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What kind of framework do you use when it comes to product road mapping?

I am a big fan of starting with user personas, then identifying a clear product strategy, which then leads to your product roadmap & features.

Step 1: Personas — For Polyvore we did a survey of women 13-35, clustered/analyzed the data, and created 5 personas of female shoppers. We worked super hard to make the personas simple and easy to understand. Each was boiled down to a picture, a few stats, her key drivers & motivations, and what behaviors she would exhibit. Then we said we chose which 3 of the 5 personas we wanted to tackle because you can’t solve for everyone. Example: The Social Shopper who is 13-25 for whom style is about self-expression and sharing her knowledge with others.

Step 2: Product strategy — Given the 3 users we were targeting, we identified common pain points and needs and desires. Then we thought about how to solve them using How Might We questions. Example, “How might we make it easy for the Social Shopper to express her style in a simple way?” We’d brainstorm and usually a bunch of themes/solutions would fall out.

Step 3: Prioritize and set product roadmap — Take the output of 2, pick the buckets/themes you want to do that quarter based on bang-for-the-buck and whatever else you care about, and go, go, go.

What was the methodology that you used in the process of narrowing down your target persona from 5 to 3?

A combination of factors, including desirability of that audience, our ability to capture the audience, with with our brand/team, etc. For example, we decided not to target one of the user types who was not really very interested in fashion at all, because it would be too much work to activate her and our product was too “fashiony” vs utilitarian to suit her needs. She would rather just Google for the one thing she needed to buy every 2-3 months.

As someone who has been so successful, I’m wondering if you can share your thoughts on work/life balance. Do you believe in it? Do you have it? If so, how?

There are definitely trade-offs I’ve made personally, but overall I think the key is the philosophy of “Do a few things well”.

Pick the things that matter and focus on being great at those. Accept the things that you suck at or don’t have time for, because no one is brilliant or perfect at anything.

At Polyvore I tried really hard to make “Do a few things well” a huge part of our culture (it was our 2nd core value out of 3 core values), because not only would it result in a simpler product/business, but also because it applied to life in general and resulted in better work-life balance.

What do you think you did best when selling yourself? What advice do you have for interviewees?

Two of my strengths are 1) I work my ass off, 2) I am reasonably good at design.

If I want to wow at an interview, I would put together a presentation with product ideas for the company because it shows 1) I’m willing to go above & beyond & work hard to win them over, and 2) it showcases my design sensibilities in the quality of the slides.

Figure out what your strengths are and make sure you showcase them well in an interview.

Any thoughts on how to come up with new ideas for a given problem in product design questions?

This is not exactly new but something I found effective during brainstorms were a warmup + brainwriting. The warmup would be a silly question like “What do you wish was in your McDonalds Happy Meal?” and seeing people come up with funny things like “zero calorie fries” or “ticket to Hawaii”, just to get the creative juices flowing and to set the tone that being a bit wacky is OK.

Then for the actual brainstorm, we often did brainwriting because it generates a higher volume of ideas and doesn’t let a few extroverts dominate the entire conversation. Brainwriting is when you have sheets of paper with prompts and people have like 1 min to write down as many ideas as possible on the paper, then you pass them around the group. After that, we’d discuss in smaller groups, identify our favorites, and present back to the group.

Btw, full credit to the awesome Polyvore PM & design team — Jason Lee, Janet Cheung, Jocelyn Lin — for running these brainstorms and iterating on these methodologies. I just got to show up and was super impressed by how the volume/quality of ideas were 10x’ed by these simple techniques.

You’ve seen a lot of successes in your career. What has been your favorite failure?

Polyvore was ultimately fairly successful as a company ($200M acquisition, solid profitable business, won a bunch of Great Place to Work culture awards, helped make fashion a bit more democratic), but the entire time I felt like I was experiencing a constant deluge of epic failure. I’ve come to realize that the nauseous feeling of “oh shit I have no idea what I’m doing, I think I’m failing” is basically the feeling of learning and rising to a new challenge.

