6x6: Product Manager Career Paths

Julia Mitelman
On Products
Published in
14 min readMay 2, 2021

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Part 1 of 6x6 series, where we share perspectives from six PMs on six questions about product management. See Part 2 , Part 3, Part 4, Part 5, Part 6.

It seems like every PM I’ve met has had wildly different career paths, and yet we all found ourselves drawn to the role. Ahead of discussions on PM best practices, I spoke with 6 talented PM friends on their origin stories.

Chaitanya S., the intern

People forget that the process of elimination is progress — if you try something out and it doesn’t work, you’re still learning and progressing towards a goal. I was fortunate to have a few internships and jobs, starting from high school, to figure out what I liked. I sold t-shirts on consignment, taught mechanical drafting as a teaching assistant, and spent two summers on Wall Street. Something about exercising left and right brain hooked me.

I studied electrical engineering and computer science in college. When I interned at JP Morgan and Merrill Lynch, there were two separate entrances at the banks: the investment banker front door and the tech side door. Banks liked to showcase their technology externally, but, inside, tech was in service of the ‘real work’ of moving money. I realised my passion was not in banking because technology was not primary to the business model. If you really want to make an impact, go someplace where what you do is core to the company.

I’d heard legendary things about Microsoft internships — you even got to meet Bill for dinner at his house! I’d used a lot of their products. Interning as a PM there solidified that this was what I loved. Internships are a two-way interview. You’re demonstrating your acumen and ability to learn by doing the real work. You also get to see if the team and company are right for you.

In August 2000, I joined Microsoft full-time as an Office PM. This was a time when software came in a box that shipped every 3 years. You had to be really thoughtful and rigorous because your arc was so long. After 6 years, I wanted to try something more consumer-oriented, so I worked on Windows for nearly a decade. It was a thrill to drive products for over a billion people. I became a people manager, which was a joy. I went on to mixed reality for just shy of 5 years, where my team and I were responsible for the core experiences of HoloLens.

I also moonlighted throughout my career — it’s important to have fun projects outside your role. My first company was a non-profit called VisionQuest, a technology forum that connected students to tech luminaries. I even got to interview my idol, Tim Berners-Lee. I published an audiobook that taught vocabulary using the mnemonics of comedy. I co-founded and was the CEO of Chewsy for several years, which let you rate dishes instead of restaurants. I was the co-executive producer of a movie. I liked to learn outside of the realm of typical jobs.

I realised early on that I’d already innately been doing product management in other pursuits. It’s about figuring out why customers do what they do, clearly framing the problem, and driving a product through the process.

Mike B., the scientist

My plan was to become a teacher. I studied cognitive science, which is a mixture of psychology and computers, in Canada. As I completed the program, the high school teachers in Ontario went on strike — they weren’t hiring. I had to find a new future quickly.

I stumbled onto human-computer interaction (HCI) at a career fair and got my first job at IBM Toronto as an HCI specialist. I worked with engineers to understand how users would use the tools that other people had decided we’d build. We were working on Eclipse and ran into a big problem in the research: the fundamental constructs were wrong. Eclipse was designed around the idea of creating a master project folder and defining your packages upfront. But most people just opened up a code editor and started tinkering around, figuring out the architecture later. It was too late for such deep product changes, so we added a bunch of refactoring tools and wizards. I was left with a deep sense of frustration that I had failed as an HCI practitioner and that this was the wrong way to build products.

So I made sure the Chief Architect at IBM understood what had gone wrong on the project, and he suggested I join the Integrated Product Management team. At the time, they worked with market strategists and customer reps, who told them what they thought the user needs were.

I made the same mistake a lot of people in the early 2000s made and studied a lot about project management. Product management is the practice of 1) clearly defining why does this product need to exist and how do we know it has succeeded, 2) aligning the team on the best possible outcome, and 3) disbanding efforts when they should be stopped.

