How To Hire First Your First Few Great Sales Reps! A 6 Point Test

We have talked a lot on Saster about how to hire a great VP of sales over many years. We've got a checklist on sasser.com you can hire, we've got interviews, we've done sessions with the best CROs in the world, from Atlassian to Digitalocean to Cloudflare to Zoom to Box and on and on and on. But I wanted to set out a few key points. When you go to hire sales reps now, later, this is less your problem. When you hire a great VP of sales, you really to some extent have to get out of their way. If they come in and hire sales reps three through three hundred or ten through a thousand, you're going to need a village. You're going to need a very heterogeneous type of sales rep. In fact, that VP of sales, if you have a good one, will hire sales reps that you would not hire yourself. They'll hire very different sales cadences, very different styles. But in the early days it doesn't work. In the early days you have to hire sales reps yourself. That will work out when you're still doing founder led sales. So let's talk about a six point test during founder led sales when you go to try to find those one or two way out there reps, the ones that actually could help sell your product in the early days and how to make sure you don't make a mis hire. Because what I see with every founder again and again is they hire someone that works somewhere great or someone that talked the talk and they end up just selling zero. So let's talk about six flags when you go to hire your first sales rep and number one we just alluded to, which is the they've only sold with a strong brand behind them. And you will learn this over the years in any type of sales, but especially SaaS is that the playbook is just so different when you have a brand behind you, it doesn't actually mean that it's easier. Look at Marc Benioff today Sales Source is struggling in this current environment to hit its plan. Half of its sales reps are underperforming. So it's not easy. Even with the most iconic brand in SaaS behind you. It's just different. It's different. I can tell you when I was a VP at Adobe we didn't even have leads because everyone in the world was an Adobe customer. It didn't mean it was easy to hit the quarter. It was just such a different cadence when everyone had heard of you. When Everyone had already used your product at some point in their lifetime than a product no one's heard of at all. And the toolkit's totally different. So whatever you do in the early days, don't hire a sales rep that has only worked in environments with very strong brands behind them. You can sort of short circuit this to startup experience, but we also need to be careful that late stage startups in many ways are sell more like big companies than they do early stage one. So be very wary of sales reps that have only had the advantage of a big brand behind them. Number two, be very careful about reps that have only sold a product that was easier to sell. And we've touched on this issue before at Saster, but boy, it is so important. And let's spend a minute talking about it. I remember the first time I learned this was with our first sdr, Sam Blond, who runs our CRO Confidential series and then became director of sales VP of Sales CRO at Brex CRO beyond that now partner at Founders Fund. But what I learned, I learned something from him. And Sam came originally, he was previously an SDR at Intact and he came to Adobe Sign Echo Sign, which I thought was a tough sale. And he said yeah, this is, it's a tough sell, but let me tell you, it's easier than selling web financials. Back in the day it was just enough easier to sell e signatures than web based financials that he flew that it was like a weight was taken off his ankles and sales just was easier. And I look for this again and again when I interview both sales reps and even sales leaders. Was the place you sold just a little bit harder? It's always hard and all startups are hard, but was it a little bit harder? Even harder because they just fly when they come into an environment that's easier. And the flip side is so true. I see this at all stack from the most junior sales rep all the way to the top. But when they come into environments that are a little bit harder to sell in, they melt. Number one is when they come into a product that's more complicated to sell. I often see folks that have sold traditional sales tools, traditional sales buyers, not easy, not easy, especially today. But most sales reps understand how a sales tool works. They're in a CRM, they're in gong, they're in all these products all the time. And so selling them, it's not selling that's easy. But they're almost product experts de facto. And then they'll come in and Sell a complex piece of developer software or context software or analytics software or security software, and they will melt because it's more complicated. So try to find folks that have sold in a harder environment and watch them fly. Take them from an environment they've sold, or it's just even a little bit easier. And again, instead of having those lead weights taken off their ankles, they'll just drag them down underwater. Okay, number three, one we've talked about at Saster so many times, but we. I see founders make this error too. Those first reps have to have sold at your price point. Now, later, when you have a great VP of sales, you can have a training program, you can have a promotion track, you can have exceptions, you can have mentorship. But when you have zero to two sales reps, there's no, there's no mentors, there's no, there's no onboarding or training program. So where do they get their training? Where do they learn how to sell? Well, they learn somewhere else at your price point. And it turns out in SaaS that even though founders at first think this isn't true, later we all figure out it is. That within a range, selling at certain price points is the same motion. Selling a million dollar deal requires convincing many, many stakeholders over many, many months. Selling a $99 product a month typically is a one or two call close and there's a spectrum of motions and energies in between them. And you at least get somewhat trained if a sales rep has sold at least 18 to 24 months at your same price point. So try to get that in your first base has sold before at least 18 to 24 months at your same price point point. 