The Wisdom Wall

“every, every healthy sales organization should be attrating the bottom 10% every year. You should be getting rid of 10% of your sales force every year.”

“Your competitors likely have a bunch of C players, so you want to go hire C players simply because they know the space? Ok, that's a short-term solve. Basically what you're solving for is you want to reduce ramp time, you want them to be able to get enabled faster because they know the domain. Fine, problem is nine…”

“Inside sales is, your sales leader is in the office five days a week, and the inside sales reps have to be sitting there. Have to be. So inside sales is an in-office deal. And, and there could be no exceptions in my opinion.”

“You should be shooting the bottom 10% of your sales organization every year.”

“We bring in a CRO pre-product. You need a salesperson to create the sales playbook.”

“If you're going to be in my interview process, you are either uniquely qualified to qualify, or you are uniquely qualified to sell. If you are not one of those two things, you are not getting into the interview process.”

“I don't want to say it's BS. I think it's backwards. You need a salesperson to create the sales playbook.”

“So you bring the engineer in, number one, it slows the process down, ok? Number two, there's risk. I don't know what this engineer is going to say to the sales guy. We're recruiting. He could say something about the product that he shouldn't say. It scares the shit out of the rep, okay? So there's risk there. Three,…”

“A reps at Oracle right now. He's selling software, right? He's selling software. That's what he's going to say, and I'm going to say, okay, are you doing pipeline generation? Yeah. I'm selling our new X product into all these Oracle accounts that have never brought X product. I'm, I'm hunting for new logos. No, you're…”

“Any inside salesperson should recognize that by being in the office, they are going to get better faster. They're going to develop faster. They're going to be better at what they are doing faster.”

“A lot of people think if I nail PLG, then I'll nail enterprise. You can nail PLG and enterprise. I just would argue that nailing one does not necessarily make you more likely To nail the other. So if you can do both, do both, but You gotta, in my opinion, you gotta start with direct sales, and then let the product get…”

“What I'd rather find is somebody that works for a company that nobody's ever heard of and actually has an inferior product and was actually able to go to the market with an inferior product and win deals.”

“I need people just to be blunt that are a little fucked in the head like I am. Like, that's what I need.”

“the other thing you want to just measure for is grit, and John McBann taught me that a long time ago. Ask them what they've been through in their life. Like, you wouldn't want to hire me. I, you know, I grew up in an upper middle class family, and I went to USC. Coming out of college, I would have looked at me and…”

“So what they do is they hire for tomorrow, not today, and if you do that, you'll never get to tomorrow. So you hire a guy for the job that you have today.”

“If you have A players in your company, and they're surrounded by a bunch of B players, and you're not holding those B players accountable, your A players will quit.”

“So across the board, if you're not hitting three times your OTE, if your reps aren't at three times, minimum three times your OTE, the unit economics don't work. Now you can give some grace if it's an emerging market, so on and so forth. You can give them a couple of years to get there, but if it's an established…”

“If you tell me five days a week you gotta leave the office at two 30 to pick your kid up from school, that is not gonna work. Unless you're gonna go pick your kid up from two 30, bring him home and come back to the office, say, alright, I can live with that.”

“Now I expect reps to do their own demos. Why? Cause you can go into Grok. And of course I'm going to go with Grok, but you can go into one of the LLMs and we can enable these salespeople from a technical perspective in a way that wasn't really possible before. And so the pre-sales part of the sales process, I think…”

“I think that 10 years ago, I would have told you that you can get away with a shitty product in a world-class sales organization. I would tell you today, I think sales execution is just as important, but ultimately, if you have a shitty product, you can't win.”

“You've just taken the company and diverted all resources to go build a list of things for a company that may or may not buy, but even if they buy, you've killed the company. Right, because you've taken all the resources to focus on one account, even if you get the account, you're in deep shit.”

