E1: SaaStr Founder Jason Lemkin on Why Revenue Leaders Must Run Towards Bad News

Jason Lemkin, welcome to the podcast. Appreciate you joining.

I am so excited to be here. It will be great. We're going to talk about some stuff that maybe hasn't been talked about before.

That is definitely the focus. 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. Today's guest is none other than Jason Lemkin, who was the founder and CEO of EchoSign, which sold to Adobe. He then founded SaaStr, which is arguably the greatest community for founders out there and is a prolific investor through SaaStr. Master fund with 5 of his first investments all going on to become unicorns and decacorns. So, uh, it's an honor to have him on, and we're going to be talking about what revenue leaders need to know about understanding and managing their board. And so if you like what you hear, make sure to follow the Revenue Leadership Podcast by clicking the link in the show notes. Hope you enjoy. But first, a word from our sponsors. This episode is brought to you by Momentum.io. Momentum is a powerful tool for turning sales and customer conversations into go-to-market data. Using GenAI, it extracts, analyzes, and automates customer intelligence across your org. The best part, it's not a new platform for your team to adopt. It integrates seamlessly with your existing stack and writes data back to Salesforce directly. Some of the most innovative companies out there, like Zscaler, Manbase, Ramp, 1Password, and even my company owner.com use Momentum every single day to capture forecast and churn risk, autofill Salesforce fields, share product signals, and track sentiment. So check it out with a free trial at momentum.io. So most folks will know who you are, but, uh, for any of the uninitiated, just give us a 60-second, uh, who you are.

Sure. I'm a SaaS founder myself, founded one of the early e-signature leaders called EchoSign that was acquired for Adobe for 9 figures way back in 2011. And then just, I was the first of my generation, the David Sachs and the Rene Lisserts from Bill and Aaron Levis to have an exit. So I just started sharing my learnings on a little blog called Saastr that's taken off. It's a big deal. We've done 10 years of events with tens of thousands of folks. I've invested in 5 or 6 true billion-dollar companies through SaaS Growth Fund, including Owner Fund, Owner, that Kyle has done an incredible job at. So I've invested about $200 million over the last 10 years. And mostly I'm just trying to run this community to help other SaaS and cloud executives do better so that, um, what seemed crazy in the early days was that we could share these playbooks and they would work at other startups, but it turns out it's true. Um, and so it's well understood today. It was radical 10 years ago. But that's kind of the mission to help share, share how you just, how to make it just that much easier to push the boulder up the hill. That's SaaStr.

That's awesome. And SaaStr was one of the most important knowledge bases for me when I was first breaking into tech and learning things myself. I think I stumbled across your name on Quora, which I'm sure is familiar. Yeah, it was a familiar story for many. And so it's been. A big part of me figuring things out. I remember so clearly reading Impossible to Inevitable and just having a book full of notes. And so it's exciting to have now partnered with you at Owner. So how many boards are you on right now and how much time are you spending in operational details with your portfolio?

Yeah, I'm not on that many boards. I think I'm on 5 boards. And I'm probably on 2 more where I'm definitely not on the board, but might actually be the most active investor. Those are situations where there's really no one helping the company too much, but the company's doing well. So I'd say 5, 5 for real legal board seats and 2 that I have a similar role. I don't enjoy being on boards. I did try to avoid it when I started investing. Um, but ultimately I came to the conclusion that if you're one of the largest investors in a startup, it's, it's, you've, you've, you've got to do it. You've got to step up and take this sort of role. Um, so I try to do as few as possible. If there's someone else that can do the role, I generally will defer to them for both selfish and unselfish reasons. Um, maybe that's TMI, but yeah, I'd say about only about 5 boards. A lot of VCs that are in big funds, this is a big difference for the audience. If you're at a, if you're at a VC at a huge fund, a great fund, you know, um, They are, they would stay, will spend upwards of 50% of their time on boards. And one of the most important things for them is being on boards. You'll see the classic one is you look on their LinkedIn and you'll see their last 20 jobs were board member, owner, board member, Shopify, board member. Then you know that like that's their job and a traditional VC that isn't that involved operationally or isn't doing other things, the maximum a VC possibly could do is 20. There just aren't enough hours in the year. And as you approach 20, you become a full-time board member.

Yeah. And, and I would imagine that you get pulled into this because you are uniquely still dialed in. I think, you know, you've been out of the operator game for 11 years, a little bit more.

Yes. Yes, that is true.

And yet anybody who follows you on Twitter or LinkedIn and looks at your breakdowns of businesses, public and private, you seem to have more operational depth than just about anybody, including the people who were most recently operators. How do you stay so dialed in? Like, how do you keep that operator edge after all these years?

It is a good question. I do think this idea of decay of your fluency is real. And I certainly think the playbook of a decade ago pretty much died, uh, during March 2020. It died in when things exploded, right, in March 2020. And then it died when things in some cases deflated. So I think if you're literally talking to someone that has been out of the game since pre-2020, and that frankly, that's a lot of the early SaaS content, I think a lot of it is pretty dated. Um, how have I kept up? Really two ways. One is it has helped to be pretty involved with a handful of pretty successful SaaS companies that have still struggled along the way, right? If it's perfect, you learn nothing. And if you run the thing right into the ground, you learn nothing. But to watch, like you said, you're going to have the, the CEO of Salesloft on, you know, I invested in Salesloft pre-revenue to watch them dump $8 million of revenue and go to zero and rebuild the company from scratch. Those are great, great learning experiences to watch owner go through like 3 different life cycles since you start. Does it? So I've been through, I'm much more closer. Most investors actually don't even understand how sales or marketing works. So I usually, and I'm curious. So, so that's a piece of it. A side benefit is while not intentional, you know, we have closed, I don't know, 100 and something million revenue of sponsors, sponsor sales at SaaStr over 10 years, maybe close to 100 million plus tickets, but tickets is more selling tickets keeps me a little bit current on email marketing and demand gen because we do have to sell 5 or 6 million tickets a year so that I don't have to fund it all. Um, And then I don't know how I feel about selling to sponsors, but you know, we need 100 to 200 of them a year and it doesn't keep me fresh in the latest tools. Like you're really good at the cutting edge of tools. It doesn't keep me, but it really keeps me fresh in terms of how are, how are buyers thinking about things? How are marketers thinking about things in particular, but also CEOs and founders. So literally being forced to sell $100 million of sponsorships for 10 years, it hasn't kept me SaaS fresh. That's investing, but it has kept me sales fresh. Like I living. You know, every single day we have a scrum with our sales team 5 days a week. So I'm with our little— and our sales team's 4 people. And it is different, but I've spent, you know, 8 years having to— the last 8 years having a daily sales meeting. It does help. It's not perfect, but it keeps you somewhat current, right?

And you're a buyer, which you've written a lot about. You were buying enough tools for SaaS.

Enough tools. Yeah. Yeah. And honestly, to answer your question, I think Being an investor in a bunch of SaaS companies that have done well, but also struggled selling $100 million sponsorships and being the buyer, I would say it's just barely enough to keep me current. Yeah. It's just, and if I wasn't curious, like if I wasn't, had a curious mind, I don't think I could be current. Right. I think you decay in about, I think your, your knowledge of, you know, I think you're lucky if you're like cutting edge knowledge of sales last 2 to 3 years. Right. Um, and maybe your knowledge of the market lasts a little longer, but then it, then it just falls apart, right? Even the restaurant industry, if you worked at Toast 10 years ago, I don't think I'd hire that person at Owner, right? 2 years ago, like the problem is it's a different market and it's too big, but at least they know that 2 years ago they know what's happening, but 4 or 5 years ago it was just a different world, right?

