Define Your Own Product Management Career Path

Many companies provide a single career path up the proverbial corporate ladder where the only way to get ahead is by moving up in title, rung by rung. In product management, this usually takes the form of something like this:

For most of my career, I worked at startups that had single-track product management career paths like this. Luckily, most of these companies were small enough that I was able to manage small teams while being hands on, defining products, and collaborating with designers and engineers to bring those products to life. On two different occasions, though, I was faced with choosing between being a manager or an individual contributor (often referred to as an IC). Both took place at different times in my career, so depending on what stage you are at, my hope is that you find my experience useful.


I joined Spinner, the world’s first streaming music service, in 1998 as one of a dozen or so employees. This was my first job as a product manager and I was thrilled to have finally made the transition from marketing to product management. We were a small but mighty team that grew the business and the company rapidly. Within a year, we had grown to over one hundred employees. I managed a team of product managers, designers, and front-end developers. It was an exciting time leading a collaborative team, as we created numerous versions of our music player that was branded for a variety of partnerships.


In 1999, American Online acquired the company. As part of the transition process, AOL brought in a few executives whose job it was to evaluate their newly acquired staff in an attempt to integrate Spinner into their organization. I vividly remember the day I was called into a conference room with one of these individuals who asked a few questions about my role and responsibilities. At one point she said “Ah, you see, at AOL, you’re either an IC or a people manager. You can’t be both. You have to choose.” I felt like I was in the movie The Matrix, choosing between the red pill or the blue pill. I knew once I made my decision, there would be no turning back.

Based on what I had seen so far of the AOL culture, I did not think I was cut out for the politics that seemed to dominate daily corporate life. Although I loved finding and hiring talented people to join my team, the work I enjoyed the most was creating something from scratch. Creating a vision, solving problems, building products that people loved — that is what drove me each and every day. I chose to give up my reins as a manager and spent the remainder of my career at AOL as an individual contributor. Looking back, I think the decision was easy because I was fairly new to product management at that time. Frankly, I wasn’t sure what the career path of a product manager even looked like back then. What I did know is that I wanted to have a direct impact on products that would be used by millions of people.


I was eventually recruited away from AOL to join another music start-up called Musicmatch. Musicmatch was another pioneer in the digital music space with it’s CD ripping and burning software called the Musicmatch Jukebox. Similar to my experience at Spinner, I managed a small team while being hands-on with the product development process. One of the highlights from there was creating an in-house usability testing facility and hiring a UX researcher to help us better understand how customers were using our products and how we could make them better.


Shortly after leaving Musicmatch, I was asked to join another digital music start-up called Sonos. When I joined in 2005, I was the only software product manager. The team at Sonos sought me out because of my experience with streaming music services. I had a strong network built from my days at Spinner/AOL and was able to leverage those relationships to establish new partnerships for Sonos. I also had experience developing software for hardware, which was an uncommon thing back then, before there were smart phones and IoT products. I jumped right in, wearing a number of hats. One moment I would wear a business development hat, negotiating with Pandora. Another minute, I would be working with a designer, sketching design ideas for our remote control software. The minute after that, I would be working with our acoustics team to figure out how we could tweak the EQ settings of our speakers to deliver the optimum sound quality.

When I look back on those days, I’m honestly not sure how I did it all, but I loved every minute of it. At some point, however, it became clear that I was spreading myself too thin and we needed to expand the team. To organize the work, my boss and I decided to split music service integrations into its own work stream. I hired and managed two additional people — one who would be responsible for the music service partnerships and the other who would be responsible for our 3rd party developer APIs and website. In addition to managing those new employees, I was the hands-on product manager for all other aspects of Sonos software. Again, I reached a breaking point where I was not being the best manager I could be to my staff nor was I doing my best work as the PM for the Sonos software. I remember the CEO of Sonos telling me that one of the worst possible outcomes in promoting a great software engineer to being a manager is that you gain a mediocre manager and lose a talented engineer. The same could be said for product managers. My boss was extremely supportive and gave me a few weeks to do some much-needed soul searching to figure out what the best path forward would be for me.

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I am a deeply introspective person to begin with. Having the time and space to reflect on where I was at this particular stage of my career was such good fortune. I figured out the right path to take by asking myself one simple question:

What are you working on that gets you out of bed?

