Working with a Head of Marketing

What this role actually does

Head of Marketing is the seat between a founder who wants a CMO and a company that cannot yet afford one. The title covers a wide range. At a fifteen person startup it means the person doing every function. At a two hundred person company it means a functional leader with three or four direct reports who has decided the CMO title is not the point. The work looks different at each end of that spectrum and it fails for different reasons at each end.

A working Head of Marketing spends the week split roughly in thirds. One third is strategy and planning, which mostly means writing and rewriting the positioning, the ICP, and the quarterly plan. One third is people, which means hiring, coaching the small team, and doing the honest performance conversations that a first time founder is trying to avoid. The last third is operator work: reviewing paid channels, editing content, pushing an email out, sitting in on sales calls, and in almost every case still holding the pen on the website.

The seat reports to the CEO in most cases and to a COO or CRO in a few. When it reports to the CEO, half the work is managing the CEO. The founder wants weekly wins, weekly numbers, and a hopeful tone. The Head of Marketing has to translate the messy reality of go to market into a story the founder can hold on Monday and not panic over on Wednesday. That translation work is not optional. The founders who claim they want raw numbers are the same founders who react to raw numbers by cutting spend, and the Head of Marketing who learns that late in the tenure gets fired for the same behavior the CEO asked for.

What a Head of Marketing does not do: run the ad account personally beyond month six, write every piece of content beyond month nine, or own the number sales owns. They also do not act as the CEO's therapist about the CRO. They do not replace product marketing with vibes. They do not treat brand as a project they will get to next quarter. If the seat is doing all of those things, it is a marketing manager with a bigger title, not a Head of Marketing.

How to brief them well

Briefing a Head of Marketing works best when the founder resists the urge to hand over tactics. The strongest brief has three parts. The commercial outcome the company needs in the next twelve months, written as a number and a segment. The constraint the founder is unwilling to move: usually cash burn, price point, or a customer segment they will not chase. The scope of the seat: whether marketing owns pipeline creation, brand, product marketing, and lifecycle, or only some of those. When the scope is fuzzy, every quarter turns into a scope argument.

Bad briefs sound like the founder read a blog post yesterday. Please launch a newsletter. Please try Reddit. Please rebrand. Please copy what a competitor is doing. A Head of Marketing can execute any of those and they will not change the business unless they map to the actual problem. The founder who briefs by tactic teaches the seat to stop thinking, and eight months later the same founder wonders why they hired a strategic leader who only executes.

The context that is usually missing from the brief and that the Head of Marketing needs on day one includes the honest state of sales, the last three months of pipeline coverage, the current state of the customer list, any commitments the founder has made to investors that the plan needs to respect, and the true state of the product roadmap. A founder who says the product is ready when it is not is going to lose their new hire in ninety days.

The best briefs from a founder end with two questions. What do you need from me. What is going to stop this from working. A Head of Marketing who is not asked those questions will still answer them internally, and the answer will show up in the plan as unspoken assumptions the founder later argues with. Asking the questions surfaces the assumptions before they become disagreements.

Review cadence + operating rhythm

Weekly rhythm

Weekly is where a Head of Marketing runs on signal. A Monday standup of thirty minutes with any direct reports, a Wednesday go to market sync with sales, and a Friday one on one with the CEO cover most of the week. The Friday one on one is the most important meeting on the calendar. It is where the founder either sees pipeline as it actually is or projects wishful thinking onto it. The Head of Marketing prepares the same three slides every week: pipeline pace against target, spend against budget, and one campaign or program the founder should know about. Anything longer than three slides on a weekly is a symptom of not knowing what to say.

Monthly and quarterly reviews

Monthly is where the seat holds an operating review with the CEO and, when it exists, the CFO. Blended CAC, payback, pipeline coverage, and content or campaign performance for the month. Monthly is also when the Head of Marketing does the honest hire, fire, and scope conversation with each direct report. In a small company where marketing is three people, monthly reviews are more about workload and clarity than performance rating.

Quarterly is planning and the honest look back. What worked, what did not, what got killed. The Head of Marketing walks in with a proposed budget shift and a proposed team change. If the founder trusts the seat, both get approved with light debate. If the founder does not trust the seat, the quarterly turns into a negotiation and the plan comes out watered down. The pattern is a leading indicator of tenure.

Annual planning

Annual planning starts eight to ten weeks before the fiscal year turns. A Head of Marketing who arrives at annual planning without a draft plan two months ahead is going to spend the first quarter of the new year building the plan they should already have shipped. The people in the room are the CEO, the CFO, the head of sales, and the Head of Marketing. Sometimes product. If product is not in the room, the plan is going to collide with product priorities inside ninety days.

Measurement (real KPIs, not vanity)

Four metrics carry the seat and everything else is diagnostic.