Yeah, totally.

Okay.

Well, let's, we're going to hop right into our 2 major topics.

So, uh, also I will say, I think that, um, having quote operators on your board has pros and cons. Hmm. A lot of cons. Um, everyone can't help comparing it to their last company. If you, if you have a CEO on your board, next CEO, they think it was like their last company. And if you have a successful VC that has only a couple successes, they always think it's like, it's all, it's always like their last company. I remember I was on, I was an investor in a company and one of the investors in Slack was on the board. This company was very enterprise when Slack was all self-serve. And he kept talking about how it was just like Slack at every board meeting and yelling at the CEO, why aren't you more like Slack? Why aren't you doing what Stewart's doing? And I kept trying to tell this very famous VC, like, it's just, it would be great if this company was like Slack, but we're selling like $300,000 to $400,000 enterprise deals with 11 stakeholders, not self-serve deals before Slack even had a sales team. And I just, you just, So that's bad. And then founders, you know, I'm very careful now. I certainly bring a lot of the lessons that I'm learning, but I don't, I don't bring my too many of my old CEO lessons that you got to be careful. And so you are kind of inheriting, if you're doing SMB and you have a CEO on your board, COVC that was an enterprise, you're going to get a weird bit of advice, right? Um, if, and then also there's sort of a deal size and then there's like different burn profiles, right? If you've got Reid Hoffman on your board, He's Mr. Blitzscaling.

Yeah.

Right. If you're a VC that has, for example, their whole career been a seed VC, they may be all about capital efficiency, right? And so you're going to get conflicting advice based on the size, based on capital efficiency. And so I think that initially founders prefer having operators on the board because it feels like them. Um, it's more comfortable. Um, but I'm actually not sure it's, it's a, it's a positive over like a financial VC. I'm not sure it's better.

Okay, that's interesting. And so the two topics that we want to explore today from the perspective of revenue leaders is very much related to this point. One is how do we understand and navigate board dynamics? And we're also going to kick off with a conversation around how should a revenue leader pick the right fit and make sure that there's alignment with the founder that they're joining? Because You've written a lot about this. It's very difficult to find fit and alignment between stage and profile segment. And so we'll, let's move, we'll move around the schedule a little bit. So you get all sorts of different advice depending on the profile. As a revenue leader, how should we be taking in this insight? How directly do you think a head of sales, head of revenue should be reacting to that type of advice from their board?

From a board, once they've taken a role.

So I'm— yeah, we'll start with topic 2, board management.

So, well, first of all, listen, most— again, I think there's 2 types of board members, folks that have been CEOs and folks that have not been CEOs and founders. And I think especially for a CRO, you need to really read the audience, right? Um, the reality is, uh, a VC, a board member that has never been a CEO is always attracted to logo, um, and a deep baritone voice and speaking with confidence. If you came out of wherever, Shopify, LinkedIn, uh, Toast, um, wherever, let's pick our leader, especially maybe a leader that was like 10 years ago, Salesforce, like it's great, but Salesforce is at $30 billion in revenue. They're always up to a, up to a point, they're going to be impressed with that. How pretty your pipeline charts are and your funnel looks. They're gonna be impressed with all that stuff. I think the more they're an operator, the more they just wanna know what your commits are. To flip it around, what are your commits? Just, and I see, and this is why I can, I can smell this in 60 seconds when a VP of sales comes in and their first slide isn't their commits. I know this just, they're not doing well. All they wanna do is, you're a startup. You don't have 2 years, right? Here.

Okay.

They start off. Okay. How was the quarter? You know, and what are you giving? You give yourself an honest grade. That's what a great startup head of sales does, give you an honest grade. How's it looking for the next quarter? And here's my honest commits. They're hard. I got an 80% chance of bringing in ServiceNow. I got a 50% chance here. Um, the mediocre ones don't give themselves a grade. They, they blame others and they have a bunch of random pipeline that makes no sense, but looks really good because there's a lot of logos in it. Just tell me the, you know, commits are, commits are obvious. I, I'm not sure that. When I started in SaaS that just this basic concept was as well known, right? To have a true commit in the funnel for sales. But it is the way all the best sales leaders present. What's your commit? What's your confidence? What's your commit? Uh, and don't run from it and don't run from bad news. And the mediocre ones run from bad news. Don't run from bad news when you present to a board. The one thing to remember, this is a lot what a lot of first-timers, 90% get wrong is, is, um, What a board wants is honesty, optimism, honesty plus optimism, not pessimism, not a Debbie Downer. Um, and they want it, they want commitment, they want honest numbers, but they know that not every week is going to be great. Like they are wired, professional investors and board members are wired for a certain amount of bad news. Too much bad news is too much, right? You lose confidence as you would in someone on your team, right? Someone on your team missed, missed every month for a year. You'd lose a little bit of confidence no matter how much you liked them. But one month is not the end of the world. VCs know this too, right? Board members know this too.

Right.

Um, and the other thing that just kills a lot of first-time VCs, even second, even third or fourth time, the one that really undermines, destroys confidence in the board, and this would be true for everyone, but especially at the board level, um, is unexpected bad news. Hmm. That destroys, that's 10 times more a confidence destroyer than anything else. If you say, listen, last quarter was great. The plan was $1 million. We did $1.2 million, but this quarter is going to be hard. And here's why. 30% of it's me, right? I screwed up. I made a couple of bad hires. 30% of it's seasonality. 30% of it's competition. It's tough. And so we're going to only do $800K this quarter. It's down. That's a hard miss. It's not a soft miss. It's not like growth is slow. It's down. And then what the quarter ends up being $850K or $900K. Okay. Well, I've gotten, I've gotten a great heads up, right? And everyone's like, okay, Kyle. Let's talk about next quarter. Like it's behind us. Who gives a shit? I mean, but when it's a bomb, when it's a bomb, and I just, it's just, you've got to learn this as a revenue leader to telegraph on bad news with a positive filter. Don't be a Debbie Downer, but telegraph it as early as humanly possible, but in a way that, that shows why, if you believe the business has velocity, why it does, like do it the right way, but no surprises. No surprises. And, um, I loved a long time ago at SaaStr, Olivia from Datadog, the CEO came in the early days of Datadog. He came to our first SaaStr Europe and he said something which sounds trite, but honestly, this is the best advice I could give to any, any revenue leader, also founders too. Run toward bad news. I know it sounds like an ism. Write it on your palm in indelible ink and look at it before every team meeting, every board meeting, run toward bad news, run toward it. This is what the best people do. They run toward bad news. Now, a lot of founders run from bad news. It's bad enough, right?

Yeah.

The classic way is when the investor updates start coming later and later, and then they don't come anymore. That's running from bad news. But CROs are even worse at it because one, they delude themselves. They can make it up next quarter or at the end of the year. They, and they commit to crazy backloaded growth numbers that are impossible. Like that's a delusional, that's a, that's a top 5 mistake folks make to the board in general is committing to a crazy plan. To make up for a miss. And two, they almost get paralyzed. They almost get paralyzed with maybe some excessive amount of intimidation and they just start making it up and they don't run toward bad news. The best ones run toward bad news. They run toward it. Right.

