Episode 352: Why Sales Teams Need Systems, Not Just Superstars (with Dickron Kherlopian)

[00:00:00] Bobby: What makes a great sales leader and how do you build a high performing sales team and a business that's built on relationships? In today's episode, as many of you are in the middle of planning for 2026, we thought we'd dive into the art and science of managing a sales team with Dickron Kherlopian, our very own Senior Vice President of Sales at commonsku.

[00:00:26] Now, Dickron is a sales team builder with nearly two decades of leadership across sales, SaaS, and financial sectors. For one example, at JazzHR, he helped grow the customer base from 2,500 to 11,000, and scaled ARR from 4.8 million to 30 million. At Goco, he led the company through a successful acquisition by Intuit after redesigning sales operations and building a high performing team from the ground up.

[00:00:51] Now, his deep experience scaling organizations through structure, coaching, and culture gives him rare insight into what makes sales teams truly excel. Welcome to the skucast, the podcast for innovators and maverick thinkers in the promotional product space. My name is Bobby Lehew. I'm glad you're here.

[00:01:09] In this episode, Dickron shares how to recruit and develop great salespeople, measuring performance beyond the numbers, and leading with both empathy and accountability, insights that apply whether you're selling promo or software. Today's episode is brought to you by us at commonsku. Over 900 distributors powering 1.8 billion in network volume rely on commonsku's connected workflow. Process more orders, connect your team and dramatically grow your sales. To learn how, visit commonsku.com. Now here's my chat with Dickron.

[00:01:38] Dickron, welcome to the skucast.

[00:01:40] Dickron: What's happening Bobby?

[00:01:42] Bobby: I'm so glad you've joined us here. For those who heard the intro, you heard a little bit of Dickron's background. What you don't know is that I've sat in meetings with him in strategy sessions and I've thought I've got to get this guy on a podcast because there's one thing the industry I think has really struggled with, this building sales teams, and you have a lot of experience building sales teams. So let's just jump right into it. You've led high performing SaaS sales organizations, as I read in the bio. And since you've joined commonsku, which is obviously a company serving the promotional products world, how do you think about applying SaaS principles to an industry that's much more relationship driven?

[00:02:17] Dickron: Yeah, I think my first instinct, and I'm gonna spitball on a lot of these answers, I think my first instinct when you ask that question is every sale is relationship driven. Obviously the promotional products industry is particularly unique because it's a lot more fraternal. A lot more people know each other. There are maybe 30 to 40,000 companies in it total versus other industries. Like if you're selling into the well-known verticals like finance or sales or HR or I don't know, tech, data security, huge massive TAMs. People don't know each other. You throw the value prop at the wall and see who you can attract. Right? In this particular case, I think personalization is key and in many ways that flies in the face of automation and scale and reaching out to as many humans as possible in a short period of time. AI should be able to help with that personalization. But what ends up allowing for that personalization is good data. You need to be able to know stuff about the people that you're interacting with and bad data, bad CRM hygiene will end up churning out some pretty silly messages to people.

[00:03:33] Bobby: Yeah, that's really, really good. We'll get back to this in a minute. What do you think, and we're gonna get into sales performance in a minute, but let's start at recruiting and building a sales team, because this is something you spend a lot of energy on. Obviously, again, everybody heard the bio, you're hiring salespeople and then we're gonna get into sales performance in a minute. Just so folks know, when you're hiring salespeople, what are the traits you zero in on first?

[00:03:53] Dickron: I'm happy you mentioned this actually 'cause the two things that take up most of my time are hiring and systems, right? You gotta, or rather in the hiring bucket I'd also put development, like post hiring development basically, optimizing the human aspect of your sales team, right? 'Cause those are the people that are gonna be executing against the systems that you put into place. So what I wanna look for typically is, number one is always someone that has a high level of conviction and passion around wanting to spend their career in sales. There are low barriers of entry in this industry to be able to get in, especially at the entry level. I don't wanna put myself in a position where I'm a career counselor. I want people who enjoy having the number on their back, can deal with the pressure. They want the ball in their hands with two minutes left and they want to take the last shot. They don't like the idea of somebody else doing that, right?

