Unfiltered: #ChooseToChallenge with Ciara Peter

Hi, I'm Jen Taylor, Chief Product Officer at Cloudflare, and I'm thrilled to be doing another episode of our Choose to Challenge Unfiltered series here. As with all of these, Ciara and I are going to engage in a conversation, but we intend for this to be a broader conversation. So you'll see at the bottom of your screen, please feel free to send any any questions or comments in and we'll try to address them in the flow. But stepping back, welcome and hello and so happy to have people here on Cloudflare TV. We're excited about this special series that we've been doing this month celebrating WomenFlare, which is our internal resource group focused on women and their allies, has sponsored and put together this series of programming. And I love it because it gives me an opportunity to get to know and speak with some phenomenal women. And I'm joined today by one of those very women. I'm joined by Ciara Peter. Ciara, can you introduce yourselves and tell us a little bit about you and the amazing things that you do? Yeah, well, Jen, thank you so much for the kind words. Hey, everyone. So I'm Ciara. I am the VP of Product Design at GameSite. I have spent the last 12 or 13 years in enterprise software and I started as a designer and then I became a product manager and a product leader. I've worked at startups of zero people, no product, no funding, you know, to really large companies. And so I experienced a lot of great things, a lot of interesting things in my career, and I'm excited to share those with you all. And now you're working on a phenomenal product, which I love. I think the world of GameSite, it's a great product and great design. So massive kudos there. Yeah. Okay. So I think of these as my conversations with superheroes, and I think all good superhero conversations start with the origin story. So Ciara, just like, let's start at the very beginning. Tell us a bit about you and your younger self and like, what were some of your first big dreams? Yeah. So I'm going to give you a really uninspiring answer to sort of lead to some thinking. So my parents were professional ballet dancers. They were actually in San Francisco ballet. So they were principal dancers in like the early 1980s. They traveled the world and then they opened a dance studio. What I realized pretty early on is that my dream was not to be a ballet dancer. I just did, I, you know, I liked it, but it wasn't the thing. And so that was kind of all I knew. My parents, they didn't go to college, they didn't have these like Silicon Valley careers. And to be honest, until my early twenties, I didn't have like career, any career aspirations. I was kind of, I kind of thought I'll figure it out. I'll figure it out. And then I was starting to worry because I wasn't, I wasn't figuring it out. So the reason I bring this up is because I think there's a misconception that you have to know really early on what you want to do. I mean, especially, I grew up in the eighties, but kids now I'm hearing like you're preparing for college in the third grade. And I don't know what that is like personally, but I guess it's just to say that, you know, you can change course at any time and sort of decide what you want to do. And that's what I did. Well, I think that's so important. Right. Cause I think there is this myth of this like lightning bolt moment. Like it's like, and again, back to the superhero, like the beginning of Superman, where like Shazam, like the light, the ice thing comes out and Superman comes out and there he is as a baby and he's fully formed as a superhero. I think, you know, we all read these, these biographies, these autobiographies of these leaders that we admire, you know, and that hindsight is 2020. And I think people sometimes forget that there's a lot of experimentation and trying things and, and kind of trying things and maybe having them not go the way you want or trying them and being like, oh, well, that totally took me some different direction. Yeah. So, so, you know, and I, you know, I can kind of also relate, right. I didn't wake up at the age of five and be like, oh, I really want to be a product manager at a technology company. Like what I do now actually didn't exist when I was a kid, you know? Yeah. So, so tell me a little bit then about like, how did you get into product design? How did that, you know, how, how did that journey go for you? Yeah. So when I was in college still like kind of at the end of college, still not really knowing what was going on, I actually was bartending to pay for school and I really, I was, I was good at it and it was the first time, you know, making a little cash and I got an opportunity to have a bar night to myself that I could promote and, you know, make it my thing. And the first thing I thought is, well, I have to, I have to make some flyers. I need to get this on website. I need to get this on email. And I didn't know how to do that. So I bought a Photoshop CD. I bought a HTML for dummies book. I had all these things at my home and I just started tinkering with them. And that's when the light bulb went off. I