Hacking Your Product Management Career

A few years ago, I watched an Olympic gymnast deliver a speech, “How to Score a Perfect Ten,” as he performed on a pommel horse. He vaulted onto the horse, did a series of moves, then said, “I get 9.4 points for getting on the horse and executing the required skills.” Then, he launched into a fearless series of 360 flips and 720 spins, suspended himself for a moment, and said, “I get another three-tenths of a point for embracing creativity and risk.” For his last maneuver, he pressed himself into a full fingertip handstand, stretched his legs and toes towards the ceiling, then concluded, “And, I get those last three-tenths of a point for extension.”

I thought this was an amazing metaphor for performing the Product Manager job at a world-class level. Below, I:

  • list the technical and functional leadership skills required to do the PM job
  • encourage risk and creativity in navigating your career through “career hacking,” then
  • describe how I built a “personal board of directors” to get full extension in my career.
That’s me, giving my “Hacking Your PM Career” talk at Omidyar Network (Filip Kaliszan photo)

DO THE JOB: The Required Skills for a PM

As the SVP of The Learning Company/Mattel, the VP of Product Management at Netflix, and the Chief Product Officer at Chegg (a homework help/textbook rental company), I have hired, managed, and developed hundreds of product managers. The job is hard: at the highest level I define the role as the ability to delight customers in hard-to-copy, margin-enhancing ways. In evaluating candidates, I focus on two separate sets of skills: the technical skills required of all product managers, and the functional leadership skills required as product managers grow into VP-level roles.

The technical skills of a product manager

Look at the list below, then force rank your skills, from “superpower” to “mere mortal”:

  • Technical: Strong understanding of technology; work well with engineers
  • Management: Light process to deliver results
  • Creative: Generate ideas that matter
  • Business: Understand how to deliver shareholder value
  • Marketing: Package & position ideas to appeal to customers
  • Design: Work well with designers; value simplicity
  • Consumer science: Deliver consumer insight via focus groups, usability, surveys, behavioral data, and most important, AB-testing

In interviews, I ask for examples of how a PM demonstrates their top two skills to establish the credibility of their claims. While I largely focus on their superpowers — how they can fundamentally differentiate themselves — I do a little work to ensure they have all the basic skills required, especially in the consumer science area.

The second list, below, outlines the functional leadership skills — those skills required to develop into a VP Product role. Again, I ask candidates to force rank the skills.

Functional leadership skills

  • Leadership: Inspired communication of a vision
  • Management: Hiring, firing, managing, and developing teams & organizations
  • Strategic thinking: Developing hypotheses for how to delight customers in hard-to-copy, margin-enhancing ways
  • Results-oriented: Proactive, “everybody grab a shovel” attitude to make things happen.
  • Culture: Understand how to leverage culture as the foundation for light process & to build world class organizations
  • Business maturity: Great judgement about people, product and business
  • Domain expertise: Experience with product category and/or stage of company.

As before, I ask candidates to give examples to verify their top two superpowers. One important note: With “culture”, there are two questions embedded in the attribute: 1.) “Do you have experience shaping culture to enable great decision-making without process?” and, 2.) “Are you a good fit for the company, given its unique culture?”

If the list of skills looks daunting, there’s good news: you don’t have to learn all of them overnight. They develop naturally, over time.

The Career of a Builder

Most product managers love building stuff. I’ll ask a candidate what they did over the weekend, and they’ll answer, “I hosted a dinner party for twelve,” or “I used my short-wave radio to talk to someone in Vietnam.” These are good examples of creative pursuits from people who love to build stuff.

There’s a natural progression in a product leader’s career, starting with “build something” and culminating with “build an industry.” Below, I outline the steps, along with the skills needed at each stage:

  • Build something: Basic design and management
  • Build a hit: Marketing and consumer insight
  • Build an org: Leadership, strategy, developing teams, and culture
  • Build a company: Cross-functional leadership, company strategy
  • Build an industry: Long-term strategy and partnerships

Looking at the list above, think about your career stage and examples you'd give to demonstrate mastery at that stage.

