E8: Sam Blond's Blueprint for Building Exceptional Leaders & Teams

Founders Fund is, is one of the most legendary venture firms out there. Uh, it's a path that I think is exciting for a lot of operators. Why leave venture and come back to operating?

Yeah, just to reinforce what you said, Founders Fund is the best. Uh, and my experience there was, uh, exceptional. Um, the people that I was able to surround myself with were the best at their craft in the world and nothing but just incredibly positive things to say about my experience there.

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.

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, Demandbase, 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. Mr. Sam Blond, welcome to the podcast. Appreciate you joining me.

Kyle, thanks for having me. You're a legend and I'm looking forward to spending some time with you.

Awesome. So before we dive in and talk about building leaders, give everybody your 60-second background.

Perfect. I grew up in Kansas City, went to University of Missouri. When I finished college, didn't really know what I wanted to do. I was lucky that my brother was in the Bay Area doing tech sales. Uh, I joined a company called EchoSign as an SDR. This is back in 2008. Uh, was again, very lucky that EchoSign turned out to be, um, a relatively successful, uh, SaaS business. Um, and timing was good also. You think about 2008, SaaS was sort of like just coming to market. Uh, Jason Lemkin was our CEO, uh, and the success of EchoSign allowed me to grow my career from being an SDR to realizing several promotions over a pretty short period of time. I was with the business for 5 or 6 years. Um, I was then VP of sales at Zenefits for 2 and a half years. Uh, joined very early, left when we were about $70 million in ARR and a $4.5 billion, uh, valuation. Um, was CRO at Brex, again joined very early. Um, left when we were about $400 million in interchange, annualized interchange revenue. And, uh, we were a $12.5 billion business. This is back in 2021, early 2022. Um, and then most recently, uh, I was a partner at Founders Fund for almost 2 years. Um, and just started my own company. Uh, so that's the, the hopefully 60-second version. Yeah. Yeah.

Very cool. I don't know if you've announced sort of what you're doing next, so maybe give people, uh, the preview on what's, what's coming up.

Yeah. I'm going to be, I'm a co-founder CEO of a startup that I'm going to build in the category of a sales system. So getting started on that, not sharing too many details at this point publicly, but really excited. Have an incredible co-founding team and we're starting to build.

Very cool. I love that. I'll be following closely. So Founders Fund is one of the most legendary venture firms out there. It's a path that I think is exciting for a lot of operators. Why leave venture and come back to operating?

Yeah, it just reinforced what you said. Founders Fund is the best. And my experience there was exceptional. The people that I was able to surround myself with were the best at their craft in the world. And nothing but just incredibly positive things to say about my experience there. I think for me, I missed and am excited to get back to operating. And so, you know, maybe at some later stage of my career, revisit the venture side. I don't, I don't know. I just know that right now what I am starting to do is, is what's right for me.

Yeah, that makes a ton of sense. What are you taking from your time in venture and applying as an operator? What were some of the big sort of reframes, seeing it from a different lens?

Well, look, I learned a lot about how venture works and so can apply that to things like fundraising for this business. I also was able to spend more time than I ever have with early-stage founders. And I think understand more acutely the problems that startups have as it pertains to customer acquisition. And then how that sort of manifests in the existing set of systems that are available to people as early founders, sales reps, and sales leaders. And as you think about sort of the technological innovation of AI and how that's going to change so much of what is status quo for the trailing several years, um, that, that really was like a guide for me in what needs to be built. And I think the experience of talking with so many early stage founders specifically about go-to-market, which is what so many people would reach out around because it's my background, um, it gave me just like a much greater understanding of the thing that I am now building. And so, um, that is a, a huge learning and takeaway and I'm fortunate to have had that experience.

Very cool. So today we're going to avoid a lot of your greatest hits, of which there are a lot. And I would encourage everybody to watch or listen to Sam Saster's talk from last year, Saster Europa talk, very different topics, but tons to learn. What I want to do is focus narrowly in on leadership and leadership development. I always knew you had an impressive alumni tree. You just sort of see them all over. They're speaking at places, but I was doing some prep around this topic and did a LinkedIn recruiter search, and that alumni is even deeper than I thought. Just like some of the names, Matt Plank, Hannah Wilson, Jameson Young, Robbie Allen, Ashley Kelly, Brandon Boyle. There is a list of people that are all VPs and senior-level operators that have come out of not a huge number of companies and are now doing super impactful things. And so I just want to spend today talking about how you think about identifying, hiring, and promoting leaders, and also how you think about building leaders. But just before we jump in, what does that list of people have in common? What are the things that when you look at your alumni, are common traits and jump off the page for you in reflection?