I think this was one of the, I put a bunch of messages out to folks to see what they would want to know from a board member, an investor. The two top things were, this topic, what, you know, how do you manage the board's confidence in me as a revenue leader? Because sometimes things aren't going to go great. And how do you— and I think this is great advice for people. It sounds like honesty and optimism. And would you add have a plan to that?

Yeah, always have a plan. And listen, if you need a framework, to present to a board. People have— I think everything can be distilled to one slide. And your one slide is, what was your commit for the quarter? How did it go? Be honest. Don't hide it.

Yeah.

If you came up short, you came up short. What went well? 3 bullets. What didn't? 3 bullets. Commit, actual. What went well? What didn't? Wow. This slide, especially if I see it ahead of time and I can read it, bitchin'. You're already ahead of 90% of CROs and VPs of sales. Yeah. What did I commit to? How did it actually go? Like my goal, my real goals for the quarter and 3, 3 things that went well, 3 things that went less well. I do a GBU, good, bad, and ugly. So I also have ugly. I like to split it into GBU, but you can just do good and bad if you want. Okay. Um, but it's so honest that rather than everything's great, I know, I know we, we set a million and it was $400,000, but everything was great, Kyle. Everything's great. Everything's great.

Yeah.

Everything's great. Um, the first startup I ever worked at, it was the first time I'd ever worked with a professional sales leader, right? He looked the part, tall, this, uh, you know, deep sea diver and offshore wrecks deep at the bottom. And every day I'd say to Michael, how's it going? He'd be like, never better, never better. In the entire year he was there, he closed zero, the VP of sales, but never better every day. Okay. Never better.

Uh, and, and that is where you lose confidence from the board.

It, yeah, you don't. And listen, here's related to it. Listen, if you want advice, way too many VPs of sales and not just first time, second time, they think they need to sell up. They think they need to manipulate the board. They think they need to have. Look a certain way and talk a certain way? No. Maybe, maybe at the IPO stage, maybe. Okay. Maybe. No. If you're a startup or scale-up, be you. Like, start with the dashboard I talked about. What was the commit? How did it go? 3 good things, 3 bad things. Every time, just present it that way. Most with a little bit of a passion, but not emotion or blame. Um, and then have the second, whatever your dashboard is, I like commits, I like this, but have it be your thing. What dash— here's the cheat code. Don't spend— talk to a lot of CEOs these days and they're often canceling board meetings or moving them because it takes too long to prepare. It shouldn't. Your second slide, Kyle, should be whatever your favorite dashboard is. How do you like to work with your team? It's brilliant. Give— that way I can see how you think. Is it a screenshot from HubSpot or Salesforce? Great. Is— do you have your own spreadsheet? Do you have a weird system in Notion? Whatever it is, if you take a screenshot of your dashboard, that shouldn't take more than 5 minutes. Should it? With a few notes. That should be it. That's so great. Okay. This is how he thinks. This is how he thinks.

Okay.

Don't sell up. Don't schmooze. People are— all your board wants you to do is grow as quickly as you can and be successful. You are aligned. It's not a game. And even if it is a game, they're going to see the emperor has no clothes. If you, if you over, if you over, if you claim things that you're not, be you. There are, there are, there are, there are CROs today that are very nerdy and math-oriented and they're almost to a fault, right? There are CROs that are more on the enterprise side that are even today are ultra relationship driven. They're like constantly hanging out with their prospects in person. Like you be you, like there are different sales, it still has different paths to success. Don't, don't act. Well, act a little bit. Like we're all acting a little bit, but don't act more than 10%. Be you. And that will inspire the confidence. Right. And like if you give too much bullshit here, trying to act too much will undermine it. Right. Um, and then the other thing you can't do about is, you know, too much fear. That's the end of it. That's the end of any head of sales. Too much fear.

When, what do you mean too much fear?

Look, startups are hard, right? And even when they're easy, they're hard because even when they're easy, the bar goes up.

Yeah.

Right. Or they're either so like, and in some ways the hardest job of all is a head of sales because, you know, it's, it's tough to be an AE, but your quota might be the same for 5 years. But your quota goes up every year, every quarter. As a VP of sales, your job gets— if you don't recruit better and better people, your job gets harder and harder each quarter. So it's hard and everyone knows it's hard and everyone's trying to watch, okay, can Kyle make it to the next level? We just want to know. There's no judging. Everyone wants a lot of the early stuff. A lot of, a lot of angry VPs of sales on LinkedIn think everyone wants to fire them. All these CEOs, nobody wants to fire anybody. I can tell you what owner, all people want is Kyle to get us to a billion dollars in revenue. No one wants anything else. That's all. Why would you, why would you want anything else? Kyle's done a good job. Why would you want anything else? Why would you? Like people, people read these irrational things into it. Um, but what you are looking for is when it gets harder and harder, like, okay, let's say, let's say Kyle joined, say you joined owner at a million. I don't know when you joined. Okay. And we're at 20 something today. And so yeah, Kyle, Kyle was very confident going from 1 to 3 and then 3 to 9. And then. But when sometimes you see that fear and you start hearing, well, I don't know, going from 20 to 30 is really, that's, that's a really big number. And in fact, in SaaS, a lot of times you're closing more each year than all the other years combined. You have to do as much work in sales this year as every year combined. And so if fear eats at you too much, you'll, you'll, you just can't do it. Right. So we are looking for fear. We are looking for fear.

I think the fear piece is rampant. The one of the questions I got the most was, well, revenue leaders are always on the chopping block when things go wrong.

It's, it's, it's not true, Kyle. It's just not true. But keep going. This is, this is what I think is one of the biggest disservices on LinkedIn and social media is this idea that revenue leaders are on the chopping block. It is not true.

So explain this from the board person's perspective, because I love this. I love this point that you're making.

Let's step back for a minute. I know, I listen, don't get me wrong. Most of the best, especially first-time VP of sales, not all, and I'll give you some stories about many of the best did get chopped. Okay. But often, first of all, often they got chopped after they got topped and they got huffy and they got quit. They quit when a CRO or an SVP of sales was, was brought on top of them. Many of the best ones I know who think they got chopped didn't get chopped. They talk about they got chopped, they got topped, and that's a different topic.

They got topped and then disgruntled and then eventually had to be moved out.

I think half the, the great stretch VPs of sales, the great ones, it's their first time as a VP of sales. They're, they're such passionate folks, these first timers. They're not machines, right? They're not mercenaries that it's tough. They do quit half the time when they get topped. It's hard, right? And, and maybe half the time they quit and another 25% of the time they almost quit. Yeah, right. They almost quit. So, but that's not the same thing as getting fired, is it?

No. And I think a lot of this comes from giving people titles and saying you're the head of sales and you, that person gets it in their mind that they are the top of the chain forever versus having an open conversation about, hey, we're going to see the founder having an open conversation and saying, hey, we're going to see how far you can take this. But this business is 5 today and is going to be 20 in 24 months. And you might be able to keep up if you're a super duper learner, but if not, it's still an incredible victory. And then we're going to bring in somebody that you can learn from.

But I think that's the right conversation. I think what CEOs don't do that they should do— I wrote this post not that long ago in Saastr, but I should have rewritten it like 11 times. If you're going to have that conversation with your stretch VP of sales, okay. Then you have to decide if you want to say something at the end, which is, listen, I don't know where it's going to go. I want you to go all the way, or I don't, right? If you can't, we may need to bring in a CRO or someone at the next, next stage. But no matter what happens, you have a job here forever.

