Episode 47: Hiring first GTM hires that last

I sat down with Harry and Uddhav from The Inflection Group - the recruiting firm behind successful hires at Coinbase, Pinterest, Snowflake, and more.

We dive deep into the biggest startup hiring questions: 

• When should you actually hire your first salesperson? 
• How do you avoid the "halo company" trap?
• Why do first sales hires fail so often?

They share stories from 300+ executive searches and explain why being brutally honest about your startup's challenges actually attracts better candidates. Plus, they reveal tactical hiring tricks that work - like putting real prospect objections in your job description. This is essential listening for any founder thinking about their first go-to-market hire.

Transcript

Episode 47: Hiring first GTM hires that last

[00:00:00]

Peter: 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 Uddhav 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 ol. And then I'll get into , some questions I have prebuilt and then we'd love to also take questions from the audience. Some of you have pre-submitted questions, so we will try to get to those as well 'cause I have them up on my screen. Um, so I'll, 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 [00:01:00] Michael Page, um, where he actually earned five promotions and. 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, gecko, robotics, snowflake, and the, and the list goes on and on.

So. Thank you Harry, for being on. Um, he's joined by Uddhav, 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, um, including one large publicly traded in one boutique company where he is 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 [00:02:00] 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 really appreciate your time.

I know your time's valuable and you could be placing candidates or engaging with clients, but I appreciate you spending time with the community too. No, 

Harry Masters: you're making 

Peter: me blush, Peter. 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. 

Harry Masters: No, thanks so much for having U.S. 

Peter: Awesome. So, so let's dive into it. Like I said, I have a few questions. I think, um, some 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, 'cause 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, I obviously love being a [00:03:00] 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, and go to market, whether it's sales or marketing? Yeah, I 

Harry Masters: 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?

So your capacity to learn something new, you know, it often takes up more of your time if it isn't something you've done before. So, uh, if you are 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, you know, when you're starting to see some repeatability. Uh, around the process. Uh, I'll throw out the 1 million a RR number here, roughly. Um, [00:04:00] and, you know, you have, you know, different competing priorities, you know, then it's probably starting to start thinking about it.

Uh, at least. Uh, I would definitely try and hire slow, uh, as well rather than like waiting till the end, till you kind of beyond your capacity, sort of at your wits ends, like, I desperately need somebody. Uh, 'cause 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, um, ability to do sales matters, uh, repeatability matters, uh, as well. Um, 

Peter: yeah, that's a good point. Yeah. You can't hire a sales person to figure out product market fit, right? Because they're not there to be user researcher. They're there to really like close deals and sign contracts.

Harry Masters: 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. Mm-hmm. So to speak. But, uh, [00:05:00] if the product can't be solved by the founder, it's likely not gonna be able to get solved by the sales person either. Mm-hmm. 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 gonna be some trial and error, there's gonna be some user research, et cetera, but, um. There needs to be some repeatability before you bring in anybody. 

Peter: That makes sense. 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, or creating the demand too? Or capturing the demand? Yeah. We 

Harry Masters: don't see founders do as much founder-led marketing as we do [00:06:00] founder-led sales.

Yeah. Uh, I 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, uh, almost even harder. Uh, to do. So I, 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, on demand gen and doing campaigns and, you know, measuring attribution and like all of that type of stuff. Sure. Uh, so 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 type of stuff 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. Yeah. So again, it's [00:07:00] like it.

It's a bit of a mixture, uh, of those things. It, it would really depend on the company's situation. I, uh, feel free to like, fire away with anything you think as well. 

Uddhav: No, I, I tend to agree with you there, Harry. Um, generalizations are hard because every company's, every founder's plight is, you know, slightly different.

But I oftentimes see if, so going back off of 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 gonna be wins, right?

There's gonna be failures. Why are we winning? Why are we failing? Are 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, you are, you need to do more [00:08:00] 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, 

Peter: Hmm. Yep. Yeah. The marketing leader also needs proof points to figure out how to message, right. And frame the value proposition. Yeah.

That's, and sometimes 

Uddhav: 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. X, y, Z kinds of companies. We don't really need marketing lift on, you know, SMB companies, for [00:09:00] example.

Peter: Yep. Makes sense. Makes sense. And, and Harry, you mentioned. Um, hire is 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, 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, and be intentional?