was like, oh, I really like this. I'm pretty good at it. Or I'm at least catching on pretty quickly. And I actually went to my manager that weekend. He was about to offer me a management spot. And I said, actually, I'm moving home. I'm moving home next week. And I just decided on the spot. So I went, I moved back here to the Bay Area and I decided to go to art school. So I did a master's at the Academy of Art. And again, during school, I was kind of helping people with different projects. For example, friends that were doing fundraisers, I would do their graphic design or build a website. And it happened that one of them worked in tech. He worked at Salesforce. And he said, hey, we have this job on our team. It's a designer. I know you do design because I had done it for his fundraiser. Do you want to interview? And I went and interviewed and the rest was kind of history. I ended up taking a contract job. And then within about a month and a half, I became a full -time employee. And I've been working in this industry ever since. It's interesting how those moments of kind of serendipity and sort of tinkering kind of can take you down those paths. Yeah, exactly. I think it's totally unexpected. I still say that it was all an accident, but I'm fortunate. And I think maybe it's not always an accident. Maybe there's something going on in the subconscious the whole time. But it's an interesting thing because you always hear don't work for free. And I recommend most people don't work for free. But that was kind of my foot in the door not having a background was doing the extra work. And I think the way that that applies is how I became a product manager. I just decided I was a designer and I saw myself instead of drawing pictures, I was writing words on the whiteboard. I loved organizing and plotting out the whole projects. And I realized that I wanted to be a PM. And I kind of just found an opportunity. I found an opportunity at this startup that was a very undefined job, just do a little product and design stuff and we'll figure it out. And I just kind of said, I'm going to take the risk and go there and put it on myself to do it well and learn it and do it right. And yeah, that's how that happened. I think it's so interesting. It's funny that you talk about not working for free and that being advice you got. It's funny, the way I got into product, I was in grad school and I was like, I want to do product management. But it was right after the dot -com bubble blew up and there were tumbleweeds rolling down the streets of San Francisco and nobody was hiring anyone. And I was at a dinner party and I sat next to this woman who's like, well, she led product at a tech company. She's like, well, I have this interesting project. I would love to offer it to you, but I can't pay you anything. And I'm like, I'll take it. And the rest was kind of the beginning of it all. That's amazing, Jen, because I don't hear a lot of people saying that and talking about that. So I'm glad to hear that coming from you. Yeah, I think it's just like the other thing I've also found, and it sounds like you had similar experiences, where sometimes it's just, I found that some of my most interesting roles and most interesting opportunities have been a function of the people I've known and the people who are sort of mentoring and helping me and kind of coaching me along, being sort of like, hey, I hear you do this thing. How about trying this thing? And then kind of having the courage to go for the interview or go for the conversation or give it a try. I mean, for you, the bold jump from product design to product management, being like, I'm just going to figure it out. That's bold. Yeah, it is bold, scary. But I'm sure you have taken similarly scary challenges sometimes. Yeah, well, and I find that like in those challenges for me personally, like the biggest barrier often is myself. Like I think that it's especially, you know, I wrestle with this kind of constant cycle of imposter syndrome, you know, and it's in these moments where you take on these new challenges where I'm like, I don't really know what I'm doing. And it's this sort of like, and everybody's going to figure out, I don't know what I'm doing. And then we kind of figure it out. But yeah, I agree. Like, I think my biggest, my biggest doubter is myself. Yeah. And that's when it's important to remember, you know, sometimes people haven't talked to in a long time because I've worked in so many, so many companies now and like had so many different roles. I was, I was probably kind of different at the beginning of my career. I was, you know, this kind of speaks to imposter syndrome at the beginning, at the beginning of my career, I was kind of like under the impression. And I think rightfully so that I had to be loud and bold and get in there and like get noticed and, and, and fight for that. Interestingly, like getting into leadership roles, especially it's kind of that, like, I think it's that like senior director arc. Yeah. When you, for me, like, I didn't realize that I was getting noticed. So all these years I've been trying to do this thing. Then