Performance.

I know that, that when you say that to people at the time, it doesn't, it doesn't really help. It doesn't take, if there is a sting, it doesn't take the sting out. Okay. And I know, but I think this is a really important thing to say nevertheless. It's like, listen, if you, you have done such a great job, Kyle, I don't, I mean, I'm making this conversation up, but let's say I was the CEO of Owner. We had this conversation like, you've done a great, like, you're a 10. You are a 10. I'm being objective for the listeners. You're a 10. And I don't know that I would have that conversation because you're SMB, which we could chat about. Cause I think folks in SMB can scale longer, but let's say we did have that conversation. Kyle, you've done great, but I don't know if you're the right guy to be our CRO at $200 million. But whether you are or aren't, I want you to be one of our senior leaders on our revenue team, period. That might not make you feel better, but it's the right thing to say if you mean it. Because then at least this, this LinkedIn mania of I'm going to get fired. I'm telling you, Kyle, if you can trust me, you're not getting fired. You may quit. You may go on to another company, right? You will not be fired on my watch. You've earned a spot here. And like, for example, the third investment I did is a company called Algolia, which is a search as a service API that hopefully will IPO in the not distant future doing a couple hundred million. The first head of sales, Gaten, he just left 2 months ago. He joined in 2014. Now his role changed. Head of sales, CRO, chief business officer, chief strategy officer. I mean, he hasn't run sales since it was like the post-founder sales level, but he always had a senior role. That's what you want. The last thing, listen, you know, Adam and Dean asked my opinion, but if I were running owner, no matter what, I don't want you leaving. You know too much about how this company works. I'm gonna find you a role. I hope it's CRO. If later it's Chief Strategy Officer or Chief Business Officer, or maybe you're GM of our SMB unit or something. Jameson, our old team, our old sales team at EchoSign, just left as SVP Sales at Gong after I think 8 years. He was the first sales hire.

Yeah.

Now I think there were like 2 or 3 CROs hired above him that maybe 1 or 2 might've come and gone and his role evolved, but he made it 8 years through all the way through SVP Sales. They kept him running this. Classic mid-market motion all the way through a couple hundred million in revenue, right?

Yeah. And massive victory for him, massive victory for the company. Like that's—

Yeah. So realize it's not that simple as getting fired. If you decide if— does your CEO believe in you? Have this conversation. And if you're a CEO, tell someone in— because there is this paranoia in sales that I'm gonna get fired. It is a paranoia. Tell— I'm not saying it's gonna work that day, but you gotta tell people you love them in life. And you, if you love your CRO, you got to tell her, him, you love them. You got to tell them no matter what, you have a senior role here. I don't know what the senior role will be at $100 million and $200 million and a billion. I don't know for sure what your senior role will be at a billionaire, but if you want to stay, you are part of the inner circle.

That's a great message. I love that. And hopefully this can help put to bed some of the fear that is definitely rampant in, in these roles and will prevent people from. Ego quitting? It went when?

It's accelerated the ego quitting. It just, it doesn't help. And I think people are just eating themselves up in their own heads and their own minds. And listen, I just, you know, whatever the statistic, the average, now CMOs are different, but for CROs, the average CRO makes it 14 months or 17 months, whatever your number. This is where averages are misleading.

Yeah.

You know, and listen, the other thing that is misleading is that, Like that somehow today because of layoffs or whatever, like it's so easy to find great people. No frigging way. It's impossible to find great people. Yeah, you can't. It's harder than ever. Most people don't want to work. Most people want to be strategists. A lot of people are angry and burnt out. It is harder than— it is easier than ever. Just get 1,000. You can put an applicant, you can get 1,000 AI applications in an hour if you want. Finding someone that wants the job, it's still only 1%. Mm-hmm.

So done the research, prepared for the call. Yeah.

If you're one of the, if you're one of the handful of leaders in a startup that truly cares about the mission, that cares about for real, that cares about the company, which is rarer than ever, the best founders never want you to go up to a point, up to a point. They never want you until unless you become a problem. They never want you to go. They never want you to go. So these numbers are misleading. No. And a good, a great CEO knows, hey, shoot, I file, I fire Kyle or Sam or Brendan. I fire them. I better fucking have someone better than Kyle right next door. How many of them have someone better?

Yeah. Yeah.

Right. So yeah, it does happen. CEOs, like you miss the number, you miss the plan and they fire the revenue team. I, and I've written this, I find firing the entire revenue team because you miss a number rarely an effective strategy. Rarely. Rarely. In fact, it often for a mediocre CEO, it often leads to a death spiral of a start. It's a start of a death spiral when a mediocre CEO fires the whole revenue team.

I hate to see it.

Because they never replace them.

Yeah.

There's just nobody.

Yeah. And so from the board's perspective, when you see struggling results, because I think the tension is always how much is the product doesn't have as much fit as we thought versus this revenue leader doesn't have it. How do you untangle that?

Okay. Never say this as a CRO. Never, ever, ever in public blame the product. That's when you're going to lose your job.

Okay.

That's a sign of a loser CRO or VP of sales, a loser one, because anyone that's been around knows that every product has weaknesses. Everyone has competition. Everyone has gaps. Sales is hard. And what's the simplest excuse? What's the simplest excuse in sales? What's the easiest one to come up with?

People don't want the product.

Product sucks. Yeah. They don't like, Yeah, if you had this feature, we could have closed Exxon or whatever, but we don't. It's a sign of a loser CRO or VP of sales is blaming the product. Doesn't mean there isn't truth to it. Mm-hmm. It doesn't mean in quiet moments, the management— you should have discussions with the management team about what you want. If you really believe the product sucks, you should leave. Mm-hmm. Like if it's really below, below a certain line, you should leave. But whatever you do, do not blame the product. It, it just, it nothing makes a CRO Listen, lying about the numbers is pretty bad. Missing the quarter is pretty bad, but just railing into the product, it's like, um, not only is it like railing into your children or your aunt or your parents, or it's just, I know that I would, I would immediately pull the CEO aside after the board meeting and say, listen, you got it. You got you. It's not going to work because if they've lost confidence, you're, you're, it's, it's a version of fear. It's a version of fear is blaming the product because it's true. It's the ease, but it's the easiest excuse.

Mm-hmm. You know, and there are situations where the product doesn't have or has fallen out of fit. And for sure. And in that, that's part of the startup journey though, is there's always competition.

You can't win. Part of being, part of being a great revenue leader is understanding your relative strengths and getting really good at your rel— where do we win?

Yeah.

Let's lean in really deeply where we win.

Okay.

Now, and then the great ones say, okay, where do we lose, but not always lose? Okay. Let's find some FUD. Let's find some counterfud. Let's find a script that, yeah, okay, listen, we're actually not that competitive in this segment of the market, but our product is easier to use. So let's just friggin go to that.

Yeah.

As great as this competitor is. Yeah, I know they have 80% market share and we, and look, people do love them, but it takes 3 months to onboard and we can get you going today. You're going to win some deals with that lead, but it's so easy to turn around and say, We can't win. Like our product's not good enough. The best revenue leaders productize. Not only do they productize where they have a competitive strength, then they productize where they lose a lot of deals, but still win some and then maximize the revenue they can get out of them. The mediocre ones lose all of the second tier and just say it's product market fit.

