Your VP of Sales Should NOT Carry a Quota

If you’re asking your VP of Sales to carry a quota when they start, then you are not ready for an actual VP of Sales. Full stop. I read a post on LinkedIn—and I’ll read it to you here in a second—that said your VP of Sales should be carrying a bag and hit a quota as an individual contributor when they start, and they’ve got to do that in order to earn their right to lead. And I want to break down why this is terrible advice and the kind of advice that you only get from people who don’t have real, deep experience in actually building out sales teams and sales organizations.

So, here’s the post. And by the way, I said it was terrible advice on LinkedIn as well in response to this post. But here it is:

"Your VP of Sales should carry a quota—at least in the early days. I’ve seen many startups hire a VP of Sales who immediately switched to executive mode. They talk about strategy, process, hiring, dashboards, but they’re not actually selling. And that’s a mistake. In an early-stage company, the VP of Sales should be close to the deal. They should be running demos, joining sales calls, handling key opportunities, closing deals themselves. The best VPs of Sales often carry a bag for the first three to six months—not because they need commission, because it forces them to understand the buyer, the objections, competitive landscape, why deals are won and lost. And if you can’t close deals yourself, it’s very hard to coach a team to do it. And sales reps know it. They can tell within weeks whether their sales leader can actually sell, and the best VPs of Sales I’ve worked with were always dangerous closers. Leadership didn’t replace that skill; it amplified it. A VP of Sales who refuses to carry a quota in the early days is a red flag."

Now, listen, this is—this is terrible advice, like I said. And for—let me just say this up front: when in this post where it says you switch into executive mode, you hired an executive. Right? So when they switch into executive mode, it means they switched into the mode of the job that you actually hired them to do. Now, I’m going to give you a few reasons why—beyond that—why this is not good advice for you.

And the first one is: no legitimate VP of Sales is actually going to take the job and actually going to do it. Because think about what it takes to get to a VP level. You start your sales career, you’re making cold calls, you’re hammering out, you know, 100, 125 calls a day. You’re getting rejected, you’re getting hung up on, you’re getting your ass handed to you—like, it is cold calling, you do that day after day. But you’re grinding it out because you know this is the first step in building a sales career. Right? That’s where I started; it’s where a lot of people I know started. And maybe it’s on the phone, maybe it’s out canvassing in the field, whatever it is. But you’re at the beginning stages, you’re grinding it out on the prospecting side of things, doing the grunt work that nobody else wants to do.

And let’s say you do that for two years, for three years, so that you can earn the right to actually start actually selling—like closing deals. Now you’re running discovery, now you’re actually out there closing deals and you’re building pipeline and you’re running the full cycle of sales. And you spend a few years developing that skill set. Right? And you start making really good money. This is where AEs or outside sales reps—whatever you want to call it—it’s where they start to make that good solid six-figure income, really expand their earning capacity, and you get good at that.

Then you discover—or at least believe—you might be one of the few people who’s actually good at both selling and managing people. Right? Like, you’re looking at it and you’re saying, "I want to keep going in this trajectory. I want to start managing people—like not just hunting and hitting my own number, but actually leading people to get their number." And the people that are good at doing that, it is definitely not everybody. And the best sellers do not necessarily make the best leaders. But let’s say you think I’m going to be great at both. You go out for management, you get promoted, and if you’re any good in sales, you probably—I mean, you’re going to go backwards a lot of times to step into management. Right? Like, the managers are oftentimes not earning as much, especially at the beginning, as top sellers.

So sometimes to get into management you went backwards in money, but you do it. You learn how to teach, learn how to inspire your team, get them focused, you know how to keep the deck clear from upper management shit—you know, like kind of keep your team free of distractions. You get good at hiring people, training people, and getting your team to hit their number. So you’re able to hit your number through other people. Different skill set. And you do that as a manager for a few years.

Then you step into a VP role because you’re good at managing. So let’s—let’s promote you. You get into VP, you get that job, and now you’ve got another layer of skill development. Right? Like, you know how to run budgets and run an actual P&L, you know, like working with C-level, working with executive leaders. And now you’re managing managers. Totally different skill set. And you’re helping managers lead their teams to hit sales. And now, by the way, your income potential significantly exceeds what you were going to do as an individual contributor. So you’re making really good money now.

And at this point, you’ve spent 10, 15 years building this trajectory. Right? And then you go interview with some startup that’s low on revenue—maybe whether they have product-market fit or not (most don’t, by the way)—and they tell you, "Hey, we’re going to hire you as a VP, but we’re going to need you to go out and hunt, and we’re going to need you to be kind of a BDR, and we’re going to need you to be a full-cycle sales rep because you need to prove that you can be a VP by being a salesperson," which is a terrible belief system to begin with. Because those are different jobs with different skill sets. And proving that you can hunt deals and close them doesn’t prove that you can manage people anyway. But, "We’re going to need you to go do that."