I remember feeling like a total failure while walking into the all-hands meeting where I was about to announce our acquisition. I felt like I had failed to produce a multibillion dollar outcome, that I hadn’t changed the way women view themselves through style as much as I had wanted, that my team would be super mad at me for having failed them.

Then when I announced it, I was shocked because everyone started cheering and was so excited. I started crying. I think it’s a good example of how you can really get stuck in your own psychosis sometimes.

What advice do you have for young/junior female PM’s that want to get higher up? I notice a lot of (unspoken) sexism in Silicon Valley and I am very curious how you’re dealing with it.

It’s both a burden and an honor to be part of a generation that’s moving things forward for women in tech. The most important thing is to do great work to prove your worth.

If you’re in a position to choose, don’t lend your valuable time/services to assholes or places that are institutionally misogynistic, or commit to helping to change them. And most importantly, make sure you pay it forward for the next generation.

Help the people who are on their way up, especially once you’re in a position to protect others (either as a woman who has advanced far, or as a man with a gender privilege).

What inspired you the most to transition from PM to VC ? And what recommendations would you have for people that might be interested in following a similar career path?

I decided to go into venture capital for 3 reasons:

1) I want to leverage all the painful lessons from my time as a founder to help the next generation of founders. It’s my way of giving back and having the most impact.

2) An important guiding principle for all my career decisions has been to maximize learning and to constantly challenge myself. I felt like I’d learn a ton by entering venture.

3) There aren’t that many women in VC, so I think there is an opportunity for me to change the ratio, but I also think it’s just a good business opportunity.

Women control 80% of purchasing power and make a ton of healthcare decisions, so if I have a slightly better innate understanding of that customer, that might actually give me a competitive advantage as a VC.

What advice do you have for starting a job at a new company, especially as the first PM at a startup?

Great PMs just figure out whatever needs to be done to move the product/company forward. At a larger company your role as a PM might be a bit more constrained, but the benefit of being at a startup is that you tend to have a lot more freedom & autonomy. Especially if you’re the first PM, I wouldn’t be afraid to just do whatever needs to get done.

For example, at Polyvore I was originally a PM, but I realized it would be more useful for me to write code in the early days, in order to free up the engineers to implement more features. So I built some of our dashboards and our abuse queue, which were easy enough for me to do and a lesser use of the real engineers’ time. I also washed dishes sometimes.

As we grew I just kept taking on more of whatever needed to get done, like answering the phone or emails from advertisers who wanted to get more traffic & sales from Polyvore. That turned into me doing ad sales and then hiring a real sales team (because I didn’t know what I was doing, but at least trying it for a while taught me what to look for). I then did the same for a few other groups.

And then one day I looked around and more than half of the company was reporting into me and then I ended up as CEO.

As a Product manager in more matured organization, we would need to negotiate with engineering group between “Product Feature” work and “Operational Excellence” work and like how much effort will go into these buckets. How you would advice for product manager to handle these situations? Any off the hand % resource effort which you have seen in your experience?

Sorry, it just totally depends on the company’s needs, so I can’t give you any hard numbers. But the most important thing is to get everyone on the same page about what the percentage allocation should be.

You don’t want your engineering managers to feel like they need to spend 80% of the time refactoring or replatforming, whereas you think it should be 80% building new features. Upfront agreement is the most important thing.

What is the most important skill set / trait needed to be an awesome product manager?

There are many different flavors of PMs and PM roles. You have to figure out what your strengths are, lean into them, and find a PM role that values those strengths.

For example, if you’re highly technical and are transitioning from eng, it might be a good fit for you to be an infrastructure PM. Whereas if you’re transitioning from sales to PM, it might be a better fit for you to be a monetization PM.

The one common thing that’s required across all PM roles is the ability to work with other people well. I’ve seen a ton of really technically talented or creative people who have a lot of other PM skills, but if you can’t communicate well or convince teams to follow you, it’s hard to be a top-notch PM.

Sometimes it still works because you’re so brilliant in other ways that it makes up for it, or because you are in a culture where people getting along doesn’t matter, but generally that’s quite rare.