The Journey Into Product: Interview with Product Leader Michael Chadwick

The journey into product can come through many different pathways. In this exclusive interview, we delve into the transformative journey of Michael Chadwick, a Montreal-based Product Leader, whose career began in copywriting and marketing, only to take an unexpected turn toward the dynamic world of Product Management.

We explore the defining moments, challenges faced, and the unique insights gained from his career transition. Join us as Michael shares his experiences and unveils the symbiotic relationship between marketing and product roles.

Michael, your career began in the world of copywriting and marketing. What defining moment compelled you to reimagine your career into a product role? Did you reimagine it? Or was it an organic career transition?

It was a bit of both. I started as a copywriter for a small shop right after getting my Master's in English, and as is the case with most startups, there is far more work than there are hands to accomplish it. In this environment, I was also tagged with managing incoming customer support emails.

It wasn’t long before I noticed trends in certain types of responses. This motivated me to play around with the products to verify their points and identify areas where we could potentially improve. This slowly transitioned into the representative “voice of the customer” in the company, and because of this sentiment, the feeling was I, more than anyone else, would be the best person to sell to them. 

So, I transitioned into the Marketing Manager role, responsible for developing internal and co-promotions with our partners and managing and executing our email lists. While this was occurring, I would also push and prod to get “quick wins” – that I knew the customers would enjoy – delivered. This new role also put me in contact with many of our partners, so I would provide recommendations based on that feedback to improve the products. 

Someone at work casually mentioned, “What you do is much closer to Product Management than Marketing Management.” I had never heard of this role before it was mentioned. I went down a Google rabbit hole, and sure enough, my colleague was right: I was talking with customers daily, identifying their problems, developing solutions through features and revisions, running tests, analyzing the results, crafting messaging around the releases, the full gamut of Product Management.

With this in hand, I asked if I could formally change my role to Product Manager, and the boss agreed. Once official, I dove deep into the role, reading every book and attending every webinar to strengthen my understanding of this wonderful field.

What have you realized is a benefit in your role as a Product Leader, having a career track that began in marketing? How has that marketing career helped you in your role now?

A good PM knows what the customer needs to have a better, more valuable experience. A good Marketing Manager knows what the customer needs to hear to engage, use, or re-engage. I find the overlap between the two is quite large, but again, I’m a bit biased. 

I have been fortunate to work with some incredibly gifted marketers, and they can make you view the product in ways you may not have considered. This shift in thinking can trickle down when identifying problems to focus on. Further, they are most commonly among the best communicators in the company, so you can learn how to position an argument or a position best during discussions with senior stakeholders. 

For example, imagine an email campaign announcing a new feature receives stronger-than-expected engagement; this can be a clear signal that surrounding features, either new or revised from existing features, could receive similar excitement. You can then compare the adoption and engagement metrics for this newly launched feature against the awareness and acquisition metrics from the announcement, and iterate from there. 

I don’t know if they still do this, but at Amazon, in place of a Product Brief, the PMs were expected to write a one-pager on a new feature in the style of a press release that the customer would theoretically read. I think that’s a brilliant approach to creating a closed loop by having what is traditionally one of the last pieces of documentation around a product, the press release, written first. This method forces the PM to start at the conclusion and work backward with the team from there.

What were the roadblocks/challenges, and how did you overcome them?

My single biggest roadblock was a mental one, and that was imposter syndrome. After officially shifting to Product Manager, I got it in my head that I needed to start doing all of the things I was already doing “the right way.” I began overthinking my approaches to collecting data. I started forcing myself to follow the frameworks I read to the letter, ignoring the particular circumstances of my marketing and company. I struggled for the first few months with the official title and thought I made a mistake. It took the advice of a mentor to say, “You are delivering and generating results based on a series of frameworks you developed yourself…you’re doing it right!” 

Beyond that, the biggest shifts came in the more practical applications of the role, such as communicating effectively with the development team, UX designers and the data teams. Related to that was also deep diving into learning the system designs of the product, such as the documented user flows and architecture supporting the technology. All of the “under the hood” stuff many people are hesitant to dig into has been essential in my experience. 

One of the best lessons I ever had early in my PM journey was a tech lead showing me in exquisite detail how the three-line story ticket I wrote actually constituted six weeks of work. He was extremely nice about it and walked me through the inflection points where we could go in several directions and the trade-offs resulting from each choice. This 30-minute discussion was one the most revealing Product Management lessons I have ever received, and I recall it whenever I begin research and ramp-up work on a new product or feature.

What advice would you have for marketers reading this who aspire to pivot into a product career?