That's great insight. And so I think the fear is like a sports team that's struggling. The GM lets the coach go and the VPs of sales tend to feel like the coach and maybe they don't have the fit or the plan made no sense and they're the scapegoat. What's your commentary on that as a board member?

Sorry, restate the question. If, if, if what, when the CRO is the scapegoat?

So yeah, I think that's the, that is where a lot of the fear comes from. It's like, well, we're not growing fast enough because my VP of sales isn't good enough. So we're going to replace him or her. And it might be a product fit issue or the plan.

Well, look, of course there can be truth here, right? And all but the great CEOs sometimes are looking for people to blame too. And all but great CEOs sometimes will blame the CRO, the VP of sales. They will. It will happen. I haven't seen the great ones. I know people are going to challenge me on this. I haven't seen the great ones do it. In fact, The great ones sometimes overprotect their revenue leader. They protect them too much. Hmm. Okay.

Interesting.

So stick with Kyle. I know he's right. I know the first couple of months have been rough. He knows what he's doing. He's doing the right things. Back off. Back off, Lemkin.

That makes sense.

They are protective because they know they need that. Like, this is it. Like, I don't know if startups are truly fun, but there's a— they're very, they're very involving, right? There is a fun element in it and it's a team sport, man. And you gotta protect your team, don't you? You gotta protect your team as the CEO. And if you start throwing your team under the bus, you can do that, but you, the good CEOs know that it's extremely costly, right? Yeah, it's extremely so, so this mythology that all these CEOs go to their board. Here's the other thing. Let's tie this together, Kyle. People, your board is important for a variety of reasons. They are not important in the way a typical VP of sales, CRO thinks. They're not important in that way. They don't run the company. They don't make the decisions. And in fact, you know, in the old days, like, I, you know, I think, you know, when Sequoia invested in Cisco, I think they threw out the first CEO and brought in another CEO. And yeah, when Kleiner went into Google, they brought in Eric Schmidt. We don't see that anymore, do we? Rarely.

No, you can't.

A little bit. Not only can you not do it for control reasons, it's not even part of, except for some like PE funds and crossover, it's not even part of venture DNA anymore. You know what happens? If an owner doesn't work out today, you know what happens if an owner didn't work out 10 years ago? Someone lost their job in venture. You know what happens if owner doesn't work out today? You move on. Okay. So, so like, don't, don't give the, if, if more than $10 million has gone into the company, take the board very seriously because that's real money, dude. It's real money, but they're not, they're not really forget about the, what? Yes. Legally they're the boss of the CEO, but that's about it. Treat them with respect, treat them as stewards of capital, treat them that way, but don't, um, but, uh, they're not making these grandiose decisions on whether you stay or go, but, but they will talk about you, like going to the point when, when the, when the closed session starts, this was my next question. So take it. The first thing that is discussed is the management team. There's no point in talking about the numbers because everyone's already pre-talked about the numbers. They've seen the deck. They already know the numbers, right? If there's something weird in the numbers, it'll be the first thing that's discussed. But actually, when the, when the closed session happens, we don't talk about the numbers. We talk about the management team. That's all we talk about is the management team. It's half of it. And others, and then other stuff, the management team. How's, how's it, how's it going?

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And what are the big questions that you're asking there? What are the things that you want to understand?

Actually, the board generally feels like they have seen enough rodeos in enough, and they may, they're often wrong because every company is different, but they've seen enough that they can, they know whether who on them and what the flags are on the management team, what the flags are. Kyle, listen, Kyle did a great job, but Adam Dean, let me just tell you, he looks spooked today. That's okay. We love him. But let's imagine we're going to— it's the third board meeting in a row Kyle's looked spooked. I'm worried. That's what I would say, right? Or for example, the other one thing I did say, for example, I think when the company was— when owners coming up on $10 million, I think the first thing I said in whatever closed session is, yeah, wow, Kyle's really coming into his own. This is really like, When he joined, I thought it might be a little early for him, but you were right. Like, he's really like, he has the skill set. He knows how to do the outbound. He knows how to do the onboarding. He knows how to work with the size customers. He knows how to deploy these pieces. Like, he's got the toolkit as you approach $10 million. And it's like, I think I said that it's not like this. It's like, it's really, it's elegant. Um, and inspiring to see that toolkit actually working, right? For someone that, you know, I forget where he came from, but you were at Shopify. It is a big company, right? So, you know, I really liked you when I interviewed you, but I'm like, I, there's a chance you're too early for him is what I said to Adam when he, when he interviewed you. I didn't know that.

He said that to me too. You, you were honest about it. Yeah.

But I literally said whenever that, whenever we came, maybe it was $8 or $10 million or whatever, but when the close session got, that's the first thing I said. I said, Kyle's really coming into his own. But that's what you talk about because at some point, you know, all that matters is the team. Once you have product market fit, it's actually all that matters before product market fit. It's just the founders, right? And then you have product market fit. And you can talk about even competition doesn't matter because the best teams will out-accelerate the competition and the mediocre teams will fall behind. You don't even have to talk about competition. You don't even have to talk about market dynamics. Nothing really matters after product market fit than the team, right? You'll either accelerate product market fit or decelerate. And so that's, and whether the board can add value recruiting, they generally can't. Um, but I do think 90% of board members know if an executive is performing above or below the line, and that's what you talk about.

Yeah. Okay.

Right. And most, a lot of times founders are pretty blind to issues. If they're first-time founders, they're often in love with logos or other things they've been oversold. Um, and, and then second-time founders, um, can just be too attached to folks either that they worked before or that have very late-stage skills. And so I do think board members can provide— the number one thing they can provide feedback on is how the management team is doing. So you are criticized. Bear in mind, CROs and CROs and other people listening, you are. You are judged behind closed doors by the board. Um, but it's not necessarily a bad thing. They do know we've seen 20 Kyles. We've seen 30 Kyles. There is some, there is some, you can start to pattern match after 20 or 30 Kyles, maybe not one you can't, right?

And you want it to work out. I think that's the thing.

That's the thing that the angry, the angry LinkedIn Aussie and Twitter Audi don't get. Of course you want it to work out. Yeah, of course. Now there's a, at the margin, and I, I'm pretty guilty of this. I'm pretty bad at this. This. When a CEO hires someone that I know is a disaster, I do have a little bit of I-told-you-so-ism, not because I want to win. I don't give a shit about it, but I want, sometimes I got to say mercy. Okay, listen, Kyle, whatever you do, don't hire this director under you. I've worked with him before. He's terrible. He's unethical. He's terrible. And you make the decision anyway. Okay. Then I'm going to provide you fairly pointed feedback because when you realize I'm right, I want you to make the decision faster. That's all I'm trying to do. I want you to make the decision faster. Because if you can decide that was a mis-hire earlier, that's not only better, that's so much better for the company to move on quickly than later. And it's actually better, even though the candidate doesn't think it on LinkedIn, it's better for the candidate.

Yeah. And you've said, you've said, uh, hiring is not the most important thing for startups. It's mis-hires.

Well, hiring is more important, but second, but if, but helping folks identify a mis-hire is a, is a high value add.

Okay.

Okay. Because you're lucky, you're lucky, you know, you're lucky if I was just rewatching an old SaaS session with, with Dev, who's the CEO of Mongo, who's a classic operator, multiple companies and a partner batteries. Like if I'm lucky, I get 60% right. Yeah.

Yeah.

