🏳️‍🌈 Pride Month: Proudflare Executive Sponsor Spotlight

Hello everyone! Welcome to our Cloudflare Executive Sponsor Spotlight today. This is our first, actually I guess second big Cloudflare TV presence for Pride Month and to help us celebrate, I'm joined here by a couple of my favorite Cloudflarians.

I'm going to first introduce myself.

I'm Jacob. I'm based out of San Francisco and I'm on our security team.

I'm joined by my co-host, Eric Allen, who is based out of Austin, Texas and is on our accounting team.

And finally, our guest of honor and Executive Sponsor and Spotlight of this session, Jen Taylor.

Jen is an SVP and Chief Product Officer here at Cloudflare and she joined all the way back in 2017, so almost her four-year anniversary.

It's really an honor to have her here today. So as I mentioned, this is all about Pride Month and celebrating Pride.

So I wanted to first get your take, Jen, like what does Pride mean to you?

Pride is about community and it's about visibility and it's about celebration.

You know, I think for me, when I think about sort of my journey as, you know, a queer woman in the world and I think about sort of, you know, kind of what has helped me kind of grow and find myself and be myself, it's the community.

It's the celebration of the community and the diversity of that community.

I think it's also about a moment of visibility for all of us.

I think that it's really important. There's a lot of power to being seen and creating opportunities for all types of different types of people to be seen.

And I think for me, it's also a moment of celebration. It's, you know, one of the things I reflect on is, you know, there's still work to be done, but we've come a long way, right?

I mean, it's, you know, a little over 50 years ago, we were in the Stonewall riots and now we're here and able to have this kind of a conversation in a corporate environment.

And it's just, I think it's important to step back and, you know, we still have work to do, but to celebrate the way that the community has grown and we've grown with it.

Yeah. I think the, you know, awesome answer that actually goes really well in line with our theme that Proud Flare has decided is going to be our pride celebration, which is to educate, uplift, and to celebrate, especially since, you know, COVID has kind of changed how we can all interact.

And I think this year is really a bit of a return to some normal pride festivities and celebrating our community.

Yeah. Yeah. It's, it's interesting.

You know, I was thinking about as, as we were talking in the, the kind of the pre-conversation around sort of, you know, the importance of sort of, you know, pride month and celebrations.

And it's, it's interesting, right?

We're going to have another experience here, at least in San Francisco, where there's no pride, there's no march.

There's no sort of that, like that has been sort of the kind of penultimate kind of cherry on the top for, for pride month in San Francisco for forever.

And it's it's been interesting to think about the ways in which the community has found ways to create celebration and connection with that in, in a time where we are all in, in sort of pockets and more fragmented situations.

So I think it's moments like this that are so important for us as an organization.

And then just even broadly outside of just Cloudflare, just the whole community.

Yeah, definitely. It's been a definitely unique year, but our community is resilient for sure.

And definitely able to find each other.

Yeah. So Eric, did you want to ask Jen maybe about how we think about uplifting some other LGBTQIA plus voices?

Oh, I was curious, or I guess we were all kind of curious about what are like, what is the importance of that?

And which voices do you really think we still, you know, you're saying that we still have some room to grow and things to like improve.

I think, what voices do you think we should make sure that they do not go, you know, unheard and or try to amplify as best as we can, even within the queer community, you know, what's your take on that?

So, I mean, I think just stepping back, I think that like, just like stepping back with the idea and the premise that all voices matter.

I mean, I'm like, of course that's true, right?

Like we can just take that as a given. And I think that that's not necessarily always true.

It's something I would like to always be true, but I do think it's important that we step back and reflect on that and that we're intentional about our efforts and that we find opportunities to invite those other voices into conversations when we have them, or we, you know, support people in finding the courage to speak up and be themselves.

You know, the world is so much better, so much richer and so much happier when we all have that opportunity.

If I look at and I think about like, you know, what are the voices that still need to be lifted up?

I think, you know, it's, you know, this time last year, we were really very squarely at the intersection of Black Lives Matter and kind of the queer community and just thinking about queer people of color and kind of making sure that when we think about the queer community, that we really are celebrating, you know, the diversity of the community itself.

You know, I think that there's a lot going on within the trans community right now and just creating visibility and acknowledgement and opportunities within the trans community and hearing those voices and putting those voices forward.

But I think it's also one of those things too where, you know, there are all types of voices that need to be heard.

And mostly I think about like, how do we help people who might be questioning or struggling?

How do we help them find their voice? That it's, and how do we help them find their voice in a way that feels right and appropriate for them?