Eventually, I got involved in open source and took a job with Mozilla as the Product Director for Firefox from v1 to v4. In most PM roles, you are translating between sets of stakeholders: your company, who wants to be successful, and the user, who will determine if you’re successful. With open source products, there’s a third audience: the open source community, which wants to accomplish something through your product or users. Early Mozilla users — mostly that third community — were technically savvy and willing to download giant browser packages. Firefox wanted to expand its audience to anyone who used the Internet. The main challenge was balancing the needs of general consumers (lighter, faster, customised) with the needs of open-source developers (revised DOM tree parser, rendering complex math equations).

At this point, I’d spent years working on something for everybody — the web browser — and this was difficult, because I didn’t know what everybody wanted. So I went on to try something more focused: software that helped geophysicists interpret 3D data they were getting back from marine seismology. After a year, it taught me that, while there is beauty in the tight coupling of product and market, it did not have the scale that appealed to me. I briefly worked for a startup in Toronto, and again it became clear that our ambitions on scale were different. I realised that, if I wanted to build products for the world, I had to go to California.

I joined Pinterest for 2 years, working on the core experience. I built the release cadence and quality tools and grew the international user base. I focused on creating cohesion across the app, since Pinterest was about experience, not just utility, and it was important to create moments of delight throughout the product.

I want to be spending my time working on something that pushes a global community forward. It’s an itch I got at Mozilla, where I’d see that people all over world, even at the Vatican, were downloading Firefox. There are few opportunities to work on something like a global standard for rail gauge, but they’re meaningful and important, because they enable trains to go from one track to another. Similarly, products that create new ways for people to communicate and collaborate and establish new communities together is super important. That’s what drew me to Facebook, where I currently help new product groups — from VR to AI to new product experimentation teams — get established internally and in their market.

I failed into being a product manager. I wasn’t good enough to be a developer, so I couldn’t just build the right things. I wasn’t good enough at graphic or interface design. But I could see the intersection between where a user problem was and what the solution space had to be, and I could carry that story.

Poorva S., the degree-educated

People joke that Olin College of Engineering manufactures PMs. Everyone had to do an engineering degree, but also take businesses classes, design classes, and pick an additional humanities concentration. It makes you more well-rounded. We had a class where we went out and studied a user group, figured out what inspired them and what they wanted, and worked to solve their problems. This is where I developed a passion to not just focus on building the thing right, but building the right thing.

I started as a PM intern at Microsoft and then spent a few years there. With a small ratio of engineers to PMs, my teams owned smaller scope but went deep into the details. Next, I wanted to do something mission-driven, and I was always really interested in education, so I joined Code.org, a non-profit startup focused on increasing access to computer science education for underrepresented groups. There were only a few PMs, so my scope was large and I had many hats — I did my own research, often made my own mockups, and did all my own quality testing. We did whatever needed to get done to make sure we were shipping the right things. For example, when we learned about GDPR, I read hundreds of pages of regulation to figure out what we needed to do, so we had a recommended plan for the professionals to review.

I’m currently working at Uber, on our Driver team. Right now, I’m focused on making onboarding a frictionless experience, enabling drivers to easily submit and validate documents. It’s a global team with many local nuances, so there’s a complexity of many stakeholders with requests that need prioritising. Even at its size, Uber remains very bottoms-up and I’ve defined new initiatives for my space, like strategies to improve driver supply.

I became a PM because of the human connection. I really enjoy learning about people and getting to know what motivates them. Knowing what to build means figuring out what the user needs and trying to solve their problems.

Anna B., the journalist

Working in journalism for 8 years, I was an editor-in-chief for magazines, worked as a political journalist in Chechnya, and worked in television — I’d never even thought about tech. But when I was at Conde Nast, we were doing a lot of work growing our web presence and I was in charge of rethinking our approach to digital content. I worked with designers, engineers, and analysts to understand how readers interacted with the site.

