The leadership rules that defined my first year as a VP

I’m not great at slowing down.

Maybe you feel that too?

Every year, without fail, Fall hits. And suddenly, we’re all wondering where the time went.

Where did the year go?

How is it already October?

The holidays will be here before you know it.

We acknowledge how fast time is moving but rarely stop to think about where it actually went or what we did with it.

So, today, I’m hitting pause with this newsletter and taking a hard look at whether I’m becoming the marketing leader I always thought I’d be.

After hitting my one-year anniversary with UserEvidence back in July, this live journaling sesh is long overdue.

Here are five rules I’m currently living by as a VP:

1. If you’re feeling comfortable, you’re doing something wrong

There’s never a moment where I feel like I’ve got everything on lock. Just when things seem under control, something new pops up—keeps me on my toes.

And honestly? That’s the way I like it. It forces me to stay sharp and keep learning.

When I started at UserEvidence, I was basically a team of one—juggling agencies, freelancers, and still deep in the day-to-day grind.

Now, a year later, as a marketing team of three, I’ve made it a point to stay hands-on. I still jump into WordPress, troubleshoot HubSpot workflows, and do whatever it takes to make things work.

Not because I don’t trust my team but because I want to support them.

As a small team, it’s about sharing the load and keeping things sane. Plus, I want to know what’s needed to get things done before I delegate and set any expectations.

2. Don’t just share your ideas, sell them

What surprised me most about stepping into this role wasn’t the marketing work itself—it was the influence work.

Being a VP isn’t just about doing or knowing great marketing; it’s about selling your ideas internally, getting the right people on board, and navigating the politics of any growing company.

It’s about communicating the value of marketing to every department, showing them how it benefits their work, and gathering their feedback to course-correct when needed.

The reality is that part can take as much (if not more) time than the actual execution—but it’s absolutely essential.

And when I think about the marketing leaders I’ve most admired throughout my tenure, the most important thing they all share is the ability to communicate in a way that makes people want to listen.

3. Be a human

I didn’t really feel like a VP until I made my first hire. When Alex came on board, it was a turning point.

Managing someone wasn’t just about setting tasks—it was about creating clear boundaries. I realized I needed to be approachable, without blurring the lines between being a manager and a friend.

It’s about being human.

I’m upfront when I don’t know something, and that transparency builds trust. It’s okay to be unsure—because, let’s be real, nobody has it all figured out.

Staying honest and curious is what keeps me on track.

4. Don’t manufacture chaos to get things done faster

I’ve seen too many leaders build teams based on chaos—fake deadlines, unnecessary urgency, vague directives.

Sure, there are things you can’t always share as a VP, but people know when you’re holding back.

There’s a difference between saying:

“Hey, this came up in a board meeting—one of the members is questioning our numbers. Can you help me make sense of it?”

And:

“Hey, these numbers are off. Why are they like this?”

Giving people context shows you’re in it together rather than just pointing fingers. It’s the difference between interrogation and collaboration.

5. Laugh at yourself

Here’s one of the biggest lessons I’ve learned in this first year: Don’t try to change into someone you’re not just because you’ve got a shiny new title.

I’m still the same person who’s self-deprecating, who spends too much time searching for the perfect GIF in Slack, and laughs at myself uncomfortably even if no one else is laughing.

The minute you start losing that authenticity, your leadership—and the work—suffers.

I try to stay involved in the nitty-gritty, laugh with the team, and never forget the importance of connection beyond the virtual Zoom office walls.

At the end of the day, it’s all about balance.

There’s always going to be more work to get done. But if you’re not enjoying the process and the people you’re doing it with, what’s the point?

Stuff I’m digging this week

• Trailer from our Drive interview series—800GB of footage, ~37 lattes from the coffee bar, and 12 interviews over two days at Exit Five’s Drive event in Burlington, VT last month. We sat down with 12 B2B marketing leaders and walked away with some epic video content.

• Voice-to-text from ChatGPT—Until recently, you could only use voice-to-text from the mobile app. Now you can use it from the desktop app too. It’s been a game-changer whenever I have raw marketing ideas for ChatGPT to make sense of and organize for me.

• New freemium plan from Navattic—Navattic launched this last month for B2B marketers who want get started with interactive demos (without having to ask finance for approval). We’ve added interactive demos from Navattic to our website and you’ll see a new demo center from us real soon.

Opinions are cheap. Proof is gold.

Episode 17 of The Proof Point ties back to rule #2. One of my former bosses (how fitting) Jason Widup, Pranav Piyush, and Megan Boone shared their best learnings for proving marketing’s impact and getting leadership buy-in.

My biggest takeaways:

• To build trust, you’ve gotta earn it. One of the best ways to do that is with quick, measurable wins that open the door to more ambitious long-term strategies.

• Don’t over-index on attribution. Mix in modeling to help capture broader trends and give a clearer picture of performance.

• If you’re responsible for setting the goals, make sure they’re realistic and achievable. Better yet, give yourself wiggle room to exceed targets and foster stronger relationships with leadership.

Listen on Spotify, Apple, or head over to YouTube.

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