Career Growth Advice from Catherine Wong, Entrata COO & CPO | From Engineer to Culture-Builder Leading with Empathy at Scale

2B Bolder Podcast – Episode 148
Featuring Catherine Wong

Episode Title: #148 From Engineer To COO: Catherine Wong On Leading With Empathy And Scale

Host: Mary Killelea
Guest: Catherine Wong



Mary Killelea: Hi there, my name is Mary Killelea. Welcome to the 2B Bolder Podcast, providing career insights for the next generation of women in business and tech. 2B Bolder was created out of my love for technology and marketing, my desire to bring together like-minded women, and my hope to be a great role model and source of inspiration for my two girls and other young women like you, encouraging you guys to show up and to be bolder and to know that anything you guys dream of is totally possible. So sit back, relax, and enjoy the conversation.

If there's one thing that becomes clear when you look at the careers of truly impactful tech leaders, it's that they don't just build products, they build cultures. They build systems and they build people. Today's guest is an extraordinary example of this type of leadership. Catherine Wong is the chief operating officer and chief product officer at Entrata, a company serving more than 20,000 apartment communities with a platform that simplifies and transforms property operations. Before Entrata, she served as the COO and EVP of engineering at Domo, and earlier in her career held roles at Omniture and Adobe, where she helped integrate teams following Adobe's 1.8 billion acquisition Omniture. She's led global teams, guided product visions at scale, contributed to MA strategy, and she's also holds multiple patents spanning data segmentation, data visualization, and SaaS data collection. Catherine is also a longtime advocate for women in technology. She's an original member of the Women in Tech Council Advisory Board and currently serves on the board of Women Tech Council, Amplitude and Human Interest. Catherine, thank you so much for being here. I have been looking forward to this conversation. And it's fun to like having this, you know. I know we're on Zoom and people can't see us, but it's so great to connect with you in person and in audio.

Catherine Wong: Likewise. Thanks so much for having me. I really appreciate it.

Mary Killelea: Awesome. Okay, so you currently serve as both the COO and Chief Product Officer at Entrada. Two roles that require vision, alignment, and operational excellence. How do you describe your work today and what energizes you most about the role and where you are in your career?

Catherine Wong: I feel incredibly lucky to have, you know, this dual role where I get to focus on the product vision and strategy, of course, which really enables what you described here at Andrata. You know, we're building this operating system for real estate and multifamily. And at the same time, it's such a team sport, which I love about, you know, product and operations because we need diverse perspectives. We have the opportunity to really pull in a variety of talent sets, experience levels to achieve these goals of delivering great products, creating fantastic experiences for our customers, right? And operationally being really hopefully excellent, right, in how we're doing all of this.

Mary Killelea: Your career spans startups, acquisitions, large-scale enterprise environments, and hypergrowth phases. Walk us through your journey and talk about some of the pivotal moments that shaped you as a leader. So let's start with that walk down memory lane kind of thing.

Catherine Wong: Yeah. So the origins, you know, my origin story, I guess, is classic nerd. I started with a degree in computer science and worked as a software engineer. Graduated at exactly the wrong time in some sense, just as the bubble was bursting, the internet bubble. And it was, I'm so grateful for it, to be honest, because it really helped me learn very quickly what it was like to work very lean and to pull together with a small team. So I worked as a software engineer, then did architecture, and got to wear a bunch of different hats because I was at a small company and I loved that. I loved the opportunity to raise my hand and say yes to things that I felt scared to do, but definitely had a support system around me. And that really informed a lot of what I was able to do later in my career. So, you know, Omnitron went public and then we were highly acquisitive. So then I got to focus on MA, which was such a wonderful experience to get to see all sorts of different companies at different sizes and stages. And I focused on the technical integration there. And then the acquisition by Adobe was yet another wonderful chapter. And there I really focused on leading engineering. And I will say I was a very reluctant manager in that I had been an individual contributor for so many years, and the opportunity to then lead teams that came about because I had a fantastic mentor, really sponsor who pushed me into it and said, you can do this. I, you know, I promise. So I got to, you know, do that at Adobe, which is a wonderful company. They helped me learn so much about what it meant to lead it on a global scale. And then I went to Domo where I got to run engineering and then product. We took it out of stealth mode. So I got to apply all the lessons that I learned in that first portion of my career, right? And apply those lessons at Domo and work with just again a phenomenal team. And now most recently in Entrada. And I would say one of the through lines through you know those experiences is the fantastic people that I've gotten to work with. I really do, I cannot understate how important it is to surround yourself with people who make you better, who you know, support you and create an environment where you can really thrive and grow. And those environments do exist out there. And I'm just so grateful for that.