He's, this is Dev. If he's lucky, he gets 60% right. So maybe 50% is a good goal for the rest of us. So I actually think you can do a lot better as a founder. I think you can approach 80 or 90% if you get enough help from your, from advisors and mentors and others. This is why I'm kind of annoying about it, because I know I'm usually right on this stuff. But then if the decision's wrong, I do want to be a nudge so that you just decide a quarter earlier.

Yeah. Which is massively impactful. I mean, I do think VCs can be a strong talent attractor. I know for me, having read your stuff for years and years and years, the fact that I would get to be involved with you was a big thing.

It may be over-indexed on by revenue leaders, but it is a talent attractor, right? It is a a talent attractor for sure.

Yeah. Well, I think these, there are some really great reframes even for me personally, our first board meeting. So this is a story that I like to tell, but never really told you. In my first full month at Owner, the results were worse than the month when I started. I was cleaning up a bunch of bad deals. I had to let 2 of the 4 reps go. We were just trying to upgrade and move to our next level of sophistication. My second month was worse than my first month, and then we had a board meeting and we had seen a bunch of leading indicators now all tracking the right way. Deal quality was up, the size, the pipeline velocity was increasing. I felt good with the direction we were going and presented it in the board meeting. And your feedback was, those are interesting metrics, but it's not revenue. So let me know when it's revenue. And let me know. For me, having been a long, long time reader, I sulked away from that meeting feeling terrified because I had read your article, your post, if your VP sales hasn't done anything in 90 days, they probably will never. And I think that is a sense that is felt with many revenue leaders. And then since the numbers started to go the right way and we that confidence was found. But I think this is a great message for folks to understand what's happening behind closed doors and understanding the board wants it to work out and they want it to work out.

And listen, just to be helpful to folks, that's good feedback for me. As time has gone on, I'm not sure this is a pop. It may be a negative attribute for me. I am much more direct than I used to be. I used to just sit there for month after month after month and just watch. I'd make one, I used to make one comment. Um, I'd be like, Kyle, I might've been back in the day. If this was like 10 years ago or 8 years ago, I might've been like, Kyle, that is great. I'm so excited for you. Um, pipeline isn't revenue, but everything looks great.

Yeah.

Like that's what I would have said, AJ. And I would have watched. Now I'm like, it's not, it's, it's, it's, it's out of respect, but I don't, I just provide the feedback and you don't, and now I don't care. Don't listen if you don't, I'm just one guy. You don't have to listen to me, but I'm much more direct. And you should be wary that, yeah, when you work, part of it's just me and maybe I should try to reset a little bit there. I feel like I run out of time to do it. Right. Yeah. You value it. Okay.

I value being direct because then I know where people stand. I would much rather operate from that.

You do. But you also said it was a bit of a shock to hear it at the same time.

It was.

Here's the thing, Kyle, only 5 or 10% of folks can take tough feedback, especially in today's world. Um, but, um, maybe the meta takeaway for folks is just realize this is a good— it's a good story. Realize for a variety of reasons, when you interact with a board or investors, you may get a type of direct feedback you're not used to for a variety of reasons. Some folks just become surly at a certain point in their career in venture. I mean, literally, I was on Twitter yesterday, I wrote this tweet that got over 500,000 views, and this famous VC just wrote that literally must be worth over a billion dollars. And we could figure it out on— he just wrote the snarkiest tweet, the snarkiest tweet. And it's not that he's really smart. It's not like there was some truth in his snark, right? I'm like, why? Just go off and buy a sports team or like enjoy your Ferrari collection. Why sit on Twitter and be snarky to me just trying to help people? So realize you may get some of that and, and try to just find the truth in it, right?

Yeah.

And don't even argue. There's not even any point arguing. Just hear the truth in it, right? There may be some truth in it. And if there's not truth in it, just talk with the CEO and just get aligned on the same page. And just then just come back and present a picture at the next board meeting or in a follow-up email. Follow-up emails are great. No one does them. And just present the picture you want to present.

Makes sense.

No one does it. Everyone says, oh, everyone got the board meeting. Kyle will be like, not Kyle literally, but Kyle Brown will be like, great point, Lemkin. Uh, I'll send you, great point, Jason. I'll send you a follow-up email on, on how we segment churn. You know how often I get that follow-up email? Like nuns. Nuns. Interesting.

And you're, so you're okay with a revenue leader then doing direct communication and feedback with you? Like what's, what's the level of direct interaction you're comfortable with? Because I think a lot of, I don't think so.

I think you should be very careful. Okay. There's a different point, I think, and this is, um, every once in a while I get a question on LinkedIn or even in the old days on Quora. My CEO is running the company into the ground. Should I go talk to the board? No, you should quit. You should quit. Uh, this is not— the CEO is the bet, 50% of the bet when investors make it's 50% of the bet. It's not 100%.

Yeah.

I mean, for some folks, inception-level betting really early, it's 100%. Even though it, even when it's inception, there's still a seat, there's still more than one founder usually, right? So it's usually multiple people, but, um, you're betting on the CEO and and as difficult as it is to change out CROs, it's 10 times harder to swap out CEOs. It's so risky. In my, in my personal career, I've never seen it work. I've never seen swapping the CEO work.

So most VCs are just going to zero it out.

They've kind of given, now listen, there are companies that are highly orchestrated, Snowflake going through multiple CEOs because that was incubated at a VC firm. It was actually started at a VC firm. But how often do you see even a CO change that isn't an intentional resignation, it's just so rare these days, right? So be careful about, for any management team, be careful about even inadvertently going over the CO's head, especially if you have concerns. Suck it up and move on. If it wasn't a fit, you know what, it's on both of you. We could talk about, but if you don't trust your CO, if your CO is a bad person or anything coming to the ground, that's on you for not having good especially a CRO has to be, has to have a good eye for talent, don't they? Yeah. It's totally embarrassing if a CRO can't figure out if the CEO is ethical or trustworthy or believable, because that's your job. You're supposed to hunt, sniff this stuff out, right? So if you screwed it up, just say thank you, give 30 days notice, not 3 hours, and just leave on good terms and go get another job. Don't, don't ever go over. There's nothing in it for anybody. And it won't work out for you if you go around someone's head and talk to me. That's different of how to communicate with a board. But if you went around Adam's head or Dean's head or someone, I would immediately, I might cut you a little bit of slack, but mostly I would lose confidence. It's just not because I'm betting on the management team. I can't run the company. I just can't do it.

That's also great insight for folks. I think that's a level of clarity that is helpful for people.

So many LinkedIn posts is my CEO was an idiot. My CEO was a moron. They're really, then, oh, first of all, are you not to blame for like, maybe, but you didn't figure that out. That's on you. Then to just leave. Life is, life is not short, but here's the thing is if you're committed, if you really want it in this world, whatever level you're at from CEO to zero down, you get another chance in this world. It turns out there's no karma. If there's, if people treat you badly, if they stole your stock, if they lied, there's no karma. They will probably go on to be successful. There is no karma, but it is, there are only, there's only so much talent in this world. There's only so many ideas. And if you, if you're good, you will get another chance. You'll always get another chance. So just go find your other chance.

Yeah. An abundance mentality.

It's true.

Um, how you doing on time?

If for some reason, listen, even for you, if for some reason Owner doesn't work out and it better, I want you to stay forever between me and the other board members. We could give you 50 opportunities in a week, right? So invest in that, right? Don't go on this angry, angry Debbie Downer, angry pit of LinkedIn. It gets you nowhere.