I think every person on that list, and we could extend the list as well. I've been incredibly fortunate to surround myself with some of my closest friends and I believe some of the greatest now sales leaders in the world. Um, one thing that really stands out with that list, and again, the sort of like extended list is everybody on that list started as an individual contributor, um, in an organization that I was the leader of, whether it was, um, Zenefits or Brex. Um, and they started as individual contributors. And I think like sort of like me at EchoSign. They were at one point or for an extended period of time, number one on the team. And so they were exceptional salespeople in as individual contributors in their own right. And then if I think about like, what, then what are the characteristics that makes someone that, the number one rep on the leaderboard? Well, look, I think some of it can't be taught. And then I think much of it is just this, in addition to like finding something you're good at, it's this mindset that like success is not hitting my quota. Success is never being satisfied and being number one on the team. And if I were number two, on the team and at 200% of my quota, but the number one rep on the team was at 350% of my quota, I was not celebrating. I was, I was in a way, like, let's just call it motivated, um, to understand what that person was doing differently and definitionally better than me. Um, and use that to drive myself to do whatever it takes to finish number one. And I think 90x% of salespeople are satisfied with being above average and hitting quota, and that doesn't get you to the level of the sales leaders that you just cited. So I think about sort of objectively, Everyone on that list was number 1 on their team as individual contributor sales reps. Subjectively, why were they there? Um, is something I just talked about. And then the next thing that comes to mind, which I think, um, there are 2 qualities that are particularly important for sales leaders that are oftentimes come along with sale, the top sales reps, but, um, not in 100% of cases. And those things are a positive attitude and a just intense work ethic. And I think the reason that those things are particularly important for sales leaders to possess is because the people that are on your team, the people that are looking up to you as a sales leader, they are going to emulate those things. And so if you are at the top of the leaderboard, but you have a reputation of being negative, complaining, anything that comes with sort of like a bad attitude, you're not going to be a leader. And the same thing is true where you can be an exceptional sales rep because of the sort of natural talent that you have. And you can decide that you are okay with being towards the top of the leaderboard, but not busting your ass. And in an organization where I am the leader, that's actually okay. Like, if you are towards the top of the leaderboard and you want to play golf on Friday afternoons, I don't care. But you're not going to be a leader on the team because the leaders need to be the ones that are early in the office, last ones out, and setting the tone for what sort of like positive attitude and hardcore work ethic look like.

Which is now a controversial opinion in the tech world, that hard work matters and we should be working hard, but we don't need to go We don't need to go down that rabbit hole.

I don't think it's that controversial. Uh, we, we, we can spend time there or not. Um, whatever you think is best.

No, no.

Uh, startups are really hard, man. Uh, like if, if you don't want to prioritize, uh, work and expect to, uh, work long hours, um, startups probably aren't for you. Now, I think like the caveat to that is that people work differently. Um, I can, I can think of specifics and I won't name names, but some of the hardest working people I have ever worked with have several kids at home and they picked up their kids from school. They had dinner with their kids, but they were online for many, many hours around those sort of events. And so it's not that everybody has to work the same way, but nobody that is progressing their career and standing out in a startup and getting into strategic leadership positions is doing so while not working hard.

For sure. I have a saying, you can't expect extraordinary career outcomes without extraordinary effort. It's simple. And so going back to these leaders, so what's the blend between, so they were clearly talented, they were in the right places, like to have that career velocity, you need to be in a winning company that's growing where roles are there. There's something about learning the brand momentum. Like, I came out of Sam Blons' org. People are going to go, okay, that person knows what good looks like. And where do you think— what do you think the balance of those things is? What's the most helpful for somebody? If I'm thinking about, I want to be a leader, I want that, how do I make the decision between jumping in and taking any startup VP sales role versus hunting somewhere with a great leader with like brand trajectory and the career momentum?

It's a thoughtful question. Um, and I am biased by both my own experiences and then the experiences of those that you cited. Uh, the folks that are my close friends and the people that have gone on to do really incredible things as sales leaders. And, and, um, again, this isn't universally true, but my bias here is that, um, as an individual contributor, um, where you come from is largely irrelevant. In fact, there are arguments to be made that if you worked in an environment and you were the number one sales rep at a product that, or at a company that didn't realize incredible success, you like figured out how to make it work with an inferior product. And so like oftentimes as individual contributors, those, those can be more interesting hires than somebody who was at one of, you know, these incredible logo businesses. Um, my experience with leaders is that I do solve for someone who has seen what great looks like. Um, and I, again, I was fortunate at EchoSign to have seen, um, what I believe is what great looks like. and if we think about Matt Plank, who's the CRO at, uh, Rippling, he, he was really strategic with me at, uh, Zenefits. Um, he, he was with me at EchoSign. I, I brought him over as an individual. And the same with Jameson Young, um, who was the sales leader at Gong. Uh, they were my first two hires at Zenefits. Um, and I think that what we accomplished—

first two?

They were the first two hires. Yep. What a duo. And Jameson. Um, and interestingly, like, you know, this is a bit of a tangent, They were two of my close personal friends before I hired either of them at first EchoSign and then Zenefits. And so like, you know, in of two, but there are actually other examples. I like hiring friends has worked well for me as long as I think the friend is going to just like absolutely crush it. Uh, and I saw something in both, uh, Jameson and Matt Blank that, um, I would be silly not to have hired them. And I'm grateful that I did. Um, I think like back to the, uh, original point, which is, and I am biased here, I think it is hard, harder for a sales leader to, um, implement great when they have never seen what great looks like. Uh, and so, you know, if you see somebody who is like a sales manager at a company that sort of struggled and they got like promoted to a sales manager, um, I think their probability of success is lower than someone who grew their career quickly in an environment of success. Uh, and at least with the group of leaders that you referenced at the top of the show, um, that has been true and I am sure there are outlier exceptions. But I'm, I'm an example of what I'm describing, and I think everybody else on that list is also examples. And so, you know, at some point I will hire a VP of sales, CRO for the business that I am building, and they will fit that criteria. And so then maybe back to the original point, if you're trying to take away learnings as an individual contributor listening to the show, I want to be a CRO. Um, I would be biased towards surrounding yourself, um, with, uh, exceptional salespeople and an exceptional sales leader in a company that's going to— that is growing very quickly. Uh, I mean, Owner's probably a great example of this right now where it's like, you guys aren't yet Rippling, you know, joining Rippling today. It's, um, people should join Rippling. It's an exceptional company. Um, The learnings that you will receive as a sales rep that joins Rippling today in 2024 are different from the learnings that you would have received if you joined Rippling in 2020. And maybe Owner is a version of, of that today where like the writing is on the wall for this type of company and they're still pretty early. Um, that is the type of environment where I would go in and I would have the mindset of, I am going to be the number one rep at the company. And if you accomplish those two things, you know, you're sort of destined for, uh, greatness. That's very cliché. Yeah.

So what was the mix in your, let's call it like scale-up phase at Brex? What was the mix of your leadership team of internal promotes versus external hires at sort of manager, second line, et cetera?

Yeah. Um, I have a, uh, strong opinion here that's loosely held. Um, and that is I heavily bias towards promoting from within. Um, at Zenefits, our first-line manager layer was 100% internal promotions. And at Brex, our first-line management layer was close. I think the learning from Zenefits And Zenefits is sort of a unique environment where we, we were growing way too quickly and we needed a new manager like every few days. Like it was crazy. The sales org when I joined was 2 people. The sales org when I left 2 and a half years later was 500. And so you can imagine like 2 years, 2 years. And by the way, like that was a mistake. So that's a different podcast. Uh, but I think one of the learnings from Zenefits, um, which by the way, I still like heavily biased towards promoting from within to the first line. Um, one of the learnings from Zenefits was just make sure that you are doing so out of want and not out of need. And there were several examples where, um, we just had this like philosophy that was we promote from within. And I think where that broke was when we sort of like looked at the individual contributor layer and we were like, all right, we need a new manager. Who is the least bad option to fill this like new manager layer? And it would be like, it's probably this person. And then we'd be like, okay. Like, and so then that's what I describe out of like need. We needed a manager, but we did not want to put that person. In a manager role. And I think that is a bit of the calculus that I would use going forward, which is like, don't promote someone out of need. And in that scenario, if I could go back and do it again differently, I would have hired from the outside instead of promoting somebody who probably wasn't ready or we weren't super excited about. What I think changes is as you get into larger organizations that you're probably experiencing today at Owner, where you need a little bit more layering. So second and ultimately like third line leadership, I think introducing outside leaders at those levels, you know, as you bring in directors, VPs, it isn't a one size fits all there where like you promote from within. There will be some promotion from within for like the true rock stars. Plank and Jameson are actually good examples of that. They became directors at Zenefits. But then I think at the sort of like, you know, VP level, introducing some experienced leadership there really pays dividends for an organization that, you know, is probably light on leadership experience.

Yeah, we're definitely in a similar space. I just hired a VP of sales a couple of months ago that was external and significantly levels up our leadership capacity to do projects, to coach, to know answers. But then we've promoted a decent amount from within to first line. But a thing we have at the end of every interview questionnaire in our ATS is heck yeah or no. And so it's similar. Like, is that internal promote a heck yeah? Like, I just promoted one of our reps, one of our— she was a BDR, then an AE, and we just made her a BDR manager. She was a heck yeah. We're like, oh, slam dunk. Like, I'm so excited to get her into this role. Versus if it was like, oh, I don't know, maybe they can do it, maybe not, then we'll go external. I think that's a great way to look at it. And the, like, I like that only true rock stars for second line as an internal promote. That's a good bar for it.

Yes. AI enables your CEO, subject matter experts, and other senior leaders to engage prospects directly, creating meaningful connections and boosting response rates. With just one click, your team can strategically involve senior staff to make your outreach more credible and effective. Empower your GTM team to orchestrate your outbound process and say yes to yes.ai. That's yes.ai.

Um, and so, uh, going back a step, what have you done to nurture people to get them ready? Like there's, so there's some talent, there's obviously a lot of talent there. But you must have had, you must have had, you must have done something really right for all, for so many people to make that leap. And so I'm curious, what, what do you think you did to nurture them, to prepare them for their first management position, to prepare them for the second thing? What was the approach there?

Yeah. So, what comes to mind is like, this is a little bit personal to me as a sales leader, and it doesn't, it's not necessarily sort of like what, what, um, what I would even try and emulate, uh, or prescribe to other— in fact, there's like a deficiency, maybe let's describe it as a weakness that I will point out. Um, but there are a couple of things that I'm good at and then something that I, uh, combination of just like haven't focused on and maybe I'm less good at. Um, and again, this is like quite personal, so it's not necessarily something if you're a sales leader listening in. That you should try and emulate. Um, I think I'm good at recruiting. Um, and so, you know, I talked about the first two sales reps that I hired at Zenefits were Jameson and Plank, like CROs of Gong and Rippling today. Um, and then there was a bunch of others. Um, like I, uh, uh, and the same at Brex, just like exceptional team at Brex. I'm incredibly fortunate to have been able to work with people that I learned from and that are better than me in a lot of ways. So I'm good at recruiting and then I'm good at, I think, creating a hyper-competitive system where people are competing with— I'm biased, but I would describe as the best salespeople in tech. And so, um, hopefully people are motivated. Hopefully people are making money. Hopefully people are successful in winning. And when you sort of like rise to the top in that type of system that I believe that I'm good at creating, it means that you are special. Um, because, um, I have recruited a group of people who are really exceptional. And I've created a system that is hard to compete in because of, I think, both the quality of the people and also the level of expectations that I have. Now, where I'm like a little bit deficient and maybe am certainly less deliberate about is this like leadership coaching. And I think that I can think of specific examples where even people on this list have come to me sort of asking for like, you know, what, what, like leader, how can I be a better leader? What, like, what, what reading materials should I read? What, like, podcasts should I listen to? Like those sorts of things. And I'm kind of like, look, Um, I'm again biased by my own experience here, which is like, I learn by doing. Um, and, uh, uh, I think most of the people, and it'd actually be an interesting question to ask some of the folks on that list, but I think that, um, most of the people on that list are in the seat that they're in largely because they took, uh, accountability and made it a priority to become exceptional leaders versus sort of like got incredible advice from me. Now, like, maybe they watched some of the things that I was doing and took the things that they liked and were able to emulate some of those things. And then I probably screwed up a bunch of stuff too. And so they like, you know, threw out the things that I did less well and tried to improve upon those things themselves. But, you know, those are the things that come to mind.

Massive talent density. That seems to be like the big thing, big theme here.

