Unfiltered: #ChooseToChallenge with Katharine Bailey

Hi folks, we are live and happy Friday. Happy Women's Empowerment Month. My name is Amada Echeverría and I'm on the Field Marketing and Events team here at Cloudflare and I'm here today with my guest, Katharine Bailey.

Katharine, thank you so much for joining us.

How are you today? I'm doing well. I'm super excited to be here, Amada.

Great, that's really great to hear. So folks, for those of you who don't know and to give more context on the theme of this show, we're very excited about this special Choose to Challenge edition that we've been running since March 8th, International Women's Day, and it's brought to you by Cloudflare's Employee Resource Group, the mission of which is to inspire and elevate all those who identify as women.

And in celebrating this month, we're hosting these episodes of Unfiltered throughout March, where we'll be chatting with inspirational women like Katharine about their insights and experiences and sharing how they forge a more equitable and inclusive world.

So Katharine, you're the General Manager of the Wall Street Journal Platforms and the Senior Vice President of Wall Street Journal Digital, and you're responsible for creating and leading a business unit around WSJ's largest off-platform membership initiatives to date in close partnership with organizations like Facebook and Google and some others.

And previous to this, you led digital product for the Wall Street Journal with a team dedicated to rethinking journalism products and experiences in order to dynamically engage the reader, so that means brand new iPhone and iPad app experiences, magazine redesign, live coverage and storytelling support, and a new curated experience for the mobile homepage.

And your team also worked with AI to optimize the digital paywall in an effort to attract new customers and retain existing ones, so this is a lot, and you spent almost 10 years in software development prior to this, which I thought was very, very interesting, and you were leading engineers in support of complex advertising processes, including rate card setup, deal maintenance, and stewardship.

And last but not least, you previously worked at NBCUniversal, SYFY Network, and IAC, and you live in Montclair with your husband Ben Selko, a documentary filmmaker, two children, and a dog.

I'm jealous, I wish I had a dog right now in the pandemic.

And so before we dive further, a quick note for our viewers, if you have any questions, feel free to submit them by emailing us at livestudio at Cloudflare.com.

You can find the banner right below this video.

So we'll get started. Catherine, what is your role at the Wall Street Journal?

So you know, in hearing you kind of talk about, it's so funny to like hear your bio, and I think one of the things that's so cool is a lot of the jobs in media didn't exist like five years ago, even three years ago, and that's probably true for the job that I have right now.

So after tech and product roles, I moved into the membership side of the business.

I really wanted to kind of really run a business from the ground up, and what's exciting is that this role really draws upon a lot of what I've done on the tech side, on the product side, and in working with big tech.

So what I do is I basically run our membership businesses that also include advertising on Apple News.

We're participators in Apple News Plus, on Facebook News, and now as recently announced as I think it was like two weeks ago on Google with Google's news product.

Great. That's an exciting new development, and that's interesting.

So when people ask you, did you always know this is what you wanted to do when you were a little girl, the answer has to be no, because it didn't exist.

So that's super exciting. Right. I had no idea. I had no idea.

Right. Everybody that thinks there's like a master plan, I'm like not so much at all, but I think you can start to get into planning over time, but I did not have a big path that I had put in front of myself in terms of my whole plan when I started in media.

That is for sure. Yeah, interesting. I think that takes a lot of humility to be able to admit that.

I know if folks want to posit they had this big plan, I always have a joke where I ask people, where do you see yourself in five minutes?

Because it's hard to plan ahead sometimes. It's like a road map. You can't do like anyone that wants a 12 to 18 month road map is insane, is what I say, because things are constantly changing.

And that's the one thing that you can probably anticipate is change.

I love that. So can you talk a little bit more about how you ended up doing this, given your resume, how's you doing many different things?

Definitely. So I always joke, and I think this dates me slightly, that I responded to an ad in literally in the newspaper when I graduated from college.

So I started off as a, I was a theater and English literature major coming out of Wesleyan and I did this a bit of a stint.

I was a dancer originally years and years ago, dancing at Alvin Ailey in the city as part of their program.

But then I ended up obviously doing theater and English led double major.

And so when I graduated, I was, I hit the pavement with my head shots. The worst kept secret though, was that I was a terrible actor, actress.

I was just horrible, horrible.

