How To Hire a $10M Team

Now, if you don't know who I am, my name is Ryan Deiss. My partners and I manage 17 companies across our $200 million holding group. So we know what to do and what not to do when it comes to building executive leadership teams. And what I'm going to show you now are the five people that you need to add to your team if you want to make the leap from 1 to 2 million to 10 to 20 million. All right, let's get into it. The big mistake that most founders make is they build a team of helpers and not a team of leaders. And. And at first, it works, right? You tell your people what to do and they do it. But as your team grows, you shift from being this productive genius with a handful of assistants to functioning more like a frazzled middle manager, constantly having to tell other people what to do and then clean up after their messes. It's like one day you're the chef, and the next day you're the chief cook and bottle washer. So how do we prevent this from happening? Or how do we fix it if it's already happening to you? First, I'm going to tell you what not to do. Don't try to hire one magical unicorn, a coo, an integrator, whatever you want to call it, to do all the things that you can't do or that you don't want to do. That's a fantasy. Instead, I want you to hire these five roles in the specific order that I'm about to give you. And as you're about to see, these aren't just task monkeys that we're talking about. These are real leaders who can manage a specific action outcome without your constant oversight. Let's get into the big five. Role number one is your head of marketing. Now, this person could be a director of marketing, a VP of marketing, a cmo. That's really just a function of how many direct reports they have. The point is, they're really owning the overall brand awareness, the amount of traffic, lead generation. And the reason this matters is because kind of everything in business is downstream from lead generation. It's downstream from traffic. If there's no leads, then there are no sales. So some of the key metrics that they're going to own are things like website visitors, leads generated, customer acquisition cost, or cac, return on ad spend, or roas. So we once had a founder in our portfolio group who they thought that they had a sales problem. I mean, their sales had really slowed, and so they were diving in. They brought us in they're like, hey, can you help us fix our sales? Our conversion rate must be down. You know, what's going on. When we dove into the numbers, what we realized is that their website traffic had basically fallen off a cliff. And it happened because it, it was largely driven by organic search, SEO, Google traffic, and that had pretty much flatlined and was in decline. But since no one at the company really owned that, no one even realized it was happening, much less doing anything to fix it. And since no one was really hearing about the business, no one was showing up, there was no one to sell to. So they could do everything in the world to try to fix their sales problem. But without the traffic, there was nobody to sell to. So, so we brought in a full time head of marketing. The traffic flow returned and they didn't really need to make any tweaks or changes to their sales process to get their sales right back on track. So this person, they really need to own all aspects of marketing. They need to own the content calendar, they need to own the campaign launches, they need to own the paid traffic and the media spend, but they don't really need to write every post or run every ad. And that's important. You, you can't ask this person to do every single thing in marketing. There's just too much going on in marketing. They can leverage outside consultants, they can leverage outside agencies, media buying teams, creative teams, but they're the person who's going to coordinate it. They're the person who's going to align the budget, they're the person who's going to align the strategy. They're the person that's going to make sure that the numbers get hit. And along those lines, a big pitfall that I want you to avoid is, is trying to outsource your entire marketing department to an agency. Agencies can be great for filling in an execution gap. So if you don't have somebody on your team who's particularly good at, you know, meta ads, then maybe you want to work with an agency or, you know, Google pay per click, maybe you want to work with an agency on that. But you're going to need someone on your team who can own the strategy and who can own the result. And specifically someone who is only thinking about you and your brand. You're going to need at some point to have a head of marketing Rule number two to go along with your head of marketing. You're going to need a head of sales or if you're more in the retail, e commerce, direct to consumer, maybe this is a Head of promotions or a head of merchandising. Now this person is obviously going to own the conversion of the leads and the traffic into customers. So that's kind of the handoff typically between sales and marketing. Marketing is going to generate the awareness and the attention. They're gonna generate the leads. Sales are gonna make sure that those leads convert into the actual money. The reason that this matters is because marketing is gonna fill the funnel. Sales is gonna pull the money out. So they're gonna own close rate, conversion rate, average order value. So we really want sales. They're thinking about not just how do we convert this leads and traffic into sales, into customers, but how do we get the people that we have to buy more. They're gonna own total revenue, they're gonna own new customers. And I can tell you, just more traffic and just more leads