ClickUp’s Jason Wooten on top sellers, procurement pressure, and leadership risk

Welcome to the Sales Compensation show where we share the latest sales performance insights through in depth discussion with experts. Season three of our show is your backstage pass to discovering how today's most successful sales and revenue ops teams support go to market strategy and improve sales performance. Plus, we'll explore what we can learn about incentives from different industries more broadly. Subscribe to hear how leaders are unlocking new growth, implementing the latest compensation trends and their priorities for improving go to market performance. I'm your host CEO of form, AI Nabeel. Alzam. Jason, it's great to have you on the show. Good to see you again. Thanks for having me. Absolutely. I always start off with a background question, you know, how did you get into this space? Sure, yeah, I took a very not straight path to where I'm at. A lot of it was was just sort of opportunistic pivots and just seeing weird opportunities and going hey, that sounds fun and let's sort of grab it. But I like to say I sort of accidentally started in sales. I really didn't know what I was going to do. I was bartender and a restaurant manager, you know, and then I it that teaches you customer service like nothing else. Yeah, it definitely there was some man, I have some stories from those days. It was fun. But yeah, I finished college and just kind of kept doing that because it's what I knew is what I was comfortable with. And the job market at the time was kind of wasn't great. It wasn't bad, but I had no idea what I was looking to do. I, you know, it's kind of, kind of clueless, you know, I was making enough money to pay the rent and I didn't worry too much about it. And one day I get a call from this recruiter at a software company who wants me to interview for what turned out to be a sales job. I didn't even really understand what it was at the time. Kind of blew the interview off, didn't take it seriously. Kind of half assed him frankly. And I was sitting around watching a football game on a Sunday. I remember the Browns were losing, so I don't remember win it. But that's what they do, right? And it's the CEO of this company and he's like, hey, we really liked your resume. And some stuff stuck out to me and it seems like you're blowing the interview off. Like what gives? I'm like, wait, you're the CEO of what? I don't know. You know, it was kind of like surreal moment and so I, I Thought about it, and a mentor of mine at the time kind of said, hey, you know, there's no such thing as a bad interview. Just go do the interview. If you don't want the job, you just don't take the job. Right? And so went in to do the in person interviews. The day was sort of just a surreal experience. We end up in the CEO's office at the end of the day, like drawing stuff on the whiteboard, arguing with each other. And I walk out of there going, that was fun. But yeah, I definitely, like, no way. Two days later, an offer comes in. I'm like, this is. This is wild. So take the job. Still didn't really know what I was doing. Certainly wasn't taking it seriously. And it turned out that I was. I was pretty good at it. Moved up through the ranks and started sort of, you know, coaching and leading sales teams in a very small company, very high growth environment. And after a while of doing that, I realized two things. The aspects of it I liked were the puzzle solving and frankly, the conflict that came with negotiating. But there were parts of it I just didn't like. It just wasn't really in my heart to keep doing that. And so one day, kind of on a dare, I took a vendor negotiation. We were buying phones. Remember when you had a phone on the desk and you had to press and dial it? We're buying a bunch of phones for new hires. It was kind of a. It was kind of a bed. It was like a joke. And so I called the vendor, I looked up some information, I just googled some stuff. And I was like, hey, you're charging too much for these phones. I get called into the CFO's office and he's like, you really upset this vendor we've worked with for a long time. Like, yeah, but he's overcharging us. Here's why. And he turns around and goes, this is your new job. Just can you just do this every day? I was like, sure. So I got to kind of take on the parts of the sales role that I liked and sort of transition out of the parts that I just weren't really in my heart. And that gave me a lot of opportunity to learn more about the broader company. You know, I had led marketing initiatives and research teams and sales teams and worked a lot with customer care teams. But I hadn't had much interaction with the finance or accounting or HR side of things. And so it gave me the ability to get involved with, you know, obviously procurement and real estate, business operations and Just sort of touch a lot of the operating side of the business that was kind of shielded for most people in sales. And in a company of that size, with the tremendous growth they were experiencing, that let me kind of build my own career to some extent and just sort of pick and choose the things that, that seemed interesting or you would get these very challenging projects that kind of raise your hand and go, I don't know how to do that, but I'll try. It's taken me to places I didn't really anticipate. It's, it's allowed me to sort of carve out roles that, that didn't exist and sort of define my own space. And that's been a lot of fun. But that early basis in revenue and sales, I think has informed my lens a lot in terms of how I look at business problems. And I think it's created an opportunity to be able to connect with the revenue side of the company in a meaningful way that a lot of people in sales can't because they don't speak the language and haven't lived the day to day. And let's face