“You can nail PLG and enterprise. I just would argue that nailing one does not necessarily make you more likely to nail the other. So if you can do both, do both, but you got to, in my opinion, you got to start with direct sales and then let the product get to where the product needs to get through and then go to PLG.”

“They hire the wrong CRO. Pure and simple. You hire the wrong CRO because you have no idea what you're looking for.”

“what I don't agree with is the rep does the land deal and walks away, and they, the customer success rep is responsible for expansion. Expansion is sales, right?”

“I'm paid off of bookings, so maybe they're only going to consume 50, but I think I can get them to commit to a hundred. Can't fault the sales guy. He wants to get paid, so he's going to go book a 100,000 dollar deal, and then a year from now, you're in deep shit, because you booked a 100,000, they've consumed 50, and…”

“If you can't make a decision on whether or not to hire somebody after two hours with them, you're the problem. Not the candidate. It's you.”

“This is the profile. I'm not deviating from it. Back to the conflict thing I said. So let's just say you hire, hire a new VP of the East, right? And he has his background or she, and he's got five people he wants to bring with him, which is a good thing because we need to hire, but he has these five people and they…”

“CEO's, CRO's got a decision. You either stand up for it right there, or you accept the fact you're getting fired in nine months. Because you know you're not hitting that number, and I promise you they're gonna blame you, and this happens a lot.”

“And if you lose A players, you don't replace A players with A players. As soon as the A players go, the rest of the A players know that they shouldn't go there. So now you're going to lose your sales org and you're going to replace an A player sales org with a B player sales org.”

“raising a round doesn't mean shit, ok? The fact that you were able to get, you know, three guys to write you a big check doesn't mean you've accomplished anything”

“My guys are not allowed to send notes. They have to call because it's the same thing. People get inundated with the crew. They have to get the phone number and make the phone call. And so I, I don't think the day of the sales rep, uh, is changing. I, I just don't. As long as you're selling something that's critical to…”

“To me, startups are life and death. And if you've not been through something like that, you don't really know. That's the other thing. Like, I want somebody that's been at a small company. If you've been at nothing but large companies, you just don't know.”

“I can't teach you how to have integrity. I can't teach you how to have grit. I can't teach you to be fucked in the head. I can't teach you how to go close new logos, but I can teach you my technology. I can. With proper enablement, I can teach you.”

“Germans want to buy from Germans. French people want to buy from French people, right? Like you can kind of get away with the UK sales force for a period of time, but usually if you want to go sell it, I'm dealing with one of the companies now, like France, Germany, Italy, they want people in their country that speak…”

“Set quotas too low, not too high, ok? Because if you have to err on one side, what's the downside to setting them too low? Ok, I blew out my number as a company, ok, I expected to do ten million, I did Fifteen million. And I paid more commissions. Okay. Probably spent more money than I wanted. I got a happy sales…”

“if your sales leader is beloved by everybody, you got the wrong guy.”

“that's the biggest shortcoming I see of a lot of leaders. They cannot stand not to be popular with the people that are beneath them. They avoid conflict, and which means they avoid making the right decision.”

“You know, can you do it with 50, a 100,000 employees to it? No, I don't see how you can do that. I just don't see how that's possible.”

“So people will say, focus on domain, focus on this, focus on scale. Bullshit. All I care about is where has this person worked? Who trained them? Do they come from a world-class go-to-market function?”

“Super easy. I'm going to pull up your resume. So help me understand. Why did you go from this company to that company? Why, what, what was the motivating factor there? Why did you make that move? Oh, well, they offered me a bigger base salary. We're done. Why did you go from this company to that company? Well, they…”

“usually you're going to need more than a couple million bucks to do this. You don't need 20, but you probably need 10.”

“Well, who designs the product roadmap? Oh, the product organization does. You got, you got problems, right? Because product organization is going to go build what they think the customer wants to buy. The person that knows what the customer wants to buy is the person that's talking to the customer. It's the CRO.”

