E13: Scott Leese on Bridging the Gap Between Founders and VPs

recruit the right way, build a team, do all this stuff. That company's worth a couple billion dollars right now. So you look back on it, it's like, what if they would have not hired me because I didn't have title insurance experience? How many people have experience selling software to title insurance folks? Not very many people. So is it, is it like an extra credit thing if I find somebody with industry expertise? Sure. But they over-index for it way too much.

Yeah, the waiting.

I'm always telling them like, find somebody who's done this same stage before, whose motor revs at a really high rate, who wants to be a builder, who knows and has sales acumen as well as sales leadership ability, who's done this kind of scaling thing before. Index for that, that kind of stuff.

Hello and welcome to the Revenue Leadership Podcast by Topline. I'm your host, Kyle Norton, CRO at Owner.com, and every Wednesday we dive deep into the strategies and tactics being used to drive success by the best revenue leaders in the world. So join me as I sit down with revenue operators to discuss actionable frameworks that you can implement in your business today with no fluff, no sales pitches, and no platitudes.

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I'm very excited that today's guest is Scott Lys, who most listeners will already be familiar with. He's one of the most followed guys in all of SaaS go-to-market on LinkedIn, and he's got a pretty sharp bio. 6-time sales leader. 5 times founder, 3-time author, 12 unicorns and exits, 12 unicorns and 11 exits to his name as an operator and advisor, and a guy with a lot of really interesting opinions, which I'm excited to unpack today. So, Scott, welcome to the pod.

Thanks for having me, Kyle. Good to see you the other day in Austin as well.

Yeah, good to bump into you. So I would love to unpack 2 topics today. One is VP sales and founder alignment. As I joked before, are a bit of a defender of the VP of Sales on LinkedIn and have a lot of great opinions about how VPs of Sales need to operate and look after themselves. And so I want to talk about how do we marry that with a bunch of the online discourse that is not so VP sales friendly on the venture capital and founder side and how we can bring those two things together, those two camps together. And then we'll also unpack the state of sales a little bit. You've got some cool opinions on where things are going and how operators need to evolve their go-to-market with respect to how things are evolving from the buyer's perspective. And then we'll get into it. So appreciate you coming on. So for folks who don't know you, maybe give them your quick 60-second background.

Yeah, thanks. Thanks again. Like you said, I was a VP of sales, head of sales 6 times, had a pretty good run. I'd say 4 of them were really successful. One of them was mediocre successful and one of them was a total shank. If you've been a VP of sales long enough or founder long enough, everybody's probably got one that, you know, they look back on and say, well, that didn't work. I I learned from that one.

One or more than one?

Hopefully only one, but for me, I was fortunate enough to just be one, you know, pretty bad shake. But yeah, I learned from all of those things and along the way starting kind of diversifying, you know, my kind of career portfolio, if you will, and got into entrepreneurship and founded a business called the Surf and Sales Summit, which is a small micro conference in Costa Rica I host a few times a year. And in 2020, started a community called Thursday Night Sales that we ran for 3 years, and it was the largest virtual sales happy hour in the world for a while. I've been building different little communities ever since and coaching founders and VPs of sales on how to get better, how to go to market, and then Yeah, my main job is I run my own consulting firm and kind of serve as fractional CRO. And I have a gal on my team who serves as a fractional RevOps resource. And we work with tech companies, primarily startups from all around the world and enjoy it. It's a lot of fun still.

Awesome. And so is the consulting business like 70, 80% of your time and the community stuff is more for fun or how, how does that get to you?

Yeah, it, it used to be a little more balanced. You know, Thursday Night Sales, for example, was a lot of work. You know, it was the community itself that you were kind of running asynchronously and having strategies and planning and engaging with the community was, was a big chunk of time. And, and then, you know, every Thursday night for 3 years, we were on, on air, so to speak, from, you know, 8 o'clock Eastern to about 11 o'clock Eastern.

Yeah.

You know, and that's, it's a big time commitment. But I've kind of backed away from spending so much time on, on outside stuff. So I'd probably say that my consulting business is about 80% of my time now. And the other 20% is comprised of, you know, maybe private coaching and communities that I'm running, Surf and Sales podcast that we run, the Surf and Sales events, some speaking engagements and stuff like that. But yeah, the primary revenue driver for me is my consulting business for sure.

And what's your ICP for the consulting?

Primarily kind of like Series A, Series B type companies, maybe some seed stage. Companies, my experience as a VP of sales was always getting things off the ground. I became known as like, maybe I'm still known as like the zero to $25 million guy, right? All of the VP gigs I had, when I went there, everybody was starting at basically zero. And in a few cases, I mean like no customers at all, no paying customers. The last, yeah, the last SVP SVP sales job I took, there was zero customers when I started. They had spent, you know, a year and a half, two years building the product and then raised money around that. But they hadn't, they hadn't closed a single customer yet. And I was always willing to like bet on myself and take this risk. I'm not a corporate kind of person, which probably shocks nobody if you know me or pay attention to things I say or how I look or whatever, but I was never going to go be, you know, that person. So I just kept going back to the beginning. I liked all the pressure, if you will, you know, if I fail, you know, the business could go out of business. If I succeed, like I'm the guy keeping the lights on. And I didn't realize it at the beginning, but I think that was the beginning of my kind of entrepreneurial spirit in a sense. You know, that building kind of phase. So I'd say probably 90% of the clients that we've worked with in the last 5+ years are, you know, somewhere in that $0 to $25 million-ish ARR marker. I'm not the guy that, I don't know, Oracle calls to like turn around their sales process. Like, that's not me.

You're not going to do an 18-month territory carving assignment.

No, that literally, I'd rather gouge my eyes out. I think that sounds like so horrible. But if you called me up and you were like, hey man, you know, we just raised like a $5 million A round. We've got, you know, like $100,000, $200,000 of ARR, something like that. I don't know how to build and scale a team. I've been hustling and doing this founder-led motion. Like, how do I go from founder-led motion to, you know, having a proper team, locking in our ICP, our buyer persona, our pitch? How do I hire salespeople? How do I hire a head of sales? When do I hire a head of sales?

Yeah.

How do I get a kind of operational rigor in place, built for scale from the start? All of this kind of stuff. I bundle in recruiting to what I do, coaching and training. Basically anything and everything in the beginning, you know, we help people install and kind of refine. So that's the majority of my engagements.

Okay, cool. So, and I would imagine like hiring an early head of sales, VP of sales is probably a common thing that you're doing along the way. So let's, dive into that as sort of our first topic. And where I wanted to frame this up is, you know, I think from my read on LinkedIn especially, there are these like two camps that just like yell past each other a little bit.

There is kind of like our political system, right? Yeah.

