How to Transition from Sales to Product Management

There has to be more to life than Sales. There was a time when I felt inspired to wake up and tackle a new challenge, but those days were in the distant past.  My brain felt like it had atrophied to the point where I was no longer sure I could do the jobs I was hiring people to do. I needed a change badly! Perhaps you’ve felt the same way while staring blankly at your monitor pretending to be busy? For me, the answer was making the transition from Sales to Product Management.

From Sales into Product

At the time, I owned an insurance brokerage and spent hours trying to train new people how to navigate our antiquated sales process. Without any formal training in product, I cobbled together a small development team to build a product to solve a problem I was having in my business. There needed to be a system that made the process 100x faster and nobody was stepping up to build it, so I saw an opportunity.

After conscribing a small team of professional developers, we set about solving this problem. The engineers had tons of questions. They wanted to know how the process was supposed to work, how we would get the data, how to validate it, format it, present it, etcetera. Having deep domain experience, answering those questions was second nature to me. The process was so rewarding that I knew that I wanted to do this work full-time and build bigger and better products with more resources. If only there was a full-time job that would allow me to do this work and get paid for it — enter Product Management.

My First Product Job Search

As I searched for my first commercial role as a Product Manager, I felt like the deck was stacked against me. My first job search strategy was a brute force attack. I applied to over 1300 positions at startups, marquee companies, and anything in between.

Much to my chagrin, very few of them even responded. It was heartbreaking. There were job descriptions I knew that I could perform brilliantly if only the recruiter could see past my current job title and listen to my transferable experiences. It was far easier for them to choose one of the other 299 applicants that had recently worked as a Product Manager at a recognizable company.

My job search had left me doubting everything about myself. Was I too old to pull this off? Were my skills that out of date? I had a fancy MBA degree, and I even knew what a VLOOKUP was. As the weeks and months went by, my dreams of career transformation began to look more and more out of reach. I despaired.

PM Agile Interview Questions

One interview went so horribly wrong that I still have nightmares about it.  The interviewer (the CEO of the startup) sat in a room across from me and the HR rep that had picked me for the interview. They proceeded to grill me for over an hour about Agile methodologies. They asked about how to correct projects that had gotten off track, and they wanted specific examples from my past experiences. They expected me to use proper Agile terminology.

Even though I had a Scrum Master certification and had spent years as a business analyst working through many of the scenarios they put to me, my answers were fumbling and paper-thin. It showed. Each successive question highlighted my lack of preparedness and the more I groped for a response, the more obvious it became that I was not the right choice. The CEO used me as a human sacrifice to teach his HR rep how to properly screen prospects for the next attempt. I was mortified, but I didn’t give up.

If you are struggling during interviews, don’t make the same mistakes I made. Don’t try to improvise your answers. Even the most basic questions about product development can throw you for a loop if you have not thought about your prior work and formulated it into a proper product response. My career in sales provided ample experience overcoming objections extemporaneously, however relying on your ability to counter punch is not a winning strategy in the specific discipline of product management, especially if you are changing careers.

How Not to Prepare for Product Interviews

There is a common thought that earning more degrees or certificates will make you stand out as a candidate. Truth is, nobody cares about your certificate. Many of the candidates you will be competing with will have the same, if not better degrees as you. Your side-project or weekend hustle isn’t what will make you stand out from the sea of applicants with years of verifiable experience. That doesn’t mean the effort was wasted; it just doesn’t translate directly into getting hired. I also thought that being part of an alumni group of like-minded PMs who also had degrees and certificates would mean endless introductions and opportunities flowing like wine. Not so much. 

There is a cadence to product management job hunting that you cannot learn by getting another piece of paper, no matter how prestigious the conferring organization. Once I started training with Product Gym, all the failures I encountered trying to figure it out on my own started to make sense. I practiced the art of interview performance theatre by working through problems with other PMs and recruiters who have been on the other side of the table, and that more than anything started to make a difference.  

In the end, it was the real-life practice that helped boost my confidence. After about 20-30 interviews using the techniques I had practiced, I started to catch the rhythm. I understood more and more how I should be framing my answers to match what hiring managers are expecting. Just like seeing results after training at a regular gym, the hours of practice and a multitude of real interviews alleviated my fears of being a product imposter. If you are serious about breaking into product and want to have a fighting chance, you need to join Product Gym and put in the work.


Justin Fowler

Justin Fowler transitioned from a lengthy career as an Insurance Broker into Product Management, working with an AI-enabled voice analytics software company. Justin is living proof that you are not too old or out of touch to learn new tricks and practice another trade — if you are willing to put in the work.

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