[00:04:49] That's number one, that has to foundationally be true. The second thing is someone that's quick on their feet, analytical and thinks while they speak. The one thing that you can never train into somebody is the ability to problem solve on the fly. They come with that already and you do a lot of that while you're in sales. Retrospectives in pipeline reviews, in performance coaching, et cetera. That's good afterwards in hopes that they implement and iterate, but you're still relying a whole lot on that person's ability to think accurately and present themselves well in a situation. Right? Trying to fix something afterwards is not as effective. And then the third thing I look for is someone that's organized and kind of takes their professional life seriously. The life of a salesperson requires a ton of organization. The biggest different, the hardest thing from the SDR to account executive or prospecting to closing role transition. Oftentimes people think it's like, oh being able to do a demo or being able to know what the product does. It's not that at all actually. If we just wanted people to demo the product we could hire high school kids.

[00:06:00] It's living that life of understanding okay, I gotta optimize my PTO around when my prospects are also not there. I need to have great work life balance because I'm going to have an exciting and stress filled and energy draining and fulfilling week and talk to a lot of people. What am I doing to defrost? What am I doing to get back in the right mind state to do it all again tomorrow? You can be a good salesperson for a day but what about every single day, 365 for 20 years?

[00:06:31] Bobby: That's good. Before we get too far in this conversation, can you explain a few different things about roles in SaaS compared to roles in sales? So in promo, you have typically business development and account executives, and there are different names for different things, but those are primarily two roles, folks that bring in the business and then folks that manage the accounts. In SaaS, there's all kinds of acronyms. Can you explain the primary roles in SaaS sales?

[00:06:53] Dickron: This is gonna be a lot of super sweeping generalizations because it depends on whether you're in enterprise sales or if you are an outside or an inside rep, et cetera. But I'll describe the funnel. How's that?

[00:07:06] Bobby: Yeah, that's great.

[00:07:07] Dickron: And you optimize roles according to that funnel.

[00:07:09] Bobby: That's great. And I wanna explain this at the front end so in case we drop any other acronyms and like SDR, anything, people will know where we're at.

[00:07:16] Dickron: Yeah. So at the top of the funnel somebody's gotta curate interest, right? Otherwise you're just yelling in a shopping mall or a parking lot and that's not an effective way to get leads, right? Nobody opens the phone book anymore. It's not very efficient. So somebody's gotta curate the interest. We have to have intent. Get on the radar of people that know how to deliver a value prop, right? And a lot of the times that's a mix of marketing departments that are using sophisticated means to get hand raisers to generate interest. Sometimes you have human involvement in curating those meetings in the form of a sales development rep, a BDR. Oftentimes an account executive will engage in that. An account executive who is a more closing role. Kind of an expensive way to procure leads because generally you want your highest paid people closing them. But if you're an enterprise it's worth your while. If you procure four leads and close one of them over the course of a quarter, if you're an enterprise, that's good ROI, right? And then all sorts of things in between. So you have to procure the interest, get those people to the table, verify the budget, authority, need, timeline. Somebody's gotta provide value, close that business, convince 'em it's the right thing to do. Whatever you call those roles from front to end is up to you. There's all sorts of ways to slice that but that's generally the process.

[00:08:36] Bobby: Okay. How do you distinguish, back to recruiting and hiring, how do you distinguish between someone who's skilled versus someone who's just been trained, who's really good in interviews?

[00:08:45] Dickron: I love this question. You have to be intentional and creative in your interviews and ask yourself like what are you measuring for? Mediocre salespeople are really good at two things. They're really good at convincing their manager that next month's pipeline is better than this month's because that's literally how they keep their job. Just survival instincts, paying bills, right? And the other thing they're really good at is interviewing all the time because they interview all the time. And so like my best reps would probably be a bad interview. Like tell me about a time when you blah blah blah. They're like I don't know dude, I just hit quota every month and crush it. Like I don't have time to tell you about a time. A lot of top performers are like that. But somebody that's answered that question eight times and just generally isn't good at it is gonna be great at answering the question.