At the time, Yandex, a big search company in Russia, had a free evening program open to anyone to become a product manager. You listened to lectures from employees and worked on a group project — it was very unusual. I joined to help my journalism career, but I liked it so much that I interviewed for an internship. After achieving some seniority in my past career, it felt odd going back to square one, but I enjoyed the work so much that I didn’t regret it for a moment.

After the internship, I worked on a machine learning (ML) team at Yandex for 2.5 years. Working on ML, statistics, and experimentation was a big transition from social sciences and languages. But I worked with a fantastic team who taught me a lot about the technical aspects of the work. My husband and I then moved to Berlin, where I became a product lead in a startup called SuitePad, building smart devices for hotel rooms, enabling communication with different parts of the hotel like the concierge and spa. It was hectic, as we somehow had 8 engineers and 8 products. But I learned a lot from working on hardware for the first time.

I spent a year at Intercom in Dublin. They had previously focused on support and wanted to expand to new audiences. I launched the new product for sales and marketing automation. For the last three years, I’ve been at Facebook, working on Workplace, where, ironically, my team at Intercom are now one of my customers (and vice versa!).

I’ve always wanted to have impact on the world. I’d been working on stories about social problems, injustice, violence towards women, about people changing the world. At some point, I wanted to change the world not just by writing about it, but by doing it, and it felt like product management could do that: create something valuable for millions or billions of people.

Shirley Z., the manufacturer

Having studied history in college, I’ve always been interested in the cause and effect, the big-picture view of things. When I interned as an engineer, I realised you’re focused on only one part of the product cycle day-to-day: the middle. But I wanted to influence how the whole thing worked. As a PM, I get to see how the product goes from conception to release and all its continuous iterations.

My first job out of college was actually in the jewellery business, doing end-to-end development, advertising, and selling. It was really interesting to see how the supply chain brings ideas to manufacturing and into the hands of people. It translated well into product management. Both have to coordinate across many stakeholders and steps to get to a final outcome and achieve a goal. Jewellery advertising required a lot of care on the conversion funnel and setting metrics correctly, which also matters a lot in tech. Manufacturing required thinking about the logistics of packaging and shipping, as in tech, where you coordinate and negotiate with many teams across product and operations. In tech, your manufacturers are the engineers and designers.

I left manufacturing for the fast pace of tech. It was difficult to break into PM without an engineering or startup background; I must have talked to 50 companies before one took a bet on me and my willingness to learn. I joined Rocketrip, a SaaS gamification platform, as its first PM, growing the customer base from 5 to 50 clients over 2 years. My role felt different every day: I was, at times, a business strategist, a designer, user researcher, data analyst, a marketer, customer service, and sales, all in service of launching successfully.

I took the learnings to my next job at Uber, where I worked on Uber for Business for nearly 4 years. I ran the gamut from improving signups, to building APIs for partners, to stabilising billing systems. I incubated a new vertical, Uber Direct, which delivered packages for businesses. Roles at Uber were much more specialised, so I had to learn a new scale of cross-functional collaboration. Negotiating across teams on priorities became really important. I enjoyed learning product craft from experts, so I got involved in Uber’s Product Bootcamp, where I created a curriculum and invited expert speakers to talk about various aspects of product management.

I’m currently leading the core checkout product team at Bolt, an e-commerce startup. Since the company is still growing, my team builds the front end of the checkout, the backend which other teams build into, and even the experimentation platform, where we own the data for checkout events. I’m using my past experiences to figure out the challenge of scaling Bolt’s product and operations to match our ambitions.

Most people outside the role think PMs say what to do and other people go do it. But as a PM, you rely much more on influence, on building relationships, than control. Honestly, if you gave a list of things to do to any person in the company, they could probably come up with a sensible list of priorities. But being a PM is about how you convince people that this is the right list of priorities.