Here are examples from my career:

  • Build something: The first software I built was “Sesame Street: Counting Café” for Sega Genesis. It sold a dismal 400 units. But I learned how to design a game and to work with both engineers and designers to build software.
  • Build a “hit”: My first hit was “Sesame Street: Elmo’s Preschool,” which was a top-selling software title in the mid-90’s. I learned how to package and position a software title — a full preschool curriculum on one CD-ROM. I also kid-tested religiously to create a simple design that worked for three year-olds.
  • Build an organization: I did this first at “Creative Wonders,” my first educational software startup. I had built a successful line of Sesame Street software and now had the opportunity to build more titles based on the Madeline, Schoolhouse Rock, and Arthur brands. I learned to give up hands-on control, to build a team, and to embrace strategy to keep the product organization focused and aligned. And based on lessons from my early days at Electronic Arts, I began to understand the power of culture to help employees make great decisions without process.
  • Build a company: I had a hand in building Creative Wonders, The Learning Company, Netflix and Chegg. As you reach this level — typically a “VP Product” role — you now participate in the definition of the overall company strategy and work closely with other functions (marketing, finance, etc.) to ensure strong cross-functional leadership.
  • Build an industry: The launch of streaming at Netflix jumpstarted today’s Internet TV industry. This stage of my career required working with partners (set-top boxes, game consoles, and HW manufacturers) as well as dedication to the long-term strategy of building a virtuous cycle that steadily built subscribers, hardware partners, and a vast library of movie and TV content.

Another benefit of this “career as builder” model: It can help you to identify which skills you need to develop at each stage, especially if you find yourself “stuck” at one level.


The previous list of skills and stages makes career advancement seem linear. It’s not. In looking at the data for how folks advance to CEO, for instance, LinkedIn concluded that the fastest path to CEO is a winding one. This makes sense: the winding path allows you to develop the skills you need to ensure cross-functional leadership and to manage folks in multiple functions.

My career was a winding path. I ran a startup sailing school during a year-off from college, graduated as an English major, then joined the mailroom at an ad agency, McCann-Erickson, in SF. I eventually advanced to account services (think “Mad Men”), left to join a design firm, then slowly developed into a marketing leader. After graduating from business school, I joined Electronic Arts as a marketer, then switched to product. Over the next twenty years, I enjoyed alternating success and failure, helping to scale both education and entertainment startups as product leader.

Framing Your Career Hypotheses

As product leaders, we’re used to executing lots of experiments to determine what’s best. We form hypotheses, test them, then form new hypotheses based on results. Looking back, I wish I had taken a more hypothesis-driven approach in navigating my career. The high level questions or hypotheses would have looked something like this:

  • Marketing Leader v. Product Leader?
  • Starter (from scratch) v. Builder (help startup with a proof-of-concept to scale)?
  • Education v. Entertainment?
  • Product Leader v. CEO?

Without being conscious about it at the time, I did test these hypotheses via side projects, by talking with folks in roles I aspired to, or simply through learning by doing. I joined Electronic Arts as marketer then moved into product a few years later and loved the role. And as much as I thought of myself as a “starter,” I concluded I was better at helping established startups to scale — I’m a “builder.” As for the entertainment v. education hypothesis, the answer is both — I bounce back and forth between the two industries.

The Right Metric?

If you embrace “career hacking,” which metrics should you measure to evaluate your career hypotheses? Let’s start with income as a proxy metric. Below, I show income over time, starting with the J World Sailing School, and ending with my current role as an adviser, teacher and part-time product leader:

My income, from beginning of career, to now.

The two periods with no income correspond to business school and my two-year sabbatical, after we sold “FamilyWonder” to Sega of Japan.

Another potential metric: A notion of job satisfaction. In talking with folks about their careers, one of the first questions I ask is, “On a 0–10 scale, where zero sucks and ten is awesome, what is your current job satisfaction?” Here’s a graph of my satisfaction, over time:

My job satisfaction, where ten is high, and zero is low.