Talk about losing yourself in a role like I never did. I was always keenly aware of the audience and keenly aware of my overall embarrassment.

So I quickly realized when I graduated after doing that for a bit and working in restaurants that I really wanted to, that I wanted to do something more on the media side.

And I answered this ad in the paper that had me starting as an assistant to the head of corporate communications at the head of Corp Com at IEC that was at the time really Home Shopping Network and a few other digital businesses.

And I think there's a lot of sucking up you have to do, not sucking up to people, but more you just have to suck it up and accept that you're sort of going to have to pay your dues a little bit in the very beginning.

And I think you learn a lot when you are working for someone as their assistant.

I think it's a really good way ultimately to have your kind of eyes and ears on the ground and really understand what it takes to be in a role that you might actually want, because you're seeing it from all angles actually.

But I think that that really started my interest in media.

And I think a common thread for me has just been this notion of being an entrepreneur or being around other entrepreneurs within pretty entrenched media companies, which I've really done within two huge companies, IEC and then later on at NBC Universal.

And so I started IEC, I started doing this Corp Com's role.

And the great thing about it was that my job was really to vet speaking panel opportunities for Barry Diller and the senior executives on the team.

And also to keep them abreast of what was going on in media, whether it was a mention in the New York Post about Barry Diller or whether it was something broader that really impacted media around, you know, the sort of like emerging e-commerce stuff that was happening at the time.

It was a really cool way to get a bird's eye view and to see the full landscape and see where I wanted to kind of fit myself.

And I think I realized pretty quickly that I wanted to try a lot of different things and I wasn't quite sure of what I wanted to do.

And each role was kind of cool and interesting and I would take something with me and then I would move into a next one where, you know, the key thing for me was continuing to learn about media, how it works, how people relate to it, both on the consumer facing side, but also how the guts of it work, you know, from the back end systems, you know, eventually working on things like the NBC mainframe.

But to kind of take a slightly more linear approach to answering your question, I answered that ad.

I worked for the head of Corp Com's for a while.

And after a year of doing that, I felt like I wanted to try my hand at something slightly more creative.

So I, you know, did sort of a kind of a semi-audition thing to go work at USA and Sci-Fi Channels to work on their creative marketing campaigns.

You know, they asked me to do something around, I think it was like John McEnroe, you know, a US Open promo.

And, you know, so I took it home.

I don't really know what I was doing. But I just tried a bunch of lines, tried to think about, you know, and I didn't and don't even play tennis, but, you know, just really kind of trying to think about what someone who's watching tennis would entice them to kind of tune in and watch this thing.

Worked on that for a while.

Got the job, which was great, and worked within this sort of creative off and on air group.

You know, becoming super familiar with all the stuff on Sci -Fi Channel, writing campaigns for the stuff, you know, really started to appreciate this total fandom and obsession with Xena Warrior Princess that was on USA at the time.

And a lot of the fair, you know, on, you know, the Star Trekkies and whatnot that tune in pretty heavily to Sci -Fi.

So that was pretty fascinating and got me, I think, closer to the consumer -facing side of things.

Did that for a bunch.

Then, you know, dot-com boom, got into that, got into what we called at the time being a web producer, which was effectively product, but called something else.

And then worked on a site called crime.com, which was a whole sort of very strange chapter in my career that we can talk about it another time, preferably with a drink.

It did involve a live jail cam, so let's keep it moving. So did that for a while.

Worked on some emerging businesses stuff, and then eventually, you know, I was working with the CTO at the time at Universal, and he was a really compelling, you know, character.

And I loved hearing him talk about technology. I loved partnering with him on, you know, things that we were trying to realize for crime.com and for other kind of emerging businesses that we were doing.

And over time, you know, he offered me a job working in technology.

And to be totally honest, I had absolutely no idea what I was doing.

I didn't really know too much about servers.

I didn't know much about writing code. He said, don't worry about it.

I'm going to, you know, send you to school for it. So I did a great program at Columbia that really kind of got me steeped in technology and understanding things from multiple different angles.

You know, what I think it did, and this was a through line kind of in my career, is I think it made me a lot more empathetic to people who are actually writing the code, to people who are actually building the stuff.

And it helped me understand really what's involved. And I ended up just managing application development for a bunch of years.

And just seeing that as, I loved it.

