How to Product: Mark Rabo

Sefunmi Osinaike
Doing a thing
Published in
9 min readMay 15, 2019

As part of our ongoing project to create a centralized resource to tell the stories of how people transitioned into a PM role (see my article explaining this here), this article series aims to provide a synthesis of the interviews we have done so far.

This article shares an in depth look into the story of Mark Rabo who never felt his lack of resume experience was a setback in his situation. His combination of experiences throughout his career made him a generalist which set him up to become a product manager.

The expected path

Mark did not know what he wanted to do at university so he decided to pick the hardest program with the hope that if he survived it, he will be able to do anything. So he decided to attend University of Toronto for Engineering science in the year 1997. After 2 days, he quit the program and decided to switch into the Mechanical Engineering field of study since he had previously worked as a mechanic while in high school. After graduating, without giving it too much thought, the next step for him was to find a job and he applied to as many roles as possible in order to get an interview and then convert that into a job.

“It was what everybody did… I was on the path! When you don’t know where you’re going, you just follow the path that you see in front of you. Go to school, graduate, get a job, buy a house, find a girl, get married and that was the path I was on.”

He worked as a mechanical engineer for 7 years and mentioned how disappointing it was. He always imagined he would get to work on sport cars or in aerospace but that was not the case, and he realized that path was far out of reach. After the company he was working for went bankrupt, Mark spent some time on the west coast to rethink what he wanted to do for a living. This was in 2006 where user-contributed content started to gain popularity on the internet. He was inspired by the story of Kevin Rose who hired freelancers to build a web prototype, went to venture capitalists to raise money and then built out the full experience of digg.com, a site for users to discover and share web content. Watching this all unfold allowed Mark to think of new opportunities to reinvent himself to go after a more fulfilling career.

“I came from a world where more experience was always better and if you did not have 30 years of experience, you were a nobody… and then I see this other side with kids like me starting companies without permission with technologies that were just there and that inspired me to go out and try my own thing.”

The adventurous path

Mark set out to create a website called Stickstickbangbang where artists could upload their work and anyone could select a design they liked and get it printed as a sticker for their iphone or ipod. He did not know how to code so he hired freelancers to do most of the work for him as he tried to bring the vision to life. He had a lot of money saved up from when he was working in the industry as a mechanical engineer which served as funding for his start up. This was the first time Mark felt like he had full control of his path, and the feeling of starting something new was invigorating. Being able to dream something up and then see the idea come to life was very rewarding as he worked through early iterations of his idea. Mark worked on this idea for 3 years with the goal to launch it when everything was perfect to him and had all the features he desired for his users. He was not willing to settle for anything less than his grand vision. In hindsight, he mentions this as the biggest mistake which resulted in the failure of his start-up.

Once Mark realized his start up was not going to work out, he let go of the idea and decided to look for a job as he needed some money. At this point he was just interested in any job that would pay him a decent amount of money. While working on Stickstickbangbang, he maintained a strong connection to the startup community in Toronto and was able to reach out to companies for job opportunities. He was offered a project management role at a startup and this position required him to enable seamless communication between the development team and the management team. After a year of working at this client services company, he left due to feeling restricted in his role. After leaving, he still did not have a clear idea what he wanted to do in his career and decided to take things one step at a time.

Mark spent the next 3 years trying out different things. He started to build a video game conference with a friend. This led him to start making trailers for video games, then eventually producing the games which involved raising money, guiding scope and direction of the projects and implementing marketing strategy. While doing that, he got more engaged with his creative side and also started freelance photography and videography projects. At some point, juggling this all felt unsustainable. He was fascinated at how authors and musicians could create content that could continue to generate more money for them for a lifetime and was interested in finding what he could do that would be a more sustaining career.

“It was tough… work an hour get paid an hour. That is a grind! You’re basically a labourer. So software was my way of making sure I get out of that.”

The path to product

Mark had a new challenge, to find the one thing that could combine all his skills and experiences into one job. He wanted to focus on one thing and was determined to find what that could be. One day, he was watching a demo for a game Google had made for their Chrome browser back in 2013 called Racer. He was very intrigued by what was built and at the end of the demo, someone who had the title “Product Manager” started to talk about the project. He looked up the title and wanted to understand what role that person had played in the game production. He concluded that it was the Product Manager who would often dream up an idea for a project and later execute it with the team that was required. As he continued to read the description of the job responsibilities, he connected with the role and felt he had similar experiences. That was the beginning of his journey of pivoting into a product management role.

