This article is based on Stu Kendall’s brilliant talk at the Chicago Product Marketing Summit. PMA members can enjoy the complete recording here. 

Contrary to popular belief, climbing the leadership ladder isn’t just about working hard or being good at your job. Plenty of talented people stay stuck in the same role for years while others seem to rise effortlessly to the top. 

So, what makes the difference?

Over the years, I’ve noticed a few key factors that play a huge role in career growth. In this article, I’ll break down what I’ve learned, what’s worked for me, and what I’ve seen work for others. By the end, you’ll have a framework to be more intentional about your next move.

Let’s get into it.

What does climbing the leadership ladder mean?

Before we dive into strategies, let’s define what we actually mean by climbing the leadership ladder. Think about it for a second – what does it mean to you?

For many, it’s tied to things like:

These are all common markers of career progression, especially in marketing. But before you go all-in on chasing these milestones, it’s worth stepping back and asking yourself: Is this really what I want?

Here’s a quote I think about a lot:

"Ask yourself what is important to you in life and why. Climbing a career leadership ladder can bring a tremendous amount of joy to your life. But it can also be riddled with stress and disappointment." – A very wise product marketing leader

Sound familiar? No? That’s because it’s my own quote – I made it up two days ago.

The point is this: before you commit to climbing the career ladder, take a step back. Figure out what truly matters to you.

Yes, career progression can be exciting. It can bring financial rewards, professional fulfillment, and personal satisfaction, but it can also be exhausting. You might reach a milestone you thought you wanted, only to realize it’s not as great as you expected.

I’m not trying to discourage you from aiming high. However, I’ve learned to be intentional about when to hit the gas – when it makes sense to put in extra effort for maximum return – and when it’s okay to ease off based on where I am in my personal and professional life.

The four key factors that impact career growth

Let’s say you’ve thought about it, and yes, you do want to climb the leadership ladder. You want the title, the compensation, the bigger team, and the cool logos. So, what should you focus on?

Here are four key factors that, in my experience, play a major role in career progression. These aren’t groundbreaking concepts, but they’re worth reiterating:

  1. The company you work for: The environment you’re in matters a lot. The opportunities available to you are heavily influenced by the company’s size, culture, and leadership.
  2. Your manager (and head of marketing): Your direct manager plays a huge role in your growth. But in a smaller company, your head of marketing – whether that’s a VP, CMO, or another leader – is just as important.
  3. You: You’re the common denominator in your career growth. How you show up, the work you do, and how you advocate for yourself all play a massive role.
  4. Your team: The people around you can either elevate you or hold you back. The colleagues you work with, collaborate with, and learn from make a huge difference.

Let’s take a closer look at each of these elements.

1. The company you work for: Your environment shapes your growth

One of the biggest factors in climbing the leadership ladder is the company itself. Some companies unintentionally create an environment that makes it harder to grow your career. Here are a few red flags to watch out for:

Signs a company may limit your growth

  • The company isn’t growing: If the business is struggling, there are simply fewer resources available for promotions, raises, and career advancement. When a company is in survival mode, growth opportunities for employees are often the first thing to suffer.
  • Product marketing gets no respect: If leadership doesn’t truly value product marketing, your career trajectory might be limited. Some of us have successfully built (or rebuilt) PMM functions, but not every company or leadership team understands its strategic role. If leadership doesn’t invest in PMM, it can impact how promotions and recognition are distributed.
  • Overstaffed functions: If the marketing org chart is packed with layers of management and there’s little room to move up, it can feel like there’s a hard ceiling on your career growth. While things can always change, being stuck in an overfilled org can make it much harder to progress.
  • Preference for outside hires: Some companies have a strong bias toward bringing in external talent rather than promoting from within. If leadership consistently fills key roles with outsiders instead of developing internal employees, it’s a sign that your growth opportunities may be limited.
  • General weirdness: Let’s be honest: some companies are just… strange. Whether it’s shady business practices, questionable leadership decisions, or VC-driven chaos, certain environments can be unpredictable and bad for your long-term career prospects.

What to look for in a company

If you’re serious about career growth, look for companies that have the opposite of those red flags. Here’s what to prioritize: