best people to lead my sales, but you're saying, No, don't do that. There are companies like Darwinian who can come in and build the scaffolding and also drives that. You know, they can build the plane whilst flying it. You know, classic. If you're saying, don't hire the big closer, should they hire a scrappy generalist? Or who should they hire scrappy generalists

Andrew Boos: 21:39

are fine, like a scrappy generalist who can kind of is okay with some ambiguity, and can solve their own problems to some degree, as long as they get enough time and attention from leadership like that. Can? I've seen that, right? That's fine. I still don't think it's optimal, but it but it can work, because, you know that person can, you know they can maybe build some of their own mechanisms to help things move. I think the big thing is, the leader needs to pay, like, daily attention. And a lot of times it feels like it's like, almost like, not glamorous enough. Like, the biggest brutal thing that I see is that a lot of founders, especially, again, I'm going to pick on technical and product founders, but they're like, a little bit above the fold, like they don't want to get on an early customer call until it's like, deep into it, and like, they don't want to prospect, or they don't want to go to the booth and meet a bunch of people. They're like, they're engineer, like they're crafting solutions and doing

Morgan McLintic: 22:29

they might not be that persona, yeah, that's not their personality type, right? I don't want to be out. Yeah, I've just hired this person to do it, and I'm paying them a lot of money, and they can, you know, they can get on with it natural to

Andrew Boos: 22:38

think that, yeah, but I've seen, yeah, the scrappy generalist with a very highly attentive founder who can do the things that might seem beneath them and at least be present for them. I've seen that work. But the main thing like, obviously, you could hire us, or you could work with a firm, yeah, but if you don't do that, just think backwards and try to get ahead of everything that person could need. Like, the most obvious example that I see a lot of is, if you think of lead comes in and then they turn into an opportunity, and then they turn into close one, like a customer, and then they're in CS. So people will hire a closer like a seller, especially from big companies, they're very usually divided, so there's like a lead gen team and a closing team and then a CS team. So they'll hire a closer because they want the revenue. Hey, we're here for revenue. We're ready for revenue. But then they don't have the lead flow coming from the business development team, and then they don't have the marketing team. Don't have the marketing team that you guys would provide either or they hire these closers, but the closers have a completely empty calendar, and they're used to just having it filled for them by other people. I guess where I'm going is, if you're going to try to do it yourself, just think backwards as much as you can to what that person needs to be successful, and try to warm those things up first. They're going to need leads, they're going to need opportunities, they're going to need materials. They're going to need some form of pricing strategy and framework. And it can't be like, let's see what they're willing to do. It needs to have some teeth to it. There's just a whole bunch of things that need to be done beforehand. And then the only other pro tip is that this is, again, like a general observation, but especially when you're in that early selling role, you need a lot of attention. You can't just leave them alone and do a daily check in once a day, like you want to go through the learnings and go through the calls and listen to the transcripts and all that stuff. So that's how you could do it, like you could do it without using a firm, right? You can do it yourself. You just have to really get thoughtful about all the inputs to making a seller successful. So even

Morgan McLintic: 24:15

though I as a founder, I've been doing the founder led sales, and I'm hiring someone here to take over that portfolio and that responsibility, it's going to free up some of my time, right? But I still need to spend that same amount of time on different things in the sales process to kind of make sure that that team works. Certainly, you know, at this early stage, because it could be tempted to say, Okay, I've hired that person, and I'm freed up my time. I'm gonna go back