I did it for almost, God, I must have done it for like seven or eight years at NBC Universal at the time, because the company sort of kept morphing.

And that's how I ended up at the Wall Street Journal, was in a technology job.

Fantastic. Yeah, we definitely love these stories of women who haven't been in traditionally tech roles, going into tech and succeeding.

So that's super inspirational. And it sounds like you're not a stranger to career pivoting and not staying in the same place for too long.

So that's just fantastic. Great. So I have another question. Can you talk a little bit about personal brand?

How have you honed one and speak to that? Yeah, you know, personal brand is such a strange thing.

It feels weird to talk about, because it sounds so, you know, deliberate in a way.

So I like to turn it around and kind of say that it's a bit more about how you would want someone to, you know, perceive you or talk about you if you weren't in the room.

And I think for me, and I think a lot of these roles that I described have really allowed me to do all these things.

It's been really about humor, for me, is everything. If you can't laugh with the people you work with, it's like not particularly interesting.

Also, just kindness.

And with that, I would say a healthy dose of empathy is probably pretty important.

And I think, by the way, is fundamental to being a really good product leader, and honestly, to just working in media, frankly.

I think empathy is pretty important, and so is curiosity.

Because as we sort of kick this off by saying, you know, nothing is a constant, everything is, or change is the constant, that it's constantly changing in media.

And influenced increasingly by big tech, as we'll talk about, I'm sure, in a bit.

Great, great. Really like that answer, and agree.

Sense of humor is, it's just great to have it work and cultivate among teams. So, there's this idea of working in the context of a company where you can reinvent yourself.

So, and you mentioned to me in the past that it's a good litmus test for a company, and it kind of tests their tolerance for not putting people into boxes, you said, and I really, really like that idea.

So, I wanted to ask you a little bit more about that.

Yeah, you know, one of the most, I think, important things when you're choosing a company, especially a company that you want to stay at for a while, is a company that isn't standing still.

You know, even if it's highly profitable, that it's really thinking about, you know, what the next big thing is.

It's diversifying, it's expanding into new areas, and it's constantly working to kind of redefine what it is.

And, you know, I honestly think that that's the reason that I've worked for two huge companies, both IAC slash NBC Universal, and now Dow Jones, you know, for my whole career.

It's because I've worked for different subsidiaries within those companies, right?

So, this is, again, you know, a proxy for the fact that they weren't standing still.

They were either acquiring, they were integrating, they were out there really thinking about, you know, how to diversify their product mix and really think about, like, who they are.

By the way, that's my daughter in her music class singing, so I apologize, though.

It sounds quite nice. So, I would say that the reasons that I've been at two companies for so long is because they really allowed me to do that.

You know, they allowed you to shape shift, and I think it's important to really gravitate to a culture that is all about that, right?

It's not just about promoting someone in a linear way, like up the ladder, right?

Obviously, I think that's important, clearly, and so is compensation, but one of the things that I think is probably the most important that I've realized for me personally is this idea of a company, like, sustaining this idea of, like, horizontal redefinition, like seeing you in a different department, seeing you in a different role, and if there is a delta in terms of some skill set that you might not have, really supporting you filling those gaps, right?

And that requires some investment by the company, but honestly, really good people are worth it, right?

And so I think that's, for me, become a really important thing in terms of seeing and looking out there and thinking about what companies would I work for, and so, I mean, for anyone who's thinking about, you know, where they want to work, like, I think always, you know, I tell people, like, starting with a list of, you know, the top five companies and then kind of moving from there, and what that exercise does, even if you don't end up working from one of them, is it really starts to help you hone in on the things that are important to you, and again, for me, it's, you know, empathy and kindness and all these value sets that are really important that have been true of a lot of the people that I work with at these companies, you know, which is interesting, because media isn't always seen that way, but then also this ability to redefine yourself, you know, I always say that a company, a really good company in that way is kind of like New York City, you know, I've lived in New York for so many years after growing up in Brazil and London, but lived the bulk of my life really in New York, and the reason that I stayed there and didn't move, you know, when I was out on my own was because New York really is, like, allows you to redefine, it's so unique that way as a city, it allows you to redefine yourself, you know, multiple times, and it can hold that, can sustain that, and I think a good company does the same thing, honestly.

