Episode 47: Hiring first GTM hires that last

Speaker A: Foreign. Welcome to Decoding Sales, a podcast where an engineer, that's Alex, Elaine and a salesperson, that's me, Peter, talk about the art and science of sales. Today I'm repurposing another one of my virtual webinars where I hosted Harry and Udoff from the Inflection Group, a search firm specializing in placing go to market executives at fast growing startups. So let's dive into this one. I'll give an intro for Harry first and then Udof and then I'll get into some questions I have pre built and then uh, we'd love to also take questions from the audience. Some of you have pre submitted questions so we'll try to get to those as well because I have them up on my screen. Um, so I'll introduce Harry first. Harry is the CEO of the Inflection Group. He has nearly a decade of experience in go to market search across both B2B and B2C venture backed startups. Um, he was previously a top national producer for Michael Page, um, where he actually earned five promotions in five years across two locations. He's led over 300 executive searches. Wow, that's a lot for companies ranging from 1 million to over 1 billion in ARR. So I mentioned they specialize in placing execs for startups. But it's not just startups because he's worked with clients like Gong, IO, Coinbase, Pinterest, Ironclad, Gekko Robotics, Snowflake and the list goes on and on. So thank you Harry for being on. Um, he's joined by Udof who's the first non co founder hire at the Inflection Group. He also specializes in go to market leadership specifically for VC and PE backed tech startups. Um, he jokes that Harry's made the mistake of hiring him now at three different places, uh, including one large publicly traded and one boutique company where he's been the top performer. Earlier he was actually in growth at Snapchat and Darktrace, um, both of whom have gone to do great things and he currently runs a music production company on the side too which we geeked out about previous to the recording. So hope I did you both justice there. Thank you for joining. I'm um, really appreciate your time. I know your time is valuable and you could be placing candidates or engaging with clients, but I appreciate you spending time with the community too.

Speaker B: No, you're making me blush, Peter.

Speaker A: Those are impressive resumes and hopefully a lot of the founders in this community also become you know, the size of like Coinbase and Gong. But but congrats so far on, on both of your journeys.

Speaker B: No, thanks so much for having us.

Speaker A: Awesome. So, so let's dive into it. Like I said, I have a few questions. I think some, um, of these I get a ton from my clients actually. Even though I'm not a hiring specialist, I do opine on go to market leadership hiring because I've worked with a lot of sales leaders and marketing leaders. And one of the main questions I get because I focus on the founder led sales stage is when do I actually hire someone? Right. I obviously love being a sidecar to deals with founders, but pretty quickly it becomes unmanageable for them to handle sales or marketing on their own. So how do you both think about that? I'm sure it varies the answer, but would love to just start there. Like when do you actually start to um, approach hiring and go to market, whether it's sales or marketing?

Speaker B: Yeah, I think there's a couple of different factors uh, that are involved in it. Um, one of which is does the founder have that experience already? Uh, so your capacity to learn something new, it often takes up more of your time if it isn't something you've done before. So uh, if you're learning sales for the first time, you might need to do it slightly earlier than someone who's done it before has sold something at a previous company and then founded a business. So I think it's not always an apples to apples comparison. Uh, generally speaking, when you're starting to see some repeatability, uh, around the process, uh, I'll throw out the 1,000,000 ARR number here roughly. Um, and you have different competing priorities, then it's probably time to start thinking about it. Ah, at least I would definitely try and hire slow, uh, as well, rather than waiting till the end to you, kind of beyond your capacity, sort of at your wit's end. Like I desperately need somebody, uh, because that's not always when you make the best decisions, uh, either. So uh, it's a, there's a couple of different factors in it. Like go to market motion matters, uh, ability to do sales matters, repeatability, uh, matters uh, as well.

Speaker A: Uh, yeah, that's a good point. Yeah. You can't hire a salesperson to figure out product market fit. Right. Because they're not there to be user research or they're there to really like close deals and sign contracts.

Speaker B: Yeah, sometimes we see um, sales leaders or just sales in general who are hired to come in and sort of fix the sales problem, so to speak. But if the product can't be sold by the founder, it's likely not going to be able to get sold by the salesperson either. Uh, so I think knowing that you have something there that you can sell consistently, uh, and that can somebody can fit into to an extent. Obviously there's going to be some trial and error, there's going to be some user research, etc. But um, there needs to be some repeatability before you bring in anybody that makes sense.