There's no one way to have a voice. There's no one way to be visible. You know, part of what your t-shirt says, Jacob, is be every color that you are.

And part of what I have always really loved and appreciated about the queer community is that it's all about being more yourself and being more you and finding the confidence in that.

And so that's how I think about visibility. Yeah. I think you hit a really good point that it's like finding that balance of showcasing the other voices, but also allowing them to say their own kind of story too, or say in a way that they are, because we can kind of sometimes get very wrapped into, you know, advocating for groups, but then not necessarily letting the group advocate for themselves.

So. Yeah. Yeah. It's, in my mind, it's about creating an opportunity for people to have their voice and not bring our own bias and our own sort of agenda into that moment.

Yeah. And then one of the last things you said, Jen, really kind of stuck with me, what you said was about, you know, making sure that people have a place to like feel loved and like self-expression.

And it kind of reminds me of the RuPaul quote that I'm sure a lot of people who've heard Drag Race have heard this now, but if you can't love yourself, how in the hell are you gonna love somebody else?

So I think it's really beautiful to help us create that space, you know, every day, but especially during June and during Pride Month.

It's really important.

Yeah. It's lovely. Well, COVID, as you've mentioned, has kind of changed how our community has been able to come together, certainly, but I think it's also really important that, you know, some viewers out there may not be aware, but this is really the second pandemic our community specifically has been through and really is still going through.

The HIV AIDS pandemic that started in the 80s and went all the way through until today has definitely had a lasting impact on our community.

And I'm kind of wondering how you think maybe COVID will also be impacting our community in a similar or maybe a different way.

Yeah. You know, it's interesting.

I can't remember. I think it might've been, it was a newspaper.

It might've been the New York Times where somebody posted a photo that was individuals dressed up in either outfits that were all black or all white.

And it was representative of the San Francisco gay men's choir back when they started.

And the different representations basically were to sort of indicate sort of of the people who were a part of that original choir, how many of them had died as a result of the HIV and AIDS pandemic.

And, you know, it was just a chilling image because, you know, there were two or three individuals basically who were still represented as being alive.

And that, it just really reminded you of the power of that.

And, you know, without sharing my age, you know, I came of age and I, and actually I came out, you know, as, you know, in the middle of that pandemic and it was, it was, it rattled the community.

And it, it's kind of the way I think about, you know, I think of a community like a house and the individuals that are, the individuals are basically the foundation that are holding it up.

And it was incredibly, it was destabilizing for the community just to have individuals in the house, like the people were dying, the foundation was crumbling.

But I think the thing that was also really powerful for me was how the community really came together, that it became an opportunity and a cause and a focus that people could really think about and move forward.

There are so many people who have experienced all sorts of different types of loss as a result of the pandemic we're living through now.

And that I think will continue to, to destabilize just the global community.

And I think that I think it will make it even kind of more important to step back and celebrate.

Like it's one of the things that's been surprising to me as communities have started to reopen is how good it feels to be together.

Right. And, and how good it feels to, to hug someone and how good it feels to, to just have that, that human interaction.

And so I'm hopeful and confident that, that, that our community, the queer community will, will be able to find those places in those ways of connection again.

It's, it's, you know, here in San Francisco during pride month, they, they light up a big pink triangle on top of a hill over the city.

And it's, it's always been iconic. I didn't realize now it had become lights.

I guess I was not paying attention. It used to just be a flag, but like, it's this big gleaming pink thing.

And it was amazing to me how that was news across San Francisco, like the mayor was involved with it.

And that like, I think that had become sort of a, I think that, that pride in the community had become really kind of a rallying cry for the broader community.

And I think that like, I'm hopeful again, that, that we'll be able to find that support.

That's, I mean, I totally, I think that's something I'm glad that, or I feel like we are going to embrace once again, like that sense of community.

Yeah. And just getting that hug.

Cause I'm definitely, this pandemic, I mean, clearly I'm an extrovert.

I'm it's like, okay, introverts, y'all had your time to shine. Now it's like, now I need to go out and like hug a couple of people, you know, fully vaccinated and all this stuff, you know, it's all good over here.

But I think that really speaks to like us as a community really having to always constantly having barriers and then breaking down those barriers to like, you know, excel and become more.

And I think I'm curious, like as to what other barriers, like, have you witnessed in the LGBTQIA plus community and how have we like broken those barriers throughout your lifetime?

Well, and again, we have the benefit of the fact that I've been doing it for a while.

But I think, you know, I think if I think about what I am most grateful for now as a queer woman is the ability to really freely be myself that like, I don't that, that I have a wife that I don't hesitate to mention that I have a wife that I don't hesitate to mention that I do that in a professional context that I feel safe doing that.