Similar. Funny how that works. There's the founder and venture capital camp, which are which view VPs of sales quite transactionally. The messaging is if they can't really drive improvement in the first 60 days, then you have to move on. You're hiring people for maybe a 12 to 24 month stint to then layer that person or replace them with the person for the next level of stage appropriateness. And there's a lot of truth and fairness to that. This is capitalism after all. And then there's another camp, which is sort of the VP of sales camp, which can be— and I'm being a little hyperbolic to make the point, but the VP of sales camp is the woe is me, venture capital is out to get me, founders are out to screw me over, nothing is ever my fault. And those two camps don't really converge on agreeing on a lot. And so you are more as a defender of VP sales, but your core customer base is founders. You spend a lot of time trying to help founders. And so you're a great person to, I think, share a message with the audience about how we can bring these two things, bring these two sides together in a more meaningful way. And so I'd love to start with VP sales hiring and how do you think about alignment? First off, how do you advise your founder to find the right type of VP of sales, somebody that they can build with for a long time? And then what do you say on the VP of sales side to find the right fit for the company for them to join?

Yeah, you'll have to help me stay on point here because there's like a million and one different angles to, to take this, this question, but I'll do my best. The first thing that I think about is I think it's very important to have somebody who's done the role help you find the person who's going to do the role. What I mean by that is so many people rely on like a recruiting firm or a staffing firm or somebody like that. And this person positions themselves as an expert. Because they've hired a bunch of people, but they've never actually done the role before. Uh, in my experience, that has not worked out well. Yeah. People that I, that I've talked to. So if somebody's looking to hire a head of sales or a VP of sales, they should go to people that they know who have done that role before and say, who do you know that you like, that you trust? You know, what are some questions that I, that I should ask? Help me complete this kind of process. So rather than relying on, on some stranger, some hired kind of guns, I think it's financially incentivized for you to accept that person. Yeah, that's right. And by the way, not just financially incentivized, like it's real expensive. You're talking about like a $40,000 or $50,000 hire in, in the like Series A, Series B kind of range. And if you're talking about bigger companies, it's probably higher than than that, right? It's no small sum of money.

Absolutely.

So that's the first thing is, you know, get referrals from people who've been in the seat before, from people that they know and trust, get help and guidance on the process, the questions and things of that nature. The second thing I would say is, Don't hire a VP of sales too soon. Very, very rarely, I mean, very rarely is the first kind of go-to-market hire a VP or head of sales type person. And that person's able to stick for, you know, let's call it 2 to 3 years or beyond 3 years, which leads to my next point, which is possibly the most important one is you've got to find a stage appropriate VP of sales. So what I mean by that is so many founders, it seems like, get advice from somebody that says, you go hire this ex-VP from Oracle. I'm just going to pick on them all day, right? You can't pluck somebody from the big enterprise and dump them into a very early stage startup and expect that to end well. These are not the same skill sets. You just hired like a VP of spreadsheets and strategy into a role that requires you to be a ditch digger, get your hands very, very dirty, do some IC type of work, do some very boring, like foundational building blocks of building a playbook, right? They're very different skill sets. And so many times I end up talking to founders after they've hired one of these ex-Oracle kind of people and it didn't work out. And they're like, I don't know why it didn't work out. And I'm like, okay, I can tell you if their motor doesn't rev at the same speed anymore. You got to find somebody who's still hungry to get in the mud and build something and still has that like fire to do all the dirty work and who has an extreme sense of urgency going on to deliver, to produce, to get stuff done. They don't, they know that they don't have all the time in the world and too many people who come from big corporate feel like, you know, these things take ages and therefore I have time. Yeah.

Your tempo, your tempo gets adjusted for sure. Yeah.

So that's, that's, that's something I try to, you know, communicate to them. The next thing I try to communicate to the founders is stop over-indexing on industry experience. This is like the bane of my existence. It's like, I'm convinced I really need somebody that has logistics experience or something like that, right? And their proxy for that information is they tried to hire somebody before who didn't have industry experience and it didn't work out. And I'm like, well, how did we prepare that person? What materials did we have to onboard them appropriately? How did they learn about the industry? How did they learn about the product? Was there a playbook in place? Was there a process in place? None of that shit is usually in place. So I'm like, okay, is it the fault of us for not preparing that person at all appropriately? Or is it because they didn't have that industry experience? Industry experience to me is the easiest thing to learn. Sales acumen and sales leadership ability is much harder to learn than it is to learn about the logistics industry. The last SVP of sales job I had, this company called Qualia, they sell title insurance software to title insurance companies and real estate attorneys all across the country. As well as like underwriters, mortgage brokers, and a bunch of ancillary people in the insurance or the real estate business. Do you think I knew anything about the title insurance business before I took that job? I couldn't even fucking tell you what title insurance was. I can barely tell you what it is now, right? But I knew how to build and scale sales teams. I knew how to get my hands dirty, figure it out. Recruit the right way, build a team, da da da, do all this stuff. That company's worth a couple billion dollars right now. So you look back on it, it's like, what if they would have not hired me because I didn't have title insurance experience? How many people have experience selling software to title insurance folks? Not very many people. So is it, is it like an extra credit thing if I find somebody with industry expertise? Sure. But they over-index for it way too much.

Yeah, the waiting.

I'm always telling them like, find somebody who's done this same stage before, whose motor revs at a really high rate, who wants to be a builder, who knows and has sales acumen as well as sales leadership ability, who's done this kind of scaling thing before. Index for that, that kind of stuff. So that's, that's some of the advice that I'm giving to, to the founders. All right.

And I would add to that sort of the stage appropriateness, the deal cycle fit, you know, you can't take an enterprise seller and ask them to do high velocity.

No. And sometimes you can have an easier time taking somebody who's done high velocity and scooting them up into mid-market and that type of thing. A little easier, but that's an excellent add-on to the stage-appropriate thing. It's like deal cycle, contract value, size appropriateness. It could be geographic as well. Like if you're running a company that sells only into Asia and I've never sold into Asia, that could be a problem, right? Because there's cultural differences in how people buy. Maybe there's language barriers and differences. Those types of things make sense more than, oh, Kyle doesn't have experience selling into restaurants, so we're not going to hire him.

Yeah. Yeah. Yeah. And I think it's interesting, the lack of scorecarding is, I think, to play here because if you don't have a scorecard and you're not specific about what you're really looking for, and have, I love your point about like get somebody who's done the role to help you shape it. But start by with that scorecard and have somebody like you shape that scorecard with you so that you're not making those massive gaffes.

That's part of that process, that interview process that I'm talking about is having that scorecard. You can't go off of memory. You know, I feel, I felt, I feel 3 weeks later. I feel like I had a really good conversation with Kyle Norton.

