👩‍💻 *Women in Tech EMEA* Leveling up with Jen Taylor

Hi everyone, I am Corinne Teasdale -Schafle, the Technical Program Manager of our FedRAMP Initiative. Thank you all so much for joining us for the last session of today's Women in Tech Day. I am unbelievably excited to host today's session with one of the most inspirational leaders I have ever worked with, Cloudflare's Chief Product Officer, Jen Taylor. To give you a bit of background, before joining Cloudflare as Head of Product, she served as the SVP of Product Management of Search at Salesforce, and has had a distinguished career in the Silicon Valley, working in product across Salesforce, Facebook, and Adobe. Jen, thank you so much for being with us here today. Thank you so much. I'm so fired up to talk to you. It's great to see you. How have you been? I've been doing good. How have you been? Good, good. You know, it's been nice to kind of get out and start seeing people again and, you know, exciting. Yeah, it's awesome that, you know, things are looking up. Yes, totally. And I'm looking forward to getting to Europe, actually, at some point. Like, the most exciting thing to me has been the fact that the borders are finally opening up. I used to spend quite a bit of time in Europe, in our London office, and then obviously kind of on the continent before the pandemic, and I'm looking forward to getting back to that. Yeah, it'd be great to see our London office and our Lisbon office. Yeah. Cool. Now, just a quick note to our viewers. If you have any questions, feel free to submit them by emailing us at livestudio at Cloudflare.tv. Again, that's livestudio at Cloudflare.tv. We will be saving some time at the end to go ahead and answer them. Now, before we launch into the hard-hitting questions, I thought we'd break the ice with a fun fact. Now, for the viewers who might not be familiar with Cloudflare traditions, it's one of our traditions to have all of our new hires share a fun fact. So, Jen, what was yours? My fun fact actually was that during college, I took some time away from university and moved to Jackson Hole, Wyoming, which is a ski town. And I had lots of odd jobs. I delivered pizzas. I worked at the grocery store. I sold lift tickets in ski mountain. And one of the jobs I was privileged to have was I worked as a whitewater rafting guy. And one of the things I came to realize as a sort of entrepreneurial young college student was that if I fell out of the boat during the ride, the tips were actually higher. And so once I figured this out, I basically fell out of the boat every day, multiple times of the day on every trip. And it was quite economically advantageous, though a bit soggy. Oh my gosh, that's amazing. All right, so from rafting to product management, that's gotta be a journey. So Jen, can you kind of share with us your path to product management? Yeah, it's really interesting. I think that the through line for me from rafting to product management is customers, it's people. Part of what I loved most about being a rafting guide was, yeah, like swimming, and I liked rafting and stuff like that. But the thing I really liked was being in a raft with eight people. We all got in and we had to find a way to work together. We had to find a way to get down the road. And we had to find a way to entertain each other and to do it safely. And so I really enjoyed getting to know people, learning about them, learning about what they were trying to accomplish and like how do we work together? And I think that's actually the heart and soul of what drives me as a product leader is really the opportunity to work closely with customers, to learn about what they're trying to do and what they're trying to experience and to move forward from that. You know, I mean, technically, you know, I'm a little bit of an odd duck in the product world, at least in the world of product today, in that like my undergraduate degree is in environmental policy. And I thought I was going to law school until I actually had some friends who graduated ahead of me and went to law school and I realized that like that was going to be a miserable experience for me. And then I had actually spent some time my senior year in the computer center. Finally, I had been reluctant to even enter the building to take statistics that I had to finish for my major. And I like totally found love, like the ability to like just in that moment leverage technology to analyze data sets and to kind of identify problems and kind of come to conclusions. It was like, you know, it's very basic in the world of technology, but to me it was transformative. And so that kind of put me on a very different trajectory. Spent time kind of all around different aspects of the business of technology, kind of in my 20s. I worked in IT consulting. I worked in investment banking. I worked in venture capital. I worked at a .com during the .com boom, and I think each one of those experiences kind of gave me a little bit of a greater sense and flavor for, okay, if I'm interested in technology and I'm interested in customers, kind of how and where do I want to play? And for me, I realized that I liked working with customers. I liked spending time with people. I liked identifying the problems that they were trying to solve. And then I love the experience as a product leader of coming back into the organization and partnering with engineering and design and marketing and sales. And all of us were huddling together and being like, okay, this is the problem we're trying to solve. How should we go about doing it? And just sort of that spark of innovation that happens through that