That's the hope. Um, and, um, again, I think, um, when you are in an environment like Zenefits and Brex, where, um, it's both competitive, but also we are growing so quickly. And you're working long hours, the just like on-the-job learning that organically happens, I think is pretty unique compared to most startup environments that oftentimes grow more slowly and are more stagnant. And so if you can get in one of those environments where again, like you're early enough that you're going to experience the sort of like rapid headcount and revenue growth. But it's also like, this one's pretty hot. So, so like you're not just hoping to pick the right thing at seed stage when there are 16 customers and there's already signal. Yeah, you want like a little bit of signal and you can get that through things like fundraising, existing revenue growth, revenue and customer growth, those sorts of things. Brandon Boyle just joined a company that has a lot of that signal at an early stage called 11X. You know, he was a great leader at Brex and he's now VP of sales there and their revenue numbers are jaw-dropping. And so then, and I think they have like a few sales reps. So like, and again, Kyle, like I think this is, you guys are a little bit more mature than that at Owner, but I think all the metrics are there.

Yeah. I give this advice a lot, is opt for quality of company over basically everything else. There's only so much you can do at a mediocre company that's growing 40% year over year and is going to expand headcount by like 15%. No matter how great you are, you're not going to go from rep to manager to director in 3 years because they won't have a director in 3 years. Like, it's still going to be 1 VP of sales and 8 reps. And so I'm often pushing people to take a role somewhere that at least has the chance. Like, it's not guaranteed. You have to compete and you're dealing with a very high standard, but at least if you are successful and stand out and have great character and mindset and habits, the opportunity is presented to you that you could go IC, manager, director. There's no path to it at a mediocre company, especially in today's environment where there's a flight to quality in venture and no one wants to fund the middle. Even if you've been a rep for 18 months, if you could go be a senior BDR, at a super hot startup that's growing really fast, that to me is the right path.

Yeah. Again, if I think back to the earlier years of my career, now I sound like an old man. I hope that I'm not. I guess I'm getting there. So think back to the early years of my career, which now unfortunately was quite a long time ago. At EchoSign, there are two things that I think led to my, my, my being a candidate to be the VP of sales at Zenefits that when I joined, like, you know, Parker Conrad was the, was the CEO, now the CEO at Rippling, like exceptional founder, the best. And, um, we, we, as I joined, we were raising our, our A from Andreessen Horowitz. It was like the hottest Series A of the decade. Um, and so my point in saying that is like, I was incredibly fortunate to qualify and have that opportunity, qualify for and have that opportunity, uh, that I did. The reasons, there are two. One is, um, something that I controlled. I was pretty good. Like I was pretty good at sales. Um, I was the number one rep on the team. I was a great manager. I was a great director. Um, something that was outside of my control is EchoSign's growth. The environment that I fortunately found myself in enabled my career to be able to grow quickly. There were manager roles that became available. There were director roles that became available, and that was because the business was doing well. And so both of those things really need to exist. I think if you want to meet the criteria for what I would sort of solve for in a profile for Who's going to be the next Matt Plank as CRO at Rippling? Um, you know, um, they probably joins as like a VP of sales, uh, at the hottest Series A-ish company.

Yeah, it makes sense. And so what was your framework for identifying and selecting leaders? So, and, and like, especially at the second line at director, what were you looking for internally and externally to know if that was a person that you were going to put in that Kevin "KD" Dorsey.