Yeah, come on. It's especially difficult.

A little more scientific about this.

Yeah. And it's especially difficult with sales because with the sort of halo effect, with the halo effect that you often see around charisma, people just gravitate to communicators and it's hard to untangle. Well, is he a problem or is he or she a problem solver? Do they have stage-appropriate experience? Do they know my deal cycles? Do they, like, you know, without that scorecard, it's really easy for the wrong things to color everything.

Yeah. And so flip side.

Yeah.

Advice that I give heads of sales, VPs of sales, it's very different. Use different kinds of questions. It's really about, are you vetting the founders? What is this founder like? Like, what's their management style? What's their communication style? What kind of boundaries, if any, do they have over sending you messages at 11 PM? You know, I remember one of my very first, if not the very first VP of sales job I had, I used to get messages at 11, 12 o'clock at night, telling me I had something due at like 7 AM, 8 AM the next morning. And I didn't know any better at the time. And I was just like, oh shit, I better do this. I'd stay up half the night producing this thing. That's like tyrannic behavior.

Isn't that part of what you're signing up for early stage? Maybe not exactly that scenario, but aren't you signing up for the intensity and the like urgency?

There's a difference between intensity and tyranny. Yeah. Sending somebody a message at midnight and saying, hey, Kyle, you have this thing due at 7 AM. That's tyranny. Yeah. That's not urgency. You tell me that within regulation hours, right? Yeah. That I have something due, fine, fair enough. You know, so these are the nuances and most people don't ask enough questions to dig into this. Kind of thing or know how to, how to figure it all out. Another one is like, how do we come up with goals? Or what goals would I be inheriting? You know how many times I talked to VPs of sales who get a new job and a couple of weeks in, they're like, so I just found out that our revenue goal is 7x what we did in the last 6 months. And our pipeline is like nowhere near big enough. And I'm on the hook for all this kind of stuff. Stuff. And I asked the founder, like, can you walk me through the math that makes this goal possible? And the founder says, well, that's what I told the board that we're going to do. So that's what we're going to do. Yeah. That is, that example right there is why so many VPs of sales, one of the reasons why so many VPs of sales last like less than 6 months.

Yeah. You have to.

They signed up for that thing.

You have to.

You have to. You have to ask, like, what is the goal you signed up for? What is the math you use to get there? Am I on the hook for that goal? Or is there like an amended kind of goal since I didn't sign up for that thing before? And then when I am there and we get into 2025 or 2026, like, are you just going to walk in the room and tell me what the goal is because you had a conversation with board, or are we, along with the CFO, going to look at past performance, certain indicators of lift, stretch my goals a little bit, of course, because we have to, you know, get bigger, but is it based on reason? Can I logically comprehend how we would get to X number? You have to dig in and ask, you know, those kinds of questions. So that's betting the the founder, then I have to think you have to vet the product. And especially in the last, call it 5 years or so, there are a lot of, you know, really neat little widgets that somehow became full-on companies that have now become zombie startup companies that can't get exits, can't get acquired, can't raise any more money. And they're running on their way to fume. You know, they are already out of the game or they're going to be out of the game soon. You know, does the product actually work? You know, everybody knows, is this like a, you know, solving real pain or is this like a nice to have? Is it a must have, need to have, or a nice to have kind of thing? Right? Um, and you know, my big shank that I already alluded to, I didn't vet the product. Good enough at all. I had done really well my first 2 times and, and candidly, I thought I could turn water into wine. I don't, I don't care what you could, I don't care what product you give me, I'll figure out a way to sell it, scale it. And, uh, you know, that, that smashed me upside the head at one time. I never made that mistake. Never made that mistake again.

And you probably didn't bail on it fast enough.

That's why I was there 7 and a half months. Yeah.

And you probably could have been, you should have been like 60 days.

If I'm being honest with you, I knew inside of the first probably month that this was not going to work out. And I should have pulled the ripcord right then, but I, but I, you know, I didn't.

We tend to be stubborn people, folks in our roles.

So, and when we're in these roles, you know, we, our ego takes over a little bit. As well. You know, we, we think that we're good or we know that we're good. We've proven we've been good before. I can overcome anything. You almost have to have some element of delusional confidence to become a VP of sales and even then to become an entrepreneur, you know, as well. And, you know, it's a good thing and a bad thing sometimes, but it's a bad thing if it means you're not doing enough to vet the product.

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And so how do you suggest that VPs of sales do that in the, in the interview process?

I would— why not try to talk to some customers?

Bingo.

Yeah.

Oh yeah.

I mean, how many VPs of sales do you think actually ask that question? I bet if we pulled on like, you know, 100 right now, less than 10 actually ask that question. If we gave them a lie detector test, I really think it's that small of a number that even ask.

I might even say less. I personally talked to customers when I accepted the owner job because I was like, this is too good to be true. I had such a great setup at Shopify. I was not trying to leave. And I sort of got pulled out kicking and screaming just because I thought I might forever regret not doing it. But I talked to customers. I'm like, Man, these guys are more fired up about a product than I've ever seen.

So somebody out there might be thinking, well, hold on, Scott, you took a job before where you had no customers yet. So how did you do that? I talked to people from the industry. I talked to people who ran title insurance companies and said, hey, I got a question for you. I'm thinking about taking on this job. What software do you use to solve this problem right now? Do you like it? What do you like about it? What do you hate about it? If you had a magic wand, what would you fix? And I had very limited knowledge of the product that I was going to end up selling, but I, you know, tried to do like an elevator pitch of sorts that I cobbled together on my own. It's like, if I had this other product that did some of these things, that would be a good thing for you. You'd switch. How painful would that switch be? I spent a lot of time, you know, talking to these types of people. I basically just cold called them on my own, on my own, on my own time. I, yeah, somewhere between like 0 and 10% of VP candidates, I think, are actually doing that. And if somebody has customers and you're a VP and you're asking the founder, hey, can you introduce me to a couple of customers so I can have this conversation? And they resist for some reason, that's like obvious red flag, right? Another thing you do is talk to, if they have reps in place already, ask to speak to the reps, or maybe better yet, ask to speak to the people servicing those accounts in account management or customer success. And again, if you get resistance there, that's a massive red flag. But even if I got resistance, candidly, I would just go around them anyways. I would just go dig people up on LinkedIn and be like, hey Kyle, I'm curious about your company, thinking about, you know, taking on a role there. Like, what do the customers say? What's the sale like? Right? Just digging into that kind of stuff.

I give that advice. I give that same advice to anybody accepting any role. It's like, if you're a sales rep, go cold message. A bunch of sales reps and be like, what's this manager like? What's the VP of sales like? If you're a manager, VP, anything.