Richard H., the explorer

I like learning things and get bored quickly, so I’ve changed jobs and cities a lot since college. I started in a business role at Amazon and realised I wanted to be more technical. So I taught myself SQL and became data-savvy. I moved to Google, doing marketing analytics, and befriended an engineering manager. He took me under his wing, walking me through his team’s code base and giving me CS textbooks to read. As part of my 20% time, I started contributing code to his team. This ballooned into two jobs, and so I transitioned to full-time engineer. But I always knew what to expect when building infrastructure, so a mentor suggested I try product management or working at a startup.

Despite having no PM experience then, one of my former roommates in San Francisco invited me to Mobike, a startup that deployed mobile bikes, which he’d recently joined as Head of Product. He’d seen me go from marketing to engineering at Google, day in and day out in the kitchen doing coding interview questions, and he had a lot of trust me in me that I could learn anything, do anything. I didn’t take it seriously at first — I wasn’t planning on moving across the world to China. But I was really interested in Internet of Things (IoT) and this was one of the biggest IoT deployments I’d ever seen. I went to China to talk to the team, and the product was just so delightful. So I stayed, as Head of International Product. I had to learn a lot, and it was rough, but at the end of the day, especially in a startup, you just have to solve problems.

I hired people and expanded the product to 15 countries. It was hectic as the company grew. I felt the growing pains. When I’d heard that earlier in my career, I’d always thought, oh that’s cute, how painful it is to blow up into a unicorn. But it actually is very painful and very personal. A startup requires you to invest a lot of yourself into the company, so people start to form their identities around it. When reorgs happen, people get promoted or demoted, and they take it very personally. It’s bound to happen because not everyone can scale their abilities at the same speed as the company. You just can’t rush learning.

A year later, Mobike got acquired, so it was a good time to move back to the US. This was just when cryptocurrencies were blowing up. Someone sent me a whitepaper on a protocol which I realised was written by someone I knew. I reached out and asked if they were hiring PMs, and after some quick chats, they wanted me to join right away. My startup experience had been intense and I wanted to take time off first, but my friend at Basis said the crypto phenomenon was moving too quickly to wait even a month. So I moved to New York as the 15th member of the team and the first product hire. Working on a protocol was like solving a logic puzzle. In the 9 months I was there, it became clear that regulations were going to come out in a way that required the protocol to be fundamentally redesigned. We decided with the cofounders that the best decision was to shut the company down and return the capital we’d raised to investors, with more than 95% not yet spent. I finally took that sabbatical, travelling and taking online classes.

Through side projects, I became really interested in using machine learning (ML) for creative pursuits like music and graphics generation. I built an algorithm that tried to identify the in-between frames of animation, so if you gave it some reference frames, it would draw in the rest. I shared it at a Google Meetup and someone mentioned a use case in the construction industry, feeding blueprints into an algorithm to automatically estimate the cost of the project. It’s hard to monetise creative AI, so I decided to fill this need instead. I became a one-man team and started collecting clients for this b2b construction object recognition software. But I just wasn’t passionate enough about it for the long haul.

During this, a friend at ByteDance — who had previously sat next to me at Mobike — mentioned a position at TikTok, and I realised I could go back to creative AI without having to monetise it myself. TikTok is one of the few companies where the core business is ML applied to the arts. So I joined this awesome job as fast as possible, and that’s where I currently work as a Product Lead. And I’m hiring now!

At first, I learned product craft by reading a lot of PM books. I became very well-versed in what people say a PM does, and the books tell you how to identify user needs and measure success, which are obviously important. But what you don’t get from these is how much you need to be able to talk to people, read them, and understand what they mean.

Being a PM is like being an API for people.

Machines have discrete protocols for what information to send and receive, and they do it at the speed of light. Humans don’t generally get that — they’re machines with different data models. They don’t know the APIs, so they just bash things at each other and some things get through and others don’t. As a PM, you have to learn the APIs, extract the information that you need, and send it back out to other humans over their own APIs so it’s useful for them.

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