don't always fix everything. One of our clients came to us really frustrated because they had tripled their lead volume. But revenue didn't really budge. And the reason it didn't budge is because sales wasn't following up. The conversion rates actually went way, way, way down. So they needed someone to come in and create the follow up process. They needed someone to come in and train the reps on this follow up process and then they needed someone to actually hold the reps accountable to follow the follow up process. Now this is just one specific system I'm talking about kind of one specific follow up process. I'll tell you, it's a full time job. Even when, and I would argue especially when things are good, tactically speaking, this person should own the entire sales pipeline. So MDRs, SDRs, the demo process, proposals, pricing, pitch decks, follow up, right? As soon as that lead comes in, they really need to own it from that point until the sale is made and it's handed off to whoever is handling the fulfillment. Now if you're running a retail, e commerce direct to consumer, this role translates a bit more into merchandising pricing. It could literally be what goes on the shelf and how are things positioned. What are going to be the seasonal items and the featured items? Again, the point is people are coming. That's marketing's job to get them there. Let's make sure that we sell them once we have them. Don't confuse a good salesperson with a good sales leader. This is the class classic mistake that businesses make. They promote their best salesperson to sales manager. When you promote your best salesperson to sales manager, you trade a great salesperson for a crappy sales manager. The best coaches aren't always the best players, but they were the ones who worked the hardest and figured out all the different angles. Same thing is true in sales leadership. And when we get higher up in sales, a VP of sales, that's when they're functioning way more like a recruiter then they're even functioning like people managers and definitely like salespeople. Point is, if you've got leads coming in and they're not converting, you're gonna need somebody to run your sales team. That person, whether they're a sales manager, director of sales, VP of sales, that person is gonna be your head of sales. Gotta have them on your team. Role number three, the third critical role is your head of product or your head of fulfillment. And as the name suggests, this person is going to own all things fulfillment, all things product. These are the folks that are gonna make sure that that you keep the promises that were made during the sales and marketing process. So if you think about it, there's really two primary functions in business. So there's the selling and the serving. And it's going to be this role that handles the serving of them once you have them. So they're going to need to work hard to make sure that they're fully delivering, but they're also going to kind of need to keep sales and marketing in check to say, hey, don't say it like that because we can't do that. At the same time, they also need to protect your gross margin. So they don't want to keep all the promises at the expense of the company's profitability. Some of the metrics that they're looking at, things like net promoter score, client customer retention, churn rate, and also what is the margin on delivery. They should be able to, you know, function and own a particular aspect of the P and L founder, CEO in our portfolio group who felt the need to personally onboard and every single client because they felt like they were the only one who could do it right. It was great. It was a great experience until they hit about a hundred customers and just the demands on the founder, not just in terms of client onboarding, but in running the rest of the business, got too much. And this founder wound up really dropping the ball pretty badly. Now fortunately, we were able to bring on a head of client services who was super systems minded. And after shadowing the founder for 30 days, they were able to take over all the new client onboarding. The clients were happy. In fact, NPS actually went up because for the first time there was somebody who was focused on only that One role, they need to be systems minded. So you're looking for somebody who builds repeatable systems for delivery without ignoring the human element. And that's really, really, really important. So they need to ensure that the product delivery is efficient and that it's profitable, but then it's also wow worthy. This role needs to be able to balance both. And so when you're talking to these people, when you're interviewing them, asking questions, how do you make sure that you balance that? You know, when they're in conflict, what wins and how do you deal with that? They need to love your customer. Don't just promote your most experienced technician to this role. More times than not, they are great at what they do, but they refuse to believe that they can be systemized because they suffer from the no one can do it quite like me syndrome. What you need is a leader who can scale delivery and without diluting the experience. And rarely is that the person you know. Your best person. Role number four is your head of finance and accounting. In every business, we basically have to make stuff and we have to sell the stuff that we made. But then we need some back office people, right? We need some back office people who are doing things like the budgeting, the forecasting, the financial reporting. And this is important because at scale, business is messy and it gets messy and it's a good thing. It's a beautiful mess. But very often this mess can create chaos and it can create