it, in most particularly in the software space, the sales organization, they have a big seat at the table, they drive the conversation, their opinion matters. And so being able to, to talk to them as a peer from a place of experience, from a place of having walked in their shoes, I think is, is just super valuable and it's, it's serving very well. Yeah. And I mean you can empathize from like a, multiple, multiple different vantage points. Right. It's like the seller experience, being on the, the purchaser side, like procurement as a process and, and being on the other side of, of the sales motion. I mean, that's perspective. It's kind of like walking up to a game table where two people are playing chess and you're not playing, but you can look at both sides of the board and kind of see what both people are up to sometimes. And you're like, oh, I'll bet he can't see that. She can't see that. But as an outsider, you can sort of read both sets of pieces sometimes and it can be super valuable. But it's, it's definitely an unusual background and I'm, I'm super grateful that ClickUp kind of recognized that and said, okay, we're going to take a chance and give you some unusual roles to mix and match here and to see how it goes. That autonomy of again, you know, problem solving and kind of piecing things together. That's where you can kind of bring creativity into the mix because you're borrowing a little bit from this playbook and borrowing from this, a little bit from over this, in this playbook, kind of create the future thing. I'm curious, engaging with vendors. It'd be crazy for me not to ask this because we're on the sales conversation show. Sure. In the times that you've played like true procurement with a vendor and you're on the, you know, on the purchasing side, how have you considered the incentives to structures that were in front of that seller that you're across negotiation table in, in your discussions? Yeah. You know, it comes up more often than you, than you'd think. And the thing that I try to explain to my current sales team is like, I know what they're going to say because I'm the one who says it like come bring me in, let me give you some insight and hear what's going on. But it's, it's a pretty common consideration actually. Now most deals are so relatively simple in terms of structure, especially in SaaS space that is pretty obvious. It's like this is the recurring revenue, they're going to get paid on that. It's not a big deal. But when you start introducing these other concepts, you know, and you start looking at multi year structures, you can tell which companies are heavily incentivizing their sales reps to sign multi year contracts versus one year. You can tell by how much the discounting ratchets up. You know, in the out years when there's multiple types of services that are being provided or there's platform versus user costs or infrastructure costs, you can tell as the deal progresses where the sales rep really focuses their time on retaining the most revenue. And so it's, it's a pretty common consideration. We, we've even had times and you know, it's, I wouldn't recommend always doing this, but there have been times that I flat out asked the sales rep on the other side for like a one on one discussion. You go, listen, I need to beat you up and I know your price can move. You need to tell me what's important to you for your compensation so that you don't feel like you're getting screwed here. But the bottom line is we're too far apart to make anything happen. The other thing that's super helpful is just when their quarters are, it's a big deal to know when you're negotiating the end of those timelines. And you can usually Google it even if they're not public A lot of times there'll be enough public statements they've made that AI can very easily tell you, oh, their quarter ends April 30th. You know, super helpful context to have, but you can't always figure it out. And sometimes, frankly, it's more of a curiosity than anything else, but it's super helpful information to have. And I think it's something that gets overlooked a lot when you're buying a car. You know the motivation of the. Of the person selling you the car. Their motivation is to make as much money as possible, but they get paid based on what they sell you. It's not just the car, but the service contracts, the financing, all the stuff that goes with it. I think people intuitively understand that motivation in a consumer transaction, but in a business transaction, they often overlook what motivates the seller. And it's a really important thing to understand as sort of the adversary is what's motivating your opponent. And so the more you can get into a state of mind where you understand how they're being compensated, once you get that, it can be very easy to figure out which levers you're able to optimize in a way that doesn't cause them so much pain that they become unwilling to work with you. It's both a blessing and a curse that there's that disconnect. Right. Like, car sales experiences feels very pushy and salesy because it's. Most car purchasing decisions are done in such short time. Yeah, yeah. It's a bad trope, for sure. The bad trope. Yeah. Yeah. But I think in enterprise sales or, you know, selling in SaaS or, you know, in the tech world, if the seller is doing a great job, they are coming in and solving your problems. And so you. The buyer and the Persona buyer could be different depending on which department they're selling into. Right. But that buyer is kind of like moving beyond or their. It's not the forefront of, like, this is a salesperson, someone that's helping me get my problem fixed. Sometimes you lose that. But I think it's very powerful in the procurement stuff to understand that context. Gets lost a lot from the sellers themselves. And it's. It's kind of eye opening. People ask