collaboration. And so I had the opportunity to step out from the work world for a couple of years and went and got my MBA, and then was very focused coming out of business school on wanting to move into product management. So I did that during my summers between business school and I've basically been in product management ever since. Awesome. Thank you, Jen. Yeah. So next question. Earlier in your career, you were the product manager of Dreamweaver. For those of you in the audience who have maybe built websites in the 2000s, Dreamweaver was the IDE for web development. It was used by hobbyists, top design firms and enterprise organizations. This is a product that has really touched the lives of millions of web developers. So Jen, can you kind of break down some of those key learnings you had from that experience of being the product manager of Dreamweaver? So still one of my favorite jobs, still one of my favorite products, and as much as I love all of our customers here today at Cloudflare, some of my favorite customers. Stepping back, if you think about the moment at which we were in, it was the late 90s, the early 2000s where the Internet was really taking off and you had this community of largely artists and graphic designers who were in many ways trying to figure out how do they make this kind of transformative shift from basically kind of creative, like physical medium to bringing that artistry online. At the same time, you had a whole bunch of entrepreneurs, some of whom had technology backgrounds, but the vast majority didn't, who needed quick and easy ways to get online so that they could express and execute what they were trying to do. Dreamweaver was a really powerful tool for the non-technical audience because it had what we call the design surface where you literally could effectively almost draw or build or color on top of it, and Dreamweaver would generate the code. It was my first real significant product management job, and I sort of walked in and I was like, oh, great, like the value proposition of Dreamweaver is the design surface, and it's amazing, and we should keep adding all of these advanced capabilities so people can visually create applications. And it was like, yeah, yeah, yeah, it sounds great, it sounds great. And the first release that I was responsible for, we released, and it completely bombed, like bombed. And, you know, stepping back, we're like, what, what happened? And it was really a humbling experience, and sort of, it was in that moment that I was like, oh, maybe we should actually go talk to some customers, you know, and so then we started this process whereby, you know, it was me, an engineer, one of our designers and one of our marketing people, and we would go on these road trips to different cities and set up these meetings with customers. And you have to remember that Dreamweaver is often used by small to medium-sized businesses, and so we were often, you know, conducting these work observations and meetings with individuals in studio apartments or in their bedrooms, and, you know, kind of all these crazy kind of different situations, these different startups that, you know, it was just crazy. Anyway, it was wonderful, but it really brought home to me and kindled for me that passion for spending time with and learning from your customers. Literally being in their physical space was just like, oh, I get it, like watching them work, like that was actually the most transformative thing, because if I like had a conversation with them and I'm like, so how do you work? They're like, well, I draw, I did it. If I actually watch them work, they didn't draw at all. Like they might, what we discovered was this whole sort of value proposition of having this design surface was kind of how people learned HTML. And what they would do is they would draw something on the design surface, and then they would actually go look at the code that Dreamweaver had generated and then edit the code. And you're like, oh, like if you change the way you think about the value proposition of what you're delivering, and just that small insight transformed the way we thought about the product and really kind of the benefit we're creating for customers. Wow. Yeah. That's really cool that you took all that information from talking with the customers and then distilled it down to that one small change that you got, your team could make, and it would really improve everyone's experience. The important thing I want to highlight is it was not me alone. And I think that's the important thing for people to really like, one of the things I've really come to appreciate and love about product management is that it is truly, truly, truly a team sport. And it's a cross-functional team sport. You know, a lot of the observations and decisions that we made around roadmap and these insights were coming from the collaboration between myself, between the engineer, the designer, the marketing folks, who are all sitting in the room with me. And it was the conversations and the debriefs that we would have after these customer meetings where kind of everybody brought their observations to the table that really sort of moved it forward. And so it also really kind of helped cement and made me really appreciate the kind of the diversity of skillsets and the diversities of opinions that often happen on a product team and made me realize kind of how important that is to actually seeing opportunity and driving innovation. Wow. That's really inspiring. I think it's really key to highlight that, you know, the diversity of opinions that, you know, bring out the best in a product