you get the acknowledgement with like a title or whatever, and responsibilities. You didn't realize I was getting noticed. And so I would still take this really bold approach and then others, you know, sometimes like I might say something in a meeting and someone would say, you know, the, the, that was kind of like aggressive the way that you said that, you know, looked, I guess that's the interesting thing about imposter syndrome is I think that women can tend to remain feeling like an imposter, even once they've gotten to that other role. And then imposter syndrome is really interesting because it takes some of these moments of realization, like, oh, like, so, okay. Yeah. No, I, I understand. It takes some of these moments of realization to realize the differences between imposter syndrome as a leader and imposter syndrome as a leader. I'm like, no, I'm just, I'm just cool. Like, I'm just, I'm just me, you know, it's not a big, it's not a big deal. Like my feedback is just, you know, my feedback is just take it, take it for whatever it is. But, you know, when you, when, when you are like a CPO or like a head of design and you give feedback people take it seriously, they reroute, they, they, you know, tend to act on it. And sometimes it's not meant for that way. So I think that that is an interesting thing that I don't, I don't think a lot of women talk about. It's interesting to think about, like, you know, I think especially when I was younger, I spent a lot of time thinking about how I kind of showed up. And then I sort of grew in my career and I sort of carried, it's kind of like, I still, I kind of joke sometimes. I'm like, I'm a kindergartner with a credit card, right? Like that's, that's, that's like my internal sort of image sometimes of myself. And it's hard to remember sometimes that that's maybe not how the rest of the room is holding and seeing me as a leader. And yeah, the way I think a lot about sort of the thing that you're touching on is sort of like, it's almost like you have to be really thoughtful as a leader about sort of almost like the volume. It's not the physical volume of your voice, but it's the volume at which the people around you sort of hear your comment and your feedback relative to the other voices in the room. Yeah. Yeah. You know, one of the things I've been thinking a lot about as a leader is sort of how do I use my role as a leader in an organization to, to bring attention and draw attention and, and sort of bring volume to the other voices in the room. And I'm kind of curious if, if kind of within the context of your organization and the work that you do, you know, if that's something you're thinking about and, and kind of how you might approach it. Yeah. So I'll share, I will share a story, which is a little bit, which I think is, is related. But a very interesting thing that I kind of like kept to myself for many years. So after I left a job so after I left job at a startup, I took a couple months off to kind of figure things out. And it was really interesting because I'd had pretty amazing male, all male managers and pretty, pretty good ones up until that point that didn't make me feel like a woman in tech. Yeah. I didn't feel like, but I thought while I'm doing this and I'm talking to so many companies, maybe I'll, maybe I'll take notes. And of course, as a product person, I will AB test things. I will create a spreadsheet and I will create a funnel of what I complete these interview processes. And, and I would, unless it was like a really bad first interview, I would continue, I would continue on partially a lot of, a lot of it for research, obviously, some of the jobs I wanted, but just to learn. And what I found, I talked to over 30 companies in this period of time which is interesting in itself. Cause I wasn't expecting that leaving company without a job. I didn't know that. Oh, okay. If you're a woman in me, I don't, okay. If you are a woman in leadership or a person in leadership, this takes a while, but the biggest thing that I learned here was in terms of how far I got in the interview process. If there was at least one woman on the panel, I got to an average of 90% or an offer. If there were no women on the panel, I got to an average of 35% of the way through. Yeah. And I just got chills saying that. Cause I don't think I've ever said that in a public forum, but yeah, the data is there. It's very, it's very clear. And so back to your question of like how to amplify voices. Yeah. A lot of the time when we talk about diversity and equality, we talk about the recruit, you know, recruiting pipeline. If anyone or if any of us are in management, you know, how do we get like great candidates of all different backgrounds into the pipeline to bring into the company? How do we have amazing ERGs? But representation on the other side is extremely important. So that's something that I've been pushing for ever since that experience is making sure that there are diverse voices represented on the actual interview panel of every, every candidate coming into the, coming into every, like every, sorry, interview and every candidate coming into