You know, I think, you know, I think first and foremost, you know, sort of the barriers that we've broken down, I've just been like, I can think about kind of a little bit differently as sort of like, first creating safety for the community, creating the visibility for the community has been incredibly those have just been sort of foundational things that I think enabled us to experience as a community and break through some of the barriers we have, because it was like, once you had that safety, people felt more comfortable taking the risk of expressing their voice and expressing who they are.

I think that, you know, so I think about, you know, just and then it's the barriers of like, barriers within the workplace and hiring practices, like barriers within the employment, like, you know, the fact that like, you know, now that you have marriage, I think that like, these are things and barriers that I've seen that like, I couldn't even have conceived of, you know, when I when I first came out.

And so it's, I look at those barriers and focus on those barriers, because they benefit me.

So like, I'm also just acknowledging that.

But I also look around, and I appreciate that not everyone in the world realizes that not all the not everyone in the in the world, not all queer people feel safety, not all.

And so, you know, I think about like the barriers we've come through, I think of is almost like the blueprint of the barriers that still remain and the work that we need to be doing as a global community to create that support to create that safety and to enable people to live and be their full and their best selves.

Yeah, that's, that's really beautiful. And I think it's really important to acknowledge that, yes, so much has happened in the US, but they're really the community globally, we still have so much more work to do to support and uplift.

I think that's really beautiful. Yeah. So, well, kind of changing gears, because you are such an important part of our organization, we really wanted and really such a role model to so many people in our organization, we wanted to switch a little bit from talking about pride to talking about your role at Cloudflare, and maybe how being a Proudflare lead has impacted how you do your job.

So would you be able to start out just telling us what drew you to Cloudflare in the first place?

Things that make me happy in my job are solving big, complicated problems that have positive social impact, and that are fundamentally bottomless, right?

And performance and security at scale to create, you know, to help build a better Internet for everyone, like, that's pretty good.

That's pretty, pretty, pretty good, pretty noble problem, pretty bottomless.

You know, like, that's a problem that's going to feed my soul.

And the second is, is that, you know, I love the customers. I think for me, you know, I, like many people wake up in the middle of the night thinking about their job.

When I wake up in the middle of the night, I wake up thinking about our customers.

And so it's really important that I like them, because I want to wake up and like, if I'm having insomnia, I want to be thinking about people and worrying about people that I care about.

But the thing that really drew me to Cloudflare, that keeps me at Cloudflare is the team.

I really, I've never in my career had an opportunity to work with people who are as smart, as engaged, as curious as they are at Cloudflare.

I feel like this is an environment where I feel I can be my best self, I can get my best work done, that I can advocate and create change.

And that's been good and important. And, you know, I love the collaboration and the air of collaboration that exists within the organization.

And so I think those are the three things that drew me. And, you know, it's one of those things where it's like, I can't believe I'm days away from my four -year Cloudflare anniversary.

And like, it still feels like I'm just getting started. There's still so much that we need to get done.

And I feel so challenged and engaged, which is exciting.

Yeah, definitely. Like a really good point. Like, I think the one word that stuck out was like curious.

And I think I feel like I tell everyone, like, we, I mean, like, we're curious about our jobs.

We're curious about other things that we're also very, like, we just share to each other and people embrace it or also like into it.

I mean, that's especially coming from being an accountant, you know, you kind of, I've seen the gambit and it's like, wow, this is like people are actually kind of like interested in things that I'm interested in, you know, so.

Yeah, no, it's, it's one of my favorite attributes of Cloudflare is the curiosity.

I think that it, it really, it so infuses our culture.

It so infuses the, the way that people engage with and respect each other and really find that common ground.

I think it also really helps fuel innovation, which is also fun.

Innovation.

I mean, first our products are like, I'm still trying to grasp our, you know, like I said, but we're curious, like, how, how do you think we build or how does like diversity, equity and inclusion show up in our various products or all the products or, you know?

Yeah.

Well, I think, so I think there are, there are some ways in which diversity and inclusion very much manifest themselves in our products.

I think first, just the variety of products we have, the fact that we're doing everything from shipping a developer platform to providing enterprise security solutions to, to protecting web applications.

Like there's a lot of diversity in the way we, the fact that we're ventured into consumer, like just the variety of ways that we've thought about and identified challenges.

One of the things I truly love and admire about Cloudflare and what I love about building product is how much of the innovation we do is ground up.

It's, it's people, wherever they may sit in the organization, identifying an opportunity or challenge.