Since Mark did not know anyone who worked as a Product Manager (PM), he looked to the internet to learn more about the role. He did early research on what successful product managers do and as he read further, he realized there was so much more he did not know. He also knew he could not just apply online for a product management job. Knowing this, he had two things to solve. The first was to fill the gap in his knowledge by learning more about product management. The second thing was to convince someone to give him a job with no prior PM experience.

To tackle the first problem, he reached out to some friends who were in tech and asked to join their company for two weeks to listen in on meetings and learn how the companies operate. His plan was to convince a couple companies that will let him come in so he could learn by being around them. He offered to grab coffees, take notes and even wash toilets to remove any reason for them to say no. One specific company was in San Francisco and mentioned they could not fly him in to shadow them. Mark responded by purchasing his own plane ticket and covered his own cost of living for the duration of his stay to show how determined he was. This turned out effective as he was engaged in meetings and was asked for his opinion during discussions. He kept a note of all the things he was learning and started to build out mock ups of his own ideas he had for products and documented cool interactions from products he admired. Mark was determined to show his work to people to get feedback so he could improve. With his notebook full of ideas, he used this to form his strategy on how to get the rest of the skills he was missing.

“I was preparing for the moment where i could maybe sit across from somebody and say… I have zero experience officially as a PM, but here is why I think I have those skills… ”

Through his network, Mark connected with other PMs and asked what he needed to do to be given a chance. He used his notebook to demonstrate his curiosity, interest in technology and working with people. He was very forthcoming of his weaknesses and was very self aware of what skills were lacking. It was very important to him to show how willing he was to learn. By doing this, he got a lot of advice on what he needed to do to fill the gaps in his knowledge and skills. He treated this like a quest and went back and forth with different PMs till he felt that he was in a good place to begin the process of job hunting.

The path to product employment

Mark got the confidence he needed to begin the process to find a product management job. His strategy had two steps; pick the top five exciting companies he would love to work for and do whatever it takes to get in front of the people he needed to in those companies.

“This was my approach instead of thinking “who is hiring?” because there is nothing exciting about sending resumes to 20 random companies. ”

By choosing companies he admired, he was more motivated to strive towards his goal of getting the job that was best for him. After understanding what the companies needed, he tailored his experience to match the job descriptions as a way to prepare for the opportunity to sit across from someone who would ask “Why should we hire you?”. After doing some research for one specific company, he was able to understand they were at the size where the CEO was likely the only product manager and was probably spread too thin. He then proceeded to make a detailed website that communicated what exactly he wanted to do for them. This was able to help him demonstrate how he embodied their core values since he aligned his narrative with what the company was working on. He also found out the CEOs favourite beer, brought it to their office and left a card with the website link he made. Later that week, he received a call from the CEO who commended him for his effort and interviewed him for the job.

Mark also reached out to people in his network to ask for a connection with product leaders in any of the other companies he was interested in. He would ask for a 15 min coffee to learn about what they typically look for in a candidate. He would then respond by showing his notebook full of relevant ideas that have been catered to the company. This showed enthusiasm, initiative and helped him engage in discussions about his thought process while building products.

In 2014, Mark got the opportunity to meet with the Director of product at FreshBooks to pitch himself.

“I told him about my experience around different groups of people, and with Freshbooks in particular, it was perfect for my actual background because I worked in a million different trades …

I knew how hard it was to like grind it out like a photographer or videographer or a contractor. I could speak the language of their customers and I’ve also been a whole bunch of them. So I have that intuition, and have the experience of what it feels like to start your own business, the fear the anxiety the stress that’s so hard to find.”

The conversation was good enough to get Mark an interview. After going through the interview process, Mark was hired as a product manager at Freshbooks.

Once Mark joined the company, he quickly realized there was more to the role than the picture he had painted in his mind. Knowing the value of continuous learning, he worked towards understanding how different teams worked together to drive business value. By doing this, he was better equipped to be successful as he grew into the role.

4 years later, Mark is now a Senior Product Manager at TunnelBear and the founder of Revere, a note-taking app for notes about people that helps you build more meaningful relationships.

Want to learn more ?

We’re two friends trying to consolidate resources for folks making a jump into the technology product/program management space from outside the industry. We have interviewed a bunch of PMs and if you’d like to hear more stories like Mark’s or other insights we find, follow our medium publication. We also started a podcast where we talk about the process of getting this all together. Subscribe and listen now on iTunes, Spotify, Soundcloud, TuneIn or Stitcher. We’d also love to hear your feedback so share your thoughts with us and like our facebook page.

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Sefunmi Osinaike
Doing a thing

Human 💡| Promoter of peace, entrepreneurship and technology!