Speaker A: Do you also feel like that's the case for marketing too? Right, because with demand gen, um, if you're doing both demand gen and sales, first of all, that's a lot on your plate as a founder and I feel like there's so much specialization in how you fill the pipe as well. Um, do you kind of prescribe the same thinking? Like you should have something that you feel like is working on lead gen or creating the demand too, or capturing the demand?

Speaker B: Yeah, we don't see founders do as much founder led marketing as we do founder led sales. I, uh, think there's probably even fewer founders that are marketers than there are salespeople, uh, usually. Uh, so I feel like marketing is a little bit more nebulous, uh, so that's almost even harder uh, to do so. I think probably less on the repeatability side, I think most founders focus on the message and the story and the narrative. They're not kind of like turning the dials on demand gen and doing campaigns and you know, measuring attribution and like all of that type of stuff. Sure, I think that's rarer. Um, but yeah, generally speaking, I think again, it depends a little bit on the business model whether you hire sales first or you hire marketing first. Like are you trying to create a new category? Does the kind of customer base need education? You know, all of that probably leads more towards marketing, uh, because it's hard to sell to somebody who does not have any awareness of your product whatsoever. That's a good point.

Speaker A: Yeah.

Speaker B: Again, it's like it's a bit of a mixture, uh, of those things. It wouldn't really depend on the company situation. Feel free to fire away with anything you think as well.

Speaker C: No, I tend to agree with you there, Harry. Um, generalizations are hard because every company's, every founder's plight is slightly different. But I oftentimes see if so going back off of um, Harry's point. Right, and your point? Uh, first, sales hire is not there to help you figure out product market fit, but what they can do is help you figure out your go to market motion by going through the motion over and over again. Right. There's going to be wins, right. There's going to be failures. Why are we winning? Why are we failing? Are, uh, we verticalizing? Is it a general, like, you know, one size fits all play? Um, so first sales hire should oftentimes come when like one, as a founder, you cannot. You, you are, you need to do more founder things. Right. Like building the rest of the company, talking to your board, VCs and so on and so forth. Um, so once you have a inflection point of hey, I need someone to take this off my plate is usually the time you, you should hire that person. But you should think about it before marketing, as Harry said, is it's like chicken or the egg, depending on what your product is, who you're selling it to, is it in a competitive landscape? Um, you know, typically I see it come after sales, but like slightly after sales. Right. Because you need a couple of wins for the marketing leader to be able to build off of.

Speaker A: Mhm. Yep. Yeah. The marketing leader also needs proof points to figure out how to message. Right. And frame the value proposition.

Speaker C: Yeah, sometimes that can come from the founder and then sometimes that can come from your, you know, your salesperson that you've hired who's, you know, giving, who's giving you data on, you know, this is working. This is not working. We need some lift for these XYZ kinds of companies. We don't really need marketing lift on, you know, SMB companies, for example.

Speaker A: Yep, makes sense. Makes sense. And Harry, you mentioned, um, hire slow too. When you're looking at hiring in general, I'm assuming that comes from seeing like a lot of mistake hires too. And in fact one of the audience members wrote in before the webinar, um, she said one of her challenges is overcoming the burn from previous bad hires. Yeah, I'm sure a lot of founders can relate to that. I can relate to that too. You know, being in early stage sales and seeing some VPs join who, you know, maybe were not the right hires in hindsight. So what are some of the mistakes founders make when, when hiring and, and why, you know, can you unpack? Kind of why you say go slow and be intentional.

Speaker B: Yeah, um, we often come in when there is some scar tissue, uh, so coming in. And often what they'll say is, you know, we had this person before, we don't want any of that.

Speaker A: Sure. Yeah, yeah.

Speaker B: Ah, and you do have to remember that it's a person, not a product. Uh, uh, as well. So, um, there's a lot of different variables with a person. Uh, uh, if we could draw somebody up in a lab, we'd probably love to do that and present them to a company. Uh, uh, so you know, they have thoughts, feelings, emotions, you know, all these other things that are outside of just what their experience is. So we'll have to put that into context. Like from a mistake standpoint. I think the biggest thing is, uh, there's a really strong draw to what I would call halo companies. So typically there are five companies in that organization space that they aspire to be that are bigger than them, have done what they want to do. Uh, so sometimes those companies can be a couple of steps ahead, sometimes they're ten steps ahead. Um, and often the appeal is to try and get whoever the most senior person is at one of those companies m which makes sense, uh, because they've been through the journey before. Um, they've been there, done that, and they're probably great, uh, at their job. However, the likelihood is that that person did the job that you're asking them to do seven years ago, 10 years ago, 15 years ago. Yeah. So if you were to try and hire that person and hire them successfully, the likelihood is they don't want to do that job anymore. They might think that they want to, uh, because now this bigger company with lots of infrastructure and resources and you know, there's some bureaucracy and all those types of things. But the reality is they're probably not going to want to go back into that player coach style role.

