👩🏽‍🏭 How to become a Product CEO

Why humility, speed and user insight are all you need to be a great Product CEO.

There are many ways to find yourself sitting with the title “CEO” - maybe you’re an engineer that now steers the ship. Maybe you come from finance or strategy.

I come from none of those. Or not directly anyways. For me it’s always been about the users - the moments of friction they experience and the products and experiences that erase them.

So the closest thing I can say is that I’m a “Product” CEO.

Only, I’ve never actually held a product role. The closest thing was probably all my years as a brand manager - steeping myself in the users’ worlds and then working with everyone from supply chain to finance to regulatory to bring it to market.

Still. After 5 years of building software, I’d say product is a unique role, with unique skillsets working with engineers and designers to create digital products that consumers will love.

For the first couple of years of building Poppy it stressed me out. I even remember one of my office hours with Michael Seibel when I pleaded with him to tell me: “How do I become a better product CEO?” and in classic Michael fashion he answered, “You do the work.” The response earned him an exasperated eye roll from me but over time I realized he was right.

Over the years, I’ll get asked the question:

How do I be a Product CEO?

I have no idea. To be honest, I don’t even know if I am, or if a “real” product CEO would call me a sham.

All I know is the the problem and the user are my religion. My north star. I don’t care a lot about what the right process should be, just that we get there.

In time, that view built up a unique but rapid building and shipping process at Poppy. New team members or outsiders would remark on how fast we built and shipped new features and products that kept users delighted. And eventually, I settled into a role I fell completely in love with.

Now, as I’m hip deep in building a vast and nuanced product, I’d say there are 3 things that I think have been key to getting better at being a Product CEO.

1. Observe and ask questions. If there’s one thing I’d say that is the key to any of my success it’s that I’m never too embarrassed to ask the dumb or the basic question. And, I’ve made it a point to hire people who are wicked smart but are also incredible teachers (it’s the sleeper value that I look for in every hire). I can’t count how many questions I’ve peppered our engineers with - because that’s always been the one function that always felt like a black box to me. So each week, during sprint plan, I’d ask them to explain why they thought a certain feature was a 13 in points vs. a 5. What made it so it added days in development. In time, this built up my intuition so that I could guesstimate how complex a given feature would be or I could think through ways to circumvent scope creep or define the requirements differently. But it started with listening and asking the questions, no matter how basic, and having the team that could teach. Even learning how to code last summer was less about becoming a functional engineer and more about becoming a better partner to build with.

2. Make it work, make it fast, make it pretty. Because I wasn’t an expert when I set out to build software, I knew I couldn’t have long development cycles. Instead, shipping quickly and consistently would be my saving grace. Because then, if my nascent judgement had led us astray, we had only invested a week’s sprint. And in time, this drumbeat of one-week sprints not only helped hone my instincts with more feedback cycles, it became a source of delight for our users who weren’t used to features being shipped so quickly.

So now, we hold to one-week sprints and keep the mantra “make it work, make it fast, make it pretty” front and center. In one week, you’ll likely be able to build a thing that “works”. Only if and when users show that they’re valuing it (by way of your core metric growing), we then put it back in in a future sprint to make it fast and make it pretty. It’s easy to think that product is about pretty. It’s not. Optimizations can come once value has been proven.

3. Never forget that product is really about the flows. The last main lesson I’ve learned is to pay attention to the white space in between the “solid” of the screens. Meaning that it’s so easy to obsess about the buttons and modals the users will be interacting with that you completely underestimate the complexity of everything that connects them. A huge part of having a product that users can’t live without is understanding how each moment connects to the next. From finding out about the product to signing up to doing the thing. Imagine where your user is - what time is it? What distractions are around them? For our current product, this means understanding that parents mostly have time for home things after the kids are in bed around 9pm. They’re wiped and just want to watch Netflix. So how does the product live and flow in this flow? Where are you making it harder for them to do what they want because it’s more “rational”? Forget rational, embrace real.

In the end, being a CEO is about managing resources, setting the vision and strategy and hiring the very best team. But for many of us, this also means figuring out the right product, especially in the early days. Don’t make the mistake of outsourcing this work just because you’ve never done it before or think you can’t.

It’s hard. You’ll feel impossibly bad at it. But by employing speed, humility and user insight, you’ll quickly find yourself building with the best of them.