inefficiencies and we need some operational support on that, specifically operational support around the finance and accounting front because if we lose visibility into cash, that is a problem. If you run out of cash, you run out of fuel, you're just going to be stopped dead in your tracks. So some of the key metrics, they need to be looking at things like net profit, they need to be always looking at cash on hand. What's the Runway, what's our budget variance? So for each of the different expense categories, are we on track, are we over budget, are we under budget? And they don't just need to be tracking it, they need to be reporting on it. So one of our clients, I remember they called us in a panic because they discovered that they were basically out of cash. I mean, they literally had to take a loan, they had to do a draw from one of their line of credit just to make payroll. And it's one thing if you know that you're doing poorly. But just the week before, they had met with their CPA and their CPA congratulated them on the great year that they were having and how strong their balance sheet was and how great their profits were looking. While they were profitable on paper, they were bleeding out cash because no one was really keeping an eye on payment timing. No one was keeping an eye on receivables. Basically, bills were coming in and the office manager was just, oh, Bill came in today. Just write a check and send it right out. And if you have a good finance person in place, they're going to do a lot better at balancing that at the end of the day. P Ls can lie, but cash never does. Now, from a tactical perspective, the role that you're probably looking to hire for is the controller. You probably don't yet need a cfo, but a bookkeeper. They're probably just not going to give you the insights that you need. They're not really great at actually managing the cash flow and providing the types of insights that you would need. And so a level up, a couple levels up from a bookkeeper and is the controller, but they're not yet at that CFO level that you know it's likely going to cost you at least a quarter of a million dollars. Just something that you probably don't need yet. Also, make sure that they're closing the books by the 10th of each month, 15th at the absolute latest. Also, they can't just say, well, here's the P and L, here's the balance sheet, here's the statement of cash flows. Not good enough. Okay, they need to point out areas of concern, areas of interest, areas of. They need to give you a summary of trends. Most business owners don't even know really how to read a P and L or a balance sheet. And even if they did, they don't take the time to look at it. So at a bare minimum, they should send you that and attach that email that you're getting on the 10th of every month. Should just be a breakdown of some insights. Your CPA is not a financial strategist. Tax accountants are not financial strategists. Bookkeepers are not financial strategists. You got to get somebody in the building who is a financial strategist. Maybe it's a cfo, fractional, otherwise, usually a controller is where we go. Rule number five, and this one might surprise you, is the executive assistant. Yep. So far everything I've talked about has been an executive level role. Direct report to you. Maybe they're a director level, VP level. In this case, we're talking about an ea. And what they really own, frankly, is the management, the protection of Your time and where they're going to live, if they're doing their job, is in your calendar and ideally in your inbox. So they're going to make sure that nothing gets put on your calendar unless you it's supposed to be there, and they're going to make sure that your inbox gets managed. Now, maybe you allow them to respond to emails, maybe you don't, but at a bare minimum, they should be in your inbox letting you know that, hey, you've got an important one here, or hey, I saw some over here that I can go ahead and respond to. They don't just reactively respond to things, they proactively make sure that things are a little bit easier for you. And that's why, from a tactical perspective, don't just hire a virtual assistant. Virtual assistants can be fine, but I really want somebody who's more like a chief of staff. And I'm not saying to necessarily hire specifically for the role of a chief of staff, but when I think about an executive assistant, you can look at the job descriptions. Whether you look at Google or ChatGPT for executive assistant versus chief of staff, look at both of them and see which one are you more looking for. Typically, a chief of staff is going to be higher salary. Make sure you don't hire someone who needs handholding. I see this happen a lot. This is a professional role. This is somebody who should actually have experience in this role. Ideally, they've been an executive assistant before. They're going to know really how to manage your life better than you do. Let's get into when do you hire these different roles and how do you add them and frankly, how do you afford them? From 0 to about 500k in revenue, you're pretty much going to need to occupy most of these roles. You might have some help, so you might have a salesperson, you might have an agency that you're working with, you might have an outside bookkeeper, so you're going to have help. But in general, from an executive level perspective, from 0 to 500,000, you're the head of all of these things. Now, from 500,000 to 2 million, this is when it makes sense to begin bringing on one or more of these roles. But you're usually going to occupy at least two. Now, what I can tell you is if you try to do three or more of these roles for any length of time, burnout is imminent. I mean, if