Yeah, I think there's, this is sort of like two things come to mind here as we're talking about, um, just sales leadership, uh, uh, as a whole. The first one is, you know, we talk about leaders scaling, um, and I think there is, there is a reputation or, um, a sort of playbook that the person that you hire to get you from 1 to 10 million in ARR, or just in the abstract, 1 to 10 is different from the person to take you from 10 to 100. And I think the biggest indicator of that, um, and when there are signs that this person probably needs to be topped effectively is one's ability to hire people. That are both more senior and better than them at the, at the respective role that they will be joining in. And the examples here, um, there are two big ones that come to mind. One is RevOps. So you're at like $10 million in ARR. Um, you want to get to $20+ this year. Like I'm just doing an example in the abstract. For the first time, you're probably hiring like a pretty senior RevOps leader. You've maybe got 15, 20 sales reps. You're doubling. You're going to be a 50, 50-person sales rep team by the end of next year, um, you really need a strong RevOps counterpart. Um, and look, like, regardless of the leveling, this is somebody with a lot of experience, probably more experience than you as a sales leader, certainly more experience than I had at Zenefits, um, and even at Brex, um, when we brought in Trishma, uh, and I think like If you can't hire somebody that their resume is like, holy shit, like that person is better than me, more senior than me, smarter than me. However you want to like frame this thing, then it's going to be really difficult for you to continue scaling. So I think like that is one example. The other example, and again, Zenefits was a little bit unique in how fast we were growing, but the VPs of sales. So, so like the, the sales leaders that either, you know, ran a segment or ran an office, uh, we opened up, uh, offices in lower cost areas like Phoenix. Um, they had far more experience than me. Uh, um, and you know, we hired somebody to run something that we called, let's just say we were hiring somebody to run like enterprise. And my experience is more sort of like transactional and mid-market. So if you think about somebody that's selling to 5,000+ employee companies, I've done that as an IC. It's been less so of what I've focused on as a leader. I've gotta be able to hire somebody that is better at selling and leading enterprise sales organizations than I am. And so then all back to the primary point here around leadership scaling, where if you want to be the indefinite leader, I think a great signal for that is your ability to hire people that are more experienced and better than you. At their respective functions, um, which a lot of people aren't. Um, and the second thing that comes to mind, um, which, which was more pointed in your question around like how then, what are the things that you solve for? Um, couple things come to mind. Um, I am a big proponent of placing a lot of influence on how candidates are sourced. And if I were to do something like, you know, I just mentioned, I just mentioned this exceptional RevOps leader that I was fortunate to have sort of alongside me running the Brex sales organization. Her name is Trishma Shah. She's now COO at the Cole Group. And, um, Charisma, uh, we had a COO at Brex at the time named PH. He came from Google. Uh, and PH was like, look, this person is the best RevOps leader at all of Google. Um, and, uh, you know, he was close with her and super helpful in sourcing Charisma as a candidate. And I'm sure influencing her to join as well. Um, but that's just an example where like, if you contrast that with let's put a job, um, you know, like a job rec on our website and get some people to like apply to the SVP of go-to-market strategy and ops position that we have opened up. Um, and again, like, I think it's an illustration, but the primary point here is I just place a lot of emphasis on in-network recruiting and sourcing candidates where their reputation precedes them in a way that like for the first, when I first met Charisma and I could use this example with 10 different sales leaders. Um, so this isn't an N of 1. I knew, like, I almost knew I wanted to hire her before the first time we met because of her reputation and how highly recommended she was. And again, like, that is one very specific example, but it is more common than not. As I look to hire senior leaders, I just place a lot of emphasis on that recruiting process and where the candidates are coming from and the reputation that they have coming into the role. So one, like, sourcing is really important. Of course, I, You know, like, here's what I would say. Like, hiring leaders is almost easier than hiring individual contributors is almost easier than hiring SDRs because you've got, you've got this like track record and backchannel reference thing to lean on. And if you, if you think about hiring an SDR right out of school, you're hiring for like, like purely intangibles. Um, and when you compare that to Charisma, you can go to her LinkedIn or whatever, you just see like, holy shit, like, yeah, that, that woman's a badass. Um, and so like, Um, that's why, like, uh, certainly hiring leaders is like higher risk and more important. You can't make, um, making a mistake there is far more costly, but in a way, picking the right person, it is almost easier, uh, because you have so much of their track record and experience to go off of so long as you can recruit. Um, I think again, going back to, uh, something that that, and there's plenty I'm bad at, um, but going back to something that I'm good at, a lot of people wouldn't be able to hire Charisma. Um, and I, I was able to get in a room with her and convince her to come on this journey with me and us. Uh, and so then I think when you're not, when like you don't have that, uh, skill set or capability, then leadership recruiting becomes much more difficult. Yeah.

That makes a ton of sense. And what about for internal promotes? So when, if you think back to the managers who you've put into a second-line position, what were you looking for in those people? Because you mentioned only true rock stars are going to make that jump. What were you trying to identify?

Well, I talked a little bit about the sort of like first-line manager qualification criteria. Um, which was that they're, they're number one on the leaderboard. Um, and they, you want others to emulate their behavior. Um, both the sort of like positivity that they bring that hopefully cascades to others in the organization and the work ethic that they bring that hopefully does the same. Um, and, and so that's like the first line, uh, qualification criteria or just like leadership, leadership criteria more broadly. I think on the second line, there is what I would describe as a level of maturity that starts to exist. And what I would describe as— here's an easy way that, here's like a sort of tactical thing that I used that others can use when you start learning. From your sales leaders. And the word strategy is very loaded and like buzzwordy, but I think like people get what it means. As an example, like, and I don't, we keep using these same examples. Okay. Whether it's Matt Plank at Zenefits or Jameson Young the same, or Brandon Boyle at Brex or Bobby Lukeman at Brex. Who sort of led segments as first-line managers, but they were, they were really executing on my strategy as first-line managers. When they started coming to me with, again, it's loaded and I hate using it, but when they started coming to me with like strategic decisions on how we should be running the organization, the segment that they were leading. And they would be, um, like, they would be things that I hadn't thought of and they would be right. Um, that's, I think, like when they exhibited the level of maturity that like, I can sort of trust this person to make decisions on my behalf. And hopefully they're even better than me because of the proximity to the business. At making those decisions. And I think that's not true almost universally when you promote somebody that was just a sales rep to a sales manager.