Looking back, I realized that I was focusing my energy on redesigning our apps and defining new features. Thinking about our customer needs, collaborating with designers and engineers, launching new products — these were the things that got me out of bed in the morning. At the same time, I was not spending enough time filling the open positions on my team. I would block out a few hours each week for phone screens and the occasional interview and then wonder why it was taking months to fill the position.

Again, I was faced with choosing between management and individual contribution. Even though I had made this decision once before, this time it wasn’t as easy. For one thing, Sonos didn’t have a 2-track career path for product managers at the time. They did offer a dual-career path for engineers, however. Another reason this was a difficult decision was my ego. At this point in my career, I had worked as a product manager for more than ten years and had some preconceived notions about my future that were based on the continuous climb up that invisible ladder. For me, this had less to do with power and more to do with money. The loftier the title, the higher the compensation.

Ultimately, I knew that money wouldn’t make me happy. What made me happy was thinking about, “How can I help people listen to more music every day?” Deciding to be an individual contributor (again!) was the best decision for me, because I was happiest having the most direct impact on the product. It was also the best decision for the company because they didn’t have to worry about further developing my management skills and, instead, they could unleash me on special projects, such as creating a ground-breaking retail experience for the flagship Sonos store in New York City.

As Shakespeare wrote,

“To thine own self be true.”

In order to know which path you should take, you need to be honest with yourself. Set aside a few days for some deep introspection. Grab a journal and a pen and ask yourself these three key questions:

1) What are your strengths as well as your blind spots?

Be open to the feedback you’ve been given, the good and the bad. Take a co-worker out for coffee and ask them for feedback. Review those performance reviews again. If you already manage people, provide them with a way to give feedback.

2) What do you enjoy doing the most?

Ask yourself what gets you out of bed every day. Is it thinking about how to help your newest team member grow? Or do you thrive when brainstorming ideas for helping your customers use your product more easily?

3) Where do you want to be in 5 years? 10 years?

Do you have dreams of becoming a CEO or starting your own company? If so, the manager track might be best for you. Perhaps you’d rather be a subject matter expert in a particular field, speaking at conferences and being sought after for your brilliant insights.

Whether you decide to focus on managing or would rather be an individual contributor, I encourage you to champion a dual-track path at your company, if it doesn’t already offer it.

Here’s what dual-track paths might look like based on my experience:

Having a track that rewards senior individual contributors helps retain a critical aspect of your company’s brain trust while ensuring people becoming managers are doing so because they want to.

In my particular case, Sonos did eventually develop a dual-track path for product managers and I was the archetype for the Principal Product Manager role. It was gratifying to be recognized and rewarded for my contributions as the most senior product manager at the company in terms of tenure and experience.

After leaving Sonos, I decided to pursue yet another career path by leveraging my extensive experience to start a consulting business. Being my own boss while having a direct impact on the success of my business offers me the best of both worlds.

Does your company offer different tracks for product managers? Have you ever faced the challenge of deciding if becoming a manager is right for you? What do you think?

Originally published at on April 23, 2018.

4 Myths About Scaling Your Business

When I joined Sonos in 2005, I was the only software product manager. The company, known for its wireless smart speakers, was founded 3 years earlier and had just recently launched its first product. At the time, Sonos had 3 offices in Santa Barbara, California, Cambridge, Massachusetts and Hilversum, Netherlands. When I left the company in 2017, the company had expanded to 12 locations worldwide, as well as a boutique retail store in SoHo, New York. During my tenure, the company grew from about 50 employees to nearly 1,500. Fortunately, the co-founders of Sonos started, led, and scaled the company successfully. Many leaders, however, have failed to scale their companies for reasons that can be explained by the following myths.

Myth #1: Scaling fast is the key to success.

Many people believe in the mantra “Go big or go home.” While this saying might make sense if you’re a professional athlete, this is usually not the best way to build a successful, long-lasting business. In fact, scaling too soon is often the cause of death for startups.

Zynga is often cited as the poster child for scaling too fast too soon. As part of their rapid growth as they sought to dominate the mobile gaming market, they hired a massive number of employees from competitor gaming company Electronic Arts while spending hundreds of millions on acquisitions such as OMGPop. The company didn’t compensate for scaling other parts of the business which became even more critical as the corporate culture tried to absorb thousands of employees from different companies.

Birchbox very recently sold a majority stake of their business because they were running out of cash. Birchbox’s co-founders have talked about how they quickly scaled the company by doubling in size each month and being relentless about feature changes. They were so focused on growth and change that they overlooked two very important factors: First, they failed to successfully diversify their revenue from selling full-size products (which was part of their original business plan). Second, they didn’t keep their eye on the competition and lost market share to newcomers such as Ipsy and Fabfitfun.