I have personally railed against the Debbie Downer LinkedIn. I'm in such agreement. I mean, humans, obviously, we're hardwired for a negativity bias. That's what is wrong with so many of our algorithm-driven platforms. And so I'm very much in agreement, like, trying to find The good instead of the bad is just such a, such a better way to operate as a person.

Yeah. Um, but, but, but, but realize, but, and just to finish the CRO thing, you are being talked about every board meeting. You're being talked about behind closed doors and you are judged. But here's another point, just so you know, everyone wants you to succeed. That's what LinkedIn gets wrong. Okay. Everyone wants you, everyone wants you to go to the distance, but you were judged before you started when everyone interviewed you. And then you're judged after each board meeting and the CRO is the most judged of all. Yeah, it just is.

Yeah. And your investors are not the bad guys who, you know, invested too much money intentionally and forced this company to take this path. There's so much blaming in the market of, oh, this CEO is a bad person because they had to do a layoff. The CEO, the macro conditions changed faster. Than ever in the history of banking policy in the US. So a CEO's just reacting to the game on the field, and that doesn't make them a bad, bad meanie.

No, there's elements of truth in it, right? There's always hints of truth, like maybe the VC's overfunded you, maybe the CEO shouldn't have, but mostly it was done for not the wrong reasons, right? And then almost, and then no one cares. It wasn't done out of malice.

Yeah.

No one cares.

I want to do a couple quick fires. How are you doing on time?

I got as much time as you want. Okay.

All right. I want to ask one question about how to identify alignment ahead of time, and then we'll get into quick fire. So, yes, you are selecting the CEO, and I think your advice on you've picked that person, don't go over their head is great. Uh, so what are the biggest mistakes that revenue leaders make when choosing an opportunity, choosing a founder to partner with, and how could they better make those decisions?

You know, it's such a good question. I was, I was literally chatting yesterday with a CRO I've known for many years since, since he was at Earth, and I sent him, just like if you stay in the game, I sent him two great opportunities over the last six months. Great. Not perfect, but great owner, great opportunities. He passed on both of them. In fact, he wasn't even willing to meet the CEO. Yesterday he sent me a deal, which, and I can tell you this company, and he asked me what I thought about it. It's good. Like, it's a good one, but it is not as good as the other two. It's like 30% worse. It's still like, this is a good job. Like, it's a great, it's a great, but I didn't send him the junk. I sent him really good opportunities. He wouldn't even meet with them. He found, he found the objections. This one isn't really what I like to do. The other one was too enterprise or too SMB. I can't remember. The first one, he's just, he's not passionate about the space. I mean, who's passionate about any of this crap? I mean, I think I was passionate about selling signatures or about selling sponsorships to events or like restaurant menus. I mean, the passion is the journey and building something great, right?

Yeah.

So my point is this guy who had all of my benefits and all my wisdom is still going to take this one that's worse than the other two. This is someone who's been around the block. I see this again and again and again and again. Again, is just so many CEOs and VPs of sales, they're shooting from the hip. They're misusing their lens and experiences and trying to judge things the wrong way. It's hard, right? So I don't have all the answers, but I can tell you, like, this— assume, unless you've been really around the block and you know exactly what you're looking for and you're sure this is the next whatever, because all the boxes are checked, right? Um, do it, but at the very end, and, and, and I might've done this with you during the interview process, find a way to slow it down and get more information. So for example, this company from the other day with the CRO I love, they gave them all the financials, but didn't quite give them all the financials. Hmm. Why do you think they didn't give them all the financials? They were sort of giving them the financials.

There's something there.

Yeah. I mean, come on. Like I couldn't, it's like, what do you think of this company? Well, I can kind of tell you what the top line revenue growth is. And I can tell you what it's burning, but I can't actually tell you how this complicated business really works. And the fact that it's not clear, it's, it's, this is something you should just learn in your process. Right. Um, and it's just very hard for, there's such an asymmetric amount of information. Right. So, um, what I personally try to do, which is only somewhat helpful to your audience, I don't know if I did this with you, but I do this with almost every executive. What I try, I like to be the, the, the one of the last interviews. And I ask him, Kyle, you've, you've, you've, how many interviews have you done? 10. Oh my God. And 4 with Adam and 6 with Dean. I'm like, okay, tell me what you've learned so far. And that sounds like a fishing question. It's actually not a fishing question because I want to learn what you didn't learn that matters. And then I tell the client every, the, the, I mean, not the, the prospect, the candidate, not the client, the candidate, everything I know that they didn't figure out. It's, it's usually a lot. It's, I'm usually shocked that by 10 interviews in, they don't know a couple fundamental things about the company, a couple fundamental risks. I feel like that's my job. And once in a while, the CEO will get mad at me for this. Once in a while. Um, I love Adam, but he did get mad at me in the very early days when I did this with one candidate, very, very early days after I interviewed. Um, and I, I, there was a candidate, this is before you started, and he really wanted like a really extensive training program at the company. And I asked him, do you know what the training program like an owner with 8 people or 6 people? He's like, I don't know. I'm hoping it's really extensive. I'm like, you know, there's no training program. And he got pretty mad at me. Um, but I think I, hopefully he would say I saved him from a mishire, right? Because he didn't know there wasn't a training program. He didn't know there wasn't a training program. Right. Um, a lot of times there's just so many things. And so, so The fact that I can do this with so many candidates after 10 interviews, I don't know the answer. Slow it down. Talk to a mentor or two. Ask for the last— so many folks don't have the last board pack or the last, or if they, or if the, the CEO feels like after 10 meetings, they won't share the board pack with you, like under NDA or like in a DocSend, then at least share the company meeting pack. If they do that, share. You're shocked that people don't even— so many CEOs don't even know what, what the data that was in the last board meeting. Why would you join a startup if you can't get access to the last board meeting when you're going to be liable for it in 60 days? Right? So try, just find a way to get, and, but, but you don't have to be pushing the first meeting. Like use your, your life experience and your spider sense. And then, and then this is the exercise I try to do. I try to almost, and I tell CEOs to do this, give Kyle an offer letter, sign it, and tell him not to, to countersign it yet. Then sit down and say, Kyle, what do you want? Here's your offer letter. Does it look okay? Is this what we agreed to in comp and title and everything? Are you cool with it? Yes, Jason or Adam, I'm cool with it. Okay. Before, don't countersign yet. Tell me what you need to know to truly believe is the right opportunity. Not enough folks do that on either side, but find a way to do it before the end. CEOs are get, especially the really driven ones get, once they, once they find that candidate, they become heat-seeking missiles. Like the Adams are great. Like he's a heat-seeking missile, right?

Yeah, for sure.

And so I know it's, find a way to like participate in that process. But if you don't know fundamental things, it's okay to ask. Not enough CROs. CROs you think are the most pushy, outgoing people, but also sales leaders have trained their whole lives to, to find that line in any deal, right? To not cross the line. You cross the line, you blow the deal, don't you?

Right.

You cross the line, you blow the deal. And I think maybe that's why they're not as good on the diligence process and recruiting as they could be, because they're very sensitive to crossing the line.

And salespeople are in general optimists. You can't do this profession unless you think that the next thing can close. And so I think we as a community get happier. And so just try to get the last board pack or company pack.