Speaker A: Sure.

Speaker B: So people always tend to want what they can't have and the grass is always greener. So it's like, oh, but this big company, there's all of this stuff like, you know, we've kind of done what we need to do and then it's like we go back again and let's do it, do it more. That can work, like, don't get me wrong. But, uh, often hiring too big too soon, uh, is the main mistake. And in an ideal world, what you really want to find is the person who's going to do that journey for your company next. Yeah, you want the next point, whoever it is, the CRO of snowflake, you want the next CRO of databricks or whatever it is. Um, that's what you want to be looking for and kind of testing for, uh, and also just trying to plan for the next 12 to 24 months as opposed to the next five to 10 years. Because lots of things can change.

Speaker A: I love that you mentioned that. Right. You need to Hire for somebody who's going to do the job today, not what you could aspirationally become in five to ten years. Right. Um, so I guess implicit in that is that you do need to take some risks on up and comers too. Right? So how do you figure that out? Right. Because, um, I don't want to lead you too much in this, but I've definitely had success in hiring folks from like the legal industry, for example. Right. They were like, I was going to become a lawyer and then they're now like a director of sales. Right. At a cybersecurity company and doing it really well. So. And so, you know, like, you know, it's hard to sometimes, um, have people feel like that is a path when oftentimes people feel like that's not the norm. But I think it can be. So how do you do that? You know, like when you're a search firm trying to hire like the next CRO. I'm sure there's a balance too. But how do you both think about that? Like, how do you hire for the up and comer? Maybe I'll give it to Udoff this time.

Speaker C: No, that's a, that's a really good question, Peter. So there's every, every recruiter has their own style to this, which I think comes into play as well. Um, but I like to. At the end of the day, we're, we're working with human beings, right? And if you're looking at an up and comer, there's only so much experience that you can actually, you know, understand about a person. There's only so much experience someone has. I think understanding the human being is oftentimes as important as understanding their experience. Right? Now, if I'm in a conversation, for example, with a candidate that I think is a good person for a foundational sales or for a company.

Speaker A: Right.

Speaker C: Um, hypothetically, it's a series A company. But as through the process of getting to know them, I figure out that, hey, look, they're interviewing with. All of the other companies that they're interviewing with are like series D, series E later stage companies. Right. That gives me a signal that like they're saying one thing, but, you know, they're, they're actually looking for something else. Right. Going a couple layers deeper and just understanding the person, like, what are their aspirations in life? Like, what motivates them? You know, very rarely will you find a job that's like, this job is what I dreamed of. It's my life, it's everything. Right?

Speaker A: Yeah.

Speaker C: Oftentimes a job is a means to an end. But how big of a Venn diagram, um, overlap can you find for how big satisfied someone will be and like how much that satisfaction will drive them to excel over and over and over again for a company.

Speaker A: Yep, yep, that makes sense. That makes sense. And there's also probably, yeah, just uh, that's really interesting that you actually look and vet the candidates too. Right. It's not just like trying to place someone um, in the moment. You're also looking at, okay, like what aptitudes do they have, what skill sets do they have? Maybe um, in, in my kind of hiring process I always tried to get these candidates to do very tactical things too, especially in the early stages, like write a cold email or like actually present my company back to me knowing that you've only known us for three weeks. So I wonder if that's also. That also gives you guys signals like how they actually behave in the interview process on just like a pure ah, skills standpoint versus like experience. If that makes sense.

Speaker B: Yeah. You know, ask people to do something tactically, um, without tons of coaching and guidance is generally a good idea. Whether that's a case study or you have them come and do a trial project or something like that so you can see how they would operate day to day. Um, but as UDA was talking about, I think like someone especially for sales, like someone's intrinsic motivations and understanding whether the job is going to give them that and it's going to drive those things is really important. Um, because the money, uh, from one company to another company, um, it might attract them in the first place. Not what keeps somebody out of an organization. Uh, it is people and motivations and is it ticking those boxes? Is it keeping them coming back, you know, day to day? Uh, so definitely for sale. Like testing for drive.

