The journey from Product Manager to Investor. An interview with Kevin Lee, Investor at Pear Ventures and Founder at Product Manager HQ

Sofia: Kevin, you have a very interesting story. Could you tell us how you got into product management and how you ended up working at Pear Ventures?

Kevin: After graduating from UC Berkeley, I spent a little under a year in investment banking. It was a technology investment banking group based in Palo Alto. We worked primarily with large private and public technology companies, advising them on capital raises, debt financings, IPOs, M&A, amongst other things. After working there for awhile, I realized I wanted something a lot more hands on in terms of building actual products. At the time, I happened to be living with an associate product manager at Google. He was the one who opened my eyes to the profession. Since my investment bank blocked all forms of social media, the only website I could access was Quora, which happened to have a lot of questions and answers around the topic of product management. That really led me down the rabbit hole of obsessive research around the field.

I ended up quitting my banking job and looking for a product manager role in an industry that I would enjoy working in. I had grown up playing computer games and managed to land a role as a product manager at this mobile gaming company called Kabam, which was just starting to take off amidst the whole social gaming boom with Zynga. Kabam had ties to Hollywood so their investors were people like Warner Bros, amongst other traditional institutional venture capital firms. Kabam built web and mobile games for a lot of popular movie industry titles. For example, they had games for The Hobbit, The Godfather, and The Fast and The Furious.

When I joined, they were in the post Series B hyper growth phase and there were so many opportunities to work on amazing games in the U.S, Vancouver, and Beijing. It was really my bootcamp and rocket ship experience as a product manager. I had a chance to lead teams across the world and got to ship very quickly. If you know mobile gaming, it’s a very quantitative PM role. You’re dealing with millions of rows of data and hundreds of split tests. You have so much data to play with so it’s a very interesting experience.

Fortunately, I had a chance to work on different products across different life cycles, from: products in testing to products that were already making millions of dollars. With established products, we were just trying to optimize, split test and improve the funnel and the metrics. I also had the opportunity to live in Beijing and help start a new product from scratch that ended up growing to become the 3rd largest revenue generating product in the portfolio.

Kabam eventually got acquired for over a billion dollars and, at the time, I really wanted to work in education, which has always been near and dear to my heart. I used to teach in high school and college. I was also on the board of a charter school here in San Francisco, as well as on the board of education for a nonprofit. I had long known that for my next role, I’d want to try to work as a PM at an education tech company.

I went to another startup called AltSchool, which is a tech company that builds software and hardware for education. It also built physical schools which meant they could quickly test their products very rapidly

AltSchool was a great experience to learn how to deal with the complete opposite end of the spectrum where you have none to little quantitative data whatsoever. We probably only had about 200 students in the schools so the products we were shipping were very much based on heavy user research, gut instinct, and a lot of qualitative data.

After being exposed to both quantitative and qualitative product management experiences in vastly different companies, I started to wonder why I wasn’t 100% fulfilled as a product manager.

I think one of the reasons was that, although you get exposure to your users and interact with a lot of cross-functional teams, it’s not necessarily a role where you’re meeting individuals face to face all day long (apart from your cross-functional teams). I’m a total extrovert. I get energized just from talking to people and getting to know them.

Venture capital was an industry that gave me the opportunity to share my product advice and learn from some of the smartest people in the world. Founders are people who are extremely passionate about the industry or the vertical that they are tackling.

These people are so obsessed that they spend 24/7 thinking about how to solve the problems they’re focused on. I’m so privileged to be able to learn from them and try to help in any way that I can.

When I was a product manager, I had always spent a lot of time going to meetups, trying to meet other product managers and learn from them. Building my network as a PM had always come naturally to me but it’s not necessarily helpful as a PM to have a large network since that’s not going to help your product succeed in the market.

Meanwhile, venture capital is an industry that actually rewards you for your network.

In venture capital, you’re often out looking for the best founders to work with, and a lot of your ability to find these companies comes from your network.

Apart from investing in new companies, you’re also constantly thinking about how to help your existing portfolio companies as much as possible. Your network will help you when you’re helping portfolio companies hire the best talent or when you’re helping get customer introductions for them.

Sofia: Can you talk about your transition into venture capital?