[00:09:25] So I like questions that test for things that you can't prepare for. For example, one of my favorite questions is like I'll list five attributes that they most wanna be known for, right? And one of those attributes is like hitting quota all the time. Another one is like being a thought leader. Another one is being well liked by your team. There's different things to kind of get a sense of where their priorities are at. I'll ask them a question that's like, what is the thing that you're an expert in that you geek out about that you stay up at night looking about, looking at it on your cell phone? Like what's that thing for you? I'll say okay in 30 seconds or less make me an expert on that topic. Because I wanna see how they're gonna pitch. Then I'll try to come up with an objection, right? Well I don't like fantasy football. It is just too much work and there's too many players to remember. Convince me why I need to spend my time on this.

[00:10:25] And so challenge them on things. And that's a good question too because you'll get a sense of what somebody's like outside of work. I've gotten some crazy responses to that question Bobby. Some non-work appropriate things. It's really good to get those things in the interview. So yeah my, and bottom line is like if you can't talk about something that you care about and convince me to care about it, how are you gonna convince me to care about a piece of software?

[00:10:47] Bobby: Yeah, right. Great point. If you love that and you can't convince me. Yeah.

[00:10:51] Dickron: Just thought questions. Read and react questions to get an idea of how somebody operates unprepared.

[00:10:57] Bobby: The reason why this is so brilliant for our industry in particular is that we typically get sucked into this. There's this misnomer that people with bright personalities that are good talkers are gonna make good salespeople. And the reality is, people that come in within the industry, often some of the best people have come from within the industry, their follow up is incredible. They're great with clients. They're speedy and responsive, and there's just different attributes than we bring in this baggage from what an old school sales rep should look like. And I love how you sort of debunk that right away.

[00:11:30] Dickron: They still need to be super tight on the follow up. They need to be very...

[00:11:32] Bobby: Well, that's what I mean. That actually that's like key, but we typically hire on personality with some of these roles rather than functionality.

[00:11:42] Dickron: Yeah a hundred percent. It is human nature. It's easy to get captivated by a charismatic person.

[00:11:47] Bobby: So talk a little bit about measuring and managing performance. So every leader has their own sort of intuitive metrics. When you think about evaluating your team, I know you pay a lot of attention to metrics. If anyone's ever been in SaaS, that's a big part of it. But also you in particular, you have a good gut and a good instinct, and you follow the data. How do you evaluate your team?

[00:12:07] Dickron: That's a great question. There's some layers to this so there's obviously just like the baseline KPIs that anybody can look at and draw conclusions, right? Obviously. But not everything is always going according to plan, right? So like understanding the story and the why behind things. I used to have a mentor and a boss that said things are never as good as you think they are. They're also never as bad as you think they are either. And so if you don't know the story behind the data you'll never understand why things are happening the way they are. And you'll make sort of very surface level decisions. And Mark Graham actually saw a sticker on my laptop that says like data is greater than opinion. And then he said you know what's even better than data? He goes accurate stories behind the data. And that's actually if you really think about it, that's what a sales leader is entrusted to provide. It's the accurate stories. Everybody can look at the charts on their own.

[00:13:00] Bobby: As someone who sat in management meetings with you, I've heard you provide context for where we're at in this quarter, what's going on this month, with different reps, performances and things like that. How do you distinguish between someone whose sales numbers are temporarily down, or who's lost the ability to drive or sell? We have a lot of people in our industry that fluctuate in their sales, so they'll have a great Q1, they'll have a slow Q2. They'll have a fantastic Q4. How do you manage that? Is it basically what you just said is understanding the through line of the business?