Yeah. And, uh, there's a lot of different ways we could go. But the last thing that I would say is in order to get alignment, you actually have to be very brave with this next question that I'm about to ask. Because I started off by saying you got to hire this like stage appropriate VP if you're the founder, right? Okay. So you're a VP of sales. Have you ever taken a company public before? Me? No. No, right? I never have either. Right? So in the interview process, I said to the founders, listen, this is what I've done previously. I've gone 0 to 25. Okay. If I get to 25 and things are going great and I want to stick around. What does that look like? Because you know as well as I do that you're going to be tempted, or the board is going to tell you, like, Scott did a great job. He's never taken a company to $200 million before. He's never taken a company public before. We might have to top him off. So I want to ask them and see if they'll be honest with me. Like, are you going to top me off when we get to a particular point and try to pull somebody in above me because I've never done that thing before. It's a very uncomfortable moment and conversation, but it's an opportunity to figure out if both parties are being honest with each other, right? In my particular case, I was candid. I was like, I have no desire to take a company public. I do not want to be here for 7 to 10 years. Here's what I want to do. I'm pretty sure that I can get you to $100 million plus valuation in, you know, 2 years or so, get you to $25 million. And at the time, at the multiples, like $250 million valuation, right? In, in under 3 years. Let's reassess where we are at that point in time, right? Let's be honest with each other. And, and that conversation was had, and that's exactly what happened. And we both decided at the end of 3 years, like I was kind of burnt out. I wanted to do my own thing at that point in time. I hired my replacement with them to ensure that when I left, it was going into good hands. And that guy had been a friend of mine that I coached Little League with, who was a VP of sales at much larger companies. And he's still there. That's 5 years. Later.

Wow. That's an awesome success story of this, which is rare.

Yeah, that's, I mean, that's a whole other kind of topic, but you know, one of the things that I did right there in hiring a friend of mine and finding my replacement was the exact opposite of what I had done in the very beginning of my career. When I left and saw things start to go south, I was like, ah, they needed me, you know?

Fuck yeah.

Right. And in reality, like stupid of me because I didn't gain anything from it. My equity lost all sorts of value. Right. There's multiple companies that I was with that lost value between when I left and when they exited. And you could argue that like, I didn't do a good job helping find my replacement and I left it up to others. And they didn't, you know, know how to find another version of me that was as good, right? So have this honest conversation about what happens when, because that conversation is often, more often than not, never had. And then, you know, some VP of sales is surprised and shocked when they get talked off and they get frustrated and they're like, Fuck this. I'm out of here. And that founder wasn't honest with them from the beginning, which creates distrust and that permeates everywhere in the team. So that's one of the difficult conversations that I try to advise people to have early on.

Yeah. And getting layered, you know, it comes back to ego. Like, you know, a lot of us have very high opinions of ourselves that you need that to do this job in many ways. And getting layered can be great. Like if you can participate in the process to find the person you're going to work for and you can help the company identify the right fit because you have so much unique information. There's a lot of scenarios in which if a company could bring in, you know, a public company CRO that you could learn from and develop under and position yourself for the next thing, like, you know, that could be a success story, but it's hard when it's a surprise. Like, it's rarely going to be received in that manner if it's a surprise and feels like you're getting—

if you want those learnings under that person because you want to go that route. Yeah, I always go back to, to like, my, my youth was spent playing sports. I always go back to like sports analogies, like I'm sure every starting pitcher would like to throw a complete game and pitch all 9 innings. Yeah, but that is very, very rare. There's a reason why they have a middle reliever, setup man, and a closer, and everybody does their job because the goal is to win. The goal is not to be right or to prove a point that you're the man or you're the woman or you're the one that can Hey, take this, you know, end to end. The goal is to win at the end of the day. Right. And if you're the person who's there for the first few years and you like that part and you don't like all the red tape that comes with being in a 1,000-person company, needing 17 signatures to change the flavor of LaCroix in the refrigerator in the office. Like, I don't want to deal with that shit. Right. So instead I'm like, well, I can put a couple chips here on the roulette table because I was here for 3 years at this company. Then I can bounce and go do it again, put a few more chips on the roulette table for a couple years at this opportunity. Now I've, I've spread, I've diversified my equity opportunities, right? There's nothing wrong with that. I just, I just implore both parties to try to be honest about it and have, and have a dialogue. So it's out in the open rather than a shock or a surprise.

Yeah. And I think that is one of the big areas of misalignment that often crops up. It's sort of equity structure. You know, if you are on a plan that has a 90-day exercise window and you were an early VP of sales at a very successful company, like the equity that you're trying, that you need to purchase might be hundreds of thousands of dollars if you've done your job. And like most of us don't have that cash just like laying around and you don't really want to maybe lay it all out on an early stage illiquid asset class. And then you're staying because you're staying, you're staying to try to wait out a liquidity event and it creates this misaligned incentive where people can't more gracefully exit versus if you said, and it's starting to be more common, but like an extended exercise window. It's like, hey, if you had this conversation with a founder, if I can get you from 1 to 25 in 3 or 4 years and you want to layer me or move me on, or we feel like it's appropriate, have I done my job? Have I earned that percent or 2% of equity? Do you think I should be able to walk away with it? Yeah. And if I don't have the cash, will you give me cashless exercise or like a 7 to 10-year exercise window?

I think that also puts a lot of pressure on this relationship because it does, because you could view all of this as like predatory behavior from venture and founders and exploiting what VPs of sales do. You know, if I very clearly said, I'm going to get you to $25 million, I'm going to do it in 2 to 3 years, and I've done that, you mean to tell me that I don't deserve all 4 years' worth of whatever amount of equity they gave me? Why do I have to sit there another year to get the full vest? Why don't I have a milestone-based vesting? Right? I talked about this years ago, I don't know, years and years ago with Max Altshuler. And we talked about this milestone-based equity vesting thing, you know, because look, when I left after 3 years, I got 75% of the equity that they had initially, you know, offered me, but I got them to exactly where I said I was going to get them. That doesn't sit well with me. And it doesn't sit well with a lot of sales leaders. And you know, the risk is not that much different in my mind between a founder and a VP of sales joining an early-stage company. Arguably more severe for a VP of sales because if you fail and you get fired or whatever too fast, it's a stain on your resume. There's not really a stain on a founder's resume if they stop being a founder and they go They try to be a whatever. They try to, they try to be, or even raise no money. The delta of, yeah, the delta of wealth accrued in the startup exit is not proportionate to the amount of value created. You know, I'd have had a couple hundred million dollar exit. The founders made like 30, 40 million. I made like 500 grand.

Yeah.