me all the time, like, well, did you. Did you escalate that ask up the sales ladder on the other side? And my response sometimes like, no, I actually intentionally. I don't want to do that. Yeah. Because the more, you know, less experienced salespeople, there's two kind of consistent things. I see there One is it's pretty easy to throw them off track with unusual ass or difficult conversations. They, they don't know how to react to that necessarily. And I think part of that is that they get sort of, they get scared by the procurement guy. And then the second aspect is by escalating too quickly, you sort of run out of escalations, right? You, you always want the ability to continue to escalate the ass as you go if you have to. You know what I try to, to tell our sales teams like what the procurement team wants to, that's a massive buying signal. Like, I do not have time to talk every sales rep of every product that we're considering for every project. And if we do, it's, I'm going to farm it out to somebody. It's going to be a non substantive discussion. It'll probably be an email exchange. At the point where you're getting someone senior in procurement on the phone to spend time with you, they've probably made the decision internally that you have the right product. Now their job is to squeeze the most value they can out of it, but it's also to get the job done when the business needs to get the job done. And so depending on how you interpret that involvement, it can scare you off because things are going to get adversarial. Sure, that's part of the process. Doesn't mean we have to throw eggs at one another, but there's going to be some natural conflict in that process. But more importantly, it means that you've done a great job of proving enough value, enough of a problem solved to the actual business owner whose budget it's actually going to come out of that they say, I want this product. I'm willing to pay this amount for it. Here's what I need to buy. And it's the procurement's team job to close that deal. And so getting scared off because procurement's in the mix and then starting to renegotiate key terms, it's just, it's negotiating from a place frankly of weakness. Generally speaking, it's often something that's overlooked. It's something that you learn more as you become more experienced, as you know, more experienced sellers, I think more intuitively understand this. It's very easy to rattle younger sellers. You know, you can see it's, it's, you know, you can just look at their LinkedIn profile and generally figure out how long they've been in the industry, how long they've been in sales. And yeah, I hate to say it, but some people are easier targets than others. But it's not hard to find that information. It's a process of information discovery on both sides. Right. Like you, you know, you look at all these things come back to incentive alignment. Like what matters to the business matter that it's more a capitalizable expense versus the, the recurring, you know, OpEx. And obviously the misalignment there from buying tech is the exact opposite because on the seller side you're trying to maximize the recurring revenue and reduce the, you know, the, the one off fees. And so it's laying out this information in a way where it's truly transparent. I mean the best procurement discussions I've had over the many, many years have been where, you know, interacting with the buyer has been an educational journey. Right. Like I'm educating them to what, how we operate and what matters to us. And they're educating, you know, us on what matters to them and you get this beautiful alignment. I mean the end of the day it shouldn't scare anyone because this is someone you're planning on working with for a long time. Yeah, it truly is like you need that information exchange on both sides. So yeah, it's got to be a two way street. And, and when sellers can prove the value and can keep the conversation there. Here's the business problem we're solving. The procurement team isn't divorced from the business problem in another department or they certainly shouldn't be. They should at least have a baseline understanding. Here's what we're buying, here's why we're buying it, here's why. It's important enough that we spent time evaluating it to begin with. The idea that all we care about is unit economics is a, it's a shield and we wear it proudly. When it's effective, it's, it's great. But you can pierce that pretty easily because they like, we have to know what we're buying and what the business case. The most effective sellers are the ones that deflect the cost conversation and move it back to we can prove this roi. This is an investment. This is you, you know, getting something out of the cash. You're turning dollars into outcomes. And those are the most effective sellers by a landslide. The ones who get rattled and just start sort of the bartering process too early. That's low hanging fruit. You can nickel and dime them all day and they'll just keep going until you've reached the breaking point. And those can be fun, but it's sometimes it kind feels like bullying somebody in the schoolyard. This is where recognizing the value alignment is very important. But you know, it's interesting because again, like, I couldn't help but ask that question because it's, again, it's so important that information like exchange in that process and it's a sales compensation show. But, you know, I did want to double click on. On. You've had all these roles you've experienced. You know, you've been a part of multiple companies that have grown very rapidly to become who they are today. Is there a takeaway that you've had across, you know, different teams, different engagements? Like, how have you thought about throughout this process? Because obviously you've worked with totally different types of profiles and individuals