Every new CMO arrives with a plan. Or they should. It usually looks something like: first 30 days to listen and learn, next 30 days to identify priorities, final 30 days to start executing against a structured strategy.
Clean. Logical. Impressive in an interview.
And almost completely at odds with what actually happens.
What the plan usually says
The standard 90-day CMO plan is structured around phases. Discovery first — sit in on meetings, talk to customers, read everything you can find, hold off on major decisions until you understand the landscape. Then analysis — synthesise what you’ve learned, identify the highest-leverage opportunities, get alignment from the leadership team. Then action — set the direction, build the team, start moving.
This framework exists for good reasons. It protects a new leader from making expensive decisions before they understand the context. It gives them credibility with the team by demonstrating they’re listening rather than bulldozing. It’s taught in MBA programmes and leadership courses because in theory it’s right.
The problem is that the organisation does not wait for your 90 days to elapse.
What actually happened
When I joined MATE the first time, I had a version of this plan in my head. Within the first week I was dealing with a campaign that needed to launch, a team member who was already heading toward exit, a channel strategy that had been running on autopilot for eighteen months, and a product launch that had been scheduled before I arrived and was two weeks away.
None of these were in the 90-day plan. All of them required decisions.
This is not unusual. In most marketing roles, especially at the CMO level in a scaling company, the organisation is already in motion when you arrive. There are campaigns live, plans in flight, commitments already made to the sales team, and a board that wants to see momentum. The luxury of a clean listening phase is largely theoretical.
When I came back as CMO in 2025, I had the advantage of already knowing the business, the team, and most of the structural challenges. But even then, the gap between the plan in my head and the reality of day one was significant. Different pressures, different priorities, different people in different roles than the ones I remembered.
What the first 30 days are actually for
Here is what the first 30 days are actually for, based on having done this a couple of times now: they are for figuring out what is already on fire and what is quietly smouldering.
Some of what you inherit will be genuinely good. Campaigns that are working. Processes that are solid. Team members who are excellent. Do not touch those things. Find them quickly and leave them alone.
What you are really looking for in the first 30 days is the stuff that nobody has told you about because they have been managing around it for so long they have forgotten it is a problem. The channel strategy that has not been questioned in eighteen months. The reporting that goes to the CEO every week but nobody actually uses. The agency relationship that everyone knows is underperforming but that predates everyone currently in the room.
You find these things by asking questions that feel slightly naive. “Why do we do it this way?” “What would happen if we stopped this?” “What would you change if you could?” People who have been in the business for a while will often tell you things in the first two weeks that they would never say once you have been there long enough to be considered part of the establishment.
The quick wins trap
One of the things every 90-day plan includes is a section on quick wins. Early results that demonstrate you can execute and build credibility with the leadership team.
This is real and important. Especially in a scaling company, there is an expectation that a senior hire will show early momentum. The leadership team wants to know the investment is going to pay off.
The trap is optimising for visible wins at the expense of correct wins. Launching a campaign in week three because you want to show activity, when the right move would have been to spend another three weeks understanding the customer data first. Announcing a new channel strategy before you have fully understood why the current one is producing the results it is.
I have watched CMOs chase quick wins in their first 90 days and spend the following nine months fixing the consequences. The quick wins looked good in the moment. They created problems that were much harder to solve later.
The better frame is this: early momentum is important, but it should come from decisions you would have made anyway, not from decisions you made early to look decisive. If the right thing to do in month three would have been to cut the agency, cut the agency in month two. If the right thing to do in month four would have been to rebuild the reporting stack, start that conversation in month one. Accelerate the right decisions. Do not manufacture wrong ones.
Plan for more than one scenario
The 90-day plan most CMOs arrive with assumes one scenario: a business that is growing reasonably well and needs better marketing to accelerate it.
The reality is that you might be walking into a business that is growing but has a serious CAC problem nobody has fully acknowledged. Or a business where the product is not quite right but marketing is being asked to paper over it. Or a business where the CEO and the CFO have genuinely different views on what marketing should be doing, and you are about to inherit that tension.
Spend some of the time before you start (or in the very first days) stress-testing your plan against different scenarios. What if the budget gets cut significantly in month two? What if the product launch that is already scheduled misses? What if the key person on the team who was described to you as excellent turns out to be the source of the main structural problem?
These are not pleasant things to plan for. But the CMOs who handle the first 90 days well are the ones who are not completely surprised when reality diverges from the plan. And it always diverges from the plan.
The comparison that actually teaches you something
The most useful thing I have found in reflecting on multiple first-90-day experiences is not comparing what I planned to what happened, but comparing what I thought the job was to what the job actually turned out to be.
Every marketing leadership role is different. Not just in industry or company stage, but in what the organisation actually needs from the function, and what it actually expects from the person running it. Sometimes that expectation is explicit and accurate. Often it is implicit, contradictory, or has not been examined properly by the leadership team before they hired you.
The first 90 days is partly about learning the business. It is also partly about understanding what version of the CMO role you have actually been hired into — and whether that version is the one you can do well, the one you want to do, and the one the business actually needs.
Those three things are sometimes the same. When they are not, finding out early is much better than finding out a year in.
Dom O'Brien
CMO at MATE and author of The Startup Marketing Playbook. Fifteen years building lean marketing teams that punch above their weight.
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