That's great, I love that analogy, and I didn't know that you grew up between Brazil and London, that's, that sounds great, we'd love to talk about that another time, and yeah, that concept, I think, really resonates with Cloudflare, we don't, you know, put folks into boxes, and I've seen, you know, people move between departments or into management or to new cities, so yeah, that sounds like I'm in the right place then, and so glad to hear that that's been productive and great for you, so I know that you are a big proponent of bringing your full self to work, can you talk a little bit more about what that means, this concept?

Yeah, you know, I think about the fact that my perception around this issue, I think, was a little bit dated for a few years, you know, I ultimately thought that, you know, and a lot of this was influenced by hearing my parents talk about corporate culture, because, you know, my mom was doing organizational development interfacing a lot with big corporations, and my father worked at Citibank for many years overseas, and I think I had this perception that you needed to, in a way, kind of check your personality a bit at the door, and put on a bit of armor when you came into work, in order to, you know, self-protect, be taken seriously, and I really think that, you know, mores have kind of changed, expectations have changed of leaders, you know, the leaders that are probably the most interesting to me now are the ones who are, you know, super open, you know, are the ones who are slight, who operate in a slightly more entrepreneurial way within a large org, or in starting their own companies, you know, who really kind of think for themselves, are unafraid to show that, and are also unafraid to kind of show emotion, you know, that ultimately makes you a better, more compassionate person, you know, being ultimately more human, and I think it brings the most out of people, honestly, because they feel like they can also be themselves, they feel like they don't have to close off a part of themselves in order to operate within the company, and I feel like I'm still learning in this regard, you know, I'm still working about, I'm still learning about the folks that I work with, you know, really listening, really understanding who they are, you need really a full picture of someone in order to, I think, you know, bring the best out of them, create an environment they want to work in, so I think it's pretty fundamental to kind of bring your full self in, and again, I think that notion of armor needs to kind of go out the window, because it just hinders you ultimately, it really does.

Well, thank you for that. So often women are told what they should or could be doing, we even do it to ourselves.

Tell me about some advice that women shouldn't follow, in your opinion. You know, smile more, you know, move to the relationship management side of the house, you know, there's like inherently feedback that women are given, that I think, you know, skews more towards a sense of expectation that they be more accommodating, that they be the ones who are the sort of note takers who are capturing everything in the meeting, and I think, you know, I've struggled with this a bit too, because I'm very much, you know, when I get into a meeting and I notice no one's kind of, you know, taking charge of the organization of the meeting or taking notes or whatever, I'll start doing it, and I think, you know, there's some nuance in there, I think that's okay to do, but I think ultimately one has to make sure that one doesn't end up being sort of an order taker in that context, you know, that even though you are doing that, you are providing a service to the team, but ultimately you have a voice that's just as loud and just as present and as anyone else is on the team, you know, but I've been told to, you know, smile more, you know, you know, sweeten up, brighten up, you know, those kinds of pieces of feedback which are inherently, I think, offensive and frankly quite unfair, you know, you don't hear people as frequently saying those kinds of things to men, that's really for sure.

Absolutely, would love to turn it around on them maybe, but okay, so when do you feel empowered as a woman to do your best work?

I think it's when, you know, I'm seen, I feel like I'm seen and heard and really, yeah, I feel seen and heard, you know, that ultimately feeds on itself and then I think I'm, you know, I'm more want to speak up even more, I'm more want to share more, but I think really looking for an environment like that is, I think, pretty fundamental.

Great, I think that's great advice and can you tell us, this might be a hard question, but can you tell us about a pivotal moment in your life and what was running through your mind?

There are really two, one of them is this acting moment that I'll just share which is probably the worst moment in my life in terms of just writhing discomfort.

I was in a play called Burn This, which was written by Langford Wilson.

As I mentioned, I was a dancer and for many years and the play conveniently has, it's about a choreographer and they built this really, really beautiful set that was made to look like a loft in New York City, you know, with cinder blocks and they actually put real locks on all the doors and I think I mentioned earlier that I wasn't the best actress and the place, I'm in every scene, the play starts with me on the stage and the buzzer goes off and I'm supposed to go let, you know, the person who's buzzing into the apartment, so the play can start, by the way, or else it'd be a giant monologue, right, which I wasn't prepared for certainly.