I'm sorry. But they did not create 60 times more value than I did. They had no revenue before I got there. No process, no system, nothing. I'm not saying I deserve as much at all. I'm just saying 60x, come on, man. I don't buy that. And so I'm a big fan and proponent of these milestone-based, uh, uh, option grants and stuff like that. I'm a big fan of. Extending the exercise period. There's no, it's predatory to say to somebody, bro, you got 30 days after departure to exercise these options or 90 days to exercise these options when they're, you know, tens of thousands, hundreds of thousands of dollars if you're a C-level person. Like you said, how many people have that kind of money, you know, lying around, right? And you lose all of them. Right? There's so many weird clauses. There's clauses in people's equity right now if they go check their grant that says, if you pass away, if you die, your spouse or your partner does not get the equity transferred over to you. It goes away. Can you imagine? Imagine. Let's say owner.com is a massive, you know, hit, hopefully. Well, I mean, it already is on its way, but let's say it's like a massive hit. Okay. Let's say that your payout is going to be worth $10 million. All right. For most people, that's like mind-blowing, generational-changing wealth for you and your family. Okay. You have a couple of kids, you got a spouse. If you get in an accident, your family gets none of that equity upon the liquidity of that.

None of that.

The clause is in there. I don't know if it's in yours. I hope not. But it's in there. It literally says it does not transfer over upon death. You know how fucked up that is? That's not right. And so all of these things, I think, are starting to be talked about a little more and more VPs of sales are starting to learn about this stuff and getting frustrated that they've been taken advantage of for all these years. And some founders are starting to make changes and adjustments and good on them. I think that they should be doing that, but this is where some of this like friction and, you know, red versus red state versus blue state kind of tension in this founder VP of sales world comes from. Right. And there's really no reason for this. We should be able to have a dialogue and a discourse around this and make changes and adjustments. We shouldn't just say, well, this is how it's always been. So that's how it's always good. That's stupid. We don't do that in any other area of life, hopefully. Things evolve, things change.

And so much of it is short-sighted. So much of it actually leads to worse outcomes for the company and the founder because you end up with a frustrated VP of sales that's hanging out for another 9 months that they don't want to hang out for just to vest or just to—

And that affects performance and could affect morale. What about the toxic VP of sales who starts talking shit about all about the company and then the reps start to hear about it and the reps start questioning what they're doing there and that dips performance.

Yeah.

Then that person leaves, takes reps with them, then the company has to find on their own a new head. This is all to the detriment of everybody involved.

Yeah.

Because every, too many people are focused on like, me, me, me, and my ego, and I want to be right versus how can we all win? Yeah. Which is what allegedly we're all here for is a win.

Yeah. And I think stuff, I think milestone-based vesting and extended exercise, it is not a giveaway. I think it is actually good for the company. It's obviously good for that CRO, but it's a good place to be as a company because you want Especially you want senior people moving on gracefully that are going to continue to be like great ambassadors of the company and not want to come and bring half their team with them. And because they did only exercise half their equity because they feel like they got shortchanged. I think that's important. I think when just going back a topic on hiring alignment for the VP sales, I think the You mentioned vetting the founders, vetting the product, vetting that journey. And then we sort of got on that tangent. The other thing that I encourage folks to do is like vet the financials. I'm like, ask to sit down with the CFO, with the growth model and go through the assumption. I had this conversation last night with a VP of sales that's looking at a role. And the advice I gave them was ask them to look at next year's model. And walk you through the key assumptions, pipeline conversion rates, butts in seats, like the really key input assumptions, and then look at it on a trailing 3-month basis and where are you at? And like ask the CFO's honest opinion of probability. And you can see like, are you— your point was what goals are you inheriting? Yeah. Well, just because it's, you know, just because the goal is 5 to 25, Seems crazy, but like, you know, some businesses do that and that would be great, but how much have they tortured this growth model?

Yeah. They, you know, that's why I want to, I want to see the math behind it.

Yeah.

You tell me 5 and 25. Okay. Show me the math. Help me understand it. Help me, help me believe. Right. And I'm open to believing 100%, you know, but if they don't have that math and they can't do that math or they won't share it. That's, that's problematic.

Yeah. Anything else that you'd add there? So vet the founders, product journey, financials.

I mean, I'm always vetting the market opportunity, you know, and I suppose people have different opinions on this kind of thing, but I'll pick on AI for a second, you know, AI content generator or whatever. There's a million and one MarTech, sales tech, AI companies right now. Like, why do I want to be a VP of sales in that space right now?

It's cool.

It's the hot new thing or whatever. There's so much competition there, so much competition and so much noise. What I tried to look for the last few opportunities in particular and specifically with investments that I've done. Are markets that are underserved, antiquated, unsexy, don't have a lot of competitors, and that means they're like ripe for disruption, right? Like I talked about software that, you know, helps title insurance companies. When I was vetting that opportunity, I asked who the top competitors were and I wanted to see the software. And the founders like showed me like, hey, here's the 3 main players in this. I remember looking at it and then looking at them saying, you're messing with me, right? There's no way. Like this thing looked like it was Oregon Trail from like 1990 dot matrix. Like it was so bad. I literally didn't believe them. And they were like, no, Scott, we're being serious. I'm like, oh my God. Like, There's not a single modern competitor in this space right now. Nobody has done anything innovative or new in this space in 20, 30 years, right? And it's in and around real estate, powers every real estate transaction. How many real estate transactions happen in America every year? So I'm like, this is a huge opportunity with old crappy software, no modern competitors. I want to go there. So I started to optimize for like vertical-specific SaaS opportunities and stuff like that, rather than the kind of hot hip new piece of sales and marketing technology, just selling to other sales and marketing leaders. Not that, you know, there's going to be winners in those sectors, but that's not how I approached it. Towards the end and not how we've approached it in my investments and some of the clients that I choose to take on and stuff like that. So that market opportunity is something that I tell people to look at strongly. Who are the incumbents? How crowded is the space? Is it hip? So therefore it's cool, which oftentimes does not equate to this is very necessary. Yeah. Right. And is it a platform? Like, do they have to use some piece of software in order to get this thing done? Because if they have to use it, then it's just about ripping and replacing versus like convincing them that they even need the thing.

Yeah.

That's less of a fight in my mind. It's a little easier and I'm always trying to optimize for like low effort, high yield all the time. Yeah. I'm not trying to do the hardest thing just to say that I do the hardest thing. I'm trying to do the easiest thing, to be honest with you, and get the most out of it.

Yeah. Yeah. And it's not binary. Like, there are MarTech companies that are going to be a winner, but if you're going to join a super crowded, crazy space, you better make sure you're joining the A+ winner. Like, even if we look at GTM Fund, So, Owner is one of the higher-profile companies. We're in that unsexy mom-and-pop restaurant space.

There you go.