Yeah. One of my favorite things is being proven wrong because, you know, you get to learn something new. I love the novelty of being like, oh wow, that worked. And it's such a powerful signal that the business doesn't rely on you anymore. Like, I think a lot of us go through this phase where we sort of do 3 jobs. Like, in my first year at Owner, I was executive revenue owner, second-line manager, and sort of first-line manager because I was in the weeds writing scripts and trying to, like, actually spending a bunch of time with reps. And the feeling I was just wrong on something that I felt sort of strongly about, but I was like, I'm going to trust my team and let's see how it goes. and they were right. And it was just like, oh, that's an amazing feeling because it lets you know that this group can now do things with autonomy without your input and get to the right answer. It is such an empowering feeling as long as you can let go.

I think this concept applies to two things that we've touched on that are sort of related. One is like, You talked about the topic we were on was, you know, first-line manager to second-line manager. How do you know that like somebody's really exceptional? It's like, look, I start learning a lot about my own business through them. And they are coming to me with things that we should do differently. We do those things and they're right. They have, you know, positive impact on growth. I think the same is true. When I'm talking to senior leaders through the interview process, which is I come away from interviews learning things about my business and with ideas that like, we should probably like do that thing. You know, I've, an interview style is preventing or presenting a leadership candidate with like some of the challenges that we're experiencing in the sales organization. And like, what would you do? How would you address this challenge? And oftentimes it's like, look, I actually like don't know what to do. Like we actually, we are experiencing this challenge and we're trying to figure out what to do with it. And there are plenty of instances where I've come away from interviews where it's like, that is really thoughtful. Like we should do that thing. And I think that's a really positive signal for, you know, hiring people in addition to promoting them.

Yeah. How you doing on time?

We're at 2:03, but I have a 2 o'clock, but let's do, if we can time box it to like 2, 3 minutes. Okay.

All right. One question, then we'll do rapid fire or a quick fire. So when you got it wrong, what usually drove it?

Give me 2 seconds. I'm going to stack this.

I should have prompted the time check a couple of minutes ago.

It's my fault because I had to get pretty for the call. Do you want to re-ask the question? Yeah. And then, yeah, cool.

So when you got it wrong, What did you learn from those? Like what drove the wrong decision when you've promoted internally or hired externally?

Well, the first thing that comes to mind on the promoted internally, we talked about a little bit before, which is this like concept of need versus want. Um, and, uh, uh, look, I would say that on it, um, said differently, I don't know that there is an example. Where a person has met the criteria that I described, which is they are number one on the team. They have a really positive attitude and they work their ass off. I cannot think of a single example where like that criteria was met and it wasn't a successful promotion. So, um, I think like, you know, uh, where I have gone wrong is where that criteria hasn't been met. And then is it, and I have made mistakes on hiring externally. The, of course, cut out this long pause. Yeah, of course. Bear with me just a second. As you can see, I'm sort of like reflecting in real time, but want to come away with, uh, something tactical here. Uh, Yeah. Um, I think there are several specific examples that come to mind. Um, and our good friend Jason Lemkin, uh, probably, uh, talks about this as well, where I have made leadership hires and senior hires and strategic hires and however you want to frame it. And I have, I have convinced myself that they are A pluses, that they are the right person. They are the best person for the role. And in reality, it was to solve for urgency. Uh, and You know, the specific examples that I am thinking of, of which there are more than one, it's like the search had been going on for too long. And I, I probably felt pressure from the CEO or like pressure from myself.

Yeah.

Just like, look, we need this, this function needs to exist and the business is suffering because it doesn't. And while in the moment, I probably would have, as I said, sort of like convinced myself, like, this is definitely the best person every time. I think if I reflect on it, it probably wasn't true. And so then I think the number one thing that comes to mind as I think of sort of like more senior leadership hire mistakes, it is trading off quality for urgency. Um, and what ultimately happens in those instances is it actually costs you far more time because if they don't work out, uh, you spend all of the time onboarding them. Uh, they hire people that may or may not be the right fits themselves. Um, it actually puts the business back further than had you just waited to actually find the right person. Certainly like, you know, easier said than done. How long do you wait to make the hire? And so that could be a podcast in and of itself.