Speaker A: Mhm.

Speaker B: It's really important. I know it's kind of almost feels like table stakes. Uh. Right. But you know, the money that they want to make, you know, what are they going to do with it? Like yeah, what are their goals? Is it to you know, buy a house, do like send the kid to college, whatever it is? Um, those are the things that people keep people coming back.

Speaker A: Yeah, yeah, it's. That's interesting. The personal motivations matter quite a bit. Right. And um, when a candidate says, oh I'm just passionate about the technology and that's it, there's probably a missing piece there and you want to understand what's going to get them up every day. Right. As well. So um, so why is there Then like, you know, there's this question in my mind. I mean, we have a founder who said, hey, like, how do you get over the burn of the first sales hire? And I feel like even in tech there's this kind of understanding that the first sales hire will never work. Like, and like that there's always going to be a mistake. Like the average tenure for a first sales hire is like probably like a year. I think Gong published something like a few years ago or was like 18 months or something, which in tech years feels like a long time. But I do feel like it's shorter than kind of other executive positions. So why do you think that continues to happen? Right. Do you feel like we've kind of made an excuse for first hires? Um, and how do you like prevent that on your side? I mean, you were kind of circling around it, but would just love to get a little bit more of your thoughts on that dynamic.

Speaker B: I think, uh, one of the main reasons is misalignment, uh, in expectations between founder and candidate, uh, in the process. So there's a natural kind of part of this where you have to sell your company and, you know, why should somebody join? But it is a balance, uh, between telling them what's great and telling them what's not great, uh, because you only tell them what's great. There is an expectation from this candidate that all of these things are perfect and there's nothing to be solved and fixed, et cetera. And that's when we talk to a candidate and say, this is not what I thought it was. If I'm going into this, this is really different to what I was told. Sold the bill of goods, all of those types of phrases. Um, so I think somebody who's motivated and interested to join your company, they will, um, understand and actually relish the challenges. So one of the questions I ask candidates is, is this challenge exciting to you? Things like that, like, that's a good one to ask people, uh, because if the challenge scares them and they don't really want to do it, that's when they're going to back away and that's when they're going to leave and the turnover gets higher. Uh, so I think a couple of core things, uh, that you can do is just set up, um, three really specific kind of smart objectives for the first three months, six months, 12 months.

Speaker A: Mhm.

Speaker B: Tell the candidate, these are what success means to me, uh, in this role. How does that align with what you can do? If they hit those things, the founder's gonna be happy. The Candidate already knows what they are. Great. Uh, and if they don't, everybody knows where they are. Mhm. As well. So I think doing those things is beneficial. And also as you're moving through an interview process, it can be quite um, it's not linear. A candidate might have other opportunities. You might have to move faster than you wanted to. Uh, there's two people involved. It's quite emotional uh, sometimes, uh, as well. So um, it can sometimes mean that you lose sight of what that success means. Uh, so if you outline success, I think that helps moving forwards.

Speaker A: Yeah, that's a really good point. I like what you said about be honest about what is going to be challenging too. Like what I used to do when I was hiring our first AES at Twingate is um, you know, like I used to say, hey, like you're going to be the first AE and we have a global customer base so you're probably going to get emails at like 9:30pm West coast time that I might poke you about. Right. And I just want to make sure that very specific scenario is okay with you. Right. Like, because like this is not like a work life balance type environment and I want to tell you that before you join. Right. So I like that because you need to like in sales too, you need to talk about your weaknesses if you're a startup.

Speaker B: Right.

Speaker A: If you don't talk about your weaknesses, they're going to find that out as an enterprise like six months into implementation. So I like that. Um, yeah. Anything else to add to that UDAV on your end?

Speaker C: Yeah, I will. So you have to give people the good, bad and the ugly about the role, but you also, that also allows people to give you the good, bad, ugly of them as well.

Speaker A: Yeah, yeah, good point.

Speaker C: And I think especially for first sales hires, a lot of it is actually about trust. Right. A founder is going to trust whoever is going to come in with their baby. Right. They're doing founder led sales, they're like hey, here's the handoff, you know. Um, and I think establishing trust in an interview process sometimes can be like very transactional because at the end of the day if someone is going through an interview process front to back, you only have like five or six hours to get to know them. Right. So how do you establish trust when you are working within the guardrail, the five to six hours? Right. If they're coming in person, it's an hour meeting, you know.