[00:13:30] Dickron: You have to hone in on what exactly you're measuring, right? So let's take the example that you brought up. Person used to be doing all the right things and now like what happened all of a sudden, right? So maybe you take a look at deals that they were assigned in a certain time period versus another time period. Did those move down funnel and how are those things different from each other? Take a look at their closed lost reasons period one versus period two. Did that mix change? Oh okay, I see more of these kinds of losses like more timing related losses maybe. Why is it that we have more timing related losses now than we ever have? Can't be macro because months ago wasn't like a different time, right? It's this person. We didn't run any different campaigns. Why do we have more timing losses now? Then you have a conversation with the rep. So you zoom in on actual differences from before and after in that particular situation. In another situation you're measuring something different and this is why it's important to really understand your data because if you're trying to solve a problem you have to think about what is the underlying data that will tell you the story about that problem and then dig into it. Then you gotta take that to the rep and there's a people management aspect of it. You have to have a good relationship with them and you have to have an honest conversation about that observation, right? If you have a really specific observation the rep can't say I don't know what you mean man. Like it was just a tough month. It'll get over. It's fine. Like I didn't do anything different, right? That's often what you're gonna get. If you have that underlying foundational indisputable data that corresponds with the behavior that you're suspecting, that'll ground the discussion, you'll be able to get to the root cause easier and have a plan of action moving forward.

[00:15:14] Bobby: Okay. I've had enough experience in SaaS and plenty of experience in promo. So I've had my feet planted in both worlds. And so speaking of sales targets, how do you keep metrics small enough to manage but big enough to remember? And the reason why I ask this, in SaaS it tends to be the needle moves to more complex. There's a lot of complexity around numbers. In promo, there's too much simplicity. You have gross sales, but there are other metrics like gross margin, gross profit, average order size, and we're not measuring those. So in many ways, in my perspective, SaaS is heavy on the complex side. Promo's heavy on the simple side. How about you? Like, how do you keep the most important metrics top of mind, and what are they for you?

[00:15:57] Dickron: You need good dashboards. They just kind of, you kind of settle on a few that tend to measure your business well. You can't be too married to any one thing because different, the interesting thing about SaaS is as a SaaS leader you need to become an expert in a new industry every five years basically.

[00:16:16] Bobby: Hmm.

[00:16:17] Dickron: So it's not promo. So like my standards for like what metrics I look at can change depending on the situation. But oftentimes you need a measure of quantity. We need a measure of quality, right? So what's coming in? How much of it are we winning? When we win it, how deep are we selling into that relationship? That typically is in the form of either product lines or average revenue per unit, et cetera. How long does it take us to do so? One of the funny things with sales cycle length is people assume an average win time of shorter is better than longer. But what happens if you have somebody that can't win the long play deals? Of course their average win time is gonna look shorter because they can't win any of the complicated ones, right? And of course if they win the complicated ones you'll see their win rate go up and you'll see their average dollars per unit go up. So they all kind of interplay with each other and it's just a matter of understanding like what are the things that you want to make sure you're optimizing in your particular business.

[00:17:15] Bobby: Ironically, I have no questions in our conversation about dashboard visibility, but this is one of the number one reasons why customers come to us. Probably one of the top three, top four is visibility and what's going on in their business, and you said that. And I've watched you wrestle with tools behind the scenes, different things we can get to get clarity, and that's one thing you did right away when you came in. I remember you submitted a report from these calls with prospects. Then we submitted that into AI of course, and found just this incredible like intelligence graph of why people want our platform, but dashboards is something in common that you share as a passion and that our customers come to us for and looking for visibility in their business. Speak more to that.

[00:17:58] Dickron: Well it just takes less time for you to get the information you need to do your work well. The point of a dashboard is the acknowledgement that these are the things I typically find myself going to. How can I get the information faster, right? Nobody wants to sit and tinker with spreadsheets all day. But yes using technology to create them for you is important, especially when you don't have the data. Like how do you do this when you don't have the data? It's very intimidating to start collecting that data because I wanna look at what happened in the past 10 months, right? So if I start those best practices now I still can't look at the past 10 months as accurately as I want to. But you have to think, huh, I can't go in the CRM and look at the top seven reasons why people are interested in looking at us, but what I can do is have AI ingest my call notes and tell me the top seven reasons from the past. It's not perfect, but it'll at least start getting you there.

[00:18:49] Bobby: So let's talk a little bit about coaching culture and motivation. What's your philosophy on coaching salespeople? Are you hands-on? How do you help salespeople overcome their own obstacles? I mean, the one interesting thing about sales, particularly in your role and in this fast paced SaaS model, is that there's a lot of psychology going on in this sales role. So what's your philosophy on coaching?