My job sat number bounces around a bit, and is often the inverse of income. Self-analysis: My experience at Netflix scored a nine for a long time, but then began to slide below seven. The reality was that as much as I was the right person to help a startup to scale, I didn’t have the right skills to advance the company to the next level. And, in the case of Chegg, I was delighted to help the company scale, to help take it public, but eventually felt bogged down by the slow rate of change in the education industry.

Another potential metric: the extent to which your work is “good for the world.” Below is my self-evaluation:

My self-evaluation of positive contribution to the world, where ten is high and zero is low.

You can see the upward trend during my educational software years and the lower self-rating during my entertainment tenure (EA, Netflix). Also, note the high rating during my sabbatical — I spent a lot of time with my two young daughters, worked at their school, and engaged in other community projects. And today, I have the highest self-rating for “good for the world,” embracing my role as teacher and mentor.

“Make it an 8”

So, what’s the right metric? In the moment, I find the most helpful metric is job satisfaction. If it’s an 8 or above, all good. If it’s below an 8, I try to figure out ways to change the job or to develop the skills that will make me a better fit for the role. But if six months go by, and my satisfaction is still below an 8, I start looking for my next opportunity.

There are a few things that helped me to navigate the long and winding road of my career:

  • I’ve gotten good at job-hunting. I’ve begun a new gig every 3–5 years, so I have lots of practice. In some cases my startup ran out of funding, we sold the company, or I was laid-off or fired — it happens to everyone. But each time I looked for something new, I found the process easier, which also emboldened me to leave jobs when my satisfaction fell below 8 for more than six months.
  • I’m good at learning new stuff. I am not embarrassed by sucking at new things and that has helped me to embrace a “beginner’s mind,” especially as I made big career transitions. Reflecting on my past, I think my job satisfaction begins to dip when my rate of learning slows.
  • I’ve been well-supported by a “board of directors” that includes both peers and mentors. These high judgment individuals substantially improved my odds for success when evaluating new opportunities.

The main advice I would give to my “younger self?” Be bold. I could have been more aggressive about pursuing my passions earlier, experimented more quickly with new ideas via side projects, and generally, been braver about taking on new opportunities sooner as my job satisfaction fell.

My last two years of “Career Hacking”

Since 2015, I think I have done a fairly good job of following my own advice. After Chegg went public, I concluded that I didn’t want to take on another product leader role — I had a strong “been there, done that” feeling about the product leader role. And, based on advice from my board of directors, I concluded I was poorly suited to take the obvious next step in my career: I rejected the notion of becoming a CEO.

I could afford to stop working, but I knew that in stepping away from a full-time role, I would still need to fulfill both my sense of purpose and social needs — two things that traditional careers satisfy. Last, I needed enough structure in my life that I would not “bounce off the walls.”

My “career” hypotheses were that I would enjoy a career as:

  • Adviser/mentor
  • Teacher
  • VC/Angel investor, or
  • Part-time product leader

I spent lots of time talking to folks in roles on the list above. But in the end, most of my learning was by doing— I tried a bunch of things to see what worked. The result is a very non-traditional combination:

  • I engage in three day/week “EIR Product” roles at fast-growing startups to keep my skills sharp, to provide structure in my life, and to fulfill my social needs.
  • I work as a product adviser at six startups, hacking with different techniques to help product leaders grow both their careers and startups, and
  • I give 5–10 product leadership talks/month. These talks convinced both Stanford and Dartmouth (Tuck) that I was serious about teaching, and I now teach at both schools. I enjoy this creative outlet immensely.
  • As for the VC/Angel route, I realized that the learning cycle was far too long for me — I wouldn’t know if I were good at it for 5–10 years. I also felt investing would not fulfill my social needs: most investors looked like “lone wolves” to me.

Today, my job satisfaction bounces between 9 and 10. Hacking my way into a fairly non-traditional career feels rewarding.


