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What mistakes, failures, or challenges in your career ended up teaching you the most?

Maureen Sitterson
Etsy Senior Director, Product MarketingJanuary 22

  1. Challenge: When I was working at American Express, I was focused on leading organic growth after we ended our partnership with Costco. This was a very challenging time for the company and we had to determine the metrics we cared about with regards to organic growth and the best way to drive them through the levers we had available. It was one of the periods of my career when I grew the most because we were truly building structure from nothing, and that was rewarding and motivating. After we set clear and specific goals and strategies to achieve them, I was responsible for reporting on our progress. I learned a ton about storytelling through data during this period which propelled me through my next few roles.

  2. POV on Mistakes: Anytime I've made a mistake at work, I've seen it as a positive, because it is so much more memorable than when things go well. Making a mistake enables me to learn how to avoid doing the same thing in the future and the painful memory of doing something wrong is the most powerful teacher.

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Hien Phan
Timescale Head of Product MarketingFebruary 13

I spent much of my career searching for something I couldn’t quite put into words. At first, I thought it was money, which led me to finance. And while finance gave me exactly that—money—it didn’t give me fulfillment. In fact, I burned out early. The 2008 recession was a turning point, forcing me to realize that money alone wasn’t enough. I wouldn’t call this a mistake; it was something I had to go through. And I don’t regret it. The skills I built during my time as an investment professional—market research, strategy, positioning—still shape how I approach product marketing today.

From there, I pivoted into consulting and market research, thinking maybe my strength was in helping companies find their answers. I didn’t land at a top management consulting firm—post-2008, they weren’t hiring. Instead, I ended up at a boutique consulting and market research firm by accident. And that accident turned out to be the best thing that could’ve happened. The firm was small, which meant I had the chance to grow fast. I rose to become a global practice area leader, leading a 100-person team focused on tech. More importantly, it’s where I met my first mentor in product and product marketing. That mentor pulled me into a startup, and that’s how I found my way into this field.

That same sense of curiosity is what led me into developer marketing. Before I joined Pinecone, I knew nothing about distributed systems or machine learning. But part of what I love about this job is that to market something well, you have to know your users deeply—not just why they’d use your product, but their entire workflow. My tenacity led me to market a vector database when no one had before. The result? We grew Pinecone from low seven figures to very high eight figures.

Looking back, my path was anything but linear. But that’s exactly how I ended up here. I realized what I love most is learning. New products, new markets, new challenges—every launch is something different. So if you’re asking about mistakes, failures, or challenges, I’d say life throws a lot at you. You won’t always see the path clearly in the moment. But if you stay curious, keep learning, and make the best of each opportunity, it will work out. It always does.

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