across sales, finance and operations. I'd love to get a little bit of color on that. My philosophy on the people. I was, it was weird. I was talking to a CEO earlier today, potential vendor, but someone who's, who's built a technology in the procurement space that's taking off, doing really well. We've been talking off and on for years about just the conceptual gaps that his product can fill. And he's been very receptive to like, hey, there's a, there's a few people who have insight and I'm going to build what you think you would buy. He's been very fortunate that, that they've now got a couple hundred employees, right? And last time I talked to him, they had like 50, 60 employees. The entirety of the conversation today was, people are my problem now. It's not building the technology, it's not understanding the market. It's not. We talked a little bit about investor expectations. It's like, yeah, there's always a little natural friction there, but, you know, they trust me to keep the trajectory going in the right direction. It's really about the people. The more people, it adds more complexity structurally, but it adds a lot more dynamics and personalities and things that take a disproportionate amount of effort to manage. And so the people who can build the technology and get the early games are not always the same people that can sustain that at scale because of all the people you insert into the middle of that equation. And so I think that any leader, regardless of their role anywhere, particularly in the software space, this probably universally applies. Almost any leader in an organization that's, that's growing or has reached some form of scale, your number one job is dealing with your people. Your promotion and career advancement is going to be based on your people's career advancement and how well they're performing. Your problems are going to be having bad people or managing them ineffectively. And so every leader across the board, if people isn't your number one focus, where you spend most of your day, then you're probably not doing yourself a very good service. Because ultimately, like I don't, I, I say this almost every day. Someone will ask, hey, what's this person on your team do? And my answer is, they do the work I take credit for now. I make sure that they get credit for it. Right. I say that somewhat flippantly, but there's a lot of truth to it. Like, I, I try to delegate as much as I can in terms of the actual work so that I have the capacity to focus on the people and first and then the systems kind of second. And so I've always tried to kind of work myself out of a job, bring up leaders underneath me who can do what I do so that I can let it go and do something else. And an organization that is growing and that's going to have newer problems every day. You know, the most complicated company that a growing organization is going to manage is the size they are tomorrow and the day after that. It's not something that happened in the past. We don't know what fire is going to burn next month. Get a pretty good sense sometimes, but there's always going to be surprises to it. And the bottom line is it's your people that end up solving those problems. And so that's always been my philosophy. Like, find, find great people. Focus on their ability to coach and work with other people first, not just their technical skill set. Develop them, move them up. If you can create the perception that you're a force multiplier, you're going to be successful regardless of the team, the company, the role, the department. If you're seen as a force multiplier, someone who ment and you're solving problems every day, you'll be, you'll be invaluable to an organization. And it's something that's often overlooked or it's. Sometimes it's seen as kind of like a secondary, like soft skill. But it's the most critical skill in leadership that there is. You know, this only scales, but it's like, you know, the first 10 people get you the next establish the quality of the next, like 40 to 50, and then the first hundred establish the quality of the next, like the first thousand people that you hire. And like that cascades out. So important you need to hire the right people. But yeah, as a people leader, you need to give them the ability to scale up and actually take on the problem so you can do more. So, speaking of people, I would love to double click on what we spoke about briefly before, before we started here and the hot take that you have in the world of sales or sales ops, because it's so relevant to the element of, like, doing right by people in the organization. I think the single most expensive, the most preventable, stupid mistake I've seen in a sales organization is the sort of automatic promotion of your top performers into a management role. They probably weren't built for that. And so I'll answer a question with a question. If your product had a documented failure rate of like 40 to 60%, would you keep shipping that product or would you do something about it? And the reason I asked that is it's kind of rhetorical, but the failure rate for newly promoted sales managers is roughly in the 40 to 60% range in the first year. And I don't think that that's a coincidence. I think it's because as a culture, sales leaders have become accustomed to moving up their top performers, but not realizing that the job they're moving them into is a leadership job. It's not a sales job. And those have different skill sets, different personalities thrive in those two roles. And they're not always income, you know, compatible with one another. You're seeing this as like the funnel of talent that you can promote from within. They know your business. They've clearly demonstrated they can sell. So I just want to double click, like, I guess, like when you think about the math of this problem, you're. You're saying