Andrew Boos: 24:39

to my engineering, get back to me with a signed contract once you go,

Morgan McLintic: 24:43

yeah, that's the dream, but no, you have to

Andrew Boos: 24:45

spend just as much time for the first 90 days,

Morgan McLintic: 24:47

at least, like, right? That's good advice. Okay, I want to ask you a question about hiring an outside firm for sales, right? Because this is a core competency for the business. Forever, I'm getting fee. Back from the market that's going to affect our product pipeline and our pricing. It's fundamental to the success of the business. My natural inclination is going to be, we need this in house, right? We need to build this muscle, even if it takes us a bit longer to do it, because it's so vital that we have it. And I imagine you get this objection all the time, whereas you're going to get me there faster, and you're going to have good ways to get intimate with the business and provide the feedback loops and all that good stuff. But ultimately, you are a third party. How do you get people over the hump of that? Because it's so tempting to go, okay, great, I can fast track this, but, you know, I'm worried,

Andrew Boos: 25:43

yeah, yeah, we get that pushback a lot. And even I can only imagine, for every meeting or engagement we have, there's probably 10 that thought about it but didn't even want to talk to us, because the common knowledge is that you should try to figure it out yourself and have it in house, which I completely agree with. I think our model adapts to that as closely as we possibly could. So we're as embedded as can possibly be. So like, we're in the company. We're building things in the company. It's as if you're hiring like, the way that we deploy is extremely embedded and extremely execution focused. So it's not like an agency where we're throwing things over the wall and, like, have our meet weekly thing. Like we're in the Slack channel or in the office, we get flown around. So the way I like to frame it is that, you know, if you're going to go and hire some folks to build out your first non founder kind of sales org, do it with us, it's the same thing. You get it all internally built. It's some heads that are going to do the work and pick up the phone whenever you call. It's the same thing. They'll take you on LinkedIn, they'll put your logo on LinkedIn, all these things, the only difference is, is through a contract and they're going to know what to do. So that's, I think it's the big unlock is that it's as if you're staffing your own team, and it is your own team, but they're going to already know what to do with their time, and they're going to kind of, in some ways, even tell you what the right thing to do will be, is to get it done right. So it's doing it right and doing it quickly with an embedded team. And then the biggest thing is that they can keep the team. So like we allow, I used to call it poaching, but you can hire the individuals if you like them. So you can think of it as a really quick way to get going, get all the rhythms and the structures all set up under your roof. And then if you like that, you can hire them and have them directly. And what most clients find is that it makes really very little difference. It's just a paperwork change, because it was all kind of theirs to begin with, anyways. But when the paperwork changes, you know, they can do some other things. They can issue equity and, yeah, do

Morgan McLintic: 27:29

other other things. Or if they're thinking this person, you can be very sure that this person is the right salesperson for you. And they'll have come with all these sort of frameworks pre installed, which is great, and I can attest to we work together on a client, and the name of the salesperson comes up a lot in other meetings. You know, we'll talk to such a website about that. To the embedding part, you're right in them. They're like, Okay, we must make sure to tell them as if they're a normal, a standard teammate. In fact, you wouldn't if I didn't know, I wouldn't know. I think that attest to that model. It's a natural objection. But if you can keep the people and you're worried about that person suddenly being pulled onto a different client from you, or getting bored moving up, then fine. I guess the flip side is also, people do move around. And if you're hiring people directly, they do swap in that instance, the impetus is on you to sub someone else in, and you might be able to do that faster because you got a team of sales people that you got a little bit more flexibility. So I like that. So you work with a lot of startups, we've talked about a few mistakes with the first head of sales, but talk to us about some of the sort of most expensive mistakes startups making when they're building a