So the buzzer rings, I go to the door, already feeling like highly aware of the audience and I haven't lost myself in this role clearly, right, so it's like the big debut night and buzzer rings, I go to the door, I start unlocking all the locks and the last lock is stuck and I can't let the other actor in to the play with me and it was several minutes of just absolute hell and, you know, parents were there, it was like a whole to-do, that was pretty like gut-wrenchingly horrible, honestly.

I would say that for work, it was a moment where I had spent months and months, you know, architecting with our team, like, you know, this whole OKRs framework and way of really evaluating our, you know, the way that our products were, you know, created and whether they were successful and really evaluating using, you know, baselines and our key results and setting targets and we had really thought this through and felt extremely proud of it and so we're sitting there and I had just done this very kind of overwrought presentation about it with my team and then a pretty senior engineer gets up and basically starts to poke hole after hole after hole in the entire framework that I have just, I felt so proud of, right, that I had just put up on the screen and it honestly took everything in me not to start crying, like, you know, there are these moments in life where you kind of, like, feel the tears coming and it takes everything to just, like, not totally freak out and be engulfed in them, so that was probably the hardest moment, honestly, professionally for me because I felt it was a very public dressing down, you know, of my, of this whole framework that I'd worked on, but I think the after for me was probably pretty impactful for me because I was so upset about that and the more and more I thought about it, the more and more I realized that it was ultimately less about the content of what he was saying, but more about the format and why he needed to do it so publicly and I ended up after a few days of kind of coming back to earth on this whole thing and feeling like I could keep it together, I invited him to lunch and I talked to him about how upset I was and why I was upset and differentiated between the content of what he had said, you know, to the room, which was very hurtful and really, you know, the way in which it was done and I was able to talk about the fact that he had some good points in the feedback that he was giving me, but that it was hard to hear them in the context in which he was giving them to me very publicly and that it made me question a bunch of different things around his motives and, you know, it ended up being a really productive conversation and, you know, I left the conversation feeling much lighter because I was really honest with the way that it had, not just the way that I felt, but also the fact that I was able to differentiate between those two things and actually take in the feedback, even though it was given to me in a really uncomfortable way.

That's great.

Great to hear that you brought it up to him and didn't just, you know, sit back and deal with it.

I like that a lot. Because then it becomes like less your issue, right?

Like, or else you're just holding it and it's painful. But if you actually share it and work towards kind of a common, you know, a shared outcome, then I think it really flips the script a little bit, which I was able to do in this situation.

Some situations not so much, but in this one I was. That's great. So we have this, so it's International Women's Day was on Monday and it's obviously Women's Empowerment Month.

So the theme is choose to challenge. And when I think about our choose to challenge movement, I think about challenging myself to lift other women up and try to lift myself up.

So we're asking this of all of our guests. How do you choose to challenge yourself?

I think actively embracing discomfort and knowing the difference between sort of self-punishing and growth.

So, you know, hang gliding, challenging myself to hang glide when I was totally scared beyond of it in Rio over my, the neighborhood I used to, I grew up in, like doing that on my honeymoon with my husband was like, you know, extremely uncomfortable.

Having lunch with this guy.

And I was very hurt by the whole thing. And he's the last person that I wanted to sit with.

But doing that and, and being open to whatever happened but putting myself in that uncomfortable realm.

Cause I knew on some level that it had, it had the promise of maybe bringing some growth to him and to me, maybe.

Also doing things like going out and seeking new skill sets and knowledge so that you're never static.

And that can be uncomfortable because sometimes it gets very, very, very seductive to stay in a role because you know it, because you understand it, because you want to kind of be a knowledge expert, which everybody wants to be.

But once you get too comfortable, that means that you're not ultimately growing.

So I would say always insert a little bit of risk-taking and discomfort in that.

And I, I, I feel as women, especially we need to heed that and really do more of that.

Cause I think we're bad-ass ultimately. I could go on and on about how amazing I think women are and how we have certain capabilities that men don't necessarily have.

I could go on about that, but, but I just think, you know, we got to feed the curiosity and we got to feed the discomfort.

Well, we have 12 seconds left. Catherine, thank you so much for, for being with us.

You're very inspiring. It's been really great speaking with you and I hope to speak with you again.

Thank you so much. It's been a real pleasure. Thank you so much.

Thank you.