it's 40, 50% of people fail at that, that, you know, in that first year. Can you walk us through it? I mean, is that just the cost of doing business? Like, how are you seeing that? Is that, that's the cost of finding good management? It's a, so promoting your, your best earner, like, it's not always a bad move. There are, there are some, some really talented people that have been the top performers that are amazing in sales leadership. This is not a universal law. Right. But in general, I view the sort of automatic bump up as a subtraction event. You're losing money on multiple fronts. Your first loss is you just killed your golden goose. So if your rep was closing, just to use an even number, let's say they were closing a million dollars a year by moving them up and having a backfill that you know is not as talented, you've got three, six, nine months of revenue shrinkage because of how long it takes for the backfill, or backfills, plural, to fill that hole in your pipeline. So you've hurt your revenue by taking your number one revenue driver off the team. The team itself actually gets worse. And there was a, there was an NABR study on this. They pulled like 40,000 sales workers and I think over 200 companies. And they found that the reps, the sort of manager who'd been promoted, their prior success was actually a negative predictor of management effectiveness. It had the counterintuitive result of making them a bad manager. And so doubling a rep's promotion leads to a decline in the subordinate performance of the team that they're leading. So across a team of like three to five, with a leader who's not prepared to be a leader, you might actually be doubling or tripling your output loss for the first year. And so you lose a multimillion dollar producer, you spend a couple hundred thousand dollars in backfill and you drag down the team output. So that's, it's like a controlled demolition that occurs. And so we call it a promotion. But the reality is it's closer to like a small natural disaster that you've created by promoting your top talent into a role that they weren't designed to do in the first place, or that they're not prepared to do it. This has to be predicated on the assumption that who is seen as a good performer is accurate. And I say that because, and I see it all the time in my past life as a consultant, in the data that we see, the definition of a good performer is tied specifically to quota attainment, which then is specifically tied to how well are you setting quotas. And there's an element of like, I'm not saying the top, top five performers, top 10% of performers, it's kind of that you have to be decently amongst. If you're not in the top 25 percentile and you're in the top five, 10%, that's a massive windfall, like weird outcome. But the top 25 percentile, there could be deviations, right? You could be talking about percentile, but really you're actually average. You just happen to be in a really good territory, you get a really good opportunity. And then I would say how much of those individuals that realized that it's more luck that they landed there and they're afraid of the next year's quota number and they're afraid of the years after quota number are actually striving for the promotion. And so is it just that you actually get like, kind of like a self fulfilling bias of like the average performers are actually striving to get to management. There might be some truth that I think if you view this as like imagine a Venn diagram, okay. Where you've got, you've got the, the individual contributor and the sales leader. Right. So what makes an individual rep really great, Right. Drive, Deal instinct. Their competitive fire? Objection. Handling the ability to sort of just, just drag a deal to the finish line. They're hunting traits. These are, these are solo operators that are designed to optimize their paycheck, their results. Yes. And assuming you've designed the compensation plan right, by them optimizing their paycheck, you're also optimizing the company's financial outcome and that's great. The idea that sales people are greedy is 100% like that should be your default. And their greed should be driven by a thoughtful compensation plan that drives to the company's revenue North Star. So assuming that your plan's not crazy, the top reps should be optimizing their personal income because that's what works best for you. But it's the skills they need to get there that, that drive, that drag ability, those hunting abilities. Now flip to the other side of the diagram. What makes for a great manager? Patience, coaching ability, Systems understanding and sort of thinking in that puzzle solving mode. Resource allocation diagnostics. A lot of times it's ego suppression which is oftentimes the antithesis of the hunter role and mentality and the willingness to see the outcome as the team winning rather than the individual wedding. And those two skill sets, there is an overlap in that Venn diagram, but it's not like the, the circles are on top of each other. There's a, there's a section of overlap, but most of the hunting skills are on one side and most of the coaching skills are on the other. Frank Cespedez from HBH wrote a really compelling piece about this. He's written extensively on this. His take is that first line sales managers are the organizational level that generates the most reports of burnout, of turnover, of failure. It's the most structurally neglected rung on the ladder. And I think that senior leaders in sales see that as being the sort of trial line that say we'll move it up, see how it goes. If they do well, we'll move them back up. If they don't, they're probably going to leave anyway. So the person that you should be promoting isn't the rep who had the highest quota attainment outcome. It's the person who's obsessed with the why of how the deal closed or the