[00:19:13] Dickron: I think it's easy to lose sight of how busy and heads down and intense the day of a salesperson is. Like even if you see just three meetings on their calendar and space around it, you know they're prepping for each of those meetings, they're doing their post-call notes after each of those meetings, they are preparing their follow-up after each of those meetings, they're doing their follow-up from prior meetings from prior days between those meetings. They're prospecting between them, right? So they're just heads down go go go go go. And they need someone to take a deep breath with in a 45 minute meeting each week where they're not doing any of those things. Especially if that someone is coming to them and saying hey, like bird's eye view, like here's how things are going with your operation. Like let's dial this up and dial that back, right? Like they need somebody to come in and help them zoom out, take a breather. So like the way you structure your one-on-ones and how you execute those as a leader is really important when it comes to coaching. So there's gotta be an element of that. There's gotta be an element of doing some deal review, knowing what deals to click into. Sales reps hate it when their manager clicks into the same deals every single week. You gotta know which ones to click into and when you click into them as you're helping them through it. You need to be able to find common threads in the gaps. Like hey I couldn't help but notice in the past three that what we talked about, the reason that you're not able to get them back on the line is because we actually don't even know what their next step was after your meeting. We don't even know what to hold them accountable to. As opposed to me saying hey what should I say, I can't get ahold of him. That's an example. So throughout the whole thing it's your job to be perceptive and come up with common themes and prescribe the right medicine to it if you will.

[00:21:05] Bobby: Yeah, I know you're a big sports guy and what's interesting, even when I'm talking with speakers, recruiting and coaching speakers for our events, one of the things I often send them is a statement about how even LeBron James needed a coach. And the reason was for perspective, because his head's down in the middle of the game, but the coach is out here looking at what's going on across the entire court. Does that feel right to you?

[00:21:25] Dickron: A hundred percent. Yeah, he doesn't want to have to worry about how many minutes the seventh guy on the bench has in the rotation or if his teammate's in foul trouble when he is busy getting double teams, scoring 40 a game.

[00:21:37] Bobby: Right. What's something you learned about motivating salespeople that you wish you'd learned earlier in your career?

[00:21:43] Dickron: That's a good one. You wanna prescribe your own characteristics on everybody as a baseline. And after you manage enough people you realize how different people are and just how much they are the same as well. And so I had a great mentor that said you, one of your biggest tragic flaws is that you always assume everybody wants more responsibility and more success and more work. And maybe you do but not everybody does. So you gotta figure out what they want, right? And there's three things that motivate salespeople from what I've seen. It's more leads, more money, and career aspirations and progression. Typically you can get away with it temporarily if one of those things aren't working, but if more than one of those things aren't working then they're not happy.

[00:22:30] Bobby: Well, I'm so glad you brought this up because I hear, I've heard this after many interviews with folks, even in the promo business. I have heard this a lot, where they try to, they're basically trying to hire themselves, which is a mistake because the business is more complex. Customers are more complex, customers are different. That's interesting.

[00:22:42] Dickron: Distributors have one similar parallel to like a founder led startup in the SaaS space. The founder or the owner CEO salesperson number one at the distributor is often trying to download themselves into like their heir apparent that's gonna take over and run it for them. And from their point of view like that's what's been successful. So it's very easy to see why you would wanna just simply clone that instead of getting super creative with it.

[00:23:09] Bobby: Right, right. Where do you feel you should invest your time? In sales reps who are underperforming that have tons of potential or reps who are performing well and there's just more they can do? Is there a trade off? This is an interesting nuance.

[00:23:23] Dickron: Yeah you don't have an unlimited amount of time. Every minute you spend doing something is time not spent doing something else. So if it takes you 50% of your time to get one person up to being a B player, right, if you could use that time to elevate three B players up to an A player, it's just smart time allocation.

[00:23:43] Bobby: So really your time allocation begins with the ROI that the business can achieve in their sales growth, not necessarily just individual rep performance.