Speaker B: Yeah.

Speaker C: So trust I think is established by honesty both ways. Right. And so the theme over here is like hey, look, as much as you want to sell the dream, right, you got to be honest about the dream as well. And you, like, oftentimes, I. I see being really helpful for, like, for the right candidate is founders being honest with sales leader, marketing leader, product leader, whatever it is, of like, hey, this is what I'm really good at. This is what I'm struggling with. Can you help me? What are you good at? What are your. What are your pitfalls? Right. Establishes trust immediately.

Speaker A: Totally. Yeah. It's so hard for people to do right in the moment. Um, but I practiced this, too, before I joined Twingate, because I'm not a Mr. Dashboards guy. Have you guys seen that blog post from Jason Lemkin where it says, like, hey, from 0 to 1, you have Mr. This. From 1 to 10, you have Mrs. This. Right? And one of the first, uh, of all, I don't really like that blog post because I think it, like, tells revenue leaders that you have an expiration on your time, you know, and you're kind of bucketed by these, like, things. But the thing I do think is interesting about that is, um, I think, first of all, a single VP can grow over, like, several years, but there are things that you don't like to do or that are energy draining. Right. Like, for me, I don't like looking at dashboards. To be honest, I'd rather be out in the field inspiring my prospects alongside my AES. So I would tell that to my CEO, uh, at Twingate, like, hey, I need a rev ops person, right? I can't just come in here and just do everything. So I wonder what you think about that too. Like, because if you do divulge your weaknesses, I think there should be an expectation of the founder that you're not just hiring a VP of a first seller, but this is kind of like a team sport. So how often do you place actually, like, multiple people at the same time? Or, like, how do you think about sequencing this? Because a weakness, I think, has to have support as well, right?

Speaker B: Yeah. Yeah. Ah, this is, um, probably more common in marketing. M. I, um, need an everything marketer.

Speaker A: Yeah, it sounds nice.

Speaker B: It does sound great. Um, and I definitely understand why, uh, that's something that people think, uh, because there's lots of different competing priorities. Like, obviously, I'm running a small company, too. I understand, uh, why you want all those things in one person at X cost. But the reality is, especially for marketing, people have majors and minors, uh, superpowers and weaknesses. Uh, so, uh, focus on what's important or the most important first, and then you start to layer people around that and create more of a team. Uh, so that's something that comes up a lot, um, in marketing specifically.

Speaker A: Yeah, that makes sense. Um, another thing I want to talk about is, is just like, let's dig deeper into the founder, VP or first sales hire relationship. Um, I think a lot of it is also the objectives, I think is great. Like you said, Harry, like, be very clear on, like, the two or three things you're looking for. The other thing that I see when relationships break apart, let's say like two to three months into a placement is very basic things like communicating over slack or communicating in a leadership setting. Right. Like, I just talked to somebody where they said their sales leader hasn't provided metrics over the last month around Outbound M and they just started the Outbound initiative. Right. And so these are things that, you know, you would think are very foundational. Um, and sometimes it just honestly takes the CEO also setting those expectations up. Right. Because there's a lot of balls that, that we handle as go to market leaders. So how much of, like, the enablement around leadership do you also help with, like, or do you do that, like, even after the placement, like, how, how does that work and how have you seen that be successful, um, at the companies you work at? Like, the communication dynamic?

Speaker C: I think it's one of those things

Speaker A: where,

Speaker C: especially at the early stage, there's no such thing as over communication. Right. Um, whether it's coming to things as minutiae as, hey, this is a new prospect. They just sent the first email. I'm going to nurture this account. Let's see where it goes. Versus, like, hey, this, this other client is at late stage. Um, you know, we, we probably going to need a week more. There's a couple of emails coming in. I'll manage this to like, hey, what does my outbound engine or pipeline look like? Right. I think you can oftentimes figure out these things in the interview process, actually, because it goes back to the signals that we were talking about of someone's intent when interviewing with you. Now, if someone is reaching out to me after an interview saying, hey, Udav, give me the feedback, right? I want to know what this company's talking about. Give me the good, bad, ugly. Um, how did this last interview, if I'm getting those signals from someone, that's something that I can speak to a founder to and point as a signal like, hey, this person's engaged. But their communication sounds, you know, is, is, is. Is there it also, you can also get signals from the founder side. So for example, there's searches where I, that I run that, you know, the founder is in slack with me on a minute to minute basis, which is great. There's other founders out there that like I speak to once a week. Right, sure. Uh, so it has to be like a communication match because some founders might actually have an allergic reaction to someone who's just pinging them all the time. Right?