“what I don't agree with is the rep does the land deal and walks away, and they, the customer success rep is responsible for expansion. Expansion is sales.”

“If you can't make a decision on whether or not to hire somebody after two hours with him, you're the problem. Not the candidate, it's you.”

“Gross retention tells me if people like my product, right? Like I understand if my gross retention is 90%, I probably have a pretty good product, right? If my gross retention slips down to 70%, I have a product problem.”

“Early stage company, look, we do, you'll do negative margin deals, right? Like we're going to do this deal, but we're going to lose money on the deal. But we need the referenceable account, and we'll make up for it later.”

“A hundred percent. You can't teach, someone's either, someone either can sell, or they can't. I can, I can, you can teach someone to be better, but if they don't have the innate ability to sell, some people are petrified of the phone, right?”

“Is that the only thing that motivates you? Because if that's the only thing that motivates you, we're done here. I have nothing, I have nothing to discuss with you.”

“That has to take place before you, before you build the product. Otherwise you could build a product that nobody wants to buy.”

“The person that knows what the customer wants to buy is the person that's talking to the customer. It's the CRO.”

“what I never want to see is, Hey, I just hired 10 reps. I put a rep in New York, rep in Dallas. And a rep in San Francisco and Los Angeles, and I told them they can have all the accounts in those geographies. You're in deep shit.”

“They are, in fact, while not as directly responsible as sales, they're still responsible for revenue.”

“salespeople are great because they're predictable. I can get you to do whatever I want you to do by setting up the comp plan accordingly.”

“If you're going to be in my interview process, you are either uniquely qualified to To qualify or you are uniquely qualified to sell. If you are not one of those two things, you are not getting into the interview process.”

“if I ever hear that a rep says, well, why aren't you hitting your number? Well, I'm not getting any leads. You ain't going to make it. So yes, they are ultimately responsible for their own lead generation, but they should be supplemented.”

“Gross retention tells me if people like my product. Like, I understand if my gross retention is 90%, I, I, I probably have a pretty good product. Right? If my gross retention slips down to 70%, I have a product problem. Net dollar retention is about expanding. So you can have high gross retention and a low NDR. That…”

“Early stage company, look, we do, you'll do negative margin deals, right? Like we're going to do this deal, but we're going to lose money on the deal. But we need the referenceable account, and we'll make up for it later.”

“Even if you have the best product in the world, you're still going to leave money on the table if you have shitty salespeople.”

“There's great companies with very shitty sales organizations, and there's shitty companies with world-class sales organizations. So the first thing you look for is what quality of sales organization does the individual come from?”

“you never want a new manager to have less than five productive reps. You can't scale the organization from 100 to 300 and not have that. What I mean is if I have a manager, he's got five reps on his team, he or she, three of those reps should be productive, two can be new.”

“A productive rep, if, if the productivity per rep is a million dollars per year, the first quarter they're productive is the first quarter you can expect them to do two fifties. So first of all, you have to, people get this definition wrong all the time. Like the second a guy does a deal, he's productive, incorrect.…”

“You can do a good job of getting the enablement to happen within 90 days, but if your sales cycle is six months, you're still gonna have ramp time of six months.”

“Somebody that's passionate about their career will know every single one of these details. They're proud of it. They hang their hat on it, right?”

“And so it makes it harder because I, again, I need more senior people, but I can't give up that ability and willingness to do the hard grunt work, the PG pipeline generation. So it makes it harder. The spec has gotten more narrow.”

“Ok, so I have to, when I'm building a productivity plan or a hiring plan for a company, I have to bake into the fact that I'm going to have six percent turnover every quarter. I have to hire ahead of that turnover.”

“So, I take my productivity, expected productivity last year, let's assume it's a reasonable number, and then I tack on 20% to set the quota. I expect my average rep to sell 1.2, I don't want everybody hitting quota, so then I'll take the 1.2, tack on 20%, and then that's my quota for the following year.”