[00:23:52] Dickron: It's opportunity cost, right? Your job is not to be a career counselor. Your job is to hit goals.

[00:23:57] Bobby: Yeah. I love that. Alright, this is a natural segue into managing yourself because leading a sales team, man, that can be emotionally taxing. It's constant energy output. And I've worked with you now long enough Dickron to, for you to basically watch you be like this. For those that are just listening and can't see what I'm doing, just an even line the whole way through. From the minute I'm at, Dickron every time I encounter him, it's this way. So how do you personally keep that equilibrium, stay sharp and motivated yourself as a sales leader?

[00:24:30] Dickron: You don't, you just look like you do.

[00:24:34] Bobby: That's a great, honest answer. I mean, that's fantastic.

[00:24:37] Dickron: I mean when you're in a position of a public figure in a company people are naturally going to look at you to see how they should be reacting to things too, right? So like something great happens, look at you how they're reacting right now. Something bad happens, they look at you how they're reacting right now. Instead of having people read too much into what's happening, you celebrate the successes but you have to keep it like this to some extent so that you maintain a level of stability for the folks that are looking up to you for that. Like you're the master of this domain, right? So if you start interviewing me like this I'm gonna think oh man this podcast is not going well because I don't do this every day, right? So I'm gonna try to match.

[00:25:24] Bobby: Yeah, yeah. Okay.

[00:25:25] Dickron: You're setting the tone.

[00:25:26] Bobby: Yeah, that's great. That's great advice. I also want to know, like you sort of gave an answer earlier to how you yourself regulate your own emotional and life through managing salespeople, and that is that you have yourself a healthy work-life balance. 'Cause you had a sort of an answer earlier at the top of our conversation about making sure people are well-rounded individuals, but leading a sales team is difficult. When you reflect on your growth though, was there another lesson you've had to unlearn from your early days?

[00:25:56] Dickron: Yeah. Actually I remember a VP of marketing that I used to work with at JazzHR walked up to me when I was in the office one day. It was like 6:30 PM and she was like you know one day when you're married with kids you're not gonna be able to do this every day like you do now. And I was like yeah yeah. Like whatever. It's always gonna be like this. I'm never gonna have more responsibilities or age or any of that. And yeah it's freaking hard now. Get your stuff done by five 30 and making sure that afterwards you spend time doing things that matter outside of work so that later on the next day you're fresh and rejuvenated and you're bringing your best self all the time. It matters a lot. And it depends on a discipline and organization too. You can't just like that just doesn't happen by itself.

[00:26:42] Bobby: Yeah. Yeah, that's really good. I'm glad you brought that up. Last question I have for you is kind of blended into a few questions here, but Brian Halligan at HubSpot, he said this on X, he said in the startup to scale up journey, he's seen three phases of sales leaders. He said there's the starter, a leader who can hire a few reps and close some deals, high res close but not analytical. Then there's the solver, a leader who can figure out the profile of the rep, hire them, train them, ramp revenue, analytical and process oriented. And then he said, there's the scaler and this is what you are, and this is what a lot of the listeners of this podcast are because they're running businesses in promo, they sort of have a CEO hat as well as a VP sales hat, or they have a VP of sales, but they're a scaler. And here's what Brian said. That is, hire a leader who can rally the sales troops, constructively collaborate with the senior team, deal with the board, and wisely move the knobs and dials on comp, territory, channels. It's high risk as inspirational and analytical. And he asked the question, does that sound right? Does that sound right to you?

[00:27:37] Dickron: Sounds right to me, but it makes it sound a lot simpler than what it actually is in real life.

[00:27:43] Bobby: Say more about that.

[00:27:45] Dickron: Yeah I mean just you know moving the knobs and it masterfully just lands on exactly where it should be all the time every time. No, it takes mistakes. It takes a gracious leader that's patient with you. And I've had those. It takes sort of moving the knob back quickly once you realize things aren't going well, right? Like it's like this, that almost makes it seem like it's like a step function. But you gotta play in the builder mode and you're a coach and you're a process builder and you have to siphon off the other stuff and deprioritize it. So it's a lot of reading and reacting and understanding what the business needs.

