You know the feeling: there’s more worth doing than there are people and dollars to do it. The list of things that would grow your business is always longer than the budget. Your revenue can carry only so much marketing salary on the P&L, and that ceiling sits well below your ambitions for the brand. Should you hire more staff? An outsourced CMO? That new agency that keeps calling you?
So the question at this stage isn’t what a great marketing team looks like in the abstract. It’s narrower and harder. Given what you can actually afford to carry, what do you resource, and how? Every dollar you commit to one role is a dollar that can’t go to another, which makes this a financial decision at least as much as a marketing one.
Each of these calls looks like a one-off: a hire here, an agency there, a freelancer to cover a gap. Taken together, they define your marketing operating model: who owns strategy, who owns execution, what capability lives inside the business, and what flexes outside it. Most founders never design that model. They assemble it.
By $20–30M, it’s usually assembled, not designed
By the time a brand reaches $20M or $30M, the marketing function tends to look like this: a head of marketing hired a couple of years ago when the company was half the size, three to four different retainer agencies working against outdated and disconnected priorities, a bunch of juniors scrambling around, specialist consultants organized around martech tools, a freelance designer or two, and a founder still spending half their time on marketing. Some of the pieces are good. Most aren’t aligned around the right tasks for their skills. Total spend is high, everyone is overworked yet output seems lower than ever, and nobody can quite explain why. Nobody made a bad call along the way. It accreted, one reasonable gap-fill at a time, until the whole thing stopped adding up.
Watch what your head of marketing asks for first
Pay attention to the reflex. If the opening answer to every gap is “we need to hire someone,” that should give you pause. It can be a sign that your marketing lead is thinking about their task list and not about the business that has to pay for it.
There’s a number every founder should understand: how much marketing salary your business can afford for each dollar of revenue. Headcount isn’t free and it isn’t neutral. Adding a role means the revenue forecast has to rise to cover it, and marketing needs to be accountable to that higher number. A senior marketer worth their seat feels that weight. They think about margin every time they spend a dollar, including the dollars spent on their own team. If yours wants to add bodies before they’ve shown you how those bodies pay for themselves, they may not be thinking broadly enough.
Start with outcomes, not categories of work
Most founders organize marketing around categories of work. They hire an email person, a paid media person, a content person, a designer, and the org chart ends up mirroring a list of tactics. That structure quietly tells everyone their job is to produce their kind of work, whether or not it moves anything.
My recommendation is to organize around outcomes instead. Decide what you need to achieve (new-customer growth, higher lifetime value, optimized product mix, whatever the business most needs right now) and put a person in charge of each outcome. Work backward from there to the jobs that actually get you there. Only then do you decide how to resource each job.
The difference shows up in who you hire and how they behave. You don’t really need an email marketer (someone who measures success by how many email projects they ship). You need a retention manager on the hook for whether customers stay and how how high lifetime value climbs. The email work is similar; how the person approaches it is completely different, because they own a result instead of an activity. Organize around outcomes and every marketing decision made by your resource gets sharper. Each resource is now in service of progress you can actually measure.
Then resource each job deliberately
With the outcomes named and the jobs mapped underneath them, the three ways to resource any given job sort out fairly cleanly.
Keep the core strategy in-house. The planning work that compounds, that understands your customer and product deeply, would be irreplaceable if you outsourced. That work should belong to an employee who lives in your business and carries its institutional memory. That same permanence is why you should be sparing with in-house seats. An employee is a standing cost whether or not this quarter is busy, so you only carry the roles you’ll use fully and all year long.
How does AI factor in? AI helps someone you already have handle a lot of the routine execution that used to justify a junior hire. I use AI heavily across my own work and think every team should be building it in. Used well, it absorbs the rote production and frees your limited salary budget for the strategic judgment roles it can’t replace.
Send specialized or variable work to freelancers. A useful test is time horizon. If it’s a problem you need solved this year but might not even have next year, that’s a freelancer, not an employee. You get a specific skill on demand and the freedom to flex up and down. You give up some context and you have to manage them. For an unpredictable workload, that’s usually the right trade.
Let specialist skills live at your agency. When the need is a genuine specialism, you’re almost always better off outsourcing it. Outside of large corporations, an agency is the best home for specialist talent, because that’s where specialists see enough volume and variety to stay sharp. Hire a niche specialist in-house at a small company and they go rusty because they don’t see enough breadth of work to maintain cutting edge skills. They only see how things worked last year, not how they could work next year.
Bring in fractional senior leadership such as an outsourced CMO to augment founder judgment. When the business has outgrown the founder owning strategy alone but can’t yet justify a full-time executive hire, a fractional leader (sometimes called an outsourced CMO) fills that gap. Strategic direction, prioritization, oversight of the agency stack, and designing the operating model itself are expensive skills. The watch-out is that a fractional leader is a head, not a pair of hands. They set direction and hold the work accountable; they aren’t the team producing things day to day.
Side by side view:
| Capability | Best for | Watch-out |
|---|---|---|
| Employee | Compounding, customer-specific, steady work | Expensive if the need isn’t stable |
| Freelancer | Time-bounded or variable execution | Needs clear direction |
| Agency | Specialist execution at scale | Needs a strong brief and an internal owner |
| Fractional senior leader | Strategy, prioritization, agency oversight, operating-model design | Not a substitute for execution capacity |
I love agencies. They still aren’t your marketing department.
You’ve heard the pitch: this shiny agency can just be your marketing department. I want to be careful here, because I genuinely love agencies. I’ve run one myself, so I know exactly how they work and how to get the best out of them. Using one as your entire marketing department is not how.