The first venture firm that I joined was called FundersClub. It was an interesting hybrid of venture capital firm and startup. It was a venture capital firm that had gone through Y Combinator and was trying to be a full stack kind of VC firm. If you look at venture firms today, a lot of them haven’t really evolved. A lot of them are still very people-driven and don’t necessarily use a lot of software. FundersClub had an engineering team, a product manager, a designer, and a venture team. We were trying to build software to improve ourselves as a venture capital firm.

I spent 80–90% of my time on the venture side, finding companies, investing in them and working with them but I also got to use a little bit of my PM experience because, if you think about it, venture capital is a product. I was thinking about how we improve our product for our users, which were founders.

A year into that, I was really itching to work with earlier stage founders. At FundersClub, the stage that we invested in was seed and Series A, so quite late. Nowadays, seed is what Series A used to be. If you’re a seed stage founder today, you’re almost expected to have a launched product with early traction and signs of product market fit. That’s what Series A used to be so everything has kind of shifted.

When I was at FundersClub, I met founders who were still iterating on the product and they didn’t have any customers. Sometimes, you’d really believe in those types of people and you’d want to invest but that just wasn’t our stage of focus. Incidentally, Pear Ventures’ founding partner, Pejman Nozad, was actually an early stage angel investor in FundersClub. I had gotten to know one of the third partners at Pear as well so when they were looking for another member for their investment team, I transitioned over. It’s been an amazing experience to be able work with very early stage, pre-seed founders.

At Pear we do pre-seed and seed stage investing. When we invest, it’s one or two exceptional founders. They’re super focused on just building a product that a few users may love. This is where I love spending my time, with these types of founders. They’re just founders in a garage or in one room, sleeping on their mattresses.

Sofia: How does your background in product management help you become a better investor?

Kevin: Because of the stage that we’re investing in, a lot of our founders don’t have any signs of product market fit (or even a product). At the early stages, they know what type of problem they want to tackle, but they don’t necessarily know what the solution is nor if the market will accept that solution.

I think a lot of the frameworks and skill sets we learn in product management are things that bring value to founders across companies. Skills like conducting proper user research, user interviews, prioritization, roadmap planning, product development processes, data analysis, etc… At the early stages of a company’s life cycle, founders are bootstrapping a product with very limited resources and cash runway. My goal is to bring in knowledge from product management to help these founders prioritize, ship, iterate quickly and hopefully build the right product that will resonate with users / customers.

When I start working with a portfolio company at the pre-seed stage, I sit down with them and try to understand how they think about building product. How do you discover the right problem to solve? What’s your prioritization process? How do you spec out new features for your engineering team now? How do you plan out your longer term product roadmap? How are you currently analyzing your cohort data to help determine what to build next? Asking these types of questions helps put a structure around the way these founders think about shipping the right products, which creates cascading, compounding effects down the line.

Sofia: How did Product Manager HQ come to be?

Kevin: Product Manager HQ is an education media company that I bootstrapped over 4 years to help provide career education for people who are looking to break into product management.

4–5 years ago, when I was obsessively scouring the internet for resources on getting into a product management role, there wasn’t any centralized resource. A lot of my learning then came from conversations with existing PMs or from random answers from individuals on Quora. Now there are a lot more PM resources, including EnjoyHQ’s blog, which is full of insights that didn’t use to exist.

After I broke into my first PM role, I decided to give back to the amazing Quorans who gave me so much advice when I was doing my own job search. I started writing for the product management topic, and over time people on Quora and LinkedIn began to cold message or email me to ask if I could meet for coffee and give them advice on breaking into product management.

At first, I took as many local coffee meetings as I could, but over time, the requests became overwhelming and I realized there weren’t enough hours in the day for me to be able to help everyone. To alleviate this issue, I bought the domain for Product Manager HQ, installed the first decent looking WordPress theme I could find, cobbled together a terrible looking logo (which has since been re-designed), and started writing articles summarizing the most common topics that kept coming up during these coffee meetings.

I started out with really basic articles about interviewing and that evolved into a weekly newsletter with curated content for product managers. Eventually, it became a community and that’s what it is today.