One of the other darlings is Ryder. They're in a super sexy hot space. They just raised at almost a $2 billion valuation. It could be in vogue, but that company has got something special figured out. And so, your vetting needs to flex depending on, I think, those things. So, The one other thought that I had just listening to you, because now we're talking about vetting 5 major areas and really going deep. And I think the challenge oftentimes is these jobs are hard to come by. And there's this Upton Sinclair quote, it's difficult to get a man to understand something when his salary depends on him not understanding it. And so basically what he means— Yeah, it's a little timey thing. But I think so much of the time we turn a blind eye to the red flags because, you know, especially if you're looking for your first VP sales role, I see this all the time. You're trying to get your first VP sales role and there's just like flashing red signals that like, hey, they don't have traction. These founders are nuts. Like, don't take this job. But it's hard to turn down the money and the role and the comp. And so having the discipline, having the discipline to, like, do these things that are hard and actually say no is even harder. I think that that's one of the important messages for potential heads of sales is like, dude, be patient.

Dude, be patient. Yeah. Don't, don't, uh, if you can. You don't ever want to come at this process from a place of weakness. That's a massive disadvantage. A place of need and a place of weakness, which leads to a place of desperation. And desperation causes you to overlook all these red flags.

Yeah. And if you can only get a head of sales job at like a pretty crappy company, don't get it. Don't go be a head of sales yet. Go be a number. I give this feedback all the time. Just go be the number 2.

Go be the apprentice. The number 2. That's right. Yeah. Or even go be the— Okay, imagine you had, you have 2 choices. Let's, in this scenario that we're talking about here, it's like, you can take this head of sales job at this like dodgy, sketchy startup that hasn't raised very much money. The founder is kind of out there or whatever. Or You can go be Kyle's number 2 and you can take an apprenticeship basically and see how things are done. See how he structures things, see how he motivates, see how he leads, see how he manages. Watch the decisions that the company makes. What kind of operational rigor do they have? How do they set up their deal stages? Literally, like, how do they close deals? How do they onboard a customer? How do they hand off a customer? All these things that you have to be a part of one day, watch and observe working with the right sales leader, and that person can become a mentor for you, potentially for the rest of your life. And a lot of people think that that's not advantageous and it's more advantageous to get that first VP title when in actuality, my experience is the opposite is true. Because if you go to wherever you're trying to go next after apprenticing of sorts under Kyle Norton, and you say to a founder, like, yeah, I'm looking for my first VP of sales gig. I had the opportunity to do it 3 and a half years ago. I turned it down because I wanted to go learn from one of the best people that's out there. And I spent the last 3 years basically in, you know, VP of sales, CRO business school. Learning and observing and watching this particular person. And, you know, a good founder would be like, well, I want to go talk to Kyle Norton and learn about his number 2. And then presumably you have really good things to say about the number 2 person. And you're like, you know, this lady is ready. She's like, you know, done everything right. She's seen my playbook, knows how we do things. Yeah, that scenario should be more important in candidates' minds than I think it is.

Yeah. Because think if you're a director-level person that spent 3 or 4 years at Brex or Vanta or Rippling or like any of these sort of high-flying, high-growth companies. Like I had Sam Blond on the podcast and the number of CROs that have come out of his His alumni is bonkers.

Yeah, that's good. That's one of the proudest moments that you should have as a leader.

Yeah.

Who doesn't want to serve? The coaching tree. They talk about the coaching tree in sports. And what you just alluded to with Sam is like all these VPs or CROs that have like learned under him and gone on to do their own thing. That's one of the things that I'm most proud of. You know, I can count almost 2 dozen people that I can think of easily that are in VP of sales or CRO kind of roles who started as reps under me and progressed to manager, progressed to director, worked with me at more than one place. That's how you, you know that, that somebody is a good person to like learn from, you know, and Sam has that kind of tree. You know, at one point in time, like, we'll talk about Kyle Norton's, like, management tree and the people that work under you right now will move on as you get older. You'll be like, oh, wow, you know, this lady is a VP of sales now. This guy is VP of sales. And those people start to come back to you and ask you more questions and stuff like that. That coaching tree is massive. That's, that's when you really know you've, you've got somebody special. Yeah.

So let's transition to alignment in the role. So I think this is a really useful view for both sides of how to think about the right fit. So now let's imagine VP sales, founder, we're working together. There's all of these tensions that we read about on LinkedIn. I think the biggest one— well, let me ask you. In my opinion, the biggest one is just like alignment on the plan. Like it feels like the biggest breaking point between these two camps is like the annual plan and the thing you're inheriting. Is there anything else that are the big points of contention in your mind?

You know, sometimes there's the strategy of it all. Yeah. One person believes we should be cold calling the whole time and the other person believes we should be, I don't know, going to events 24/7. So the strategy is oftentimes lacking in alignment. There's the measurement. There's founders in particular who want to know all the details because they want to know the conversion rates and they want to know the math and the science behind everything. And there is a version of a VP of sales out there that doesn't want to measure anything and just wants reps to like have the freedom to do what they want to do.

They shouldn't be a VP of sales then.

Yeah, tell me about it. But this is like the new age way of being a VP of sales. It's like, what? I swear to God, bro.

Oh my God.

Yes.

That's a separate podcast then.

That's a whole other, uh, podcast, but yeah, there's a difference between like letting reps have the freedom to do some things that don't scale or are very hard to track and measure and just like throwing out almost all KPIs and not worrying about like, you know, activity metrics and stuff like that.

If you're listening to this, please don't do that.

Don't be that person.

Measure things. The math is the math.

Yeah, exactly. Okay.

So GTM strategy growth model, the measurement is an interesting one.

Measurement is sometimes And then one of the things that might surprise people is actually, I would say, is communication.

Yeah.

Yeah. Yeah. Here's what I mean by that. In my experience, when founders don't know what's going on and they don't get regular updates, they get anxious and they start pestering you as a VP of sales and they want to know everything and they pick apart everything. And It's just because they don't have the information and they don't see it right in front of them every day. It's not necessarily because you're not doing anything. The problem is you're not communicating what you're doing every single day to them. You need to proactively be communicating all this stuff, right? The moment the founder has to go to you and be like, Kyle, you know, what's the story with all this numbers? What's the forecast? You're fucked already at that point in time. Yeah. Because they've had to stop whatever they're doing to think about it and ask you. And they're asking you because they don't know where to find the information or you're not putting it in front of them every single day.

Yeah.

One of the smartest things that I ever did is I used to just send this like 2, 3 seconds little recap at the end of every single day.

Yeah.

So I found it because I wanted my founder to leave me alone. And so I felt like if I proactively tell him like, Here's what I worked on today. Here's what I got done. Here's the challenge that I'm trying to overcome, whatever the 2 or 3 sentences were, right? Yeah. I found that they would leave me alone.