I would say you are much closer than you realize. A large part of the skill set necessary to be effective in marketing, like communication, how to test hypotheses, and understanding the customer’s wants, needs, and pain points, are requirements to be effective in Product Management.

The one challenge a marketer new to product must face is a fuller understanding of the technology. Not just the technology pertinent to their product and market in general but technology overall. System design, APIs, SQL, databases, the works. Learning to communicate with developers effectively is a skill in and of itself, and the more you can correctly communicate with them on their grounds, the more effective you will be in negotiating with them and shaping what is ultimately delivered. 

Once you are on the product side of things, you are tasked with breaking everything down to its fundamental components. Another great piece of advice I received many years ago is, “To a Product Manager, every product is a collection of features. To a Developer, it's a collection of services. And to a UX Designer, it’s a collection of flows.” You need to be mindful of the interplay and healthy friction that needs to exist within the team to navigate and make the best decisions for the problem and the solution. 

Fortunately, you should have a team of knowledgeable people around you to assist in this process, so you don’t need to know every granular piece of the puzzle. If you are executing Agile and Lean Thinking correctly, you are bringing just enough to the conversation to build the solution together. 

I have onboarded and trained many PMs in my career and one of the things I always advise is to “know enough to be dangerous.” This role rewards the curious and the empathetic. You’re off to a fantastic start if you have those two traits

What advice do you have for Founders or CPOs who decide to hire a marketer into a product role? What should they be concerned about? 

My career in product has focused mainly on B2C, so there might be other unique considerations with B2B products that I am not considering, but if there is one thing they should look for, it is someone who is more concerned with the problem than the solution. I believe that should be true for everyone in the company. The role of the marketer is to communicate the solution after all. I believe it is understanding the true blockers and pain points that prevent the customer from being that more idealized version of themselves that will inspire the best angle to connect the user’s problem with your product.

Any person considered for a product role needs to be intensely curious, a self-starter, and an aggressive learner. There are just too many facets to Product Management that a PM needs to balance to be effective at the job. Someone who isn’t actively looking to expand their knowledge and awareness is someone I can’t see maintaining the role for long. If you have the sense that potential hire won’t put in the time to continually learn and refine how to run compelling customer interviews, A/B tests, story writing or product briefs, lo-fi mockups, post-mortems or whatever specific toolset that specific Product Manager role requires that person should not be considered. 

While I don’t subscribe to the ‘mini CEO’ tag, the role gets sometimes labelled with; the implication behind it that the person needs to have a robust understanding of all of these components is very, very true.

What should employee onboarding look like to help them ramp up faster?

The best way to onboard a new PO or PM is through a series of crash courses with small work assignments, starting with the macro and progressively burrowing down into the micro. Along the way, I am sharing the particular ways of working of the company and how it all connects to deliver the end result. The thing I find awesome about Product Management, which can also be overwhelming for newcomers, is just how many things you are expected to know and leverage to be successful. 

Even for a seasoned PM, giving them a product and throwing them in the deep end will provide lacklustre results. So, for a hypothetical new PO hire, completely new to either the role or the market, I would provide an evergreen slide presentation of the market, the main competitors, along with the feature sets and value delivery each one does to differentiate each other. I would then assign them to run a market and competitor analysis independently to see what insights they find. 

After that, I moderated one-on-one chats with the team lead, the UX designer, the QA, the data analyst, and the marketer so they could talk about the product from their unique perspectives. While that is happening, they should pick up what they talk about, what words and terms they use, etc. Some of these chats might have small assignments at the end, like reviewing and taking notes of the asset library customer interviews or recent bug or incident reports. And before long, they’re shadowing the Agile Scrum ceremonies and seeing how tickets are broken down, stories and briefs are written, tests are documented, etc. The unique ways of working that every company has. 

Each week, I would decamp with them to discuss what they have learned and answer any questions. This process would be over the first 4 to 6 weeks, with the next 4 to 6 weeks setting them loose to begin executing in the role. 

The goal is to provide a 360 review of every relevant facet of the company that comes to bear on their product and how they, the Product Manager, stand in the middle of it. Depending on the role and experience, it may not be as thorough, but at the same time, there would absolutely be some version of this approach. The only difference would be its overall length. 

Thank you to Michael for sharing his journey. It serves as a roadmap for those contemplating a similar leap—showcasing that the bridge between marketing and product roles is traversable with the right mindset and skill set. Whether you're a marketer eyeing a pivot or a Founder contemplating the integration of a Marketing Manager into your product team, Michael's insights provide valuable guideposts.

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