Speaker A: Yeah, yeah.

Speaker B: So I think that's interesting actually.

Speaker A: Yeah, yeah. I've only been in the environment where founders are pinging me every minute, so. But, but you're right, it's like a mat. It's a communication style. It's like not good or bad either way. Right. Like just because you're pinging your VP every two days, it doesn't mean that's a bad thing if your VP can kind of like carve their own path and not need that like constant iterative approach.

Speaker C: Yeah. So yeah, for example, if a founder is like, hey, my biggest pain point is I need someone to take sales completely off of my plate. Like let me know how you're doing. I need to see performance metrics and all that. But like I need you to run it. That's a different problem to like, hey, I want a salesperson who's going to be in the trenches with me. We're going to co sell together. Um, we're going to figure out what the go to market version looks like. It's a, it's a different like problem. Different flavors of the same vanilla ice cream, if you will.

Speaker A: Yeah, that makes sense. That makes sense. Um, so, so we talked a little bit about how we judge like VPs of sales CROs who have been on rocket ships and um, how that's not necessarily the end all be all right because you need to have like these soft skills and hard skills as well. Um, on the founder side, I'm curious. Uh, so like I'll just kind of tell you the situation. I feel like there's, there have been so many unicorns, you know, within tech, you know, especially like let's say like 10, 15 years ago. It was like people were just like getting exits and, and making a lot of cash. But then I feel like bad behavior of CEOs has been okay, almost like accepted. You know, you think about like the deal rippling espionage situation. Like you see the headlines from 11x right around like falsifying customers and um, I promise there's a question here. But the thing I think we're kind of getting over is like these like valuations. And Adam Newman for example, from WeWork, he just raised like what, $100 million from the same investors for some reason, I don't know, like, that just blows my mind. And like, for me being kind of in the industry for like over 16 years now, like I wouldn't touch those leaders with a ten foot pole. Right. Um, so I wonder, are candidates starting to become savvier around that? Do you feel like with like it's much more of like I want to like engage with this person as a human versus like, like is it not working as much where you're like, hey, this person had like an exit two startups ago. So like this is a rocket ship, you know, I feel like a lot of recruiters would use that in the past. But I wonder if you guys. I'm hoping actually you guys take a little bit of a different approach because I think like the whole industry needs to come around to the fact that, hey, it's not just an exit that you should be chasing. Like you actually need to be excited to work with this person. Right. So what do you all think about that? I think we're still behind the times there, but I'm hopeful that folks like you will help with that.

Speaker B: Yeah, I kind of see it as a professional matchmaker to an extent.

Speaker A: Uh, I like that term. Yeah.

Speaker B: People to people leave companies that don't typically leave people. Uh, and you see that in sales a good amount. Right. Where you see cohorts of people go from one company to the next company to the next company together.

Speaker A: Uh, you mean people leave people, not the company is what you're saying, by the way.

Speaker B: Right? Uh, yeah, yeah. So I'm just saying like there's a connection like between people to people whereby, um, they tend to stick together. Uh, right, right.

Speaker A: Or like there's that saying like you leave your manager, not the company. Right.

Speaker B: Yeah, yeah, it's like, yeah, this is kind of like a band of brothers.

Speaker C: Totally.

Speaker B: Uh, almost. So definitely coaching and like educating that as much as possible can be really easy to get blinded by like a really good offer. Like for example. But I have seen a pattern, uh, in some companies where companies who don't have the best cultures often pay the money m they need to. Yeah, because that's how they attract people and that's, that's okay. Um, you just have to be mindful that that isn't something that's going to keep you there for a very long period of time because then you're going to be Looking for the next best offer and the next best offer and the next best offer. If you're moving from company to company all the time, all of a sudden you become significantly less desirable.

Speaker C: Yeah, yeah, Saw that with Meta. Not, um, a great example for like startup founders, but Meta used to pay a golden premium because people didn't want the black dot of Meta on their resumes. Right. Like engineers, software developers didn't want.