a company. Yeah. Yeah. That was kind of astounding to me. That's amazing. That's amazing. And, and how the organizations respond to this is, is this, is this something where you, you feel like you sort of bring this to the table and people like lean into it and are fired up on it or is it, is it been, are there, are there places that have been, are there aspects of it that have been challenging and what are some of the challenges been? I don't, I don't think, unless I show someone the spreadsheets or like I really share kind of details of this story. Yeah. It's hard for them to understand. Yeah. I don't, I'm not saying that people don't believe me. I think you do, but I think people in like recruiting and HR organizations really are mostly focused on the pipeline because that's what, that's what people talk about. So if I do recommend it, at least for my roles and at least for, you know, the adjacent roles of people working in my organization, I have been successful in, in, in, in bringing that on. Yeah. But you know, it takes a lot of, it's like a rule number one of marketing. But I, but I like to apply it to many things is repetition, repetition, repetition. It's like people who, so Jen, you spoke at our, at our Gainsight conference for product. And so, you know, I'm, I'm sure you've done your share of speaking. I have tried to do some speaking in the last, you know, five years and I've gotten to do some keynotes and, and great things, but I was pretty scared of that and definitely have gotten more comfortable, gotten more comfortable over time. Yeah. But, oh my gosh, I lost my train of thought. I'm so sorry. See, I was, started talking about public speaking and then I, like, I don't want to, I don't want to, I don't want to go there. Yeah. And then I completely lost my train of thought. So I'm so sorry, but I'm not embarrassed because, you know, you gotta embarrass, you gotta embarrass, oh yes, I remember. Okay. So repetition, you see these people that are doing all this public speaking and you're like, oh my gosh, how do they remember that? All that stuff. They're so like smart and amazing. And yes, usually they're smart and amazing by the time they get to a point where they can do public speaking. But what I also realized is that most people who go on like a tour and they do, maybe they do five speaking events per year. They're mostly saying the same thing, but mostly giving us pretty similar presentation with some tweaks each time. Yeah. So that was like a great lesson in repetition that I started to do. And like, that was a, that was a thing that helped me to get a lot more comfortable is I'm not trying to memorize really much. Yeah. My first, the first like product presentation I gave at a keynote, I was new to the company. I was a month in and I had a seven minute spot. I'm like seven minutes, nothing. And I like tried to remember every word because I didn't know the product. And that was like anything you're seeing on stage and you're like, I forgot the word. Yeah. Yeah. So that was like, that's something that I have that's something that I have been able to modify and like get a lot more comfortable with over time. I sometimes people are like, wow, you know, you did such a great job with public speaking. I'm like, if only I could like show you a video of like my first big public product kind of keynote spot, like I was a brand spanking new product manager. I've been doing it for like six months. They put me up on stage. I'm like, oh, you know, I'll wing it. I'll figure it out when I get on stage. Like, it's gotta be easy. It looks, oh my God, like bombed big time. And there's really nothing like bombing to make you feel like, okay, that's never going to happen again. And then it's just been, for me, it's, it takes practice. It takes practice. It takes work. Like people forget that like as a leader and as somebody in an organization, like you're like a duck, you're constantly paddling under the water, you know, to kind of, kind of make the things happen that look elegant on the surface. Yeah. Yeah. Agreed. Yeah. Okay. So hold on a second. So, so last we left you on your adventure, you, you had transitioned from, from product design and product management. You you've taken that leap. Now talk to me a little bit about the leap then for you from being an individual contributor to really, you know, being a VP of product design at a very successful company. Talk to me about that journey into leadership. What was that like for you? And what are some of the things that helped you along the way? Yeah. So I think the journey and leadership, the, the, the biggest learning was well, actually doing it at a startup. So I'd had like a very, a lightweight management role at Salesforce. I managed a team of about five people. But that wasn't, it wasn't scary for me. But like going into product and becoming a product, like head product at the same time was really scary, but that's what I wanted. So I just, half of it was like, I had observed, I'd always reported to product managers and so I'd observed them and I knew like, okay, I knew for about a year before that, that that's what I wanted to do. So I was paying a lot of attention. So I was able to go in and I took this because there was just two young, brilliant engineers, but they weren't like organized or operationally they didn't care about operational things. So I just started by doing what I could. So first, what I first, what I could do is it was a product that I knew the space. So I put together a presentation, just how I would explain a strategy that I was trying to, you know, convey. They agreed with it because I, because I did a lot of research. I asked the right, I asked all the right questions. I asked stupid questions, you know, in my research process, because that's what you need in order to create a good presentation. So, so that's why I created this vision thing. I didn't really know what that was. And then when I got on board, I saw the engineers working and they were having like, they were just kind of working, but, and we had a little bit of a plan, but we didn't have a roadmap. So I just went in and I said, well, let me start. I'm just gonna start kicking the tires and Jira. And I just started creating the sprints and looking for opportunities to do things that others didn't want to do, like that were, you know, oriented towards that role. So we actually got our series A funding on my second week. And I was like, okay, I was like, I'd like to hire a product manager and a designer. And like, I just did it. And we grew from, we, we grew to a team about 15 people on the, you know, on the product side with designers. I had a head of design that reported to me. I had product managers. And I think like, one of the things that made it most successful is realizing early on that just because you don't have a certain experience, like actually one of my PMs, he was, he was more experienced than I was. He was kind of more senior than me, but it's about like, what's our goal? Why would you want to come to this company? Like, do we have those shared goals? And the shared goals, him was like, he'd been working in the corporate world for a long time. It was the first time going to an early stage startup. And I said, Hey, you have a really great opportunity here to do a lot of different things, work at a startup. And he, he agreed with that. So I brought what I could to the table. We learned together. And that was it. It's not about like, it's not about being better or necessarily more experienced than people. It's about figuring out how all of your, all of your goals work together and working hard and being, I mean, for me, like if I made a mistake, I was, I would usually like say, Hey guys, I made this mistake. Like, what do you think? Let's talk about it and same with them. And so that's how we learn. That's how we learn together. Yeah. No, I think it's the importance of a team is, is critical. And like, you know, I think about like my journey into leadership and even just the, the, the role I have now, you know, I am where I am today because a lot of people took the opportunity to sort of mentor and advise me and give me advice. And, and, and I felt really supported. I felt like I had, I felt like I had a team, right. And, and now, you know, I I'm so honored by the team I have today at CloudFlower. I had the opportunity to work with some just phenomenally brilliant people and I'm learning from them constantly. And it's so fun. It is so fun. I learn something from my team every day. Yeah. Yeah. Yeah. So, you know, stepping back, you know, one of the things people talk a lot about is, is really this notion of mentorship and allyship. You know, how has that been a factor into the work that, you know, kind of your development as a leader, you know, or the, the way you approach being a leader and mentoring others? And I think like mentoring, well, mentoring is, is interesting because women, a lot of the time are told like, find a mentor, you know, choose a mentor. And sometimes, like I've been in situations where I've kind of been placed with someone that I am mentoring and like, you know, like it doesn't click right away. And so I guess what I, I guess what I like to do is find people, like find people who I think have potential and just talk to them about my really like early days, really stuff, like just kind of like embarrassing things. And I'm like, this is how, or like, this is how you do it, or this is how you, this is how you, you know, maybe you want to, maybe you want to think about like how you talk to certain people or just tell them they're doing like sometimes just telling people they're doing a great job. Is it like, I don't, I mean, I don't consciously think about mentorship, but I think, but I do it. Yeah. And the way that, the way that I try to do it is just by sharing everything I possibly can with people who are, who are early on, like, yeah. In a transparent way. Yeah. I can't believe the time has flown by. Like, I feel like I could keep talking to you for another like two hours. This has been such a fun conversation. Thank you so much for taking the time to talk to us about your, your path to leadership and your approach. And it's been a pleasure. Yes. Thank you so much.