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Two Years In: What I Wish I Knew on Day One

What actually changes when you go from startup PM to enterprise PM (and what stays the same)

Author

Stefanie Brown
October 10, 2025

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👋 Hey friend,

Two years ago this week, I started at HubSpot as a Product Manager.

I remember sitting in my first sprint planning meeting, nodding along like I understood everything, while internally panicking about whether I’d made a huge mistake leaving my startup.

At the startup, I knew everyone. I knew the product inside and out. I knew which Slack channel to drop a question in and who’d answer within minutes.

At HubSpot? I didn’t even know where to find the roadmap.

The thing no one tells you about joining a bigger company: The first six months feel like controlled chaos.

But here’s what I’ve learned after two years: that “I have no idea what I’m doing” feeling might actually be your biggest advantage.

The Risk I Took Because I Didn’t Know Better

Six months in, I was leading the global go-to-market strategy for our Analytics Suite launch at INBOUND.

Let me be clear: this was huge. More teams were counting on me than there were people at my entire previous startup. The stakes were high. The process was intense. And I was drowning in impostor syndrome.

I remember thinking, “Everyone here has done this before. They know what they’re doing. I’m just faking it.”

But here’s the thing. Because I didn’t have the weight of past launches hanging over me, I took bigger risks. I pushed for things I probably wouldn’t have pushed for if I’d known “how it’s always been done.”

And it worked.

That launch taught me something I carry into every project now: Sometimes not knowing the “right way” gives you permission to find a better way.

What Actually Changed How I Work

When people ask me what’s different about being a PM at scale vs. a startup, I used to say “more process” or “bigger impact.”

But the real difference? It’s about turning feedback into insight, not just collecting it.

At my startup, I heard customer feedback constantly. I was close to it. I thought that meant I understood it.

At HubSpot, I learned the difference between hearing pain and diagnosing patterns.

Now, I aim for 5 customer calls a week. Not just to listen, but to look for patterns. What are three customers saying in totally different ways? What’s the pain underneath the feature request?

AI tools have made this easier (I can analyze call transcripts faster now), but the discipline of looking for patterns instead of just logging feedback is what shifted how I build product.

💡 Quick Tip: Next time you finish a customer call, ask yourself: “What pattern does this fit into?” before you add it to your backlog. If you can’t connect it to a pattern, you probably need more calls.

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The Part That’s Still Hard

Going from 1 team to 2 teams was tough. Adding a 3rd one? Still figuring it out.

The biggest challenge isn’t the work itself. It’s the meetings.

My calendar looks like Tetris on hard mode. And the hard part isn’t just finding time, it’s figuring out what I can say no to so I can say yes to the most meaningful work.

I’m still learning this one. But here’s what’s helping:

Ask yourself: “Am I the only person who can do this, or am I the only person willing to do it?”

If it’s the latter, it’s time to delegate or drop it.

📌 Try this today: Look at your calendar for next week. Circle one recurring meeting and ask: “Does my presence here create unique value, or am I just a warm body?” If it’s the latter, skip it or send someone else.

What I’d Tell My Day-One Self

If I could go back to that first week, here’s what I’d say:

1. You’re not supposed to know everything yet. That’s the point. The learning curve is steep because the opportunity is big. Lean into it.

2. Your background is your edge, not your weakness. Coming from customer-facing roles means you understand pain firsthand. That’s a superpower, not a deficit.

3. Great managers exist in every chapter. You loved your startup manager. You’ll love this one too. Great leadership isn’t about company size.

4. The “messy middle” never goes away. Launches will still feel chaotic. Priorities will still shift. The difference is you’ll get better at knowing which plates are glass and which ones bounce. (Thanks to my manager for that one.)

5. You don’t have to choose between craft and community. You can be a great PM and build something beyond your day job. In fact, doing both makes you better at each.

Quick Reads for Scaling Your Impact

Challenge: Reflect on Your Own Two Years

Whether you’re two years into a role, two months, or two weeks, take 10 minutes this week to answer:

  1. What’s one risk I took that worked out because I didn’t know “the right way”?

  2. What’s one thing I’m better at now than I was six months ago?

  3. What’s one thing I need to say no to so I can say yes to more meaningful work?

Write it down. You’ll be surprised what you realize.

💡 Pro Move: Share your answers with your manager or a peer. Sometimes saying it out loud helps you see how far you’ve come.

Two years in, I’m not the same PM I was on day one. I’m not supposed to be.

And honestly? I’m excited to see who I’ll be two years from now.

See you next Friday,

– Stef

💬 I’m mentoring on ADPList! If you’re breaking into product, navigating a new role, or just need a sounding board, you can book a free session with me right here.

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