Yeah. Um. We 

Harry Masters: often come in when there is some scar tissue. Yeah. So coming in and often what they'll say is, you know, we had this person before, we don't want any of that. 

Peter: [00:10:00] Sure. Yeah. 

Harry Masters: Yeah. And you do have to remember that it's a person, not a product as well. So, um. There's a lot of different variables with a person.

Uh, if we could draw somebody up in a lab, we'd probably love to do that and present 'em to a company, but we, 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 I also 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 like, what I would call halo companies. So typically there are, you know, five companies in that organization space that they aspire to be, that are bigger than them, have done what they want to do that. So sometimes those companies can be a couple of steps ahead.

Sometimes they're 10 steps ahead. Um, and often the appeal is to try and. Get whoever the most senior [00:11:00] person is at one of those companies. Mm-hmm. Which makes sense, uh, because they've been through the journey before. Um, they've been there, done that. And you know, they're probably great, uh, at their job.

However, the likelihood is that that person did the job that you're asking 'em to do seven years ago. Mm-hmm. 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 wanna do that job anymore. They might think that they want to.

Mm-hmm. Uh, because they're now this bigger company with lots of infrastructure and resources and you know, there's some bureaucracy and all of those types of things. But the reality is they're probably not gonna want to go back into that player coach style role. 

Peter: Sure. 

Harry Masters: Yeah. So people always tend to want what they can't have, and the grass is always greener.

So I was 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 [00:12:00] 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 wanna find is the person who's gonna do that journey for your company next.

Peter: Yeah, good point. 

Harry Masters: You want the next, whoever, it's the CRO of Snowflake, you want the next CRO of Databricks or whatever it is. Um, that's what you wanna 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. Uh, yeah, because lots 

Peter: of things 

Harry Masters: can change.

Peter: I love that you mentioned that, right? You need to hire for somebody who's gonna do the job today, not what you could aspirationally become in five to 10 years, right? Yeah. Um, so I guess in 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 wanna 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 gonna [00:13:00] become a lawyer. And then they're now like a director of sales, right. At a cybersecurity company and doing it really well.

So, so, you know, like, you know, it's, 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, I think it can be. So how do you do that? You know, like when you're, uh, 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 RUddhavlph this time. 

Uddhav: 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?

Peter: Mm-hmm. And 

Uddhav: 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 [00:14:00] 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 skills or for a company, right?

Um, hypothetically it's a series a company, but as through the process of getting to know them. Yeah. 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? Mm-hmm. That gives me a signal that like, they're saying one thing, but you know, they're, they're actually looking for something else.

Mm-hmm. 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. 

Peter: Yeah, 

Uddhav: oftentimes a job is a means to an end, but how big of a Venn diagram overlap can you find for how satisfied someone will be and like how much that satisfaction will [00:15:00] drive them to excel over and over and over again for a company.

Peter: Yep. Yep. That makes sense. That makes sense. And there's also probably, yeah, just for, that's really interesting that you actually look and vet the candidates too, right? It's not just like trying to place someone. Mm-hmm. Um. In the moment, you're also looking at, okay, like what aptitudes do they have? What skill sets do they have?

Mm-hmm. Um, in, in my kind of hiring process, I always try 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 U.S 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 skills standpoint versus like experience, if that makes sense. 

Harry Masters: Yeah. Asking people to do something tactically, um, without tons of coaching and guidance is generally a good idea. Whether that's a case study [00:16:00] 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 gonna give them that and it's gonna drive those things is really important. Um, because the money from one company to another company, um, you know, it might attract them like in the first place.

Sure. That's typically not what keeps somebody at an organization. Uh, it is people and motivations and you know, is it ticking those boxes? Is it keeping them coming back, you know, day to day? Uh, so definitely for sales, like testing for drive mm-hmm. Uh, is 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 gonna do with it? Like, yeah, what are their goals? Uh, [00:17:00] is it to, you know, buy a house, do like, send their kid to college, whatever it is. Um, those are the things that people keep people coming back. 

Peter: 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 gonna 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 aisle will never work. Like, and like that, there's always gonna be a mistake. Like the average tenure for first sales hire is like probably like a year. I think Gong published something like a few years ago where it 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 [00:18:00] 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, and how do you like prevent that on your side? I mean, you were kind of circling around it, but we would just love to get a little bit more of your thoughts on that dynamic. Yeah. 

Harry Masters: I think, uh, one of the main reasons is, uh, misalignment and expectations between like 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? Mm-hmm. But it is a balance, uh, between telling them what's great and telling them what's not great. Yeah. 'cause if 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. You know, we talk to a candidate [00:19:00] and say, you know, this is not what I thought. It was like, I'm going into this, you know, this is really different to what, you know, I was told, uh, sold a bill of goods. You know, all of those types of phrases. Mm-hmm. 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? Mm-hmm. Okay. Things like that. Mm-hmm. Um, like that's a good one to, to ask people, uh, because if the challenge scares them and they don't really wanna do it, that's when they're gonna back away and that's when they're gonna leave and the turnover gets higher.

Uh, so I think a couple of like core things, uh, that you can do is just set up, um, three really specific kind of smart objectives. You know, for the first. Three months, six months, 12 months. Mm-hmm. Tell the [00:20:00] 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 what they are mm-hmm. As well. So I think doing, doing those things is, is beneficial. And also as you're moving through an interview process, it can be quite, um. You know, it's not linear.

You know, a candidate might have other opportunities. You might have to move faster than you wanted to. Uh, you know, there's, you know, two people involved. It's quite emotional, uh, sometimes. Mm-hmm. 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, uh, moving forwards.

Peter: Yeah, that's a, 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 [00:21:00] AEs at Twingate is, um, you know, like I used to say, Hey, like you're gonna be the first AE and we have a global customer base, so you're probably gonna get emails at like 9:30 PM West Coast time that I might poke you about, right?

Mm-hmm. And I just wanna make sure that very specific scenario is okay with you. You. Mm-hmm. 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, um, I, I like that because you need to, like in sales too, you need to talk about your weaknesses if you're a startup, right?

If you don't talk about your weaknesses, they're gonna find that out as an enterprise, like six months into the implementation. So I like that point. Um, yeah. Anything else to add to that AV on your end? 

Uddhav: Yeah, I will. So you have to give people the good, bad and the ugly about the rule. But you also, that also allows people to give you the good, bad, ugly of them as well.

Ah, 

Peter: yeah. Yeah, good point. 

Uddhav: And I think especially for [00:22:00] first sales hires, a lot of it is actually about trust, right? A founder is going to trust whoever's gonna come in with their baby, right? Mm-hmm. 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 guardrails of five to six hours, right? 

Peter: Yeah. 

Uddhav: Even if they're coming in person as an hour meeting, you know? 

Peter: Yeah. 

Uddhav: 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 wanna sell the dream, right?

You gotta be honest about the dream as well, and you like, oftentimes what 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 [00:23:00] struggling with.

Can you help me? What are you good to? What are your, what are your pitfalls, right? Mm-hmm. Establishes trust immediately. 

Peter: 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 zero to one you have Mr. This from one to 10 you have misses this. Right? And one of the, I, I, first of all, I like, I don't really like that blog post. 'cause 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, I think first of all, a, 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 [00:24:00] field inspiring my prospects alongside my AEs.

So I would tell that. To my CEO 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? A weakness, I think has to have support as well. Right? 

Harry Masters: Yeah. Yeah. This is, um, probably more common in marketing. Mm-hmm. Um, I need an everything marketer. 

Peter: Yeah. I need 

Harry Masters: someone. And that sounds nice.

It 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 [00:25:00] small company too, like there's. I understand, uh, you know, 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, uh, or the most important, uh, first, and then you start to layer people around that and, you know, create more of a team. Uh, so that's something that comes up a lot. Um. In in marketing specifically. 

Peter: Yeah, that makes sense. Um, a 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 [00:26:00] 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, and they just started the outbound initiative, right? 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.

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, 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, at the companies you work at?

Like the communication dynamic? 

Uddhav: I think it's one of those things where especially at the early stage, the over, there's no such thing as overcommunication. Right? Mm-hmm. Um, whether it's [00:27:00] coming to things as minutia as, Hey, this is a new prospect. They just sent the first email. I'm gonna nurture this account.

Let's see where, where it goes. Versus like, Hey, this, this other client is at late stage. Um, you know, we, we are probably gonna 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, ol, give me the feedback, right? I wanna know what this company's talking about. Gimme the good, bad, ugly. Um mm-hmm. How did they like 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 of like, Hey, this person's engaged, but their communication styles, you know.

Is, is, is, is there. It also, you can also get signals from the founder side. [00:28:00] 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?