Generally speaking, growth cannot be forced. Sure, scaling is often an indicator of a company’s recent success, but be careful not to believe that a causal relationship exists between the two variables. The companies that scale effectively are patient, and they strike when the timing is right.

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Myth #2: More developers = fewer problems.

Somewhat related to myth number one, is a problem that I encountered during my early days at Sonos. It was one of the few times I saw the company struggle to scale. There was a point when the ratio of software developers to product managers at Sonos was 50:1. It was recognized that this was a problem and there were even jokes made about cloning me. The fact of the matter is that it was really hard to hire good software product managers who met the high quality bar that Sonos had established. When I asked the head of engineering to scale back on hiring until we could bring on more product managers, I was laughed out of his office. The ratio did improve over time, but it took a long time to get there.

A key lesson from my experience is that companies that are focused on doubling the number of employees month over month or year over year need to be careful not to overlook certain functions or departments. When you add more engineers to crank out more features, you’ll need more designers to create the user experiences for those features, you’ll need more marketing people to tell the stories behind why those features matter and you’ll probably need more customer success people to help your customers deal with changes.

Myth #3: Innovation slows down the more you scale.

As companies get larger, especially once they go public, their appetites for risk usually shrinks. Public companies become laser-focused on hitting their quarterly numbers and limiting risk is a big part of their strategy. However, it doesn’t have to be this way. Just look at Google. Founders Sergey Brin and Larry Page have stayed closely involved in the management of the company while maintaining a commitment to innovation. They have done this by committing to research as well as fostering internal idea incubation.

When Apple announced the iPhone SDK in 2008, the Sonos product team quickly reacted to what would be a huge market change by making the bold decision to embrace mobile and launch a free mobile app despite selling its own remote control product for hundreds of dollars. By pivoting quickly and spinning up a product team that could design and develop for a completely new software platform, Sonos was able to ride the wave of innovation that was enabled by the iPhone. Sonos eventually phased out its hardware controller in 2011.

Myth #4: Money makes it easy to expand to new markets.

This myth is also similar to growing too big too fast. Often when companies receive an infusion of funding in their early years, they are tempted to spread themselves thin and introduce products and services to address adjacent markets. But when you are scaling your company, it’s best to stay true to your mission (and hopefully, your company has a clear mission) and stay focused.

Think about the great startups that have grown into huge businesses. Google was all about search. Amazon just sold books. When I was at Sonos, we would often be asked by customers, retailers and the press when we would have a product for video or for cars. This is when our leadership team really shined because we would always stay true to our mission of filling every home with music. That has allowed the company to successfully scale in a very intentional way.

The odds of being truly great at one thing are low. Don’t make it even harder by spreading yourself too thin.

Warby Parker is a great example of a scaling company leading with its mission statement. Since launching in 2010, Warby Parker’s founders stayed true to their roots by offering designer eyewear at a revolutionary price, all while leading the way for socially conscious businesses. They haven’t launched a shoe line and they don’t sell handbags. They just do one thing and they do it extremely well.

If you are a product manager at a startup, you are likely to see your company struggle with some of these myths. If you want to be a great product manager, use your skills of influence and critical thinking to identify these potential dangers before they arise, and help your leadership team understand these pitfalls. One way to do this is to create and share a well-planned roadmap that explicitly outlines your company’s core initiatives for the foreseeable future. While this is a great way to explain to your team what you will be working on, it also communicates what you will not be doing. For example, if you are a product manager at Warby Parker, you could explain “We’re not launching a shoe line” in the next 3 years. Letting your stakeholders know what is off the table can be just as helpful as letting them know what you do plan to build.

Another thing you can do is to be aware of your company’s hiring plans and speak up if you detect any imbalance in projections. There is no magic ratio of product managers to developers, but knowing the pitfalls of unbalanced teams will help you advocate for what is best.

Finally, be willing to let go. Be willing to let go of your ideas. Be willing to let go of your preconceived notions. Be willing to let go of that product that sustained the business, but will ultimately become an anchor that drags down your business. Stay focused and stop chasing unicorns and rainbows. Because the best way to scale like the Amazons and Googles of the world is by doubling down on what works, just like they did.

Originally published at on May 17, 2018.