Andrew Boos: 28:40

sales team. Yeah, the one that I described earlier, where they hire the closer without thinking of anything around it, that's the most common by far, and it's just so miserable and expensive. It's like a quarter, two quarters, three quarters of lost runway. And then even when you figure it out, then you have to, sometimes they'll even make it twice. So then they'll hire a BD team, but they still don't have a marketing team, so then it's like they got to get that full thing set up that's right before they start thinking about closing revenue. So that's by far the most frequently made mistake. There's a big problem, especially with folks that come from large enterprises, like founders from big enterprises will often over architect the living hell out of their sales system before they even have $1 of revenue. So they'll have this incredibly well built out sales territory mapping, and the CRM will have all these automations, and they'll have, like, very intricate pricing tables and all this stuff. They'll have documentation for everything. And then it falls flat, and then they have a really hard and long time to adapt and evolve. And then it's also just made even more challenging because now they have to rebuild all their stuff. So every time they make a little course correction, which takes a while to begin with, it takes even longer and is even more expensive, because they have to re architect everything. So like my big thing for the first couple million, you got to come in with some humility, you have to come in with conviction, with whatever pricing model you have, but be ready to make some changes and then ship a new model. Ship a new way to structure it. You. And, like, I wouldn't architect much until you have, like, substantial repeatability around how you're doing things.

Morgan McLintic: 30:05

I like that one because it's almost the opposite of the other one, right? Hiring the big closer with no instrumentation or processes, right? And this is the opposite. Hey, I've seen what sales look like in my large organization. I came from IBM, and we need this pricing and these battle cards and this flow of different lead flow models and all this stuff, because at any point, we're going to be deluged with all this inbound, because that's what a sales organization looks like in their minds. Yeah, we're just going to get a slightly smaller version of it, so it's almost the opposite. And that takes time to build, and you spend a lot of cycles on that. And as you just said, rigid

Andrew Boos: 30:40

and very rigid, yeah. And actually, I see it as kind of even a further perversion of the same thing. Like, I don't see them as offsets. I see them as the same thing. So what they're doing is they're building the hell out of their closing, out of the finish line, like the finish line of the race, like they have everything built around the finish line, but they don't have the rest of the track built yet. So they'll have territories, and they'll have battle cars and all this stuff, and they'll have their CRM will have different drop downs for what type of license it is, and all that stuff. But they don't even know if anyone cares about that, or if those pricing models are acceptable to customers. There's just, it's all built around the revenue, the dollars, but they don't have all the inputs to dollars yet.

Morgan McLintic: 31:14

Yeah, fascinating. The pricing models are changing so much now because it's so token based, yeah, and burned down models, all the different billing models that you're starting to get, and so that, I think that's probably amplified now more than ever. You just talked a little bit there about what something I would say feels like scaling, but just that slows it down. It's like building out this complex process really feels like work, and just digging foundations here, because this mighty emphasis is about to rise. Are there other things that you think that startups will often do that feels good, but actually it's just a bit unnecessary. Oh, I have so

Andrew Boos: 31:54

many rants about this. Oh, there's two really big ones that I just see all the time. One of them is, I see, especially in the early days, there's a very different voice and Persona when you're speaking to a prospective customer and when you're speaking to a potential venture capital, like a VC investor. And so I see that voice just people self sabotage without even realizing it, severely on both sides of that all the time and so and just to illustrate that, like so the way that you speak to a VC is, you know, you can speak in sort of lofty things. It's like the Grand tectonic plates of the industry are shifting. It's like a TED talk, you know, it's like some, like, lofty intellectual thing, and you're also kind of pretentious and talking down a little bit like you're like, Yeah, well, at grad school at Harvard, I discovered this thing, and then I found the best scientists in the world and the economic shifts were just right. And VCs eat it up. They kind of like being talked down to a little bit. It's like, Oh, I found someone smarter than me. They love it right now. Do that to a customer buddy. They're going to hang up the phone so fast. They don't want to be spoken down to. They don't want to hear about tectonic shifts of any nonsense, like they don't want to hear about your Harvard degree. They could give a shit about any of shit about any of that. In fact, if you make them feel small, they're not going to want to be around you at all. And so like, it's like you got to suck up. It's like, you know, your boss, like you got to suck up to them, laugh at their jokes. Like you can't outshine the Master. Don't outshine the customer. VCs like to be outshined a little bit because they want to invest in something that's shiny. I see people screw that up all the time, and usually it works itself out. But for the first like, your seed, pre seed, I see it all the time. Usually by series, a

