This month on Medium: Jessica Ratcliffe

Each month, we profile an awesome PM writer on Medium. Our first subject: Big Health’s Jessica Ratcliffe, whose “Coffee with…” series spotlights leading women in the field.

Jessica Ratcliffe’s Medium posts tap into San Francisco’s amazing community of product managers…and caffeine lovers. Each week, Jessica grabs coffee with an awesome woman working in product management, then writes up their chat on Medium. Although her Coffee with… series is only a few months old, it’s already featured interviews with some of the most inspiring women in product, from Slack’s Merci Grace to Tumblr’s Bo Ren to Asana’s Jackie Bavaro to Medium’s Cara Meverden.

Jessica herself has a fascinating product management story: she first got the idea for GaBoom, a peer-to-peer video game trading platform, when she was only 15, and officially launched her first business (and product) at 19. Originally from the U.K., Jessica now works at Big Health as a product manager on their sleep-improvement app Sleepio. We talked about puzzles, coffee dates, and her own favorite Medium writers.

What do you love about being a product manager?

Product management is like a massive puzzle. One after the other, you’re just finding solutions. And that applies both to something that’s working well—it’s like, “How do we optimize it?”—as well as to something that isn’t working so well. It’s understanding why and then finding the solution. I just love the iterative process of identifying a problem, digging into why that problem exists—what is causing it, what is driving it—coming up with what solution could fix it, trying it, and adapting and iterating as you go. Because the first thing never works.

What inspired you to start publishing on Medium?

I’ve always loved meeting people for coffee—meeting for knowledge, basically. This goes way back to starting GaBoom, having no idea at 15 how to start a business. I moved to San Francisco 18 months ago, but I actually visited a couple years prior when I was at the end of running GaBoom. Moving back out about two years later, I picked up those connections and was able to meet a bunch of new people. And so I was having these coffees and thought, “Hang on, the stuff that we talk about, it’s not just relevant to us—we’re the people that just happen to be here having coffee.” That’s kind of where it came from.

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Why did you decide to spotlight women in product management?

It really just happened. I went to girl geek dinner at Slack and heard Merci Grace speak and she was using the Women in Product Slack group as her demo tool for showing off new features within Slack. That was the first time I heard of that group. I joined, and immediately that was how I was meeting people for coffee. And so it sort of naturally progressed.

What have you learned about product management from writing on Medium?

It’s more about the people. I’ve definitely learned stuff, maybe without even realizing it, in each interview. We’ll pick up particular themes. For example, the one with Anna Marie Clifton was very non-PM-focused—it was more about positivity and resilience. And then Bo was talking about imposter syndrome and how she goes about tackling that. With Cara from Medium, that was a big one for me. She explained how she never sets milestones, developers always set milestones. Even when you’re already doing that, just hearing elese somebody say it was really helpful.

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Do you have a favorite piece that you’ve written?

The one that was a particular favorite, but not necessarily because the content was better than any of the others, was my chat with Suzie Prince. I met Suzie within a month or so of moving to San Francisco. We meet for dinner every other week or so, but it just becomes about what’s happened in between the last time that we’ve seen each other. And so it was very rare to be like, “Way back when, at the start of your career, tell me about how you did X.” This was an opportunity for us to actually have that conversation, and I was like, “Man, you’re cool.”

What do you personally look for when reading about product management?

I tend to read stuff that’s actionable. Something that is applicable no matter what company you work in, no matter what size. Whether you’re a PM that has a whole team of PMs or a single PM. Whether you work with 10 or 20 or 50 engineers—or not. Things where you can basically from that go away and start trying.

Who else should we be reading?

One that stands out for me is Julie Zhou from Facebook. I also enjoy Hunter Walk’s writing. Ellen Chisa. Bo Ren. And Jackie Bavaro, obviously.

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Read Jessica’s posts

What I’ve learnt interviewing 10 badass product managers

Although this is a roundup post, it’s also a great jumping-off point for Jessica’s series, since she outlines her top takeaways from all those coffees.

Coffee with Merci Grace

Jessica started her series on a (very!) high note: by interviewing Slack’s Group Product Manager Merci Grace.

Coffee with Bo Ren

Bo shares her thoughts on imposter sydrome, MBAs and finding “content-audience fit” when writing about product management.

You know what? Just read all of them.

Order an Americano and start browsing.

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