why of how the deal didn't close. It's the one that geeks out on the process, that does the informal coaching with their peers, that understands the product at a systems level, not just conceptually. In a deck, they might only be hitting 90% of their quota or they're just over 100, or they're, they're maybe just at the edge of that 25th quantile. So they may not stick out as the obvious best performer, but that doesn't mean they don't have skills that transfer better across the diagram to that, to that coaching Persona. And I think that that's what's often overlooked. Your best closer has got the instincts of a shark. Your manager has to have the instincts of a shepherd. They're not the same animal, they never have been. And no amount of leadership training can turn a shark into a shepherd in 90 days. Right. It takes a long time to do that. Takes a lot of investment coaching. And so the idea that a shark can flip the switch and just become a shepherd because their title changed and now they have people and so they'll naturally get it. Some people can do that. There are success stories out there, but most people are going to struggle with that transition. And then to make things worse, what happens when they fail? They see it as career suicide to move backwards in the same organization. So what do they do? You either let them go or they see the writing on the wall and they exit themselves to go to another company. Or what do they, what do they do? They either look for the same role that they're still not prepared for, but that new company might provide that onboarding and people training to them as part of their cultural training that they didn't get from the promotion because it was assumed that they knew it. Or they take, they go back to an individual contributor role, earn potentially more or whatever the case might be, or hedging their bet financially. But their talk track is, hey, I've been a leader and that makes me a much more effective closer. Right? Which may or may not be true, but they're still defaulting back to that shark Persona that's in their blood, that's natural to them. So they're probably going to be successful, successful there. The other mistake that I see is that we've sort of demonized this idea that the first line manager can't go back to an individual contributor role. If anything, from time to time, when that happens, it should be celebrated. We tried Something. But you're still committed to us, we're still committed to you. Let's move you back to the role that makes the most sense for us and for you do. And then we'll find an appropriate manager who has those. The, the. The skill set, the instincts and things like that to do it. And it's not even always a matter of failure. I've known plenty of outstanding contributors who've moved into. To sales leadership. And genuinely, they're good at it or they're okay enough that, that like, they'll be fine. Like they're not. It's not a house on fire kind of situation, but they're afraid to take that step backwards. It's. It's an ego trip for them or they just find that they don't like it. And that's kind of where I landed is myself was I got into that role and I realized that there were a lot of the people aspects of it I liked, but there were a lot of like structural aspects of sales management that just weren't sort of weren't for me. Right. So I was fortunate enough to find an off ramp to another role where I could use this, the skill set that was naturally in me. But that's unusual. You know, a lot of people in sales, they stay in sales and it's move up, move down, or move sideways to another company. And so by sort of, again, demonizing is probably a little strong. But we certainly don't create cultures generally where we allow people to move backwards back to that IC role in a positive light. They're seen as a failure or a quitter or, you know, some other negative connotation. It may not be accurate. It might just be that, hey, they didn't like or weren't good at that role, but they know what they're good at. They still love you, they still love the company, they still want to contribute. So you have to be able to find that path backwards for them. If you're going to treat FLMS as a testing ground, you've got to create a way to allow people to move backwards and maintain their dignity. It's almost like a trial period or player coach mode before you get the full promotion or something like that. I mean, the interesting thing here is there's so many things that are set up to not work. You talk about the different type of skill sets and the profiles, right? The shepherd and the wolf, different roles, different profiles. There's also different comp. Structure, right. Like if you think about it, you're like, everything is almost at Risk. When you're an ic, then you go up to management and now, you know, 75, maybe of your, of your comp is kind of like tied to that base or of your previous comp because you just got this promotion, 75% is now like just there. And maybe the person could have evolved, but they're now in a much cushier spot. And so all of a sudden, did you take incentive away? Did you? You know, there's so much that has to be like, thought through and structured in a way that leads to success and an off ramp so that you don't lose out on that, that talent. And I think a lot of that, that comes back a lot of times to a misalignment of motivation. We, we kind of touched on this earlier in terms of understanding the seller's motivation and the buyer's motivation. There are some people who perform really well in the IC role and their motivation is still not necessarily the income, it's still the success of the team in the organization. And so it's easier for them to make that transition and still maintain that focus and that drive towards outcomes where someone who is strictly focused on their own personal