Hacking your career requires a series of relatively quick decisions to determine “best fit” for you. You need to be self-aware about your skills and what fulfills you, plus you need the ability to evaluate different roles and industries. Given that no one possesses complete self-awareness and that it’s difficult to develop expertise in multiple industries, it‘s a bad idea to go it alone. This is why I developed my own “personal board of directors.”

I wasn’t conscious of the notion of a board of directors until I fought my way back onto the playing field after my two-year sabbatical. But at this point, I set up two conversations/day with past colleagues, role models that inspired me, entrepreneurs, VCs, recruiters, and people whose judgement I valued, in order to figure out “what’s next?” In the end, there were 5–10 people I consistently kept in touch with to help identify a meaningful career path. You can think of these folks as my board of directors.

Here are a few examples of how my board helped me over the years:

  • I understood that I needed a strong sense of purpose and enough structure in my life not to “drive my family crazy” via conversations with Joel Jewitt, an Amherst College alumni who graduated a few years ahead of me. I met Joel during my sabbatical and he shared the story of his “retirement” at age 40. He detailed the “intervention” that his young kids and wife staged for him — begging him to go back to work — and this story had a lasting impact on me.
  • Irv Grossbeck is the “dollar a year” professor of entrepreneurship at Stanford who invented the cable TV industry and graduated from Amherst College thirty years before me. During one conversation, he looked at me and said, “Gib, can I be honest with you?” After a hesitant “yes” from me, he continued, “You seem too nice to be a startup CEO.” The feedback resonated with me, and in a single moment, Grossbeck released me from the notion that I had to be CEO before my career ended.
  • In my last few years of career hacking, it took me a bit to get going. I took a long walk with Patty McCord (she ran HR at Netflix) and I said to her, “I am having a hard time finding non-traditional roles.” Her reply, “Just tell them what you want.” Shortly after that conversation, when recruiters called, I responded, “I’m willing to take on a product leader role, but only for three days a week.” It felt audacious, but it worked.

Establishing Your Board

I have maintained a personal board of directors for fifteen years. Here’s what I have learned:

  • Invest in good times. It sucks when you only reach out to people when you need their help. Do it persistently and consistently — in good times and bad.
  • Encourage candor. Your board’s job is to help you to see your blind spots and to give you realistic insight about what may be good vectors for you. Sometimes they need to be brutally honest with you — accept their feedback.
  • Listen carefully. I can still play back dozens of career conversations that fundamentally impacted my career. Your board is there for you— listen.
  • Refresh/upgrade often. Navigating your career requires different skills at different stages. Your peers and mentors will “age out” and you’ll need new board members to navigate the ever-evolving landscape of a hi-tech career.
  • Seek diversity in both thought and experience. This helps cover your “blind spots.”

My board of director includes both peers and mentors. Here’s what I have learned in recruiting both:


  • Reach out to peers for mutual support. They navigate issues similar to you and help you to avoid the same mistakes they have made, and vice-versa.
  • Seek peers in similar functions, stages, and companies. This improves the odds that they will deliver timely, relevant insight.
  • Keep in touch with past colleagues. Make an ongoing effort to stay in touch as you switch from one company to another. This is my richest source of board members.


This is what I look for as I add mentors to my board:

  • Extraordinary judgement. These individuals have demonstrated phenomenal decision-making through ongoing, high-level career success at world-class companies.
  • Broad skills & network. I have VCs and CFOs in my network, for instance, because I have found them to be extraordinarily helpful in evaluating the likelihood of financial success for startups.
  • They are trustworthy. Over time, as personal chemistry develops with mentors, I share my secrets with them, and vice-versa. They need to hear these secrets in order to be truly helpful.
  • They are both candid and caring. Like Irv Grossbeck, my mentors share critical feedback with me because they care about me and my long-term career success. But candor without caring, or vice-versa, isn’t sufficient. You need both.

