Culture and Organization
March 1, 2023
min read

From Engineer to Engineering Executive: An Unexpected Journey

Recently I had the pleasure of sitting down with Masumi Nakamura, Vice President of Engineering at Mercari US. We wanted to discuss his experiences from starting out as a contributing engineer to becoming a Vice President of Engineering at Mercari. Below is part one of a retrospective look at his journey.

An Indirect Path

Nick: You're currently the VP Engineering at Mercari US. Can you tell us a little bit about your journey? How did you get here?

Masumi: In my case I would say that I am typical in that I discovered managing people through organic opportunity. I have found that a lot of people tend to fall into that path through starting off as an individual engineer, doing contribution work, and then as opportunities come up you end up being the person who people look to out of availability or necessity in what you would call peer management or what some places call a team lead. 

The journey to becoming an executive isn’t always necessarily a straight line and can include going on and off that natural path as a team lead. Earlier in my career at Cisco Systems when I was cutting my teeth as an engineer, there were elements where I would end up leading/acting as a project manager in the capacity of organizing the project. This was important for me because it allowed me to develop the skills necessary to manage people and resources. Later on in my career when I was working at various startups, I had to own that portion, and when I joined other startups, I would even fluctuate between high technical and some level of team management. Throughout my career I have always believed strongly in the statement “an engineer is always an engineer”, meaning at its core the engineering mindset is about solving problems. This doesn’t have to mean always through true invention but sometimes through practical orientation of engineering principles that can be applied to the managerial role.

Masumi Nakamura, Vice President of Engineering at Mercari US

The Better Ways to Build Leadership Skills

Nick: Could you tell us your thoughts on leadership? What's important for other engineers to know?

Masumi: While I feel these skills should largely be taught in a more structured environment, in my experience it tends to follow a more classical apprentice model where you learn from example and feedback from a more experienced leader willing to take you under their wing. Business schools are attempting to solve for the management skill problem. In many ways they have been successful, but specifically for the startup area, thorough management coursework is still a newer concept.

Here is an interesting way to look at the concept of management skill training. It is not like going for gold at the Olympics with a clear end goal in mind. In many cases it happens very organically over time. To grow and learn this skill set, it is critical to take advantage of the opportunities as they present themselves. You can’t just pick up a guitar and expect to be able to play the guitar. You have to train at it. Therefore, it should be recognized that if this is a path you may want to pursue, it is important to proactively train for new leadership opportunities as you search for them, not only after you find them.

Successful Management by Staying True to Yourself

Nick: What's the biggest thing you've learned being a leader? What advice would you give to engineers who want to follow a similar path?

Masumi: The breakthrough of why I wanted to become a manager and how to use that as motivation didn’t happen as a “eureka moment” as you might expect. It was more of a journey of self-discovery. This helped not only assure me that I made the right choice but contributed to shaping my personal management style.

It was essential for me to discover who I was going to be as a manager to be successful. Introspectively, I pondered the question of why as a manager I should try to be anything different than I am as a person. I enjoy cooking. I like to tinker. I enjoy creating things. That underlying motivation to solve problems and create things in life and as an engineer became the driving force behind my motivation to become a leader. Now I’d use that same concept to create a team, department, or company to solve a unique problem. Of course, the intricacies differ, but the concept is very similar.

For someone like me (and other engineers that are driven from a first principles orientation) once the underlying motivation is clarified then action follows. Taking on the responsibility of acting to fulfill the needs of the greater group, truly owning the need to solve for the problem set, understanding the elements of what the team members can and cannot (or will not) do, and who and when communication needs to be done are all things you automatically begin to do and seek to understand. Typically the phrase “ask for forgiveness not permission” tends to come to mind, but i would modify that with the phrase “ask for forgiveness not permission and broadcast widely before and after you act”.

Becoming an Executive

Nick: What's the single biggest thing you would attribute to your success in becoming an executive?

Masumi: Once I started actively pursuing the executive path, I learned the main differences between being an executive versus being a manager. I’ve read a lot of books on the subject, but I feel I truly became an executive after going through a kind of transformation. In fact the tricky part is that the difference is clearly stated in the name of the mindset (by definition) but knowing a definition and acting within it are very different. An executive makes decisions as the primary job responsibility and the manager manages. Though managers and non-managers constantly make decisions their end goals are different. The difference here is that the executive mindset is always about the end goal of making a decision, while a manager’s end goal is to manage the situation. To this end not only is the orientation different but the toolsets are  very different as well. 

In my case a mentor helped me to break away from the managerial mindset to the executive mindset.  I found this so critical that when I was trying to make the jump to executive, I contemplated it during the interview process when considering new opportunities. Part of the overall decision process; was there someone to show me the ropes, knowing that I was a newbie executive and coach me on what that means? How would I be able to move past that to a more proactive executive mindset? Getting to that stage without a coach or mentor is possible but it tends to take much longer.

In part 2 Masumi recounts his growth as an executive to an executive mentor and provides advice on knowing when is the right time to make the switch to a more managerial or executive trajectory.

Nick Pereira
Nick Pereira is the Communications Manager for Product and Engineering at Mercari. Based in Connecticut, Nick has been in the global digital communications space for both tech and cybersecurity for over 10 years. His experience ranges from communications and digital marketing to UX design, web development, and product design.