And it's that curiosity that sort of helps bring those ideas to the table.

And I think just the diversity of ideas that make themselves available within the organization and that we build on top of.

You know, I think we strive within the organization to really leverage the, the breadth and the depth and the perspective and the voices from within the organizations as we, as we build product.

It's, we pride ourselves on the fact that like, you know, we try to user test everything.

We dog food everything. And we, we try really intentionally to listen to all of the voices across the organization and to fold that feedback back into the product.

And then, you know, very similarly try to do the same, same with customers.

I think it's, I, and I think that there is a very tight relationship, very tight correlation between the diversity and curiosity of Cloudflare and the rate of innovation and product delivery that we have.

And I, and I don't think, I don't think another, I think that that is, is integral to the company.

I don't think any other company can, can mirror that.

Yeah. And the kind of what you talked about too, and talking about community and especially how we think about Pride Month, making sure that everyone's voices heard, everyone's voices uplifted.

We really do, I think, as we develop products, we ask our customers and we ask employees, we really try and take in a ton of different sources of feedback so we can make some of the products that really suit the needs.

You know, and we move fast and we don't always get it right, but we try really hard to learn from those experiences and like pick ourselves back up, like fix it and get going.

So, yes, absolutely. Yeah. So how, how soon after you started Cloudflare did you get involved with Proudflare specifically and what kind of prompted you to step into more of a leadership position with us?

Well, you couldn't keep me away. Like, honestly, let me at it. So, you know, it was really, it was really interesting, you know, when I started, you know, one of the things I do whenever I start a new job is I really try to get a chance to meet as many different people as I can.

And it was probably within the first two weeks of my time here, I was having a one-on-one with somebody and they're like, you know, like we just been having a very like professional conversation at the end.

They're like, you know, we don't have a queer, you know, organization here at Cloudflare.

And I think it would be great if, if we could do that.

And I, you know, I'm really hopeful that you, you know, you might be able to, to help make it happen.

And I was like, oh yeah, like, yes, absolutely. Like, and then actually Andrew approached me and said, you know, we're thinking of starting this organization, Proudflare, would you be willing to be our executive sponsor?

And I'm like, heck yeah.

Like, let me add it. And it's you know, there are many things I love about my job.

There are many things I love about Cloudflare. There are many things I find rewarding.

It's actually the work that I do with Proudflare and the community of Proudflare that, that I am most excited about.

I'm, I'm happy I got to contribute in some small way.

And you know, the leadership within the organization right now, like, you know, I follow them more than, more than, than I provide, you know, leadership as an executive sponsor, but you know, I'm really, I'm honored to be a part of it.

I try to make sure to create positive visibility for the organ, for Proudflare within the organization.

So yeah. Yeah. It's awesome having you as an executive sponsor.

Anytime, like even this interview, you're always so eager to just help and get involved in any way.

All the members definitely appreciate that, especially coming from the top down.

Yeah. Yeah.

Confidently say that we have the sponsor with the best shoes. I'm just saying, just putting it out there.

I mean, I don't know if you're, I don't know if you have any, you know, if you have like any cool shoes on right now, but if you ever want to showcase them, you know, just like let us know.

But, but so we, I mean, clearly the road to an executive is, I mean, everyone probably comes up to this kind of position, like in their own kind of like pathways, all kinds of stuff.

But we're curious as to like, what were the different roadblocks that you have encountered throughout your career?

And what kind of mentality did you have in order to like go, like, you know, overcome those blocks or, or not even blocks, but, you know, I guess there'll be more like, why are we, because clearly you went through them.

So yeah. You know, if I think about like roadblocks I encountered and things I went through, I think the first, like, I think the biggest roadblock for me in the growth of my career has continually been myself.

And, you know, I'll be honest, I find it very difficult early on in my career to be out and to be myself at work.

And the way that that manifests itself is I didn't feel comfortable sort of, I do my best work when I'm in flow, when I'm like not worrying about it, I'm just riffing, I'm just like, whatever.

And what I think I found myself early on in my career was spending a lot of time being kind of like, can I say this?

Can I do this? Like, you know, and, and I think it's, it's been being able to find confidence and, and find voice in doing that.

I didn't do that alone. I had, you know, I am a big believer in having advocates and mentors and having people help you sort of kind of break through that.

And that I think was, was, was a big step for me. I think the other is, you know, another poison that is like, you know, there are lots of steps that don't go as planned along the way.

And I think, you know, some of the barriers I had were just overcoming those moments when that wasn't awesome.

I didn't show up as my best self or, you know, that, that, that didn't have the outcome I wanted and being able to find a way to sort of pick up and move on.

