10 Signs You Shouldn’t Hire a Sales Rep (or VP of Sales) Candidate: A Checklist

Recruiting has changed for sales reps over the last few years. I didn't totally get it until a comment on a LinkedIn post I'd made the other day from a CEO said, Listen, before March 2020, every single sales rep would do research before in an office interview. No one ever came to the office without having done a Google search, watched a video, checked out the website, seen a demo. He's like today the bar for an interview is 10 seconds. You hop on a zoom. And that nobody really does the work before an interview. Some truth to that, a lot of truth to that. In my experience, no matter what, people just interview differently, they interview faster, it's more furious, there is less put in. So I thought I would help you with a checklist, a checklist of 10 signs. You just shouldn't hire a sales rep and this is especially true in the founder led sales days when you hire a VP of sales that you trust, that you believe in, that puts points on the board, be more flexible, let her or him hire who they believe in for the most part. You can't micromanage a great VP of sales. But and here's a bit of a, bit of a learning, almost a paradox in the founder led sales, you almost have to micromanage a bit. You need a very particular type of sales rep that can be your right hand person that can get it done for you. And if you, you could and you can hire a different type of person in the founder led stage, probably all that matters is that you would buy your own product from them. As we've talked about, they can come from different backgrounds, they could be a bit mid pack, they could be a bit shabby, but they have to be someone you would buy your product from. So with that let me give you 10 signs, 10 quick tells. Just don't hire a rep in today's world. Okay, number one, and this, this one is among others may maybe a little controversial to some, some will challenge it, but let me tell you, this one is completely true. Do not hire a sales rep if they're late, if they're late to the zoom, if they're late to the interview. And why look, why, why can't you be late? What's the end of the deal? Now let me distinguish between sending an email 15 minutes before meeting saying I'm sorry I'm running late or I'm sorry something happened, I'm sorry, I'll be there, I'll be there, just a few minutes late, sending that email in advance, apologetically, that's one thing. But The CEO just sitting and waiting for five, seven minutes for someone to show up to a zoom. Why is that not okay? I'll tell you why it's not okay. They're going to be worse with your customers and prospects. They're going to be even later. They're not going to follow up with them. And that just makes you look terrible. You will lose deals. It is the world's worst message to send to a prospect. That their time is not worth it, that they're not worth it, that you're not even going to show up on time. The best founders are always early. And the best sales reps know it matters too okay. Too. And we hit this at the beginning. Don't hire any sales reps you wouldn't buy your own product from, period. And this may sound quirky, why? Why? I'm not exactly my buyer. No, but if you're in the founder led sales and you've closed 10 customers, 15 customers, 20, 30, you know what works and doesn't up until that point. Now you wanna, you wanna experiment, you wanna be creative, you wanna learn from bringing some seemingly experienced person on your sales team. But I gotta tell you, whenever I talk to a founder and they tell me the first two reps didn't work out, the first five, eight out of the first ten didn't work out, I always ask them one simple question. Okay, I know you liked her or him. I know they had a great LinkedIn, a great resume. I know they talked the talk and knew NRR and ACV and ARPU and all of this stuff, but would you have really bought your own product from them? And the founders always say no, you're right. I hired Jason because he came from Twilio. I hired Linda because she came from Datadog. I love those companies. I loved her experience. But I know I wouldn't have bought my own product from it. It's much too complicated. You have to be too much of an expert. You have to know this, you have to know that they never understood it. They never got there. So don't hire any sales reps you wouldn't buy your own product from. They won't work out, number three. And this one's going to be a bit controversial. I wrote this up on LinkedIn a while back and at first a lot of sales leaders and a lot of or maybe sales executives said this was silly, but then they came around and said, yeah, you're right. A sales reps got to be able to sell you this pen. Now, I don't mean literally the Sell me this pen exercise of like literally sell me, sell me, sell me this, sell me this phone, sell me this pen. I mean sell me your product. And in the old days when interviewing was done differently and a lot was done in person and in the office, usually at least by the second interview or sales rep would come into the room and sell the SaaS product, sell the product to the rest of the company, do an actual demo, stand up, even click through it, do it the way they would do it in real life. I rarely see that today. And it's fine of course to do it over zoom or to do it however. But too many folks