Peter: Mm-hmm. Yeah. Yeah. So I think it's. Sorry. That's interesting actually. 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 ma, it's a communication style. It's like not good or bad either way. Mm-hmm. Right? Like just because you're pinging your VP every two days, it doesn't mean that's a bad thing.

Yeah. If you VP can kind of. Carve their own path and not need that like constant iterative approach. 

Uddhav: Yeah. 

Peter: So, yeah, so 

Uddhav: 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, I need you to run it. That's [00:29:00] a different problem to like, Hey, I want a sales person who's gonna be in the trenches with me. We're gonna co-sell together. Um, we're gonna figure out what the go-to-market version looks like. It's a, it's a different like. Problems, different flavors of the same vanilla ice cream, if you will.

Peter: 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. Mm-hmm. And, um, how that's not necessarily the end all, be all right? 'cause 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. [00:30:00] You know, you think about like the deal rippling espionage situation, like.

You see the headlines from 11 x right around like falsifying customers and, um, the, I, I promise there's a question here, but the thing I think we're kind of getting over is like these, like valuations and, and Adam Newman, for example, from WeWork, he just raised like, what, a hundred million dollars from the same investors for some reason?

I don't know, like that just blows my mind. Yeah. 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 10 foot pole, right? Mm-hmm. 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 to [00:31:00] go. 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.

Mm-hmm. 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, will help with that. Yeah. 

Harry Masters: I mean, I kind of see U.S this like professional matchmaker, like to an extent.

Yeah. I like that. I like that term. Yeah. Like people to people. Yeah. Uh, people, people leave. Companies, they don't typically leave people. Uh, so, 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. Uh, because you mean 

Peter: people leave, people not the company is what you're saying 

Harry Masters: the other way around, right?

Uh, 

Peter: yeah. 

Harry Masters: Yeah. So I'm just saying like there's a connection [00:32:00] like between Sure. Uh, people to people whereby, um, they tend to stick together. Um, right, right. Yeah. Or like they, 

Peter: there's that saying like, you leave your manager, not the company. Right? Yeah. Yeah. It's like, uh, yeah. 

Harry Masters: This is kind of like a, a band of brothers.

Yeah, totally. Um, 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 patent, uh, in some companies where companies who don't have the best cultures often pay the best 

Peter: because 

Harry Masters: they need to.

Peter: Yeah. 

Harry Masters: Uh, 'cause that's how they attract people and that's, that's okay. Um, just be mindful that that isn't something that's gonna keep you there for a very long period of time. Mm-hmm. Because then you're gonna be looking for the next best offer and the next best offer and the next best offer. And if you move from company to company all the time, all of a sudden you [00:33:00] become significantly less desirable.

Mm. Yeah. Yeah, somewhat. Um, I saw 

Uddhav: that with meta, um, not 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 it. 

Peter: Oh, interesting. Interesting. Mm-hmm. Because it was just known that the culture was not great.

Uddhav: Yeah. Yeah. You take it, you 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 could go anywhere else from there. 

Peter: Yeah. Yeah. I, I feel like Apple kind of has a same, similar dynamic mm-hmm. 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 reputation. Mm-hmm. They're just doing fine. Right. But, um. Uh, you know, startup reputations, I think can, can spread. Right. Do you see that as well, like the word of mouth around bad leadership, [00:34:00] right.

And the soft skills. 

Uddhav: 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, there's power in this kind of like unsolicited. Thing, but back channels, founders and companies back channel candidates all the time, 

Peter: right?

Uddhav: Mm-hmm. Mm-hmm. Especially if it's a first hire or if it's a strategic hire, you want to know previously who've people who have worked with the person that you're looking at, what their experience was. Right now there's different weight to back channels. Sure. Candidates have also started back channeling founders as best they can.

Yep. You know, so if, if someone has a specific reputation, whether it's good or bad. Whether it's like, Hey, they're 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 [00:35:00] started using it.

Peter: That that makes complete sense. I get a ton of questions about my advisees all the time. Mm-hmm. Right. Like, why aren't you joining full time? Like, was there something going on there? Right. And and for me, the reason is 'cause I'm not joining any company full time, but like there are, I'm gonna be honest, right.