An agency is excellent at delivering against a brief and genuinely bad at writing one for itself. That’s the heart of it. Hand an agency a sharp brief and clear direction and you’ll get strong work. Ask it to decide what your business should be doing, and you’ve handed your strategy to a team whose incentives only partly overlap with yours. Agencies drift toward the work that’s fun, the work that wins recognition, and the work that makes them money. They do act on your behalf, but that still isn’t the same as making the call an in-house person would make — someone with a deep, complicated understanding of your customers, your margins, and your trade-offs.
So an agency is a great pair of hands and a poor head. Keep the head (the strategy and the brief) on your side of the table, and outsource the hands.
There’s a second decision hiding inside “use an agency,” and it’s big enough to deserve its own conversation: one large agency or a few small ones, a single all-in-one shop or separate specialists, media and creative under one roof or split apart. Designing that agency stack well is a project in itself. Your first step is to know the question is there, and that the answer should fall out of your outcomes rather than out of whichever shop pitched you most recently.
Before you commit to a hire, ask five questions
Before you add a permanent role, expand an agency, or convert a freelancer into staff, ask yourself five questions:
- What capability does the business actually need over the next twelve months? Not the role you want to fill. The output you need produced. Capability is defined by output, not by title.
- Is that capability stable enough to hire against? If you don’t yet know what good looks like for this function at your scale, you can’t hire against it, and hiring before you understand the function is one of the more expensive mistakes a founder makes.
- Who would evaluate the work? If the honest answer is “the founder,” and the founder doesn’t have the time or the expertise to judge it well, the role isn’t ready to be filled. A seat no one can coach or hold accountable is a seat that drifts.
- What’s the right commitment shape? Work you’ll use intensively for nine months and then less is an agency or a contract. Work you’ll use steadily for years is a hire. The wrong shape costs you either flexibility or quality.
- What’s the smallest team that gets you through the next twelve months? Most founders overbuild. The smallest team that meets the real requirement, with deliberate gaps filled by fractional or agency capacity, is almost always cheaper, more flexible, and easier to course-correct.
A $9M founder who didn’t need a VP
Take a founder I’ll describe in composite: a consumer brand around $9M, growing 25% a year. He was convinced he needed a Senior VP of Marketing and had started interviewing, but was having trouble attracting a great candidate to a brand his size. He was looking at around $275K in base salary before he loaded benefits and employment cost — well more than a $9M brand can carry.
Two hours of those diagnostic questions changed his plan. He couldn’t describe what the VP would do in the first ninety days beyond “take marketing off my plate.” His existing agencies were producing fine output, but no one inside the company other than him could brief them or hold them accountable. He was the only one who could, which is exactly why he needed help. And frankly, he’d never managed a senior marketer, so he had no real picture of what “good” looked like at the VP level for a brand his size.
The right structure for the next twelve months wasn’t the SVP. It was a fractional senior leader — an outsourced CMO — for strategy and agency oversight at around $120K a year ($10K monthly retainer) paired with an in-house marketing director around $140K to own the day-to-day management and execution. He got both a senior brain and an execution owner for less than one loaded VP salary, and the arrangement flexed as the business clarified what it needed. At 25% growth, a full-time VP still wouldn’t have penciled out a year later. In another year or two, once the brand is bigger, he’ll be able to afford and attract the right full-time hire — and he’ll know exactly what he’s hiring for.
The CMO/VP role is the seat to think hardest about
One role matters more than the rest: the top person who decides what to resource and how, owns the outcomes, and writes the briefs. That seat rewards range — someone who’s worked across more than one brand, in both big companies and lean startups, ideally outside your category, since the freshest growth ideas travel across industries. Unfortunately, that kind of senior, margin-minded judgment costs a price a smaller brand can least afford to carry full-time. That’s when an outsourced CMO or fractional CMO service makes sense.
Three signs you’ve outgrown your setup
A few tells that your setup has outgrown its stage. You’re still making the strategic marketing calls yourself — allocating channel budget, briefing creative, writing the quarterly plan — well past the point you should be. No one can say cleanly what each agency is on the hook for, so they drift toward whatever looks good on the monthly report. And every new initiative needs a new hire or a new vendor, because nothing in the current structure has the room or the authority to absorb it. Same root cause each time: the function was assembled, not designed.
Where this leaves you
If this is starting to sound like more than a simple hiring decision, that should be your takeaway. Designing a marketing organization around your real outcomes is a genuine piece of work. You define the outcomes and break them into the jobs that achieve them. Then, you need to go responsibility by responsibility to decide what belongs in-house, what flexes out to a freelancer, and what goes to an agency. You set goals that match, work out where your existing people fit. You take an honest look at whether your current mix of agencies is the right one. A marketing org should be built top-down, on purpose, because the structure shapes every marketing decision that comes after it.
Want a second set of eyes on whether your setup fits your goals?
That’s the whole point of my Marketing Org & Tools Review, which is one of my Fractional CMO services. I look hard at how you’ve actually resourced your marketing (your team and their job descriptions, your agencies and freelancers, the tools in your stack, where the money goes), and tell you whether it serves your goals or just accreted over time. You come away with a clear view of what to keep in-house, what to flex out, what to cut, and where to reorganize around outcomes.
I’m biased, of course. I’ve built my own career around the fractional CMO model, so naturally I’ll tell you a flexible senior brain has its place. The less self-serving truth is that the right marketing org for your business is genuinely a project to figure out. Most founders have never had the chance to sit down and design it on purpose. If that’s the project you’re ready for, let’s talk →.