are skipping the step entirely. They they will get an offer letter out, hire and bring on a rep that has never had to demo selling the product themselves. This used to be something 100% of VPs of sales and sales managers would make reps do. It was understood as a sales rep looking for a job. You're going to have to put in a few reps, you're going to have to prepare, you're going to have to come before you got that offer letter with a demo. You're going to have to be able to demo the product at least at some mediocre level. And I find 9 out of 10 VPs of sales often skip this step today. And almost 100% of founders don't. Don't. If. Listen, they don't have to sell you your product in the first meeting. They don't have to sell it to you until you're a couple steps down the process if you want. But if after two, three, four interviews and you're and you're going to give them an offer letter and you're going to trust them with your precious leads if they can't do a basic demo, a decent demo, if they can't watch a few of the ones that are already on YouTube that your team has already done. If they can't listen to a couple gongs and they can't do a B plus job of selling your product, all the onboarding in the world isn't going to get them there. Not in the early stages at least. Point four a little bit related to the prior points. Don't hire any reps that do no research before the first meeting. Don't, don't. I hear too many excuses this day. I hear too many. I didn't have time, I didn't have this. And listen, it's just too easy to do research today. It's too. You just fire up the browser, go to and companies have so much great stuff on YouTube today. Almost every SaaS vendor, almost every vendor's got some great demos, some great videos, explainer videos on their website, on their YouTube. I'm not saying sales reps need to do four hours of research before a first call, but way too many do nothing. I'll show up to a first call and the question will be, tell me what you do. No, that's not my job. You're in sales. You've got to sell yourself. You've got to sell me or us that you can actually do it. So when they do zero research before the first zoom, when they're this there with their mug, with their mug to listen, don't make the hire. Don't make the hire. They'll do it just as bad with your prospects. They. They won't research your prospects and customers before meeting, and they'll show up with no good ideas. They won't bring solutions to meetings, which is the job of SaaS sales today. Hey, number five, and this one may sound funny, but I see too many reps that, that aren't going to do it. That struggle with your tech. They struggle to get into your zoom. They struggle to figure out how to use your audio. They struggle to use whatever meeting technology you do. They struggle to watch the demo. I'll. I'll send folks, or I'll. I'll send folks a YouTube link to something and they'll say they had trouble reading it, like their computer wasn't working. I know you laugh, guys, but I see this. 10 or 15% of the time, someone can't use the mixed calendar link or the mix max link. They couldn't do the scheduling. We're selling technology. If the sales rep candidate can't use your technology, it just ain't going to work. So I know you laugh, but it's pretty common. Don't make excuses. Don't laugh when they say they couldn't figure out how to get your calendar link to work or the YouTube link didn't work on their computer. Don't make the hire. There are other computers. A sales rep that wants a job can go find another computer where the calendar Zoom link works. Okay, 6. This one may be the most triggering of all to some, and I really don't like that word triggering, but it's become part of our Lexington. Don't hire a sales rep with another job. Don't hire another sales rep with another job. Now, listen, I'm not going to win the debate around sale side hustles. We did a survey on Saster, LinkedIn the other day to over 2,000. Over 2,000 sales professionals voted. Over half said they had second jobs and side hustles drives a lot of founders nuts. It drives me nuts. As founders, we know, we know that if you're doing two jobs at once, you're not going to be great at either of them. That's my life experience too with folks on my teams that have worked multiple jobs. None of them have been number one. None of them have been number one. And even when they have, they flamed out because the demands of the other side hustle and job have overwhelmed them from time to time. But listen, I'm not really talking here about a small thing they do on the side or some vending machine or real estate job they have. I'm talking about folks with another job. Don't hire somebody. I'll give you a fun extreme example. This is more for a VP of Sales than an ae. But you know, the other day I interviewed a VP of Sales candidate and he violated a bunch of these rules. So all 10 of these applied for VP of Sales as well as just individual contributor AES and I. And I'd asked his VP of Sales if he'd had a chance to review the YouTube link that I sent him. He said, I got about 10 minutes through. Is interesting. I have a few questions. So that's a good sign. We talked about, you know, did a little bit of research and said, why'd you only get through 10 minutes? He's like, well, my CEO really needs me for a big pitch on Monday. I had