financial outcomes may end up in a spot where they get apathetic to having that, that drive that they, that they used to have when there was more on the line. So I think there's some truth to that. I think, you know, everybody's different in terms of their motivation and their mix. You'll also find different phases of people's life, different financial motivations that come with them. You know, I'm at a point now where like, I don't, I don't really care that much about financial outcomes. Like, like, could I go find something that pays more? Yeah, sure. Do I want to? No, not really. I enjoy doing what I do and I enjoy the people that I do it with. And I want to coach this team and these people and make them as successful as they can be. It doesn't mean that one day, you know, years down the road, I might say, hey, I've done enough here, it's time to do the next thing. But for the time being, my motivation isn't, you know, finance isn't the top motivator for me right now. That wasn't always the case. And in the future, that also may not always be the case. And so people evolve through different seasons of their life and their motivation is going to shift around too. And so we have to be careful not to just box all salespeople in to those motivations. And understand that they're human. And that can be a really tricky thing to do. Fortunately, there is a prescription to kind of fix this. Right. One is the idea that you floated to sort of this dual track like kind of trial period is where it's not necessarily a pure management role and title, it's more of a mentoring role. Take a little quota away, tie that income back to other people on the team, let them mentor sideways, see how that goes. It's a good way to hedge the bet and do a trial run if things don't go well. It turns out they're not very good at that. You've learned a very good lesson and you haven't spent that much money. Exactly. Very low cost. Yeah. And you haven't created a situation where now they're at risk of leaving because of the indignity of the, the de promotion. Another thing that's really critical is, is hiring for management aptitude rather than what their quota attainment was. You're making a bet on it. When you promote someone, you're making a bet on who they're going to be in the future. And while their past performance does inform their future aptitude, it's not the only indicator. And so acknowledging that those skill sets may have some overlap but are, you know, generally not crossed over by, by, by. Many people make the, the sort of interview process, make it an interview process, don't make it automatic and focus really on the management and the coaching aptitude that they have as the core skill set because that's the skill set that will drive their future performance regardless of how great they, their past performance must have been. And then if you're going to promote a closer and there are great closers out there that have long glorious careers in sales leadership and then people shouldn't be discouraged about, about that. Right. You've got to invest in the transition period. You have to invest as much in them as you would bringing in an outside external sales leader. You've got to make that same investment to someone internally. You have to know that you know, it's not a two day off site with trust falls and hey, you're a manager now. Now you need a structured program. They need an experienced mentor that's been through that transition. You need regular level skipping feedback. You need an explicit permission for them to be able to struggle early on and have that option to prevent them from churning out of the organization and take that step back if it comes to it. So you've got to normalize the ability to step back without the stigma if you're going to do it. But you have to resource them properly. You can't pretend that because they knew how to hunt as a shark that now they know how to shepherd, because they don't. They may have some crossover, but if you enable that like you would for most other roles, you'll have much better outcome. And, and oftentimes that's, that's skipped. You know, you're moving up. You've been here three years, you know everything there is to know. Here's your Google. And there's an aura around that person. Right. They're usually the top performer, so they're seen as, you know, it's almost. You almost don't even want to bridge the, the hey, well. And then the people that they're coaching see them as being sort of infallible because they were the top performers, right? And it's like, well, yeah, they were doing the job that they were doing. Exactly. That doesn't make them the best at doing the next job that that comes. And frankly, quick litmus test. If they don't want to be evaluated by their leadership potential and they don't want an investment of how to make that transition in a structured program to move them from individual to manager. They just told you everything you need to know about their ability to lead people and deal with adversity. And they should continue to be an individual contributor. And there's nothing wrong with that. It's okay to have a career individual contributor in sales who is always the hunter, who never wants to be anything else. If you find them, keep them, pay them a shitload of money, have a great time, don't feel like they have to move to management to be successful. They don't. The business case in the ROI fully think it through is very high to kind of put a proper HR program around, kind of the scaling of talent throughout sales organization. So hot take. But that's like any good hot take. The logic behind it makes a lot of sense. So I'm glad that you share that, Jason. And yeah, I agree with how underutilized or underthought it truly is. I just want to thank you again for jumping on the show. And before we close out, I always ask two questions. So