sales rep

“So, you know, and a lot of times sales reps do this where there, there's clearly a bigger opportunity, but they're optimizing for their commission this quarter and they're actually leaving a Big pile of money on the table because they're optimizing for their c…”

“I mean, if you distill everything down to the essence, we're sales reps as venture capitalists.”

“I think the one thing to call out is it's the cheaper route. You're not going to give away as much equity. You're not going to be probably paying these people in very early stage, high amount of cash”

“So a great rep typically would come to me in a one-on-one and say, you know, Jean, my target is X. I'm going to need to close 20 deals to hit that. You know, here are, at this point, the ones that I think are likely to help me get to that number. Here are the …”

“You know, it's hard to trust a single individual's point of view on what the pattern is. And so I do think you're going to want two to three folks to sort of corroborate that pattern as being, you know, true versus sort of a single individual's point of view, …”

“I always get nervous about sales reps who think they've got it all sorted out, and want to keep you at arm's length, because the best ones typically know where they can leverage other people in the org, and really want to do that.”

“My lean, Harry, head of sales first, because I think a strong head of sales can do four things really, really well. First, they create that sales playbook that you asked about earlier, where the CEO is leading by example, but that head of sales goes Creates th…”

“Personal ownership means a real understanding. I'm part of a bigger picture. My number is my manager's number is my segment leaders. Number is my head of North America's number is part of the company number. And that's a very big thing. And that's hard to teac…”

“First, make sure they've sold at your price point. A sales, if you're a five K ACV startup, do not hire someone from a million dollar a year group, no matter how much you love them. It's the wrong toolkit.”

“What makes them Tenex, and it took me a long time to figure this out, they can change their playbook. 90% of sales reps, and this works out the bigger you get, they sell exactly the same way.”

“I think if you really need to rely on sort of like having people with the same cohort to drive competition, I think you may have hired the wrong people in my opinion, right? Because in that early stage, I'm actually trying to foster more than anything, a cultu…”

“If you can't be successful as a founder selling your product, how can you ever expect someone else to be successful?”

“I think the thing that goes wrong is when You've got a team focused on one segment and you ask them to dip a toe in the water of another segment. And it's very hard for any one person to both do, you know, high velocity bottom of the market deals and also do s…”

“No matter how much you say the stove is hot, people still want to touch it in order to find out that it's really hot, and so it's my job to make sure the burner's on simmer and not on high, so it's not a catastrophic wound.”

“So you need to create space for them to fail when the stakes are low so they can succeed when the stakes are high.”

“I think they should make that first hire as soon as they have a product that they really want to be testing out in the market, and so I think it's a lot sooner than a million ARR, to be honest.”

“Great sales reps know exactly how they did every year. Like, I can tell you, okay, and this year, in 2007, I did this, and I made this amount of money. . I was number one on the sales board. I was number two on the sales board note three. John Holbrook beat me…”

“I think you should hire more than one at a time for a few reasons. Less about the competition. I think they're, you know, that's kind of going to happen maybe naturally, but it's more about you can work. It's work for scale. I think if you're onboarding one pe…”

“A good sales rep uses us as a pawn. I always say, I'm an actor in the sales reps movie. They're the director. They can use me however they want. If they make me the director, good luck, and you're probably going to fail.”

“You don't make the software. So your only job is to sell the software. You're not a technical resource. You don't help customers deploy. So this is kind of the, you had one job argument, right? Like you had one job. And it's like, let's just remember, that's w…”

“The hardest case is not firing somebody who's not selling. That's easy. The hardest case is keeping somebody who's not selling.”

“In the same way, like, if you're expecting to hire people off the street, expect their super high turnover rate, it's just, you know, there's a 98% chance that each hire is probably not gonna work out.”

“I have a lot of situations where I had a rep that was in there for three or four months, and we weren't sure, and they weren't hitting it, but we gave it a shot, and seven months in, they were toward the top, and they stayed there.”

“If they're going up for a week and go down, yeah, we probably need to make a cut. But if they're staying there, this is taking a little while, let's hang in there. I think we're going to get there.”

“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 to discuss with you.”

“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 re…”

“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…”

“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 sh…”

“And I think many leaders will maybe disagree with me, but I don't think you can create urgency. Like you can create fake urgency. And if you have urgency to hit your number, that's not the urgency your prospect has.”

“I believe sales experience is overrated. I think When you are a highly tenured rep, I think some people believe that. It should be weighted the most when hiring a sales rep. I don't think that is true. I think there are other characteristics that I would weigh…”

“I would almost hire a marketer before you actually hire your first sales rep, maybe 18 to 24 months in advance, so they can get better work.”

“The sales reps that are coin operated are the ones you don't want to hire. The sales reps that have that insightful IQ that you talked about want career development. They want challenges. They want to figure out how to get, like, coached and mentored. That's w…”

“Even the best sales reps I know, depending on whatever segment you're in, you know, their win rates are anywhere from 15, 20%, maybe 30, 40% of the absolute highest end.”

“Most sales reps in the world use ChatGPT, perplexity, LLMs in their private life, but they can't use in their professional life.”

“And I think AI is going to drive so much more company creation that there will be a consistent demand For these roles, because the economics of the roles get better. There's more companies that need sales reps.”

“As long as humans are buying software, I think you need humans to sell software. So we definitely use AI to become more efficient, but we're going to hire quite a few folks because we're going to go big, so.”

“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.”

“You should have got ahead of it, and I would say, take your time and hire only eight people. Otherwise, it's gonna come and get you at a certain point, where again, you created a bad culture”

“They're not all money motivated, and you can't make the mistake that they all are. You have to sit down and understand what motivates someone. So if you drive into an account with them, used to call it windshield time. You don't look at your phone And check yo…”

“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.”

“The job of a sales rep, they get their book of accounts, right? And every year we've created more focus around them and we've done, we've had to do ruthless prioritization on like which accounts are we going to really go deep on. But once they get their accoun…”

“I, if those are the two options to choose from, I would take the person with the experience doing the deal, because I think the industry experience you can teach with, to the person who's got, you know, the right willingness to learn and the curiosity, and obv…”

“I tell every founder this, I'm like, hire two at a time, because then you'll actually see Is one, you hire one, you're like, is it good? Is it not good? I don't know. If you hire two, it's pretty clear whether one's good and one's bad.”

“A lot of these people who have these entitlements, they're going to have a bunch of young kids come up And steal their lunch because they're going to go out and want to work because they're desperate to work. So I do think it's going to change.”