100%.

And they wouldn't pester me because they weren't sitting there going, I have no idea what Scott does every day. Yeah. Because I'm proactively telling them.

And this is the most important thing. This is the thing that founders care about the most. Is money coming into the business? Are we growing? And you can't expect them to just have like blind faith.

And what are my people doing, especially in a remote environment now where you're not in the office? These two factions, there is a faction of founder VC world that wants everybody back to the office, right? And they think every rep is at home, like, you know, doing Pilates all day and watching Netflix. And rather, rather than working, right? Well, if you want to perpetuate that sentiment, don't communicate to the founders what's happening. You want to dispel that sentiment, communicate all the things that are happening. Show, show them all the things that are happening. Don't make them wonder. That's where problems happen. Right. And the other piece on communication. On communication is, you know, from the founder on down to the VP of sales, it's like you can't give people 900 different level 1 priorities in a single day. You can't, you can't as a founder say to Kyle Norton or say to Scott Sharp, hey, I want you to solve X, Y, Z. And then 2 hours later, you send them a Slack message that's like, I really need you to do this other thing. Oh, I need this thing done by 5 o'clock today. You can't constantly ask them to shift their priorities around all over the place. Nothing will ever get done. They'll always be in a reactive state with like cortisol level 9,000 because they're stressed out, right? You can't send them messages that don't respect their boundaries or their personal life at all, right? If I get online at 6, 7 o'clock in the morning and I have 900 Slack messages from my boss already. That's not good, right? If I get online at 9 o'clock at night and my boss is sending me a bunch of messages because he sees I'm online at night, that's not good either. You can't send people a million messages over the weekend when they're not expecting it.

Or yeah, I will say it's just about expectations because there are some companies where you're like, hey, we are 1000% all in. That's all we're going to do. And there's a bunch of these companies that have been super successful because they operate faster and more urgently. But back to the original point, you got to know going into it, like, are we signing up for 11 PM Slack messages? Like, I don't mind getting those personally. Like, if you want to talk to me at 11 PM, I'm usually working.

You're a good soldier. The longer you've done this gig, and this is probably alignment as well as some of the The jadedness that comes, like when you've done this 6, 7 times and you're 40-something, 50 years old and you're getting 11 PM Slack messages from a 22-year-old founder who just graduated from Stanford, who has no comprehension of what your life is like because you just, you know, went to a high school football game and you've been in, you know, with your family from 6 to 11 PM at night. Like you don't understand these persons, this person's life whatsoever. You're not going to get the best out of this person. And if you're a VP of sales, taking on a gig in that environment, like, what are you signing up for? You don't want to work for that, that person, that person is all in 100%. They have nothing else that they're focused on. Right? Well, the founder might say, well, yeah, so, so should, so should Scott. Scott, you should be all in as well. I don't care how old you are. I'm like, listen, dude, you're going to make 60 times what I'm going to make. Okay. I don't have the same incentives as you to work 24/7 on this. Let's be real. Yeah. So I understand your point, but there's also a point where founders need to understand where people are at in their life and they need to respect some of these boundaries and that's actually going to get the most out of them. Burning me into the ground because I don't mind 11 PM messages right now is not a long-term strategy for success. And I promise you, you're cool with it right now. You're significantly younger than me. Your kids, if I can't remember if you have kids, but I think you have, you know, little ones, right? Talk to me again in 10 years when they're like teenagers, preteenagers, and their practices don't start until 8:30 at night. And they don't get home until 10 o'clock and you're eating dinner like you live in Spain because it's 10:30 at night and you can't get to bed before midnight. And if you start getting messages at midnight from your boss, you're not going to feel good about that. I assure you.

Yeah. Expectations.

It's all expectations, stage alignment, and having these awkward, difficult conversations at the beginning. So both parties know what they're getting into.

Yeah, my founder doesn't do this. I was like, dude, send me messages whenever you want and I'll respond to them. He knows I've got a family. It's like, if I don't respond, I'll respond when I can. And he's never really infringed on my— like, he's never did the triple tap, send me a message. Did you get this? He's cool.

But I'm okay with that.

But I personally don't mind the sense of urgency. I think that to build great companies, you do need a high motor, high sense of urgency, and it's my job not to get stressed out about it. I'm a very extreme ownership person. If you're sending me those messages and I don't like it, my job is just have a conversation like, hey, I got kids, I don't get home from practice. When you don't hear from me, just know that I'm going to get back to you at the earliest possible time. But sometimes that's the next morning. And I think like the—

Yeah, I think if everybody has that level of expectation, that's totally fine.

Or just have the conversation. Don't sit and stew in it. And I think that's sometimes the challenge. Like I, when I met—

That's like any relationship, right? Yes. One or both parties are are upset over something, they say nothing, and it just builds and builds and builds and builds until it explodes.

And then you're just assuming the worst of the other person. I hear this at dinner sometimes, and I share this feedback. I'm like, how directly have you shared that with your founder? It's like, well, I mean, and so that's a no. You haven't said like you haven't gone back with the data, with, you know, like clear, you haven't clearly articulated why, you know, this go-to-market strategy might not be the right fit or the communication style. And I think one of the things revenue leaders need to learn to do is just like better communicate with low stakes, low anxiety cortisol levels. And just have this grown-up conversation. And this article I wrote on the Substack is like the difference between a revenue leader and an executive. And this is one of those things. If you want to be taken seriously as an executive, you got to have uncomfortable conversations. You got to be able to say these things. And then if your founder is like, that sucks, I don't agree, no way. All right, that's a different conversation. But we as a group, I think, need to do probably a better job having big girl and big boy conversations about some of that stuff and not grumble about it. So we only got 9 minutes here. I want to ask one more question about alignment because I think a lot of it comes down to sometimes the growth model you mentioned at the beginning. Hey, I told the board we want to do $10 million next year. And sometimes that's not reasonable or probable, which is going to be problems at some point. So how do you talk to both founders and heads of revenue of how to get to the right number together that is not like a sandbagged VP sales friendly number, but it's also not this crazy thing that no one has a shot at hitting?

Yeah, I mean, it's a lot easier if you have If you have data, because then you can use past performance as some type of predictor of the future. If you don't have that—

And oftentimes the new model is, oh, it's just, well, 3x win rate and we'll double the pipeline.

