Sales Rep

“As I spend more, more time in there, I very quickly realized that it's not that big of a TAM and that world is ending very, very fast. On the other side, Sharath had spent a lot of time in Philippines in his previous job, so he convinced me that no, customer s…”

“Because it turns out that in a lot of these companies, you have reps doing 10 or 20, thirty million.”

“I think we have 10,000.”

“We have 17,000.”

“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.”

“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.”

“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…”

“Why do I want pessimistic? Because I don't want someone with happy ears. If you're happy ears and you're nice and everyone's nice and you like everyone, well, guess what? There are gonna be a bunch of deals that you're not gonna get because people are gonna li…”

“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.”

“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…”

“Yeah, because of the 50, 50% failure rate, I think that's exactly right. So yeah, even, even, even a taller order, go, order, go find two people that are good. But yeah, I think that that's right because, you know, one in two will fail.”

“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.”

“It's better to give a precious lead to an ad to a B plus AI than to give it to someone in sales. That's going to quit, not show up or screw up the deal.”

“What we're seeing in, in a lot of those long tail customers is let's move all of those to digital, or let's even move all of the, you know, the high volume, low touch historical buyers to a hundred percent digital, because then our sales reps can make it go fi…”

“There's no excuse for a sales rep or a CSM or a support rep to not have context about your account, to know what you're doing.”

“I think it takes a lot of work to get that last mile good enough where you would say, Hey, we're actually going to feel confident actually having the AI act as the sales rep or act as the CSM in these equations where it's going to get there. It's going to get …”

“Most sales reps want to earn 80% of what they can for 30% of the work.”

“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.”

“The only problem is it's entirely wrong. And, you know, you have like a sales rep that is adding their own like subjective Experience about the account. Like they may want to influence the sales manager to think that the deal is going to close, or they may be …”

“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.”

“I don't think they have a job next year. I think most, I think they're going to quickly lose all and they're not going, and I don't think they're going to step up and become AI experts.”

“Because your AI, at least by next year, is going to be better than 80% of sales reps. Not the best.”

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

“Particularly in medical versus just small, medium-sized business, you know, finding decision makers is much tougher. You know, office managers and front desk staff, people at these medical practices are trained To keep sales reps and people away.”

“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.”

“One of the things that I've seen very consistently in terms of being one of the biggest growth drivers at companies I've worked at, it's having highly tenured reps. Those reps are the ones that tend to have, in my experience, Tend to have the highest in rep pr…”

“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…”

“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.”

“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…”

“No one does reference checks since March, 20, 20. No one asks sales reps to do demos before they hire them anymore.”

“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.”

“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…”

“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…”

“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…”

“We're gonna see, like, the certified real human, which can be the new, like Parmigiano-Reggiano of, like, sales. Well, like, hey, like, this is a stamp. This is, like, actually a meat bag that's talking to you, and some people are gonna like that. Some people …”

“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.”

“Reps spend about 75% of their time on non-selling time. If you measure the hours that their customer facing, it's 25%, sometimes even less.”

“We made decisions based on a spreadsheet. We had a historical data on rep effectiveness in 20, 20 and 20, 21 in finance plugged the number going from 10 reps to 14 reps into the spreadsheet. And the spreadsheet said this was what was going to happen when we go…”

“In founder-led sales, unfortunately, you can't hire the diverse type of rep that a great CRO or VP of sales can hire. They have to be narrow. They have to be people that work on your wavelength, that talk the way you talk, that can do no look passes, that you …”

“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.”

“If you're running a new CRM startup, you can run circles around 98% of the sales reps at Salesforce or HubSpot, right? They have the brand, they have the partners, they have the integrations, but they cannot answer the questions you can answer.”

“So you need to hire One rep and you've got to hire two because otherwise there's no AB test. You have to AB test humans. You have to AB test humans. You've got to hire two as hard as it is.”

“Those first couple reps have to be people you would buy your own product from. That's it. Now we can talk about other criteria. We can talk about normalizing for deal size. We can talk about industry expertise. We can talk about all this kind of stuff, but whe…”

“I think you will regret it if you don't hire these first couple sales reps that have a couple years of experience. If you're in B to B with B to B sales, they need a couple of years of experience and they need a certain amount of maturity.”

“It's usually 50, 50, right? 50% base, 50% bonus for a sales rep.”

“Ultimately a sales rep's got to bring in four to five times what they take home. Okay. So that one forty's got to be six, 506 hundred or more. The more enterprise you are, the bigger the multiple has to be and the higher the comp, but it's got to be three to f…”

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

“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…”

“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.”

“However, that's the number one predictor of how stressed out somebody is, not how responsive their customers are that week, not how many deals they're closing that week. It's the health of their relationship with their manager.”

“If you hire someone from something that is great, but easier to sell and yours is harder, they will fail almost always.”

“If lead rejection rates actually start to go down, it might mean that your leads are just not getting followed up with.”

“Do leads pick up the phone and want to talk to your team at expected rates? This is mainly a training issue. That where reps might not know how to speak the right language to prospective customers, or might not understand what customers are looking for.”

“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…”

“You need to get them signed now. Like, if they are perfect, like, why should you wait the week? What are they waiting a week for? I don't know. They just wanted to think about it. What are they thinking about? Get them in and be aligned on this. So this is sup…”

“Not everyone needs to train exactly the same thing. I think that's the original error that you do. You have these boost sessions where you get everyone in and you're training negotiation. But maybe 50% of your team already know how to negotiate. Why spend two …”