Just try to get all the data. Try to get as much. Here's a fair— at the very end, if you have to wait till your offer letter and say no more games, I'm not going to play any games, I don't need any side letters or anything, I just want to know as much today as I'm going to know in 30 days. Yeah. And a different version of this, the one of the, it's not quite the same, but the best diligence question I ever got from a VC as a founder years ago, my first start, I got the best question ever from any VC. Best question ever. Sat me down. He'd given me a term sheet. I hadn't signed it yet. We hadn't signed it. It was just draft. We had breakfast at a diner on the weekend and he said, Jason, tell me what I'm going to learn at my first board meeting that I don't know today.

That is good.

It is good. That you need to find that out as a CRO or an executive too. But before you sign your offer letter, be as educated as you will be 30 days into the job. It's a fair ask of the CEO, even if they're cautious, even if they're worried, whatever. Some people, people get too paranoid. People think so much stuff's confidential, which you can just find on Google. So be it. Don't, don't cross the line. But once you get the offer letter, just sit down and say, I just wanna know what's there. And. If, if, if this is going to be someone that's going to have your back for years, going to the start of this conversation, if they're going to have your back for years, they'll share it all with you. If they're not going to have your back, they won't share it with you.

Hmm. That's great.

Okay.

Rapid fire, and then I'll let you go.

Okay.

What is the best piece of advice you would give to a CRO starting at a new company? They're getting their bearings. They want a fast start. What's the best piece of advice for them?

You got to start with, we got to start with two hires already in your back pocket that are great. Otherwise, you're not ready for the job. Not enough time. It's not enough time to go find 2 people, hire a bunch of recruiters, and interview a bunch of random people you've never worked with. Maybe it wasn't true of you, but I gotta tell you, I've never worked with a great sales leader that wasn't constantly recruiting a group of folks under them, and they want to go to the next job with a small team, at least to start. If that's not, if you do not have 2 people, you're not ready. Maybe the great IC, maybe you can join as a director somewhere, inherit a team. You're not ready to be a head of sales.

Makes sense. What do you wish you knew as a leader that you've only come to understand much, much later? If you could go back and give yourself advice 10 years ago on the leadership front.

I was lucky my first two management teams, the core teams were so good that I didn't know what mediocre looked like or merely very good. I didn't get spoiled. I got confused. It took me a while to really see what everybody knows that's been in the game a long time, which is even hiring a B+ or an A--, it's just push on. Don't make the hire as painful as it is. Don't make the hire.

And it is painful sometimes to have that headcount open.

It's painful to have it open. But you know what's more painful is literally digging the hole out in 6 months.

Yeah.

Yeah. It's so painful. And when you hire, the hole is always deeper than you think. Everything is true that they hire the Bs, hire Cs, and Cs hire Qs, and Qs hire Zs. Everything is true. And we all get tired. And we all lower the bar and it was a bad idea pre-2020. It's a worse idea today when we, the market is flooded with, um, we, we were just Amelia that runs Saastr and I with you. We were just, I just had talked to this great CRO, sort of CRO, CMO, you know, weird hybrid, but, but she'd done very SMB where you can kind of overlap too. Very intelligent, knew Saastr, loved it. And, um, it was a right kind of a good, good phase in her life where maybe she wanted to do something different and could work on this community. In the end, she's like, Yeah, but actually I only want to work 14 hours a week.

Okay.

So, uh, I'm not exactly sure where I went to the story, but you just don't lower the bar. There's what I mean by that is there's so many ways to lower the bar today. So if you, you know, so just, just have the gap on your team. That's the number one thing. Have the gap on your team and you've got, but the great leaders still find a way to fill it, but realize there may be a multi-month gap, which is brutally painful that you have to do yourself.

Yeah.

Right. The bandaid never— there is no bandaid. There is no bandaid in leadership.

No.

Maybe that's the lesson. There's no bandaid in leadership.

And it can be personally tormenting to have that spot open and get to the end of a process and not have that individual. I had to go through this 6 months ago. We went through the whole entire process. Didn't have a pick and we started from scratch again and found somebody incredible. This was the exact person that we were looking for from the start. It took me a full extra 90 days and wasn't fun. But yeah.

And if you're not a great recruiter, it could be an extra 180 days or an extra 270 days. Yeah, brutal. But a Band-Aid is worse. Yeah, there are almost no effective— this is why I'm so— I do believe there are There are a time and a place for some fractional assets, but not as band-aids. As augments, it works as little bits and pieces, little hints, little flakes. There's a role for a fractional, but as band-aids, they all want to be band-aids, but it doesn't work. They don't, they won't own it. Band-aids don't own it.

What's the hardest lesson you've had to learn?

In all the whole career?

Yeah.

I think the hardest lesson to learn, um, uh, is that almost no one cares. And, but you gotta, but when you find someone that actually cares about you in tech and whatever, just, just try to work with them forever if you can. Not people are not out to get you. It's through this conversation. They're not out to fire you, but really nobody really cares, right? They don't care. There is no karma. There's no nothing. People that have treated me poorly over my career for the most part have done extremely well. Successful people that have, that have stolen millions of dollars from me, that have done very unethical things, that have signed documents they weren't allowed to sign. That have done so many things I really don't want to talk about. They've all, they have had no karma. They've just gone on to be more and more successful. No karma. Um, and, uh, it's tough because when you, when you, this whole, the whole startup thing is built on trust, right? You can't have enough information. The teams are too small. You have to have trust. And the longer you go on, the more amazing experiences you have, but also the longer you go on, the more people breach that trust, right? Or they just don't care. You think they breach the trust, but the truth is they just, They just don't care. So, um, there's probably fewer people that you can really count on in the distance, but if you can, there's something, there's something to be said for keeping the team together as long, as long as sometimes they got to leave the coop, right? Sometimes they do have to go, but try, if I had to boil it all down, try to keep the best people at least 4 to 5 years. Promote them, give them the title, give them the whatever. Don't let them go before 4. Sometimes the best people have to leave before, don't let them go for 4 to 5 years. I mean, I remember our best director of engineering in the old days. I had to grab in the parking lot when he was going to leave and take another job by his neck and dragged him back in the office and said, what will it take to keep you? I don't know if that would work today, but don't let them go. Don't let them go until they have to go because it's just, it's their time. Right.

And then keep them close. I mean, you've kept so many of your EchoSign tribe close.

As much as you can keep them close. Yeah. And then that's, that's, That's the lesson of that I can think of. And there's no karma, but keep the few folks. But it is a system of trust. And so the ones that you can trust that are also good, you know, try to work with them for 20 years if you can.

That's awesome. All right. Well, we'll wrap there. So many great takeaways. I certainly hope people walk away from this episode with a new understanding and view of their board. As cheering for them, wanting them to be legitimately successful and understanding the dynamics behind closed scenes, behind closed doors. I think that will be a great message for folks. How can people find you? They want to learn more. Where should they go?

Just go to Saastr, Saastr.com, or whatever works for you. Just, you can just, just Google it, whatever works, whatever medium, the YouTubes, the Instas, LinkedIn, Twitter, events, LinkedIn, yeah, whatever, wherever you consume content, podcast, just search for that weird name Sasser.

And the book is still good. The book after these years still hangs up to scrutiny. I still recommend it frequently. It's in my top leadership reading list that I give to folks, Sales Acceleration Formula, Impossible to Inevitable, a couple leadership basics. So I'd also encourage people to to read, read it because it's a good one.

Maybe it deserves a third edition. That's a good, that's a good question.

It holds. It stands the test of time.

All right.

Well, Jason, thanks for the time. This was—

Thanks, Kyle. This was great. Really appreciate it.

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.