4 and this one sort of summarizes some of the prior points, but it's another point on your checklist to make sure you don't make a hiring mistake. Make sure your first sales reps have sold without a ton of support. It's another sort of line. Typically at companies that are 100, 200, 300 or more people, they start to develop rev ops and sales ops. Typically teams with more than 10 sales executives start to have a rev ops and sales ops. And they'll also have other functions like sales engineers that help them demo, and they'll have solution architects that help them deploy and they'll have a really built out customer success and enablement team. You probably have none of those if you're early stage. And even if you're not quite early stage, you may only have a subset. So I see sales reps again and again. And it's no fault of their own. Come out of environments with a lot of support and drown at smaller startups. And again, they don't even know. They often don't know because they think they have no support. They think they have no help. They say, hey, that silly four week training I had was stupid and my boss was dumb and the sales engineers never showed up and I couldn't get any help. And they say that. But going from a smidge of help to no support at all, boy, I just see that failure again and again. So they have to have somehow worked in an environment if you have no sales support, where they can thrive in that environment as well. 5 and again, this one in a way is a remix of the prior four points. But if your industry is much more complicated than the one they've sold to before and we hit, we hit on that in the second point of a product that's easier to sell. But be wary of taking folks that go into more complicated environments, folks that it is not. Listen, I don't. Domain expertise is overrated. You do. You can teach anyone with, with a brain over 60 days, 90 days, even just by osmosis, even just doing customer calls and listening to gong and participating in meetings. You can, you can learn the 10 or 20 most important points in almost any industry. But selling in a regulated industry, in a complicated industry is very different than a simpler industry. I've seen again and again in companies I've invested in that are in environmental science, that are in financial services, that are heavy regulated, that are in niche industries, higher reps from regular old SaaS, companies like normal SaaS companies selling tools we know all the time and they fail because of some of the reasons up above. But they also just don't know how to learn the nuances of a very complicated industry. So it's a variant of the prior points. But be wary if they come out of a very simple industry and yours requires a lot of domain expertise. I don't think you need to be an engineer to sell to engineers. I don't think you need to be a physician to sell to physicians. But I do think you have to have done a more complicated or nuanced sale to a different type of stakeholder to survive or rather to thrive in a complex environment. And point six and really you can throw out the prior five points if you want when you go to hire your first sales rep. And I've said this multiple times on Saster over the years, but I can't say it too many times, which is when as a founder, you go to hire your first sales reps, and this will change again, going to where we started the discussion, this will change when you have a VP of sales. But when you go to hire your first sales reps yourselves, make sure, no matter what, even if they haven't sold at your price point, even if they seem to need some support, even if the industry they come from is more complicated, even if their last job was easier, you can bend a lot of rules if you would buy from them yourself. And you have to make sure that you don't bend any rules if you wouldn't buy from them yourself. So what I mean is, be calm as a founder, if you're doing founder led sales, even if you're doing it poorly, at least if you've closed 10 customers, 15 customers, 20 customers, 100 customers, at least you know how to close those customers. And leads are so few and precious in the early days that if you don't trust one of your first sales reps with these precious leads, they will fail. You won't train them, you won't enable them, you won't trust them, they won't grow, they won't learn. And this is also your spider sense. It's your sixth sense when you're interviewing them, when you're viewing that person that comes from that fancy SaaS company that you admire that knows all the acronyms and claims, they know all the people in the industry and they read Sasser every day and they're so smart and worldly and knowledgeable and they post on LinkedIn seven times a week. But if you would you buy your own product yourself, you've already talked to a hundred prospects, 200 customers, you know who will they buy from, and you know who could do it better than you, or at least as good as you. So hold out, don't settle, pass. If you would not buy from any of your first two potential sales reps yourself. But with a big caveat, when you hire a VP of sales, she or he will hire people you wouldn't buy your own product from. You have to trust them to build up a playbook, to build up a system to handle, again, a more heterogeneous type of rep. But, but to kind of wrap this up, whenever I talk with founders where their first reps aren't working out, or often reps three through six aren't working out, when, when they found one or two to work out, I always ask them this question. Well, those reps that didn't work out, would you have bought your own product from them. And the answer is always, no, I wouldn't have. So that, ultimately, is the most important screening test of all. Get that right, and you'll probably hire a couple of great reps to take you to the next level.