Morgan McLintic: 33:26

founders have figured it out, right? I'm trying to sell a vision, whereas what the buyer is trying to buy is a solution to a problem. Like, we're not taking over the world here. I'm just trying to keep my application up. So I don't care about the tectonic shifts in the way that this is,

Andrew Boos: 33:41

yeah, they're talking way lofty to like Steve in Nebraska, who just wants to go on break 15 minutes earlier, you know what I mean, and they'll, like, lose the deal immediately. Now the flip side also doesn't work either. So if you're like, a friendly, eager beaver, nagging sales guy like that works fine, because you're kind of like, Hey, I'd like to help you out. Hey, when can I get time on your calendar? Like you're kind of the needy help like that actually is fine for sales like that. That's how you get on people's calendars to begin with. Do that to a VC, and they'll think you're pathetic and they won't want to talk to you. So, like, it goes both ways, you know. So if you do the whole like, suck uppy, like, eager beaver sales guy thing to a VC, they'll think that you're not interested. They're like, this can't be a hot founder. They're lacking confidence.

Morgan McLintic: 34:17

They've got no vision. Like, yeah, what are they doing? You know, it cuts

Andrew Boos: 34:20

both ways. So that's the first one. And then the second thing, the second brutal thing that I just see founders do all the time is, I think you alluded to this before, but, like, they'll do this busy work that, like, feels glorious, but it doesn't do anything for moving the business forward. I mean, the most egregious example of this, I had this one client a long time ago, and he was so proud of being bi coastal, and he wouldn't shut up about being bi coastal. Oh, yes, we have a corporate place in New York, and we have a corporate place here in San Francisco. And, oh, I'm speaking on panels. Oh, I can't talk. Oh, the next week, I'm speaking on three panels. Meanwhile, the business was cratering and, like, they were so caught up in this, like, busy, important, lofty thing. And and having presence and being a lead and being known and speaking on panel, going to these communities, like they would go to Davos and Switzerland and try to get into these loft of the Milken thing in LA like they were just going to all these fancy things. And the rest of their employees were begging for input and begging for help, but they're like, Hey, listen, I'm doing really important things right now. You're going to have to figure it out, buddy. I've seen that so many times in different ways, and it's just brutal. It makes me want to hurl like whenever I see it. It's such a shame, because usually they could do so much better if they just focused on the unglamorous things that really move the business forward.

Morgan McLintic: 35:31

Yes, keep the main thing the main thing, and not always success theater. It looks like we're doing so well, and that's fine, as long as you're doing well, how does because everyone's thinking, how do they do it? How on earth does this person do it? And the answer is, they're not doing it. They're just turning up to the conferences that they paid for, and that's what they're not actually doing, the nitty gritty bit of selling, it

Andrew Boos: 35:53

shows in the revenue. Like, that's why I love being so close to the revenue. And we invest a fair bit, and we're just laser focused on what the what story the revenue tells. So if we see the fancy stuff going on and their revenue is flat, nope, like, I don't want anything to do with that company, and there's no way to hide that. And people even try to this is another kind of side ramp. But people are getting pretty clever with how they structure their presentation of their revenue, too. And I'm ruthless with that. There's this new term contracted, Arr, I don't know if you've seen that come up. Yes, it's essentially fraud. It's like we wrote in a contract that if they were to get up to 100 seats, this is what we would charge per seat. But then they tell investors that they have, oh, we're in contract for

Morgan McLintic: 36:31

this, much as if it's booked revenue.

Andrew Boos: 36:35

That's a lie. People will go and raise money on that. And then all these other founders like, oh, man, I suck. I'm not at 10 million in contracted Arr, in the first year,

Morgan McLintic: 36:44

neither are they. Yeah, this isn't actually money in the bank. Yeah, we, we do see this a fair bit. There's normally a number that is indicative in each sector about the profit per whatever that sort of key economic unit is that you can drill into and just stick to that. Just stick to that. But yeah, yeah, on your investing side, you're in the sales side, you can see what's going on and, oh yeah, don't lie to me, dude.