Which goes back to being honest, upfront. Mm-hmm. Because CEOs should probably be thinking, Hey, like, if you back channel me, this is probably what you're gonna hear about my weakness. Mm-hmm. And then you could get ahead of that, right? Mm-hmm. So, so that, 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 onto stage if you'd like. If you want a 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, and you've already kind of said a lot on this, but is there one final [00:36:00] 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.

Harry Masters: Yeah. Um. This is gonna sound really basic. It's something that is often missed. Um, don't just write a job description. Uh, typically those are like amalgamated from other job descriptions somewhere else, and then just like put together. It's like, this sounds good. And people are using like chat GPT for it now, probably, right?

Yeah. 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 [00:37:00] you want the person to actually come in and do, you know, as opposed to just the skills that you want 'em to have.

Mm-hmm. There's a difference between those two things. Uh, so my one piece of advice would be do that upfront and to 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 gonna flip flop back and forth around, you know, do we need a product marketing person or a demand gen person?

You know, do we need this type of sales person or this type of sales person? Um, that will make a big difference. Um, and also will keep your team aligned too, because you're not gonna be the only person who interviews them. So, uh, aligning everybody on what needs to happen with this hire mm-hmm. Is the biggest piece of advice.

And it sounds really simple 'cause it is. But often that doesn't happen. Yeah. 

Peter: Yeah. That's great Advice goes back to like be as tactical as possible, right? Yeah. I have a 

Uddhav: very specific example for this first search I'm running right now. So got connected to a [00:38:00] company that was looking for their like founding sales person 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? What's wrong? 

Peter: Mm. 

Uddhav: And then just through understanding their sales motion. So these guys have a, they're looking very technical, founding, go-to-market salesperson.

Right. Which is a very, very small band just in of itself. Right. So I understood their interview process, and part of their interview process was like a technical co-selling kind of a interview. Mm-hmm. And, uh, through that process, I, 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 I see. Or Codeveloping with their prospects. So I was like, Hey, let's like give me some audio recordings of a [00:39:00] typical sales call.

And so the CEO props to him sent me voice recordings of like actual customer conversations. I use chat GPT. We ran four of these prospect calls through chat, GBT, and we're like, Hey, what are typical questions that, oh, wow, you would not, that's great. And so 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 the right fit. If this is something that makes sense to you and is is exciting to you, let's chat. It's been a game. Oh, that's 

Peter: amazing. Wow. 

Uddhav: It's been a game changer. 

Peter: I feel like everyone should do that for every single job description.

Mm-hmm. Actually, I love that. Mm-hmm. Okay. 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. 

Uddhav: Mm-hmm. 

Peter: That's awesome. That's amazing. I can send 

Uddhav: you a copy of it. 

Peter: I would love to see that actually. No, I appreciate that.

For [00:40:00] sure. Um, awesome. Well, that, that was amazing advice there. Anything else from you RUddhavlph, on like words of wisdom for founders who are thinking about their first go to market hire? 

Uddhav: Again, a generalized platitude, but oftentimes you don't need a head off. You don't need to have. Mm-hmm. You need, especially 

Peter: in the early stages, right, 

Uddhav: 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 a head of, even though transactionally, it's more meaningful for U.S. 

Peter: Sure. 

Uddhav: 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, we'd rather have someone a little bit junior who's like actually doing it.

Hire someone who you trust to 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 [00:41:00] 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 skillset or higher for tomorrow's problem tomorrow.

Peter: Yeah. Yeah. I love that you guys do that. 'cause 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.

Mm-hmm. Which is unheard of in startup land, right. I think there's a VP of marketing at Tail Scale, 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.

Yeah. 

Harry Masters: When you think about it for U.S, like people are hiring U.S to help U.S help them impact the trajectory of their company. Yeah. And doing that with a person. Uh, so candidate success is of the most [00:42:00] importance to U.S. So yes, like search firms are made to make a placement, but for me slash pass, it doesn't stop there.

So that's why we have this like candidate success program that we run, uh, like quarterly post-placement, uh, just to kinda temperature check how everybody's doing and are we aligned on 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.

Mm-hmm. Uh, that's my like goal for every search. Nice. Amazing about like getting to Okay. Accepted offer of done. 

Peter: Mm-hmm. Yeah. 

Harry Masters: I love that. I love that 

Peter: about you guys. Yeah. I could, I could felt that kind of genuineness in, 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 [00:43:00] 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 ol, I'm gonna 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.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. 

Harry Masters: Love it. Thanks so much for, uh, for having U.S.