To date, Product Manager HQ has helped thousands of people break into or significantly improve their chances of breaking into product management and has been featured in many publications including Forbes and Huffington Post.

Sofia: Do you remember what it was like getting your first PM job? You mentioned you had a roommate who introduced you to it, but how did you actually get your first job?

Kevin: I really push the idea of the ‘T-shaped product manager’. Generally most new PMs learn a lot of the fundamental product manager skills — product planning, execution, post-launch analysis. When you couple that with the vertical part of the T, such as industry or domain expertise, that can really give you a significant edge as a PM.

My vertical part of that T, when I started out, was that I grew up playing games and enjoyed talking to folks working in the gaming industry so I already knew a lot about the gaming space and how people built products in gaming companies. When you couple that with the base knowledge around product management I had been developing, gaming companies like Kabam were willing to take a chance on me despite me not having any PM experience.

My advice to anyone trying to break into the industry is to leverage your personal interests and use that to your advantage. If you really care about healthcare, go build a reputation in the industry as a healthcare expert. Interview health care professionals and organize meetups. Couple that with a little bit of knowledge on fundamental PM skill sets and you’ll have a huge advantage in the interview process.

This is exactly what I did when I was trying to break into education tech. I had no prior education tech PM work experience. While I was still at Kabam, I spent a whole year on nights and weekends hosting education events. I would go to education meetups and meet all these different stakeholders. I would talk to teachers. I would talk to superintendents. I would talk to education investors. I hosted an event called Startup Weekend Education where I got 300 people to spend a whole weekend building education companies and brought in education judges like the CTO of Oakland Unified School District.

I also joined the board of a charter school in San Francisco because I love working with students and I wanted to really develop empathy with various types of stakeholders in the education industry. When I then started going to interviews, a lot of these ed tech firms were really impressed by my passion for the space and were willing to overlook my lack of ed tech PM experience.

Sofia: Kevin, what would be your advice to PMs who want to take their careers to the next level, perhaps moving into leadership roles?

Kevin: One thing I don’t see enough PMs doing is leveraging mentors within their company or outside of their company. When I was at Kabam as an associate product manager, I immediately started looking for relevant meetups and communities. It’s actually one of the reasons why I started the Product Manager HQ community.

If you look at some of the most established companies out there, like Google, Amazon and Facebook, they have very structured PM programs that they’ve developed and refined over many years. When you join one of those companies, you basically go through a regimented program that teaches you skill sets that progresses you through different PM levels.

Not a lot of other companies in this world have that, so how do you give yourself that advantage? You have to surround yourself with the best to become the best.

When I started this community, I wanted PMs from different types of companies to share best practices and knowledge with other PMs from smaller companies that don’t have those kinds of resources. You need to find a mentor, inside or outside your organization, who is a lot more senior than you, someone you really respect who can guide you in the right direction.

You’d be surprised at how much you can learn from cross pollinating with different industries. Just because you’re a PM on a SaaS product doesn’t mean you can’t find an external mentor who’s a VP of Product at a consumer company. The things you can learn from them are probably relevant to you. These days, if you’re an enterprise SaaS company, trying to do a bottoms-up model like Slack, you need to get into the hands of employees who then push your product to the top because that’s where you’ll sell your enterprise plan. A lot of the growth tactics used by consumer companies are therefore relevant to B2B companies today.

As a PM you also don’t have a quick feedback loop so how do you know that you’re doing well in your role? One way you can find out is if you talk to fellow PMs about the situations you are in and collectively discuss how to handle these situations.

Another tactical tip I would recommend is to create a personal roadmap for yourself. Say you’re a level two PM — you should talk to your manager and ask what skill level they’re expecting from a level two and what you need to do to get to the next level.

Then, every quarter or so, map out each of the skill sets under what it takes to be a level two or a level three PM and note down what you did in that period that you think fulfilled those particular things. Also note down what you could improve on.

Then rate yourself on each skill set and ask your manager to rate you so you can compare. Do this every quarter and eventually you’ll have built a mini roadmap for yourself that can show that you’re improving over time. We’re so used to creating roadmaps for our products but we don’t create them for ourselves. We should. Showing your progress is what’s going to get you that promotion.

You can follow Kevin on Twitter here and join Product Manager HQ here