to do some work. I'm like, I see really needed you. So what's going on with, with your CEO? You know, are you transitioning out or what's the plan? He's like, no, no, I want two VP of Sales roles. I'm looking for two at the same time. I appreciated his honesty, but there's a lot going on here. The fact that he could do 10 minutes of the project but not 30 minutes of it because he wanted the other job, because he wanted two VPs of sales job. It's an extreme example. This was my first one where someone came out and said, hey, I want to simultaneous full time VP of Sales roles. That's an extreme example. But look, I'm not going to argue the side hustle thing. The ship has left the station. When sales reps could all work from home, half of them or more started working multiple jobs on their computers. It's happened. It's been over four years. It's not going to change. But if they're literally working two jobs at the same time, don't hire them in a startup. Just don't. They're never going to get good at your product. Here's what I found. They never put the time in to become product experts. And if Nothing else, your first 2, 4, 5, 10 sales reps have to be product experts. They have to be solution architects, they don't have to be coders or engineers. But they have to know how to use your feature. Poor, not that great product that does have a 10x feature, that does have something differentiated. They've got to convince folks to buy it when no one's really heard of you. And if they're working two jobs, I don't ever see that happening. They're at best, at best mid pack in the early days and, and usually worse. And the other flag here is, I'll bring this up with folks. I'm like, how? How do you think you can do two sales jobs at the same time? They're like, well, it's just selling. I don't really need to know the product as long as I understand the customer's problems. This is the great conceded sales. I don't have to do the work, I don't have to learn the features, I don't have to know how to do a demo. I don't have to do anything because I have empathy. I, I know my customer's problem. Their problem is that their API doesn't work right or their financials are inaccurate. It's not enough. Great. A lot of customers know they have issues around financial reporting or financial controls. But if the rep can't tell me why their product will solve it, they're not going to close anything. And too many reps cut steps. Too many reps joint take jobs that they shouldn't take. For products that are too complicated or not the right fit for them because they think they can understand the problem. That's a start. But you have to understand the problem to provide a solution. But in sales, your job is to provide a solution, not just to identify and understand problems. Okay, sign flag seven that you shouldn't hire a rep or VP of sales. And the more I go through this, the more I think this applies to anyone up and down the stack in sales and frankly, probably for any role. Don't hire folks that are really angry about their last role. And this has always been an issue, but the last couple years it has become far more common. Look, so much change, so much change. We went through lockdown and Delock down and a boom in 2021 and a de boom in 2022, and then layoffs and then in 2024. We're in the era of the efficiency. And it's like, I think in the last few years, we've been through four or five huge rounds of change. Far more change, far more faster than in my whole career in sas. And the folks, a lot of folks, one feel like they got a raw deal. A lot of folks feel like they work too hard for a lot of money. A lot of folks don't really want to work that hard anymore. There's a lot of issues and there's a lot of angry folks. And the reasons they're angry. I have some empathy from, and in some cases, I have a lot of empathy from. But too much of this, it breaks people. And, you know, it's always been true that a little chip on your shoulder is great for first, for your top hires. A lot of your top hires. Your, your great VP of sales, your great, your great ae. They're going to have a chip. Hey, man, I was, I was at this great SAS startup, but they didn't see my greatness. I, you know, I was top 20%, but they never invited me to President's club, blah, blah, blah. They got a little chip. Little chip is great. A big chip. I start to worry about. And then when it's beyond chips and it's bitterness and they tell you how their last CO was terrible and their VP of sales was awful, there's. There's usually a lot of truth in those stories. A lot of CEOs are flawed. A lot of CROs are flawed. I'm flawed. You may be flawed, but if they tell you too many of these stories in the interview, don't hire them. They will come in bitter. They will not get out of it. Your job cannot be a sanctuary for bitterness for folks. It just can't. There may be places for that, but it's rarely your startup. And the folks that are this bitter and angry about their last job, they can't throw themselves enough into your startup, into the chaos, the lack of training, the. The dynamicness of your environment, they just never get there. So have empathy. But when, when there's just this constant anger, this, this, this belittling of their last roles or jobs. Don't hire them. Don't hire them. Okay, last ones. Number eight. Trust me on this one again, one