“The usual problem is, my new logo ACV is not where I want it to be. All my reps are doing is focusing on expansion. Why? Because expansion's easier than opening a new account.”

“salespeople are great because they're predictable. I can, I can get you to do whatever I want you to do by setting up the comp plan accordingly.”

“If I'm a 10 K ACV, then I'm, I'm exclusively inside sales and I better be able to keep the cost of sale low. Otherwise, to your point, I can't justify it. The unit economics don't work.”

“It's sort of a rule of thumb. My reps should be able to generate three times their OTE. So if your OTE is 300 rough numbers, you should be able to get 900 K in productivity.”

“If you have a field sales organization, and you have 10 reps, and the productivity is 600 grand, you better not be hiring. You need to, you need to get that productivity, and until such time as either you get that productivity up, or at least can look at the data and see that it's trending in that direction, and you…”

“Inside, I'd like to see 90 days. Outside, six months. Reality is, it probably trends more towards nine months in enterprise.”

“So at 10 reps, do you need an enablement person? Probably not. And each, each circumstance clearly is unique, but at 30 to 40, yeah, you better start to think about it.”

“your SEs will start to depart before your reps. And when your SEs start to depart, the reps know that the SEs know more than the reps know about the product. Right. So you'll see SE start to depart and the reps will start to follow.”

“if you're going to scale like that, you can't have 10 interviews per hire, right? It kills the productivity.”

“Most of these guys are now reaching a point where they've made so much money where they may not want to go back and do this again. So you have to look for the next generation.”

“salespeople, as good as they are, is capturing and understanding the data. That doesn't mean they're necessarily great at creating content. So what you want them to do is capture all of the information, feed it back into product marketing and let product marketing create the messaging.”

“So if you look at a 10 K ACV, well, that's definitely not a field sales rep, right? If, if I'm a 10 K ACV that I'm, I'm exclusively inside sales and I better be able to keep the cost of sale low. Otherwise, to your point, I can't justify it. The unit economics don't work.”

“My reps should be able to generate three times their OTE. So if your OTE is 300 rough numbers, you should be able to get 900 K in productivity.”

“So if you have a field sales organization and you have 10 reps and the productivity is 600 grand, you better not be hiring. You need to, you need to get that productivity, and until such time as either you get that productivity up, or at least can look at the data and see that it's trending in that direction, and you…”

“Inside, I'd like to see 90 days. Outside, six months. Reality is, it probably trends more towards nine months, uh, in enterprise.”

“So at 10 reps, do you need an enablement person? Probably not. And each, each circumstance clearly is unique, but at 30 to 40, yeah, you better start to think about it.”

“Having a rep that loves his day job is, is very difficult in our environment because nobody likes doing pipeline generation. It's not fun. It's a grind.”

“If you get managers saying different things and selling it differently as the reps are going through the process, what happens? You lose credibility. Hey, this manager said this, this manager said this. What the fuck? Now I just don't believe anything you guys are saying. So you gotta get that. You gotta nail the…”

“when you're hiring at scale, you have to hire. Because if you can't hire next year's forecast, not this year's, but next year's forecast is shot. Now you're going to the board saying, I got to lower the number. I know we raised off of doing 200 next year. I get it. I'm sorry. I can't hit 200 because I'm 50 heads behind…”

“functions like a, like an outside salesperson. You can't make them be in the office. I don't want them in the office. I want them in front of customers.”

“Sales engineers are going to, and so what will happen is your SEs will start to depart before your reps. And when your SEs start to depart, the reps know that the SEs know more than the reps know about the product, right? So you'll see SEs start to depart, and the reps will start to follow.”

“Don't get greedy and try to put the rep into a position where you're expecting revenue before you should expect he or she to be enabled. Commit the time and resources and understand it's going to take this amount of time, this amount of resources to get our reps enabled. Do not take shortcuts.”