Yeah. Then I say to them, well, how? What is the change or tweak we're going to make to triple our conversion rate? Is there a, is there a new feature that is badass? Is there a new integration that was causing us to lose deals? So what is product doing to triple our win rate? What is marketing doing to contribute to tripling the win rate? What is CS doing to contribute? What can sales do? What can I do? What am I coaching, training, onboarding, teaching, enabling? Is there some new piece of tech that we just bought that we think is going to contribute to tripling the conversion percentages? Is there something in the market that has shifted that suddenly everybody, you know, needs this thing? Like Zoom, for example, when the pandemic hit, right? Like, okay, market conditions have changed massively. We have a huge tailwind. It makes sense for us to, you know, triple our conversion rates or whatever. But in the absence of those things, how? Help me understand how and why we're signing up for all this growth and increased conversions.

And how do you do that without it sounding like excuse-making? Because I think the founder side of this, and this is something that Lemkin said on the pod, he's like, when you see fear, when you see fear in a VP of sales, like oftentimes they're cooked. And so if the board and the founder is looking for signs of fear as a sign, like, hey, this person just like doesn't believe, they don't think. And like, you know, sometimes the perception is, well, like, you're the VP of sales, you're supposed to figure that out. How do you get them to— how do you as a VP of sales have that conversation without it coming across as like, well, do you want me to figure it?

Do you want me to figure it out? Or do you want me to do all of the work? Required to fix it. They're very, they're two very different things. Because part of me figuring it out is me enrolling help and assistance. Knowing I can't do everything myself. That's not fear. That's just me saying, I'm a human being. I'm one person. In order for this to work, I need some help from product. I need some help from marketing. I need some help from CS. I need some help from the CFO, maybe to give me some budget to buy a tool or whatever. Right? That's utilizing the team around you. That's utilizing resources that you have available and accessible. And then obviously it comes back to what are the things that I can do to move the needle? You want me to triple all the conversions? Why does all of that tripling have to come from me? Other people should be doing things in the company to help enable me to triple our conversions or triple our revenue.

Yeah.

How much of that is coming from me? I don't know. As much as, as much as I can. I got, I'm not afraid of that. I'm going to do everything I can and come up with a plan that says, okay, this is how, this is all the stuff that's 100% in my locus of control.

Yeah.

And I can get us to, you know, 2x. Yeah. So the other 1x part has to come from these other areas. I don't think that's excuse making. I think that's reality. Yeah. And you know, I, Jason and I don't agree on lots of stuff. There's some stuff we do, do agree on, agree on. I don't know the context of that quote about once you see fear in somebody's eyes, they're cooked, but, um, it depends to me. How did that fear get placed there? If you purposely scared the shit out of them and terrified them, right? You don't blame the person who's afraid. You fucking caused that mess, right? If you have a logical, sound, reasonable dialogue and walking them through math and data and saying, this is where I think you can go. And, and then that VP of sales has fear in their eye. Then I probably agree with him. Right? So that's, that's how I, that's how I, uh, kind of approach it. How much of that can I own? What are the things that I can do? That's where I start there first. And then I say, what can this person do? And what can that person do? And what could this person do? And how will these things impact? I'm putting the puzzle together because my job in my mind My job is to help us get there. It doesn't mean I have to play hero ball and do everything myself.

Yeah. Oftentimes the advice I give here is yes and. If you get given a pretty crazy plan, be like, yeah, we can do this. And here's what I need. I need like $10 million in marketing budget and I need CS to get us to 10% like a 10% increase in NRR. And then you just say like, yeah, yeah, we can do it and here's the plan. And then the response is oftentimes, oh, well, but like we can't do that and that. Like, oh, okay. Well then let's modify. But if you start with no, oh no, I can't and they have to do this and they have to do this, then it falls apart. But like this, I think what you're saying is similar. Like, Be like, yeah, we can do it. But like, and here's, and here for that to be true, here's what, yeah.

Yeah. It's okay. I hear that. Here's what I can control that will contribute this much so we can do it. I'll get us this much on my own. And here's what I need from all of these different resources in order to get there. And if they say, well, they can't do that. Then my response is, okay, well then help me understand the alternative. Help me understand the alternatives. What am I not thinking of? What do you see that I don't see? Right? And then, okay, maybe we need that. Maybe we need to modify the plan. Yeah.

Awesome. Um, like I suspected, we only made it through this one topic, which is, which is great. Uh, there's so much here, but I really think this is a useful conversation that I hope founders and VPs of sales, uh, really take to heart. So, Let's do a quickfire. So short answers, couple key things. What did you learn much later in your leadership career that you really wish you knew as a young leader?

That winning is what matters, not my own performance.

What do you think separates a good CRO from the truly great ones?

I think the ability to develop people who can and will replace you one day, that coaching tree thing that, that we touched upon.

Yeah.

Because I think at the end of the day, your job as a CRO, VP of sales is twofold. The first one is to hit the numbers that you're supposed to hit. And the second one is to help everybody underneath you get to wherever it is they want to go next in their life and in in their career. And that's that developer of people.

Totally agree. What's the hardest lesson in leadership you've had to learn?

Hardest lesson in leadership.

One that's stung to learn.

I mean, at the end of the day, it's all your fault. That's very difficult to accept. You know, even if, if Kyle, if Kyle was a tyrant, well, it's my fault. I didn't vet properly that Kyle was a tyrant. Yeah. You know, I think that's the hardest thing is that whatever the mistakes are, whatever the results are, whatever my own happiness is, that's on some level, in some way, shape, or form, I contributed to that.

Yeah.

And it's kind of my fault. And life-changing when you learn Yeah, yeah, whether you could probably, for most people, continue to learn it throughout your whole entire life. Yeah, at least in my case. Yeah, yeah, yeah, I'm still learning.

Um, what's the best thing you've read in the last 12 months?

Ooh, best thing I read. I'm blanking on the name of it. I think it's called Escape from Auschwitz, actually. Oh, I, so I have lots of sales books back here behind me, but they're actually not the books that like inspire me the most. So I like reading, you know, about history and people basically overcoming like absurd odds to make it out. And anyways, this book is about the first two people to ever successfully make escaped from Auschwitz and their journey and then what they went and did in their lives afterwards.

That's awesome.

Really, really difficult read, but really inspiring.

I bet. Well, Scott, this has been awesome. I have a ton of really interesting notes here. I think there's so many great messages to share with folks. The one in particular that I hope people take home is just the importance of vetting. It's like, spend the time vetting, really get to do your diligence on companies that you join and get clear about expectations. How can people find you? Where should we send them?

The easiest place is just find me on LinkedIn. I'm actually really good about responding to people who send me DMs and connection requests and stuff like that. So if I get a a real message that's not automated or bot-driven or whatever, I will respond. So hit me up on LinkedIn.

And lots of good stuff on there that people can learn from. Well, thanks for coming on, man. This was a blast. Appreciate you spending the time.

Thank you for listening to the Revenue Leadership Podcast. If you enjoyed it, don't forget to subscribe and you can find a link in the show notes and be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.