that many will challenge me on, but then later concede I'm right. Don't hire a VP of sales or a sales exec that's constantly on LinkedIn all the time now for VP of sales, a certain amount of this is good. It's good for recruiting. It's good for folks to understand who they might go work for. It is good to have a little bit of audience on LinkedIn for management I think. But if you have a CRO or VP of sales that's posting seven or more times a week, these ones never work out. They never ever work out. And sales reps that are constantly giving advice with 18 months of experience, SDRs that are telling you on LinkedIn how to run your business, not never ever hire. These folks, the VPs of sales and CROs that are constantly on LinkedIn two to three time posts a day, don't really want to do the job anymore, they don't want to sell. And the SDRs and AES that are posting constantly about how to be great at sales, they want to be influencers. It's just the reality. And I know folks will challenge this but, but you don't want to hire the ones that are there all the time. A VP of sales that does a couple posts a week, that are smart, that are thoughtful, that ultimately help her or him recruit, I'm all for it. But once you cross the line into influencer and there's a lot of them, influencer, course, seller, whatever, don't, don't make the hire. Okay, last two. These ones are important. Number nine, do not hire a sales executive where your product is much more complicated and than the last one. Trust me on this one. This is a mistake we all make again and again and again. When you hire someone who, whose last product was super hard to sell and yours is merely hard to sell. Like hard but less hard than last one. It. It's like a weight is off their, their shoulders. It, it's like, it's like you've cut off, cut off some weights from their feet and they just fly. They just, they just fly and you know, same blonde CRO at Brax. We've done so much together. Our CRO Confidential series when he was our first sdr, he flew when I worked with him in the very beginning as sdr. And there are a lot of reasons he flew. Sam is great if you follow any sasser stuff. But he also came from as hard as we were in the early days, as hard as selling E signatures from he came from intact which eventually had a billion dollar exit. But selling financials on the Internet was even harder than selling contracts on the Internet. So he came in and he just thought this job was easy. It wasn't easy. It was hard, but it was easier than his last role. The flip side is take a sales executive that has only sold to themselves, only sold sales products. Have them sell a developer product. Have them sell that complex vertical SaaS product, a security product, a compliance product. Some can do it, some can do it, but you better make sure most cannot. Most cannot. There's not enough time in a startup to jump into in a selling environment that's harder and more complicated than the last one. They'll cut corners, they won't learn it, they'll think they can, and then they'll just start drowning two to three months in. Okay, last point. Ten, last flag. And this is one that may appeal to you as a founder a little bit, but you can't make the hire. Don't hire anyone in sales from SDR to AE to director to VP to CRO that doesn't care about money. That money isn't a top reason to take the job. Now, of course, the higher you go in the org, the more important equity is. A lot of CROs will push you really hard on equity day. But that's still money, folks. It's still money. Don't hire an AE that says, listen, I'm, I'm here. I, I'm here for the customers. I don't really care that much about money. Maybe that's good in customer success, maybe it's great in support, maybe it has a good place in production. I've never met a sales rep that performed well that didn't care about money. In fact, it's almost sad. A lot of the best sales reps spend everything. A lot of the sales reps will make hundreds of thousands, half a million, maybe a million a year. And at the end of the year, they've got nothing left. That's a bit of trap of a tragedy and we should do more to help them. But it's kind of what you want. You want someone that is so focused on money that they are going to not rip off the customers. There are some issues there, but that they will get good at their craft, they will get efficient, they will call the customer back, they will map out the org, they will figure out the 20 stakeholders at the company. If you don't care about money, you're not going to do 20 demos, you're not going to figure out every stakeholder. You're just going to figure out when the person that inbounds is the wrong person, that it's, that it's closed lost when it wasn't. When it could have been a million dollar deals. You want sales? Sales is about a lot of things. It's about the game. It's about a craft. It's about getting good at it. It's about learning to love the. The learning to tolerate the L's with the W's. But it's got to be, in large part about money. So run from sales reps that don't care about money. My ten flags. Trust me. Just. Just. It's so hard these days to find great people. It's so hard to find a match. And again, we're recruiting so fast and furiously over zoom that we skip a lot of steps. But Here are my 10 tips to make sure you don't regret a sales hire.