in the industry, I guess, who would you most like to take out for lunch and why? I would say Rosalind Santa Elena, who's the founder of the Rev Ops Collective and also hosts the Revenue Engine podcast. She's been a top performer and marketing influencer for years. Built the Revop Collection Collective like from scratch. And what I like about her is she's one of the few people in the space that can talk about aligning sales, marketing and CS without making it seem like it was, like, written by AI for a TED Talk. Like, it's very. It's very real. She simplifies things. And in an industry that loves to over complicate everything, it's an undervalued skill. So I'd love to pick her brain about where she thinks the direction of go to market and sales and rev ops is heading in the coming years. And I also love to compare notes about how AI is sort of just burning the playbooks, right, that we know in a faster manner than I think anyone ever anticipated and how to sort of stay ahead and keep up with that. Because we spent a lot of time investing in the playbooks and in the scripts and the process and the systems that go with it. And AI is just transforming things at a speed that I think everyone sort of knew was coming. But now that it's happening, it's like, wait a minute, I knew the car could go this fast, but where. Where's the barf bag? So I'd love to pick her brain on. On sort of the future of. Of. Of where this is all heading. I had the privilege of doing a roundtable with her a few years back and she's definitely. Oh, did you know the domain? Yeah, yeah, we hosted one in. In the Bay Area. And this was again, like several years ago. So it. Well before kind of all the actions happening now. But second question is, what book, podcast or resource have you found tremendously helpful for you and your career that you'd want to share with the audience today? One book that sticks out is the 21 irrefutable laws of Leadership by John C. Maxwell. And it's fundamentally changed my perception of leadership and my perception of people. It was actually an accident that I read the book. I was going through this men's sort of ministry leadership program with my local church, and the book had been taken out of the curriculum. But I didn't know that, and I was trying to be ambitious and get ahead of the reading schedule. So I read the book and then found out later that it wasn't on the list for that particular course. But it was one of the happiest accidents that I've ever had. It was truly one of the most effective leadership books I've ever read. And I think the core of it, it really is that that leadership wasn't always about being the best performer in the room. It's about making everybody else a better performer. And he talks about these laws of like empowerment and explosive growth. And those gave me a different perspective on how to be a secure leader that gives power away because by building the scale, that's how you develop both your leadership muscle and your leadership leadership brand. You don't want to manage followers. You want to empower new leaders to sort of rise up. And so that's really shaped how well I've been able to build teams and some of the things I'm talking about today. And the other thing I appreciated is Maxwell talks about things from not the whole book, but certain sections of it from a faith perspective. And that's important to me also because that deeply resonated with me and it shouldn't scare anybody off from the book. The leadership principles are universal and it's, it's a very small section of it that did that. But that was how I sort of accidentally stumbled into the book. And so my takeaway there would be, you know, if you find programs that are designed to challenge you, even if they're outside of sort of the strict business environment, you should still take advantage of those opportunities too, because you may like I, through this brotherhood course at my church, found this great business book that I never would have read otherwise, sort of accidentally. And I've been able to take a lot of those teachings and move them back into the business world. They've been tremendously effective. And so education can come from any area of your life. It doesn't have to be just, you know, your boss's personal reading list. And so, you know, that was one that's really stuck with me recently. In fact, some of the best learnings that I've had that I've applied, you know, back to my work has been things that I've learned outside, you know, experiences of experience outside the day to day work that we do and certainly added to the list for myself as well. But just want to say thank you again, Jason. This was really enjoyed the conversation. I think it's a very impactful one to kind of bring perspective and thoughtfulness and especially for the people that are listening to the show on the sales ops and sales comp side. I think having that perspective in conversations around designing incentives and structures for those that are shifting from that kind of IC to the leader type role. I mean, there's certainly, you know, a path that can be done and supported through incentives where, you know, that player, coach, model or you know, the multiple solutions that we talked through. And so I think this is this is a very fun conversation for me and I think it's very insightful for those that are listening in and just want to thank you again for taking the time to jump on the show and share that with the audience there. Yeah, been a pleasure, appreciate talking to you as always and I'm sure we'll catch up on some other crazy topic in the future too. The Sales Compensation show is brought to you by Forma AI, the sales performance management platform that fully integrates sales planning with rapid scalable incentive compensation management. 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