because it's not just one person that can make something great. Yeah, absolutely. So Jen, that kind of brings me to, how would you like define your leadership style? Would you be able to give us like an overview? My approach to leadership is I hire really smart people that I aspire to work for. I delegate and empower them and get the heck out of their way. I think that's really, you know, of course, along the way, you know, you provide scaffolding and stuff like that. But, you know, for me, I love building product. I really love building teams and I really love helping people get started in their product management career and being a part of their growth. That to me is always really powerful. You know, it's interesting. I was, I have a son who's about to go off to university and I was talking with him about what he wants to do. And, you know, he said, well, I want to be a doctor or a lawyer. And I was like, well, you know, keep an open mind because the thing that you might find really makes your heart sing might be something that you have no awareness of now. And it's, you know, what I do now, I mean, at least it's like Cloudflare didn't exist when I was in university, right? And so I think for me, it's this discipline, this career is something I never really imagined when I was younger, but I also at this point couldn't imagine doing anything else. So you brought up like entering like the workforce and just, you know, starting your career as a product manager. Are there, is there advice you'd give people who are considering product management? So people, I'll answer it in a slightly different way, which is people often ask me when I'm hiring, like, what do I look for? And I think that that's kind of a good way to kind of understand a little bit of sort of what I think some of the critical skills are for product managers. You know, I think, you know, one thing I'll say for sure not is, you know, I think that kind of going back to diversity of opinion, diversity of thought, diversity of experience, I think great product managers come from all types of disciplines. If I look at some of the most amazing product managers I've worked with, yes, some of them have technical degrees and some of the products that they work on really demand that. But, you know, I've got English managers, I've got history majors, I've got accounting majors, I've got, you know, you know, comparative literature majors. I think, you know, really for me, when I step back and I think about what makes a product manager great, I think first and foremost, it kind of ties into this customer orientation and most specifically like skill number one that I look for is the ability to listen. Because I think great product managers need to be able to listen to what they're hearing from customers, listen to what they're hearing from engineers, listen to what they're hearing from designers and find a way to kind of synthesize that and kind of be able to kind of consolidate that into clarity around what's the problem we're trying to solve. Listening is a really valuable skill. Listening is also really hard. And, you know, a lot of it is listening to, at some degree, what is not necessarily actually said directly, but being able to sort of interpret and understand. Second skill then is communication. And that's the sort of flip side, but it's, you know, communication to drive collaboration with a cross -functional group. Product management is the ultimate art of management. It's the ultimate art of managing through influence because people are like, you're responsible for the product, but you actually have no direct responsibility for anybody that is actually responsible for making that happen. Like that all happens with engineering and design and marketing and program management. And like, you know, so you need to be able to communicate and collaborate and bring those folks to the table. And then I think that the last one for me is just the ability to ruthlessly prioritize. We will never have enough information to completely meet. You'll never have 100% clarity of information. You'll never have clarity of we should do this or we should do that, but you always have more to do than you have time or resources to do it. And so product management is the art and the skill also of figuring out how to make decisions, how to prioritize, and kind of how to make those decisions and run with them and be at peace with them. So you mentioned communication, listening, and prioritization. Are there skills that aspiring product managers can hone that would, you know, help them become better product managers? It's interesting. You know, I think it varies a little bit by organization. I think if you look at Cloudflare, you know, we have very technical products. And so at Cloudflare having some depth of understanding and technical aptitude and the ability, you know, product managers at Cloudflare collaborate really closely with engineering. And so having a certain level of depth and aptitude with the technology and the ability to kind of have those conversations with engineering is critical. That's not true necessarily everywhere. The interesting thing also about product management at Cloudflare is the other side of this, the other thing that folks need to be is really good storytellers. You know, a big part of what drives inspiration and innovation with the engineering team and with the design team and everybody is the ability to bring to life the problems we're trying to solve. But then also at Cloudflare, you know, product managers are the folks who are writing the blog posts, who are thinking about the positions, are