And you’re going to look at that—a VP who’s been at this for 10, 15 years, who legitimately has all the skills that I just talked about, knows how to hunt, knows how to run discovery, knows how to close, knows how to manage, and knows how to manage at an executive level—they are going to say, "No. I did it, and I don’t want to do it." That’s reason number one.

Reason number two is you create a conflict of incentives. And in sales, incentives is everything. Like Charlie Munger—you know, Warren Buffett’s partner who’s passed—had a, you know, say, "Show me the incentive and I’ll show you the behavior." Like, you can trace everything back to incentives. And you create a conflict of incentives when you go about this and hiring a VP and ask them to sell. Because you tell the VP they’ve got to come in and build a sales team and go out and sell.

Right? So one of those is a long-term investment where they’ve got to build playbooks, they’ve got to build processes, go out, recruit people, train people, get them on-ramped, up to production, get them selling, and everything else. Right? That’s the VP side of this. The other part of this is immediate: you go out and sell stuff, you make money, you get paid. Now think about those two incentives. People need to get paid. Right? That’s just human nature; it’s just who we are.

So what do you think they’re going to focus on more? Well, they’re going to focus on getting paid, which means the priority that you really want—which is building a sales team and a sales organization—that takes a backseat because they’re not getting compensated for that in the short run. Like, that’s something that they’re going to get paid for in the long run. What do they get paid for in the short run? They get paid for selling stuff, which is what they’re going to focus on.

And the bigger conflict is, if they’re selling and they’re hiring people to sell, they’re literally competing with the people that they’re bringing into their team. So who gets that lead that comes in the door? Who gets prioritized in the round robin? You’ve created by design a situation where you’ve got the fox guarding the henhouse. And what happens every time—the "VP" comes in and they sell because that’s what they’re incentivized to do—that’s going to consume their time. The sales organization doesn’t get built, or both things get done half-assed. Right? Like they’re halfway building the sales organization, they’re halfway out there selling, and you don’t get either thing that you actually want. Okay, that’s reason number two.

Reason number three—yes, this whole topic fires me up—the third reason, and maybe one of the most important ones, is if you need your VP to carry a quota, you’re not ready for a VP. Right? Like, that is a symptom of not being ready for a VP. Because you’re saying, "Hey, I want somebody to come in and build the sales organization, but what I need right now is somebody to come in and close deals and make money." Well, then that’s the problem you need to solve.

If a VP of Sales who’s asked to come in and build a sales organization—they need time and they need money to do it. I’ve done this several times. And that means as a business owner or as a CEO, you need to hire the right person with the right skill set to do that job. And it’s not cheap. Like, remember the trajectory that I just went through? Like, when you develop those actual skills, like, you know your value if you can actually do that.

So it’s not cheap, and it takes time. Which means you’re paying a healthy salary for an extended period of time that doesn’t have immediate ROI. And there’s nothing wrong with that as long as you can afford it and as long as you have the cash flow to do it properly. The problem is most people don’t. And so they hire a mediocre VP who doesn’t really have all the skill set necessary to do the thing, then ask them to carry a bag because they can’t afford to give them the runway they need to do the job properly. Then they come in and they start focusing on earning their own commission and they’re only partly focused on building the sales org. Both jobs get done half-assed and mediocrely—whatever—and if you’re a founder, if you’re a business owner and you think you need a VP of Sales but you need them to sell, what you need is a salesperson. Right? Like, that is a symptom of the fact that you aren’t ready for a VP of Sales. And you’re not going to get the right one because you’re not going to give them the sufficient space they need to do their job effectively. Right? To be an actual manager or hire a manager and then—and in all of that.

So, that’s the sign that you aren’t ready for the VP yet. And that’s okay because the fourth and final reason I’ll say here is: you’re the VP. If you’re the business owner or you’re the CEO, you are the VP of Sales, whether you like it or not. When you hire the salesperson to solve the sales problem, that salesperson needs management. They need leadership. They need systems in place to be effective. And that’s virtually every salesperson—even highly experienced salespeople. And that means either you are the VP of Sales and/or sales manager, or you need to hire like a fractional sales management system or program or something to help you manage that particular salesperson.

And that is how you get to the point where you can go hire an actual full-time VP to help you continue building out that sales organization as an organization. And I can’t emphasize this enough: solve the problem that you have. Don’t go try to hire a VP and get somebody who’s not a true VP but then ask them to sell, but then they’re still aspiring to be the VP so they don’t really want to sell, they want to be VP—it just becomes a shitshow. Keep it clean, keep it focused. And I’m telling you, this comes from experience. Like, I’ve seen this story play out so many times, I’ve been part of this story playing out so many times, and I have so many of my colleagues, peers, friends who can vouch for this because when it’s battle-tested, you know how bad this advice is. So, anytime you hear "hire a VP and have them carry a quota," just know you’re probably listening to somebody who doesn’t have enough experience in actually building sales organizations to know better. Rest my case. Hope it helps. Adios.