[00:28:24] Bobby: Yeah. And I see you almost kinda said, I don't wanna put words in your mouth. You almost kinda said you dip in and outta some of those roles at times, depending on what the business needs. That's interesting. Finally, one last piece of advice. Now a lot of us are heading into 2026 as we record this. It's early November. There's lots of business planning, there's lots of goal setting, targets, things like that. And if you could give one piece of advice to a promo sales leader trying to boost their focus on their sales team. So maybe they're sitting here thinking, we want to amp our sales and a lot of us do this. We're like, we wanna grow sales. And then it's a matter of where they as a leader should focus and spend their time. So, as a last piece of advice, they're planning for 2026. How would you encourage them heading into the new year?

[00:29:08] Dickron: Make a plan.

[00:29:10] Bobby: Okay.

[00:29:11] Dickron: There's gotta be a plan. It trickles down to what makes sense, right? If I have X amount of opportunities last year, I won X percentage of them. I got this much revenue from each one and thus it ended up landing me at whatever revenue I did. Okay. So if I want to improve my win rate maybe I need better presentations, maybe I need a higher quality prospect, whatever, maybe I need a better human that's actually delivering the pitch. If I want to increase the pool of demand that I have at my disposal maybe I need to go to more events, right? Okay. It costs me this much to go to those events. Does that cost justify the expansion of the top funnel demand gen? How does that trickle down to the bottom? If I keep my win rates at this level or if I raise my win rates, right? So each of the dials on those things get turned up or down, hopefully up, based on actual real life changes that you make. Nothing is actually never gonna get better. Like those things will not get better on their own, save for macro things, right? Like the interest rates going back down to zero. But generally like those things aren't going to adjust upward on their own unless you're actually making business changes that correlate to them.

[00:30:20] Bobby: And speaking of that, as you plan for 2026, you're putting out an annual plan. Is your instinct to evaluate that more on a quarterly basis as far as where you as a sales leader makes dramatic or big changes? What's your rhythm as you head into the year and you set this big hairy goal of growing 30 to 40% or whatever it might be? How are you evaluating that as you move along through next year?

[00:30:42] Dickron: It's not just me, you gotta get all the stakeholders involved, right? There's different participants in different parts of the funnel. A head of sales will typically get together with their head of demand gen or head of marketing and say hey, can you provide like a safe bet and ambitious bet of like where you think demand, what do you think demand is gonna look like month over month, right? And there might be different people in charge of that depending on the channel of acquisition, right? And then you as a sales person are like okay I have this much coming in. Here are the additional things I can do to get more to come in. Now that we understand that do I have the right headcount to meet it? Do I have too much? Do I need to hire more? If I hire more, when are those people over the course of that year going to be fully ramped and making an impact? If I have a bunch of new people does my win rate now go down? Does my average ARR now go down? Hey let me talk to product. What does your roadmap look like? Oh major release is coming in April. Great. That means my average ARR, average revenue per unit might increase because we now have more product to sell starting in April. So like every part of the plan has to be correlated to something that makes sense.

[00:31:48] Bobby: I love this.

[00:31:49] Dickron: You can't slap 30% on last year and say we're gonna do it because we're gonna do it.

[00:31:51] Bobby: Yeah. I love this because what you really said, the key to unlock strong planning is this collaboration with your colleagues. Because in promo what that looks like is we're selling an account, we're selling a million dollars worth of promo into this account, but we're only working with marketing. What can we do to work with HR? What can we do to work with purchasing and what are the other stakeholders within our own organization that can help move that needle? So lots of cross collaboration going on before you can actually finalize those plans.

[00:32:14] Dickron: Yeah.

[00:32:15] Bobby: That's good. Dickron, thank you for the time, man. We could, I know we could have talked for an hour. Thanks for joining us to talk about this. It's huge as we head into 2026. So it's a big service to our customers for us to just think about sales. We'll have some easy steps from this conversation in the show notes that we'll add from our conversation with Dickron. But thanks my friend.

[00:32:33] Dickron: Yeah. Thanks Bobby. Appreciate it man.