Andrew Boos: 37:08

Like, I'm the last guy you want to lie to revenue about.

Morgan McLintic: 37:12

Okay, this is great. So just as we wrap here, I want to ask you what sort of one sort of contrarian belief that you have about sales that most startup founders might disagree with.

Andrew Boos: 37:23

I actually think AI is going to help with some of the tactical stuff, but I think selling is going to come back to in person IRL, maybe even local like I think software is going to be so commoditized that you might have some startups in Austin and some startups in LA that maybe do the same thing, and you might want to work with the one that's closer to you. I think we're going to you. I think we're going to keep going in that direction. I'm a little out on a limb there, but like, I'm seeing signs of that. You think that,

Morgan McLintic: 37:47

because there are going to be, there are so many startups who are doing fairly similar things, and sales is orienting towards being local, yeah, that those companies are going to establish a home territory in their city or in their state, and others aren't going to be able to get in there because they're going to have their local stuff.

Andrew Boos: 38:07

They're not invited to those dinners, right? Like, I think I'm a little out all in there, but I'm seeing bits and pieces of this conclusion. So yeah, like the company that's like the company that I mentioned here that does two dinners every night in parallel. Good luck trying to really build mindshare here, but there's probably, in fact, I know that there are almost identical competitors. There's like, four other almost identical competitors. Now, the one in New York might get most of the New York like, there's going to be almost, like a little bit of a convergence back into local at least for, like, the high dollar, high trust things. I also have this kind of thesis that it's going to evolve on the scale of how high trust the decision is. So like, for a small dollar amount, like, if you're buying $100 on a credit card every month, you don't need to speak to a salesperson that you can use, like AI. You can have an AI salesperson for that, no problem. But for like, 10 grand and up, you're going to want to speak to somebody. You're not going to risk your career over a bot conversation. And then even more, at the 50 100, 200 grand, 500 grand, 500 grand, like these really big enterprise deals and contracts like you've had many in person meetings, usually. And I think that's not going anywhere, if anything, I see what I just described, where there might even be kind of more, almost a regional bias towards

Morgan McLintic: 39:12

customer base. Do you think that the low bar on what can be automated with AI? You said, yeah, like 100 bucks a month. 200 is the AI bar at the bottom going up like 1000 bucks a month, 5000 bucks a month? Does that go up over time as people get more confident with that's a really

Andrew Boos: 39:30

information maybe, first of all, just inflation.

Morgan McLintic: 39:35

Yes, because my sense, my sense is that it that it will, we'll get more confident. We'll get more and that doesn't mean that the role of sales goes down. It just means it more important at the higher end. But you know, people just get more confident, and they need to move fast, and having a decision and implementing something is worth right, the offset of the risk.

Andrew Boos: 39:54

Yeah, Tesla. Tesla really made some waves. You can buy a Tesla online, and most people do, and that's you. Most Americans second largest expense in their lives is their car, right? So, okay, so yeah, I think there is some validity to that. I think over time, the dollar amount will go up, but that's going to be slower moving than how fast technology is advancing.

Morgan McLintic: 40:11

Yeah. Okay, listen, Andrew, I really enjoyed the conversation with you today. Thanks for sharing some of the thoughts there. If people want to get in touch with you,

Andrew Boos: 40:18

where should they go? Yeah, well, I'm all over LinkedIn. So Andrew Bose, B O, S, I post a lot my email. I mean, I can just give this out. My email is a B for Andrew Bose, my first and last initial@darwinian.com darwinian.com is our website. There's also a form you can submit, and we monitor that very closely. Yeah, reach out. I mean, I'm pretty responsive. I get it all and we can, we can chat further. That'd be great.

Morgan McLintic: 40:41

Landreaux, thanks for your time today, and thank you all for listening. We will see you all next time you.