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Stumbling Into Product Management


Ten years ago, if you had asked me what a product manager did, I'd stumble into some form of "manages products." Which is, of course, the same as saying I have no fucking clue. Turns out, I did know, but I didn't know through traditional exposure. Almost nothing I've learned in my career has come from traditional exposure.

I've written about how starting your own company can help you become a better product manager. But that's just one way to stumble into product management. I've stumbled so many times and in so many different ways in my career. Fortunately, most of my stumbles have carried me forward, and that's the best you can hope for. I do think you can position yourself to stumble forward more often than you stumble backward if you commit yourself to progress. When walking or running, if you pitch your body forward just a few degrees, you're going to stumble forward if you happen to stumble.

I don't expect this stumbling adventure of mine to be a good fit for everyone. I'm not sure I would even recommend the circuitous path I took. But I wouldn't be where I am without taking this exact path. That much I'm convinced of.

The first thing I have done well in my career is focusing on the customer. Everyone says that, but you have to live it for it to be true. When I graduated with my bachelor's degree, the only thing I knew for sure was that I wanted a 9-5 in an office after spending the previous 7 years working at a grocery store. I think it was probably a blessing that my 9-5 job came in the form of working in an insurance call center. The people calling in were, invariably, not happy. So, ending a call on a positive note was a challenge. But it was a challenge I leaned into.

As you might imagine, leaning helps you stumble forward.

Even though I was helping customers over the phone, most of those customers interacted with the online web app for reporting and managing claims. This exposed me to user experience issues and opportunities. I wasn't in a position to solve those problems (or even relay them considering the size of the company), but I filed them away in my mind. Eventually, I took a promotion to work on the Customer Experience team for the very same web app that I had been exposed to you tangentially through conversations with customers.

In this role, I was helping shape the product, but it wasn't "product management." I researched customer journeys, reviewed user surveys, watched session replays (back when those were new and exciting), and worked closely with the User Experience team in conducting user experience tests.

My title was business analyst, but I was working with engineers and suggesting new features. I was even helping QA releases. Some of this was beyond the scope of my job, but, once again, I leaned.

Eventually, my family and I were ready to move on to new adventures. Serendipitously, I had read a Medium post by one of the co-founders of a company called SlideRoom before we moved to Dallas. The company, as it turned out, was based in Dallas. My resume did not suggest that I was ready to jump into the startup world, but I took a shot. After months of talking with the founders, I was eventually offered a job as…

An account manager.

Still not product management, but with startups, a title doesn't normally reflect your daily duties. My time as an account manager and eventually Director of Account Management was less about sales and more about talking with customers every day, helping them through support and demos, and helping shape the product roadmap based on this feedback. I was the frontline, and once again, focusing on the customer helped me stumble forward. We worked in two-week cycles, had backlog grooming, had roadmap planning, and more. I participated in all of it alongside the CEO.

While working at SlideRoom, I taught myself to code and launched an app. This was my first product where I had customers I could speak with. I had launched previous companies, but they were all very removed from the end user. This new app I built and launched allowed me to talk with customers and prospects. I learned what people wanted, and—because I built it myself—could make changes quickly based on feedback.

With my newfound coding skills, I moved into a hybrid software engineering role. I still spoke directly with customers and had influence over the backlog, but I could also contribute to building the product. Still not a product manager, but a little closer to the product.

Eventually, I decided to go full-time working on my app. As I mentioned before and have written about, starting your own company is a great way to get into product management. It's the "normal" path, but it's another stumble forward. I would go on to start another company after this one and was in charge of all product decisions. However, when that company failed and we shut it down, I had a decision to make. Would I try to find a job in product management or contract for a company in product management or something else?

I made the only logical decision I could make. I decided to contract as a software engineer.

I like coding, but I don't generally like coding for someone else. That said, I knew the fastest way to get back into the startup game was to contract as an engineer. And that worked. I contracted for a customer feedback analysis company then eventually moved on to contract for Pinata.

It was at Pinata where I got to flex all of my product muscles. I was writing code, but I was also jumping on phone calls with customers frequently. I became Pinata's first full-time employee and quickly transitioned into a full-time product role. My stumbling had finally brought me into the mythical product manager role. As Pinata grew, so did I. I grew into a product leader and a manager, rising to head up the entire product department at Pinata.

My path did not involve going to school for computer science or product management. I didn't get an MBA or any certifications. In fact, I went to a for-profit college, got a business degree, then eventually went and got a master's degree in creative writing. It was almost like I was giving myself no choice but to stumble my way into whatever it was that I was going to do.

And it's worked well so far. Let's see how much farther this stumbling can take me.