Welcome to Evidently—the bi-weekly newsletter where I share my biggest hits (and get honest about my misses) as a first-time VP of Marketing. If this was forwarded to you, join the 5,000+ people who apparently enjoy watching me figure this job out in real time by subscribing here.

At some point, I realized I was spending more time explaining decisions than actually making them.

I remember walking out of a meeting thinking I’d just spent thirty minutes explaining something I had already decided. Not debating it. Not working it through. Just explaining it. 

None of the questions were unreasonable on their own. That’s what made it hard to push back. But after a while, it started to change how I worked. 

More prep. More slides. More context. More time explaining things I already felt good about.

Eventually I caught myself thinking: why does this feel harder than it should?

Most marketing leaders have a familiar explanation for moments like this. “The CEO doesn’t get marketing.”

It’s a common complaint, and it usually ends in one of two places:

1. You blame the CEO

2. You quietly start thinking about what else might be out there

Sometimes those conclusions are fair. Sometimes they’re necessary. But they don’t leave much room to actually do anything about the situation.

When you’re already in the role, the market is tight, and you still care about doing good work, neither option feels great. So you keep going. You try to make it work. You tell yourself this is just part of the job.

What I didn’t understand earlier in my career is how much this can take out of you over time.

How it actually shows up

This marketer vs. CEO-who-doesn’t-get-it dynamic rarely shows up as a blow-up. 

It shows up in smaller ways. Questions that slow things down. Decisions that don’t quite feel final. Extra check-ins that weren’t there before.

You’re still on the hook for the outcome, but you don’t really have the room to operate the way you should.

That’s exhausting. Not dramatic burnout. Just the steady drain of explaining your thinking over and over instead of doing the work.

You don’t notice it right away. You adjust. You get clearer. You explain more. You tell yourself this is just what managing up looks like.

But slowly, the job changes.

You’re not building momentum anymore. You’re focused on how things land. You’re not really leading forward. You’re defending decisions. That’s the part that wears you down.

I learned this the hard way when I presented my first UserEvidence marketing budget, just over two years ago. I made the mistake of showing the spreadsheet line by line. Every category. Every tool. Every event. Every experiment.

It was way too granular. And the moment I did that, I lost the “room”.

Instead of talking about the bets, we went line by line. This agency versus that hire. One event versus another. Whether influencer marketing made sense at all, instead of whether it made sense for what we were trying to do.

I ended up defending individual line items instead of owning the portfolio. That one decision changed the whole dynamic.

I wasn’t allocating across brand, demand, events, experiments, tools, and headcount anymore. I was explaining why each line existed. And that’s 100% on me.

The job of the marketing leader is to decide how to place the bets and how to allocate the portfolio. The job of the CEO is to decide whether they trust you to do that.

When you skip that distinction, you end up explaining instead of deciding.

What people really mean when they say their CEO “doesn’t get marketing”

When someone says their CEO doesn’t get marketing, they’re usually not talking about tactics.

They’re talking about trust. About not being trusted to run the function. About having their judgment questioned by default. About owning the outcome but not the decisions.

Here’s the uncomfortable part: so much of this is self-inflicted.

Not because the CEO is right. And not because the marketing leader is doing bad work. But because marketing is easy to second-guess. Everyone has an opinion. Everyone thinks they understand it. A CEO wouldn’t tell an engineer how to write code, but they’ll happily weigh in on headlines, positioning, and campaigns.

If you’re not clear about what you’re doing, why you’re doing it, and how it ties back to company priorities, someone else will fill in the gaps.

Usually the CEO.

Not because they want control. Because uncertainty creates involvement.

One of the biggest things I got wrong earlier in my career was assuming CEOs question marketing because they don’t understand it. Most of the time, that’s not what’s happening.

They’re reacting to how confident you are in the decision, not the decision itself.

The real cost of being second-guessed isn’t frustration. It’s that your job quietly shifts from making decisions to explaining them.

That’s when the job slowly turns into something else.

I didn’t notice it happening in the moment. It just showed up in how I spent my time. Less time deciding what to do next. More time making decisions sound safe.

What actually helps shift the relationship

Once I saw what was happening clearly, things changed. I stopped treating every question like pushback. A lot of them were checks on my judgment and how I’d respond if something didn’t work.

Marketing is a series of bets. You don’t know exactly how they’ll turn out. The goal isn’t to remove risk. It’s to show you’ve thought it through. Autonomy doesn’t come from being right. It comes from trust.

And once trust starts to slip, everything feels heavier. Decisions take longer. Progress slows. You end up spending energy in places that don’t actually move the work forward.

If you want more autonomy, you don’t argue your way into it. You change how you show up.

The biggest shift for me was stopping the endless explaining and starting to set the direction. Instead of reacting to questions, I came in with a point of view. Here’s what I think matters right now. Here’s where marketing is focused. Here’s what’s working, what’s not, and what I’m willing to bet on.

That changes the conversation. You’re no longer stuck justifying decisions. You’re giving someone something to react to.

It also forces you to be honest with yourself.

If you can’t clearly explain why you’re doing something, that’s worth paying attention to. Either the work isn’t as solid as you think, or it’s not actually what the business needs right now.

Both are fixable. But only if you’re willing to look at them straight on.

Knowing when it’s not flexible

Early on, I thought sharing everything was the answer. It wasn’t.

All that did was invite feedback on decisions the CEO didn’t actually need to be involved in.

The real work is figuring out what they want to see, what they want to weigh in on, and what they’re actually comfortable leaving with you. That doesn’t happen by being vague or by hiding things. It happens through direct conversations and clear lines.

Sometimes you do all of that. You bring clarity. You deliver wins. You rebuild momentum.

And the autonomy still isn’t there.

That’s not you failing. That’s you learning the difference between misunderstanding and misalignment. 

Misunderstanding is usually fixable with clearer communication and expectations. Misalignment is deeper. Different comfort with risk. Different definitions of success. Different expectations of what this role is supposed to be.

What finally helped me was being honest about how my role feels day to day.

If most of the time the work feels productive and the relationship with a CEO moves things forward, some tension is normal.

If you’re constantly tired, constantly explaining, constantly feeling boxed in, that’s not just the job.

Once you see that clearly, the decision gets simpler.

You either change how you’re showing up and reset the relationship, or you stop pretending it’s going to turn into something it’s not.

Stuff I’m digging this week

• The feeling of being off the marketing grid for the last three weeks on my honeymoon. 12/10 recommend.

Hold up—what does UserEvidence do again?

Most companies have great customers. What they don’t have is a way to activate them.

So the stories, the insights, and the people who would actually help end up scattered across decks, tools, and Slack threads. Things get messy. Quotes get lost. Advocates get overused. Deals slow down.

UserEvidence fixes that.

We give your GTM team one platform to activate your customer base. You can find new advocates, capture customer proof, and publish original research— then use all of it where it actually moves the deal forward.

• Advocates — Activate your best customers without burning them out.

• Evidence — Verified, believable stories and results buyers actually trust.

• Research — Original long-form research content that shapes your narrative.

UserEvidence makes it easier for your team to use your customers in the channels and moments where trust matters most.