Speaker A: Oh, interesting, interesting. Because it was just known that the culture was not great.

Speaker C: Yeah. You take it, take it for a couple of years, you take the golden paycheck for a couple years, you get that experience on your resume and then you can go anywhere else.

Speaker A: Yeah, yeah. I, I feel like Apple kind of has the same similar dynamic. Right. With like paying a premium, but I don't really find people excited to go into work every day. Right. But as a startup, that's even, I think, more important to think about. Right. Because Meta and Apple can probably afford to kind of have that reput. They're just doing fine. Right. But, um, you know, startup reputations I think can, can spread. Right. Do you see that as well, like the word of mouth around bad leadership.

Speaker B: Right.

Speaker A: And the soft skills.

Speaker C: Yeah. So on this theme, so we kind of facilitate this. But think of something that companies do a lot that candidates historically haven't done. And there's a lot of power in this because there's power in this kind of like unsolicited thing. But back channels, founders and companies back channel candidates all the time. Right. Especially if it's a first hire or if it's a strategic hire, you want to know previously who people who have worked with the person that you're looking at, what their experience was. Right now there's different weightage to back channels.

Speaker A: Sure.

Speaker C: Candidates have also started back channeling founders as best they can.

Speaker A: Yep.

Speaker C: Uh, so if, if someone has a specific reputation, whether it's good or bad, whether it's like, hey, they're a great strategic CEO, not great at operations, or they're great salesperson, not really good on the product, whatever it may be. Candidates are now privy to that, that tool as well, and they've started using it.

Speaker A: That, that makes complete sense. I get a ton of questions about my advisees all the time. Right. Like, why aren't you joining full time? Like, was there something going on there? Right. And, and for me, the reason is because I'm not joining any company full time. But like there are. I'm going to be honest. Right. Which goes back to being honest up front because CEOs should probably be thinking, hey, like, if you back channel me, this is probably what you're going to hear about my weakness. And then you could get ahead of that. Right, so, so that's super helpful. Well, for the folks who are in the audience, definitely feel free to chime in with any questions in the chat. I'm starting to round out my final questions here. Um, so please feel free to chime in. You can also come on to stage if you'd like. If you want to live, ask a question. Um, but I'll leave the chat open. Um, but yeah, let's start to kind of round out the conversation. This has been awesome by the way. Thank you both for being so open, um, with your ideas and your time. Um, but, and you've already kind of said a lot on this, but is there one final piece of advice from each of you that you would give to founders looking to hire go to market in the early stages. Like if you could give like a word of wisdom, I think that'd be a great way to start to round this out.

Speaker B: Yeah, um, this is gonna sound really basic, something that is often missed. Um, don't just write a job description. Typically those are like amalgamated from other job descriptions somewhere else and then just like put together and it's like, this sounds good and people are using like

Speaker A: chatgpt for it now probably. Right? Yeah.

Speaker B: Well, I mean, the job script's just a list of responsibilities. Normally, um, if you're really serious, uh, about hiring somebody great and making them successful, put something in place. Whether that is, this is the mission, these are the outcomes and these are the competencies or you know, something specific, uh, around the objectives of what you want the person to actually come in and do as opposed to just the skills that you want them to have. There's a difference between those two things. Uh, so my one piece of advice would be do that up front and just be really clear and intentional, uh, around that because that will set you up for success in terms of who you're hiring. You're not going to flip flop back and forth around, do we need a product marketing person or a demand gen person? Do we need this type of salesperson or this type of salesperson? Um, that will make a big difference, um, and also will keep your team aligned too, because you're not going to be the only person who interviews them. So, uh, aligning everybody on what needs to happen with this hire mhm is the biggest piece of advice. And it sounds really simple because it is, but often that doesn't happen.

Speaker A: Yeah, yeah, that's great advice. Goes back to like be as tactical as possible. Right?

Speaker B: Yeah.

Speaker C: I'm a very specific example for this first search I'm running right now. So I connected to a company that was looking for their like founding salesperson for about three months before we got introduced. And uh, they're in, they're in Brooklyn. So I like physically went there, spent some time with the CEO and I was like hey, like you've been trying this for three months. What, what's up?

Speaker B: What's wrong?

Speaker A: Mhm.