thinking about the positioning, are thinking about the narrative of what we're doing and why we're doing it. And using that as a way to kind of inspire others to act and deliver, but it's also the ability to inspire and drive, you know, customers to be interested. So I think storytelling, and I actually think writing is a big part of what product managers do. Cool. So when we think about a good product manager and we think about a great product manager, what do you think defines that boundary? Customer orientation and kind of the kind of prioritization and decisiveness. Those two things, you know, the places where I see product managers get lost in struggle is when they lose sight of the customer and they lose sight of the opportunity. The other place where I see product managers struggle is when they kind of get stuck a little bit in almost analysis paralysis and they can't kind of crisply just make a call one way or another to kind of bring focus to the team to deliver. On the flip side, you know, the best product managers are ones who, you know, are very comfortable and happy spending time with customers who also really, the way I like to talk about it is they can tell you what their customers eat for breakfast. Like they know their customers really, really deeply, both on like a personal level, but then also really just have a good sense and good feel for them. And they're able to bring a lot of that energy and that understanding back into the organization to help people understand, like this is what we need to focus on. This is what we need to sort of shy away from. Cool. Very cool. Thank you. So switching topics a little bit. Jen, you were recently appointed to the board of directors of Freshworks just after the company's IPO in late September of this year. What does it mean to be part of a board of directors and what learnings from your own career do you bring to the board? So it's an honor and a privilege to be a member of the board at Freshworks and I'm thrilled. It's a great group. It's a great company. It's a great experience. I think for me, what I bring to the board, what I hope to continue to bring to the board, really kind of two things. One is just, as we were just talking about, sort of product orientation, providing kind of input and guidance to the organization as they continue to think through their product strategy and their growth strategy and their customer strategy and being a sounding board and a resource for the team and for the company as they continue to do that. So bringing kind of the diversity of experiences I have from servicing individuals who come with a credit card and buy a product to people who are buying product in other countries and using it in different ways to really that transition to service larger organizations and to launch new products. Kind of the sort of, I bring the sort of experience I've had and sort of the war stories in the videos. The other is, I often say there are lots of different types of product leaders and sort of my superpower as a product manager is really operationalizing and scaling and helping young organizations with tons of innovation really think about kind of how do you sequence that innovation? How do you find the right cadence? How do you structure the right roadmap? How do you find the right collaboration with engineering to get it built? But also how do you do that with go-to-market? And so working with young, innovative companies like Freshworks who are growing so quickly being a sounding board for some of that sort of operational and strategic growth as well. Awesome. Yeah. Now switching kind of topics again. So I know you're passionate about the environment and I know you were becoming, we're thinking about law and environmental law. So with your career today, like do you think that you've been able to bring that passion and match it with Cloudflare or even on Cloudflare? Yeah. So it's interesting. I think that I weave that passion in, in some ways that I think have been kind of powerful and unexpected for me. So one of the things that I got really into in high school was backpacking trips. And I did like NOLS courses and Outward Bound courses and I had the privilege to do those sort of longer term journeys and explorations. When I got to university, one of the things I did was lead backpacking trips for other students as part of sort of the onboarding and orientation experience. And it was a little bit like rafting, right? Being in the outdoors, diverse group of people thrown together. You have to get from point A to point B. Somebody's carrying the cheese, somebody's carrying the bread, somebody's carrying the oatmeal, somebody's carrying the tent stakes, somebody's carrying the tent. Like, how do you make this all work? How do you agree which way you're gonna go? How do you, and I think for me, those types of journeys were, I think very important to me in understanding how much I liked being a part of building teams, building teams of diverse people and finding ways to work together to accomplish something. On a more tactical level, I feel very fortunate in that my career has enabled me to live and work in San Francisco. It's a beautiful city. It has provided a really challenging kind of career environment where I've been able to sort of, there are lots of intellectual stimulation, lots of opportunities for professional growth, but it's also someplace that's beautiful. And I can kind of easily kind of find that work-life balance and easily get out and do the things that I'd love to do, whether it's going for a hike or going skiing or continuing to try to learn to surf, which I will do at some point in my life. Right now, I just swim with a surfboard, but I think it's also created an opportunity for me to have a little bit of that kind of balance. You know, Jen, I think you spent too much time falling off of rafts. I think your body's a little- On the rafts, stay off the raft. Yeah. Let's be consistent here, please. Wait, you're trying to tell me I'm supposed to stay on the surfboard? That's what I'm supposed to be doing? You know, it's unclear. Your body is a little disoriented at this point. It's a good point. I hadn't thought of that, but I'm going to fold that into my surfing now. Stay on the board. Stay on the board. Yeah. All right. One more question, Jen. So how has your gender played a role in your career trajectory? Sorry, struggled with that word. Yeah, no, I struggle with trajectory. So there you go. Like, it's, you know, I think it's, if I step back and I think about it, I think being a woman, I think in some ways, the societal expectations around sort of conversation and discourse and socialization, I think fed into a little bit of the customer orientation that I found. I think I've also been very privileged to grow up in this industry at a time when there were lots of other women who had come before me, who I think really had tough rows to hoe, as they often say, but provided phenomenal mentorship. I'm actually, it's funny, the story of how I got into product management was I was actually at a dinner party that a friend of mine was throwing and I was doing a marketing internship and I was hating it. And I sat down next to this woman who turns out was a director of product management at a place then called Macromedia. And we got chatting and I was like, oh yeah, I'm doing my internship, like not loving it, I really wanna do product. She's like, oh, well, I got an internship I can offer you. Like, I can't pay you much, but like, I would love your help. And really opened a door for me. And I think that, you know, I think that was my first kind of true, true, true product management job. I think there are many, many women who have created those opportunities for me, who've been great sounding boards and great resources. I also think that I'm lucky to be growing in my career at a time when people have come to understand and appreciate the power of diversity. And I think, you know, probably when I first entered the workforce, there was less of a focus on that. The notion of being different was a liability. I actually feel like culturally, we're getting to a place where being different is an asset. I think very specifically at Cloudflare, being different is like, that's right, that's what we're all about, right? And that like, we really value that diversity of opinion, the diversity of folks within the organization. I think that like, I think in many ways, I kind of found my home at Cloudflare as I think about my career progression in that I feel very welcome, I feel very empowered, I feel very heard and I feel very seen. And all of that is in a positive way for kind of just who I am, so. You know, I think when you mentioned women helping women, that really resonated with me. And, you know, I hope that at some point in my own career that I can also provide that to other women. I think that's, you know, a really important thing as we move forward. And then you also mentioned that Cloudflare really, you know, loves diversity and really brings it forward. And I think that is a key part of our culture. And I'm, you know, that's something that gets me out of bed every day to come work here, so. It's interesting, you know, I can't remember exactly how he says it, but one of the things Matthew, our co-founder and CEO often says is that, you know, none of us are kind of, you know, none of us sort of fit the type, none of us really fit the mold. And I think we're all like, yeah, that's right. We don't fit the mold. And that's a big part of what I think enables us to be as innovative as we are. You know, we come at it, we all come at it from a different angle. And I think that's where you see that virtuous cycle of diversity, of thought, diversity of who we are, sort of the freedom and support to be who we are, I think is a huge part of what helps facilitate the innovation within the organization. And like, I'm just, I'm thrilled to be a part of it. And I take the responsibility of, you know, continuing to drive diversity and growth within the organization for the team here very seriously. Definitely. Well, Jen, any last thoughts? No, no last thoughts from me. Any last thoughts from you? You know, I'm gonna try and stay on the raft. Stay on the raft. I think that's, I'm gonna make a little post-it. I'm gonna put that on my desk. Stay on the raft. Of course. Yeah, good. Well, thank you so much for doing this. It was a pleasure. You know, we get a chance to work together all the time, but we don't really get a chance as much to chat. And so it's been great to spend some time with you. We don't, you too. Thank you so much, Jen. We, I mean, I know everybody in the audience really enjoyed you sharing your experiences and advice today. And I know that I really did. So thank you so much, Jen. And before we wrap up, I do wanna note for all of those of you watching, the Cloudflare product team is growing. So if you're interested in joining Cloudflare, please check out our career page on Cloudflare .com. Oh my God, I totally dropped the ball on that. Thank you. Yes, we're actively hiring. Join us now. Come work with me and Corinne. You can be part of the conversation. Awesome. Thank you, Jen. Awesome. Bye. Bye, y'all. Hi. Hi. Hi. Hi. Hi. Hi. Hi. Hi. Hi.