Yeah. Okay. Quickfire. What do you wish you knew in the first, in your first VP of sales job that you came to understand sort of much later?

Well, I'll give an illustration and then it's like a bigger concept. So, The illustration is I came from EchoSign. EchoSign was acquired as a private company in 2011 by Adobe. We did not have sales ops at EchoSign when we were acquired. So I think like different time than today where sales ops is like, or RevOps, everyone frame it is, is like, you know, universally applicable to startups at a certain scale. And Adobe gave us a couple sales ops people to help and they were not good. Um, and I think because of that, I had this like hugely negative association with sales ops. Um, and they really screwed stuff up. Like there were, there were periods of times where leads weren't being routed to reps and everybody was like scratching their heads. Like, how did leads go down 50%? And it's because the sales ops person, like put in a new qualification in a system that like routed leads to like a dummy invite. It was crazy. So, my experience was like very negative. And then I got to Zenefits and everybody that I talked to when we were like 10 reps, 15 reps, 20 reps, they were like, you've got to get sales ops. Like you don't have anybody that's like dedicated to systems and process and like helping you on the analytical side and like all this. And I was like, no, trust me, I've seen sales ops and we don't want that. And I was obviously wrong. We eventually got there and huge, huge impact, both its benefits and its wrecks. Like, I can't speak highly enough of the influence that strong RevOps has on a go-to-market organization. But I think the meta point is that I was sort of like, I had had this experience at Echosign that guided a stubbornness or decisioning at Zenefits ultimately that was like wrong. And I should have been more open to considering alternatives and not being sort of like so set in the way of things that I had seen work versus not work. And so that's probably like the bigger point. I wish I was just like sort of, uh, I was probably quite rigid in my thinking and felt like I knew what I was doing and everything that I was doing was right and those sorts of things. And I should have been more open to considering alternatives and doing things differently. Cool.

Last question. What's the most common advice you give to new leaders and mentees? Hmm.

Um, some of it's situational, right? But I think like, um, maybe we'll go back to something that, um, has helped me in my career, which is, um, you say like new leaders, here's this thing that I observe. Oftentimes I will see somebody be promoted to a manager or be promoted to a director. And, um, the, the like reaction is sort of like an I've made it. Uh, you know, like there's this thing that I've like really been working hard for, for the last 36 months at this company. And like, I've finally reached the mountaintop of being a sales manager. Um, and my advice to those people is like, this is just the beginning. And, um, the, the like second that you are satisfied with your accomplishments or where you are. Is the second that your growth will be stunted. And so, um, just like never be satisfied, always remain hungry. And I think to apply that to something that happened with me and, and part of why I left being a CRO, left Brex, joined Founders Fund is for the first time in my career, I felt satisfied. With what I had accomplished as a sales leader. Um, you know, I was CRO, doesn't like get a lot more senior than that as a sales leader at a company that I joined at Series A that became a $12.5 billion company. Like, um, that, that's, that's like a pretty good, it's going to be hard to emulate that, um, as a sales leader. And so for the first time ever, I was sort of like, all right, like, I feel like I've kind of done it. Um, and so I knew that I needed a new challenge. And part of that was what drove me to do something different. Um, but, but I, I'd never, I didn't reach that point of satisfaction, um, until like much later in my career and until I had sort of achieved what I described in that CRO role. Um, and now I'm sort of back to like, actually there's something much bigger than, uh, being a CRO, that role, like you, you should be a founder and CEO. Um, and so that is the sort of like new motivation for me. And I think if you have that mindset at every step of your career, which is like, This is just the beginning. I am not satisfied. I'm going to do whatever it takes to get to the next level. And then ultimately what I aspire to be as a leader and with my career.

Awesome. This was great. I've got a whole whackload of notes. My few of the takeaways that really stand out is this idea of need versus want in terms of promoting people. And being absolutely certain. And I think the message around talent density will definitely be one that people should take away from this. Just stack talent and the best people you can, let them compete, and good things will happen. So I really appreciate the time. This was awesome. Really pumped we could dive into this topic. So thanks for joining.

Kyle, I appreciate you having me. And as I said, you're somebody that I look up to as a leader and really impressed with all that you've accomplished as an investor and owner and getting these updates of you just crushing it. And so congrats on all the success.

Thanks, man. It means a lot coming from you. And I got a little ways to go to catch up to some of your track record.

Well, I'm well on your way and congrats on all the success. So I'll talk to you sometime soon.

All right. Thanks.

See you, man.

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.