Speaker C: And then just through understanding their sales motion. So these guys have a, they're looking for a technical founding go to market salesperson. Right. Which is a very very small band just in it of itself. Right. So I understood their interview process and part of the interview process was like a technical co selling kind of a interview. And uh, through that process I figured out that that was the linchpin in their interview process because they would like get really suave, you know, salespeople get up to that technical piece and then they would drop after the technical piece because this company specifically had like a pal has a palantir way of co selling with their or co developing with their prospects. So I was like hey, let's like give me some audio recordings of a typical sales call. And so the CEO, props to him, sent me voice recordings of like actual customer conversations. I Ah, use ChatGPT. We ran four of these prospect calls through ChatGPT and we're like hey, what are typical questions that oh wow, that's great. On the job description on the last page is like hey, you know we are being very selective about this hire. These are the following questions that you will typically expect to answer live on a prospect call. Wow, this gives you pause. Probably not fit. If this is something that makes sense to you and is exciting to you, let's chat. It's been a game.

Speaker A: Amazing.

Speaker C: It's been a game.

Speaker A: I feel like everyone should do that for every single job description actually. I love that. Okay. You're giving me ideas for my coaching too around like how you can create an onboarding guide. Right. For new hires around Objection. Handling or FAQs. Mhm. That's awesome. That's amazing.

Speaker C: I can send you a copy of it.

Speaker A: I would love to see that actually. No, I appreciate that. Um, awesome. Well that, that was amazing advice. There anything else from you Udof on like words of wisdom for founders who are thinking about their first go to market hire.

Speaker C: Again, a generalized platitude. But oftentimes you don't need a head off. You don't need. You need.

Speaker A: Especially in the early stages.

Speaker C: Right, Especially in the early stage. There's been a couple of different, um, companies that I've been working with even in just the last two, three months where we have dissuaded a company from hiring ahead of. Even though transactionally it's more meaningful for us.

Speaker A: Sure.

Speaker C: Right. Rather than having like someone go for a short stint and just not be aligned and like kind of ruin someone's life for six months instead of having that or have someone a little bit junior who's like actually doing it, hire someone who you trust and give the sales responsibility to obviously over the course of an interview process, but you oftentimes just need someone to like hit the ground running, knock on some doors, help you figure out how you're selling and then you can like think about either promoting them down the line if you have a belief that they have that skill set, or hire for tomorrow's problem. Tomorrow.

Speaker A: Yeah. Yeah. I love that you guys do that because then it gets them to come back to you too in the longer term. Right. And I think in my first call with Harry, I was excited because he pulled up like multiple go to market hires, I think VPs of marketing. And he was like, yeah, these guys have been here for two and a half years which is unheard of in startup land. Right. I think there's a VP of marketing at Tailscale, which coincidentally was a competitor of ours at Twingate. Um, and they did great with marketing. And he's like, yeah, this guy's been there for like almost three years. And I was telling Harry like, oh, we've been through three marketers in three years.

Speaker B: Think about it. For us, like people are hiring us to help us help them impact the trajectory of the company and doing that with a person. Uh, so candidate success is of uh, the most importance to us. So yes, search firms are made to make a placement, but for me, us, it doesn't stop there. That's why we have this candidate success program that we run, uh, quarterly post placement, uh, just to kind of temperature check how everybody's doing and are we aligned in the objectives that we talked about. Um, because our business is about reputation, recommendations, referrals. So if somebody comes in and does an amazing job, that's what we're trying to achieve.

Speaker C: Mhm.

Speaker B: Uh, that's my goal for every search.

Speaker A: Nice.

Speaker B: Getting to. Okay, Accepted offer, done.

Speaker A: Yeah, I love that about you guys. Yeah, I could felt that kind of genuineness in our initial conversations. Um, and your track record shows for it, so I think that's a great place to round things out. This was awesome. I learned a ton. Thanks for kind of riffing with me on go to Market hiring. I don't think there's like, a magic bullet. Right. It's. It's all kind of dependent on the situation that you're in. But I love how intentional and human you guys are being about it. Um, for the audience, if you'd like to reach out to Harrier Rudolph, I'm going to put their LinkedIn profiles in the show notes once we actually, uh, publish this. And then you can also check out their website. It's the inflection group dot com. Right. Um, so definitely check them out. They're happy to have a conversation. Even if you're not quite yet feeling like you're ready for hiring, they can at least get you in the right mindset. So, again, appreciate you both for being friends of the community and for spending time with me. Hopefully, we'll do this again.

Speaker B: Love it. Thanks so much for Sam.