you're functioning like a true CEO, you should have no functional responsibility. And by functional responsibility, I mean you shouldn't be over the marketing function, the sales function, the product function, the fulfillment function, the finance function, all these are functional responsibilities. As a CEO, you should own none of them. At most, during a transitionary phase, maybe you own one. Ideally, you own none. So now that you know the five roles that you need to scale, let's talk about when to hire each. So step one, what I want you to do is I want you to hire for your biggest bottleneck and to decide what your biggest bottleneck is. I want you to ask this question, Is my business demand constrained or is my business supply constrained? Now what demand constrained looks like is we just need more leads, we just need more customers. Supply constrained means, for the love of God, please don't send any more leads. Please don't send any more customers. We can't fulfill the ones that we have right now. And businesses very often we'll switch back and forth. I mean, it's frankly common that you solve your demand issue only to wind up in a supply issue. But for right now, what is it? Which is it for you? If you're demand constrained, then you're either going to want to go with either ahead of marketing or ahead of sales based on whether you need more top of funnel or bottom of funnel. In other words, do you need more leads or do you need to sell more of the leads that you have? If you're supply constrained, then go with that head of product or that head of fulfillment. Now the reason that we want to start the moment that you hire for this role, they should pay for themselves almost immediately. Because what I hear from people all the time is, yeah, Ryan, I get it, I know that I need these people, but they're pretty expensive. And yeah, every one of the roles that I just described is at minimum going to be a six figure person. It's going to be a six figure hire. The great thing about talented people is, number one, they all come with a 12 month finance plan. And let's say you got to pay them $200,000 a year. That's a lot, right? But you don't write them a check for 200,000 on day one, okay? You're going to pay them one month at a time. The other nice thing about really talented people, they have an immediate impact. And that immediate impact has a very rapid roi. So if you've only ever hired entry level people, individual contributors, low level people, what you find is like, yeah, they're inexpensive, quote unquote, but you got to invest a lot of time in them, you got to manage them. They're going to ask a lot of questions and they're not really going to move the needle that much. They might take some work off of your plate, but the ROI really isn't going to be there for them very quickly, if at all. So if you're demand constrained, you bring in ahead of marketing, you bring in ahead of sales, they should very, very, very quickly, within the first 30, 60 minimum, 90 days, make some changes, make some additions to be able to offset and pay for themselves. Really simple, but same on the fulfillment. On the product side, they should make some enhancements to increase and improve the capacity so that almost immediately they pay for themselves. And not just pay for themselves, but they should return a positive roi, which is good because this gives you enough to afford to move on to step two, hire an executive assistant. Now that you have your first real executive on your team, I want you to free yourself up to do whatever job the hire you made in step one isn't doing. Let's say that you hired a head of sales to come in, and they're coming in and they're rocking and rolling. Invariably, as soon as they come in and they start doing a really good job, that's going to create additional stress and strain on fulfillment. So you're going to need some additional capacity yourself to help in that. That's also going to enable you to move on to step three, which is to hire for the next biggest bottleneck. So whatever you solve for in step one, if you solve for demand, then let's get a supply person in. If you solve for supply, let's get a demand person in. Now step four, we could scale your support team, specifically finance and ops. With the core business functions taken care of, you could turn your attention to the back office. And look, while these roles may not make you a lot of money, if you've got a great controller, a great head of finance and accounting, they will definitely help you keep a lot more of what you make. And at the end of the day, that is just as important, if not more important. If you're sitting there thinking about, okay, what are my weaknesses? Okay, I'll hire somebody to do my weaknesses. That's going to help you grow. Scale is hiring for your strengths. If you want to scale, learn to recruit people who are better than you at doing that one thing that you believe that you're the best in the world at. So don't hoard tasks and don't hire helpers who enable you in your task hoarding. We got to stop doing that. I want you to build a real executive leadership team. I think you're going to be shocked at how fast you can grow and how little you need to work to do it, and frankly, how quickly it can pay for itself when it happens. If you want help structuring your leadership team or figuring out who to hire next, that is exactly the kind of thing that we do for our clients. So check out the link down in the description if you'd like to learn more about what it is like to work with us. And if this video helped you out, go ahead and hit subscribe. Maybe tell a friend. That'd be great, because we've got a lot more tactical founder first content coming your way.