Pipeline created by marketing, cut by segment. This is the number the founder cares about, the number the CRO argues about, and the number that either earns marketing a bigger budget or loses it in the next planning cycle. Head of Marketing owns the definition of what counts as marketing sourced pipeline. If the definition drifts, the number is meaningless six months later.

Blended CAC and payback window. Total spend divided by new customer count, and months to payback on gross margin. At a Head of Marketing scale, blended is more useful than fully loaded. The seat is trying to answer whether the next dollar into marketing is faster than the next dollar into sales headcount, and blended CAC settles that argument.

Content or channel yield. In a small company, five channels are running at once and only two are working. The Head of Marketing needs a monthly view of pipeline yield per channel and a bias toward killing the ones that are not paying. This is where the seat proves it can make hard calls. A seat that cannot kill a channel is a seat that is about to be told to kill everything by finance.

Team output and cycle time. How long does it take marketing to ship a landing page, a campaign, a launch. When cycle time is three months for something that should take three weeks, the seat has an operator problem it is hiding. Cycle time is the honest measure of whether the team has enough people and enough clarity.

Vanity metrics that look impressive and do not help include follower counts, subscribers, MQL volume without SQL conversion, and event attendance without pipeline attached. The Head of Marketing who reports vanity to the CEO is teaching the CEO to ignore marketing numbers, which becomes a problem the day the seat needs the CEO to believe a real number. Any metric that cannot be traced back to pipeline or retention in two steps is a distraction at this scale.

Compensation + career path (honest ranges)

Head of Marketing comp sits below CMO in every band, and the gap is real. The seat trades executive comp for scope, ownership, and the shot at the CMO title in the same company.

Compensation bands by market

Mid market. Series A to early B, three to twenty million ARR. Base 170 to 230 thousand. Bonus 15 to 25 percent. Equity 0.15 to 0.5 percent. Total cash 200 to 290 thousand. Most of these seats are player coach, meaning the person still writes and edits. Bonus is usually pipeline plus a qualitative rating from the CEO.

Tech metro. Series B and later, twenty to seventy five million ARR, roles based in Austin, Boulder, Denver, Chicago, Atlanta, or hybrid. Base 210 to 280 thousand. Bonus 20 to 30 percent. Equity 0.10 to 0.30 percent. Total cash 250 to 360 thousand. Team size two to six, with a first hire usually being demand or product marketing depending on the motion.

Coastal enterprise. Series C onward in San Francisco, New York, or Boston. Base 260 to 340 thousand. Bonus 25 to 40 percent. Equity 0.08 to 0.25 percent. Total cash 320 to 470 thousand. This band often uses Head of Marketing as a title for someone the board is testing before promoting to CMO. If the promotion path is not written in the offer, it usually does not happen.

The typical next step is either CMO at the same company, CMO at a smaller company, or VP of Marketing at a larger company. The lateral move to VP at a larger company is often the safer career choice because it puts the person under a real CMO who can teach the board level game before the next promotion. The direct jump from Head of Marketing to CMO at a bigger company is possible and it is the move that most often results in a two year exit, because the person skips the layer where they would have learned to run a functional org of eight or more.

Common departures. The eighteen month exit when the CEO wants a CMO. The two year exit when the promotion to CMO was promised and did not happen. The clean exit at three years when the person has built enough to take a CMO seat somewhere else. Anyone in the seat longer than four years without a title change is usually looking, whether they say so or not.

Common ways this seat fails

The seat that never gets promoted. A founder hires a Head of Marketing with an implied path to CMO and never has the promotion conversation. Two years in, the person realizes the title will not come, applies out, and leaves for a CMO seat at a smaller company. The founder blames the market. The market rarely deserved the blame.

The seat that hires too early. A Head of Marketing lands, sees three functions to build, and hires a director in each within ninety days. Six months later the funnel is not working and the company has burned twelve months of runway on payroll. The right first hire is usually a strong operator generalist who can do the work while the seat figures out which specialist to hire next.

The founder who cannot let go. The Head of Marketing writes a plan, the founder red lines it, the plan gets executed at half strength, and the founder blames the plan. The seat that stays in this pattern for more than two quarters becomes a project manager for the founder's ideas. The way out is either an explicit boundary conversation with the CEO or a resignation letter.

The seat that never picks a lane. Brand needs work, demand needs work, product marketing needs work, and the Head of Marketing tries to fix all three at once with a three person team. Nothing improves. The seat that picks one problem, ships against it for two quarters, and only then moves to the next problem, outperforms the seat that tries to boil the ocean by a wide margin.

The seat that never earns finance's trust. A Head of Marketing who cannot answer a CAC question live in a meeting, or whose numbers change every time they show up, loses budget in the first hard quarter. The finance relationship is not glamorous and it is the relationship that keeps the seat funded. The Head of Marketing who does not schedule a monthly with the CFO is teaching finance to distrust marketing.