The "Head of Marketing" Trap: Why This Hire Almost Always Fails
Before launching Tactile, I sat in the "Head of Marketing" seat myself more than once and I have a love/hate relationship with the role. I appreciated the full oversight it gave me early in my career, but through my work at Tactile, I've watched it collapse under mismatched expectations many times.
The "Head of Marketing" job post is one of the great startup rites of passage. Founders hit a certain milestone (a fundraise! early users! a nudge from their board!) and decide it's time to "get serious" about marketing. Enter the Head of Marketing, a title that sounds like a milestone hire but is usually a mirage.
Here's the pattern I see: companies hire a Head of Marketing to outsource uncertainty. They haven't answered core questions about product, ICP, or go-to-market, and they hope one hire can do it for them. When the timing, scope, and expectations don't align, the role fails predictably.
For this essay, I talked to founders and marketers who've lived this, drawing on my own insights as both a marketer and advisor to high-growth startups. The pattern is remarkably consistent: the company is still shaky on product-market fit, but already expects CMO-level outcomes. They want a leader who can set strategy, own brand, run demand gen, analyze funnel data, and launch partnerships — but they've budgeted for a manager, and the candidate they end up hiring is somewhere in between. The disconnect is baked in from day one, and it plays out in three ways:
The Expectations Mismatch
Companies want CMO-level strategy and execution at a manager-level salary with a director-level candidate. As one former VP of Marketing told me (she asked to remain anonymous), "Marketing is not a faucet, but that's how it's treated and the Head of Marketing is often expected to produce results immediately, sometimes overnight. That's not how marketing works. I recently saw a real job posting that included tactical work for everything from video production, to SEO expertise, to implementing digital ad campaigns, to sales enablement. This isn't a 'Head of Marketing,' it's an entire department crammed into one person."
That “department in one person” dynamic came up again with another perspective from Kt McBratney, GP & Head of Community at Renew VC (former founder, former startup CMO and first marketing hire): "A common mistake I see startups make with their first marketing hire is expecting one person do strategy and execution on every channel and customer stage. It's a recipe for burnout, but it also dilutes momentum since one person cannot be a fulltime content creator, email marketing, demand gen, events lead, product marketer and PR lead. Founders should know what the 1-3 KPIs they need the marketing hire to support, and then let them test and iterate to maximize those before adding more."
The Timing Problem
This role gets posted too early, before the business knows their needs or their ideal candidate profile. As David Garcia, CEO and Co-founder of Veep (and former CEO of New Stand), puts it: "Startups often conflate marketing with advertising and hire a mid-level generalist to chase growth before truly understanding their ICP, pricing model, or channel mix."
Shamir Allibhai, CEO & Co-founder of Eddie AI and former CEO of Simon Says (acquired by Meta), experienced this firsthand: "If we'd hired a Head of Marketing right after our seed, the role we needed then would've looked nothing like what we needed six months later — and definitely not what we need now. When you're growing fast, experimenting, and still sharpening ICP and product, chances are that hire won't last a year. When you're pre–product-market fit, you need new users, but marketing is not the #1 problem. There isn’t enough work for a Head of Marketing and they’ll become a distraction. You'll be scouring for work for that person when you should be focused on talking to users and building your solution. And then if you’re so lucky to find PMF, it’s doubtful they will have the skillset to support a post-PMF company."
The Authority Gap
The title sounds senior, but the role rarely comes with real power. Garcia notes that "structurally, the role is usually scoped too narrowly without authority or influence across product, pricing, or positioning. This makes success nearly impossible." Without the authority to actually prioritize or make strategic decisions, even talented marketers get stuck executing someone else's fragmented vision.
The overarching issue is perception. Marketing remains the least understood function inside most startups. To engineers, it looks fluffy. To sales, it's just lead-gen (or making decks look pretty). To founders, it's whatever they most recently read in a fundraising deck or on the First Round blog (no shade…).
"Internally, marketing is often seen as a service function rather than a growth partner," Garcia explains. One anonymous former marketing executive put it bluntly: "I don't weigh in on HR strategy or legal contracts, so why does HR feel entitled to weigh in on campaign development? Marketing is a strategic function, but it's treated like a service and in addition, weirdly, everyone thinks they're an expert."
Without buy-in, a Head of Marketing is left pitching for a budget they'll never get, working across functions that don't respect the work. That's how marketing becomes the scapegoat when growth stalls.
The Rare Cases It Works
Ever so often, it does work! But the conditions are very specific:
The company is close to product-market fit, with a clear ICP and early traction
There's alignment on what "marketing" means right now
The hire is accurately leveled, which matters for expectations
The person is a builder, and spikes in the right areas: a scrappy generalist who happens to over-index in the function that is most critical for the business
Garcia confirms: "The hires that succeed usually own their own swim lane, operate with clear cross-functional influence, and are brought in at the right moment, often after PMF."
As one founder told me, "I've seen exceptions, the rare case where a hands-on generalist happened to spike in exactly the growth area the company needed. But that's luck, not strategy."
What to Do Instead
The better move is often to delay. Garcia recommends that "pre-PMF, companies should rely on fractional talent with deep go-to-market experience to test channels, validate ICP, and build early systems." Allibhai echoes this: "Start with a senior fractional leader who can flex with your needs and pull in specialists from their network. Then, once your broader strategy is clear, bring in someone with category depth, say, a VP of Marketing with a brand spike."
If you do hire full-time, set the bar differently. Success in the first 30 days shouldn't be "grow pipeline." It should be: clarify ICP, sharpen messaging, stand up analytics, run one or two channel experiments. Build a foundation to scale.
As Garcia puts it: "A better approach is to scope marketing as a strategic function from the outset and bring in fractional leadership to test, learn, and evolve until the full-time role is clearly defined."
The Bottom Line
The "Head of Marketing" fails because it's usually a placeholder for uncertainty, a way of asking one person to answer questions the company hasn't yet answered for itself. The rare cases it succeeds are when the timing, the scope, the person, and the expectations align. Because here's the truth regardless of title: marketing can't fix a lack of product market fit or a lack of clarity, it can only amplify it.