But I think it's, I think the final barrier for me was, how do I say this?

It's kind of, the way I think about how I got through is kind of like going towards the light, right?

It's, it's, you know, choosing, choosing what I wanted to do and how I wanted to do it, but then opening myself up to, and who do I want to do it with, rather than just sort of saying, oh, I need to go work at that organization, or I need to take that role or whatever, really stepping back and reflecting on where places that sort of, I feel light, I feel welcome, I feel engaged, you know, and I think, you know, I give a lot of credit to the organization that Matthew and Michelle have built.

I think from the very beginning, you know, they were very focused on, on creating an environment where I felt like I could do my best work.

And they're, they're always really receptive and helpful there.

And like, I appreciate that.

Something I really liked that you said was, you know, focusing on finding mentors and finding people who can help support and uplift.

What are some of the qualities you look for in a mentor that you would recommend people look for?

Because I think that's kind of gets overlooked.

Sometimes they can really help unblock things for you in your career.

Yeah, for me, personally, I needed somebody who was kind and gentle and could at the same time totally kick my ass.

You know, I think I needed someone for me, I needed, I needed, you know, for me, personally, I really needed somebody who would push me and who would challenge me, but could do it in a way that didn't shut me down.

That was sort of like, okay, like, okay, like, maybe, but are you really trying your hardest?

Like, really? Like, have you thought about that again?

Or like, that looks like it's getting all worked up.

Do you really need to get worked up? That would basically, you know, have the power to hold a mirror up to me and sort of challenge me and the assumptions I had about myself.

Yeah, that's, that's really interesting. I like that.

The helpful guiding challenging to help, you know, uncover more about you and maybe what your wants and needs are.

It's really, it's important. And it's also that, you know, that I talk about mentors, I also think about mentors kind of being going one step beyond and being advocates.

And I think there also have been many people in my career who've, who've seen opportunities, created connections, been an advocate for me.

And I think that's something that I really strive and aspire to do for for other people in my community is, is to kind of pay that forward.

You know, so for me, you know, I love being a mentor.

I love being an advocate. I love, I love helping in any way I can, because I'm very confident that my next boss is somebody, you know, in the organization of Cloudflare that like, that I will go work for in the future.

Oh, love that. Love our internal community building. It's so good. So then I guess with that, also, like, what I mean, so, you know, getting, making sure that, like, find advocates for yourself, but also, I would say, for, to, I mean, I guess some of us would like to possibly be executives in our futures, but it's like, you know, just let's get real.

But it's like finding advocates, but what other kind of or skills or mindsets do you think we, people that want to reach a certain level would, should kind of cultivate now or like, what are some strategies and books maybe that you read or like, I don't know?

Yeah, I'm miserable when it comes to reading business books, because like, I can't, I can't, I can't, like, I can't do it.

Like, I love some, I love me a memoir. Like, I'll just be like, I'm going to be like, full on about that.

And I like traffic TV and I read people magazine and like, okay, there's like, there's just all that.

I think the things that the two skills that I personally had to do a lot of work on as I grew my career, but I think it really benefited me, both have to do around communication.

The first was learning how to listen. I think it's, I think very early on in my career, I was like, oh, I want to be a leader.

I know, I know everything.

And, and actually, I think the thing that really helped me grow was realizing that I didn't know everything.

And that like, it was learning how to listen to different voices within the organization, different people, and really be able to kind of quiet myself down enough that I could actually hear it and internalize it rather than barrel right through it.

And I think the other part of that communication for me is learning how to ask questions.

Because a big part of, of the work that I do now is, you know, again, surrounded by phenomenally talented people who are closer to everything than I am that know more than I do, you know, using, using opportunities to kind of follow the curiosity, follow the questions as an opportunity to learn and build alignment.

Those are the two things that I really focused on as, as I grew in my career.

Yeah, that's, that's beautiful.

And kind of aligns with so Cloudflare's five capabilities, we got our culture by and one of them, it's my personal favorite is being curious, which is something else that Eric's already mentioned, just really using the questions to help guide and help to learn more.

I think that's really beautiful.

So, well, we're just at the end of our time here now, kind of crazy how 30 minutes just flies by so quickly.

I feel like I could be on here talking to you for another hour or so, but, you know, we all really appreciate you taking time out of your really busy schedule to talk with us and to help you on Cloudflare TV.

And I think we all want to wish everyone watching out there a happy pride and make sure to tune in for the rest of our Cloudflare TV segments the rest of this month.

Thank you for, for doing this and happy pride, everyone. Awesome. Thank you. Bye, everybody.