Finding and developing mentor relationships

The most common question I get about building a board is, “How do I connect with mentors?” Here’s what I’ve learned:

  • Don’t ask them to be your mentor. You need to nurture the relationship until at some point, they simply become one.
  • You don’t get what you don’t ask for. Dare to reach out to people who inspire you via LinkedIn and other resources. One out of ten times, you’ll get a “yes.”
  • Strengthen weak links. Mentors can be school alumni, folks who share your interests, or leaders from past companies. Over time, figure out ways to get to know them better to develop a more meaningful connection.
  • Figure out how you can help them. I have had mentors who wanted to better understand companies that I have worked for, or were interested in very specific domain expertise that I have. In the last few years, some have needed help finding jobs for their kids.
  • Be both clear and realistic about what you seek. I have targeted professional speakers, asking them how they got gigs with 5,000-person audiences, or asked VCs to share their list of current investment theses. Don’t bother with vague questions like, “Know any good jobs for me in SF?”
  • Do your research. If a person has written a book, read it. If they’ve produced podcasts, listen to them. This provides opportunities for you to give them feedback — a simple way to begin a mutually beneficial relationship.
  • Be both patient and persistent. The people you seek as mentors are busy. Keep your emails crisp and if you get a response, follow up quickly.
  • Know and adhere to business conventions. Understand the mechanics of the two-sided intro, for instance, so you can demonstrate both your discipline and knowledge. Don’t ask for a job in an “informational interview” (but do ask for the names of 2–3 people who may be helpful to you as you extend your network).

In the long-run, I don’t find much difference in how you develop and maintain peer or mentor relationships — the lines begin to blur. In both cases, manage these relationships with updates, notes on topics your board may be interested in, and extend an invite for coffee the next time you are in the same town.


As an aspiring world-class product manager, here are your go-do’s:

  • Do the job: Develop your PM skills. Assess both your technical skills as a product manager, as well as the functional leaderships skills required to grow into a VP role. Stay focused on your superpowers to clearly position yourself for best fit roles, but occasionally “shore up” key weaknesses that blatantly stand in the way of success.
  • Embrace creativity and risk: Hack your career. Outline the key hypotheses in your career, and find ways to test them, either through your day job, side projects, or informational interviews with folks who enjoy roles that interest you. Let “job satisfaction” be your one true metric, and consistently work to “Make it an 8.
  • Extend your career: Build your personal board of directors. Given that there is no such thing as “one size fits all” for careers, build a board that can provide meaningful insight, based on knowledge of you and their perspective on different functions, career stages, and industries.

I will leave you with one final thought — what I call the “2 a.m.” test:

What projects do you find yourself engaged in at two in the morning? Put another way, is there something you are so passionate about in your work life that you can’t not do it? The answer can provide a career hypothesis to explore and test.

During my second year of business school, I built prototypes for kids educational games late at night. Two years ago, at two in the morning, I found myself creating new product leadership talks. In the first instance, this “2 a.m. test” was a substantial clue for my career hypothesis that I’d like to build children’s educational games. In the last two years of my career, this test framed the hypothesis that I’d like to teach.

The cool thing about the “2 a.m.” test is that if you are truly passionate about the idea — you can’t not do it — your passion for the idea will drive both the necessary intellectual curiosity to explore the opportunity, as well as the determination to see it through. These are two critical attributes all companies seek when hiring product leaders.

What comes to mind when you think about this “2 a.m. test?” How might you begin to test hypotheses formed by this seed of an idea via side projects, informational interviews, or by diving into a new job in this area? Be bold.

Please “clap” to make it easier for others to find this essay. I’d also love it if you could give me feedback on the essay by clicking here. (It takes you to SurveyMonkey and only takes one minute.)

If you’d like to learn more about career hacking you can watch a one-hour presentation by me on the topic here.

Thanks for reading this 2 a.m. missive and many thanks to Flori Fischetti, Shaun Young, and Dan Balcauski for their editing help.


Gibson Biddle

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