Mary Killelea: It sounds like such an incredible journey. And I don't know if you could have been, you know, I don't know, your 10-year-old self or or or 21-year-old self. Could you ever imagine the path going that way? No, I had no idea.

Catherine Wong: No, I had no idea. And I think part of, you know, what I talk about a lot is it's hard to become what you can't see. I feel really lucky and fortunate almost because I had no idea that these jobs even existed. I didn't know what it meant to be in business or, you know, in aspects of this world. I'm the daughter of immigrants and I'm so grateful for the lessons that they helped instill in me around, you know, hard work and taking every opportunity that you can and so forth. But I would say to answer your question, you know, like the 10-year-old me had no idea, even the 20-year-old me really didn't know. And I think, you know, what I love about this podcast and the work that you're doing is I just think it's helpful. I learn by seeing other journeys, you know, and other experiences. And it really helps to expand my mind as to what is out there and what the opportunities are.

Mary Killelea: I love that because I agree with you completely. I think we can continue to learn from each other and inspire each other.

Catherine Wong: Yes.

Mary Killelea: You've advanced in senior leadership, obviously, in industries and environments that historically might have been more male-dominated. What do you attribute your mobility upwards and mindset and habits? Like you, you got where you were today because of obviously hard work. But what else was a driving factor for you in a world where there weren't many women?

Catherine Wong: Yeah, I think some of it was really coming to embrace and understand that me being different was actually more than okay, that it was pretty great. But I will say I didn't start off thinking that way. I thought because I felt different, I looked different, you know, sounded different. At first, I'll say I probably tried to kind of mask that. And I tried to fit in. And, luckily I was surrounded by folks and had some mentors who really tried to help me understand like, hey, your diversity and in your diverse perspective is actually going to drive a better outcome. And I do believe that the business outcome is stronger when we have different voices. It can be different generations, it can be different, you know, backgrounds, different walks of life, different disciplines that we each studied in college. But I do think it leads to a better outcome. And so I think a lot of my leadership journey was, you know, grounded in starting to embrace that my voice was going to be different and that it was actually helpful to vocalize that instead of trying to dampen it down, right? To do that. I think the other thing that really helps, and I see this with up-and-coming leaders as well, is when folks are really able to communicate well and build relationships well. This is a team sport. This and it works better, right? If you have a culture and an environment that you promote where people feel like they can be open, they can be transparent, they can be vulnerable. That's when you know great ideas really come to the surface. And I think we all have an opportunity to, you know, speak up and really advocate for that kind of a culture and environment.

Mary Killelea: I absolutely 100% agree with you. I think diversity just makes business better, makes people better, makes you know the community better. You've led teams across engineering, product, integration, and architecture and operations. How do you think having been exposed to all those different elements of the business have helped you as a leader to scale technology and people?

Catherine Wong: I love this question because I think, you know, so much of it is, you know, reflected in a lot of what we use as a product philosophy, which is we try to develop empathy, right, for the audience and for or the customer or the user, you know, and when we get to sit in different seats, we actually become very empathetic. You know, I remember being an engineer and, you know, getting requirement documents from the product manager and thinking, well, you know, I would love for it to be more specific or or whatever it may be. And then when I finally sat in that seat as a product manager and stared at that blank, blank sheet of paper, I developed empathy really quickly for, oh, that's hard. We're sitting here and you know, now I've got to, you know, kind of look at it from this perspective. And I think when we're able to do that, it really helps strengthen us. You know, Cheryl Sandberg in her book, she referenced the, you know, it's not a ladder, it's a jungle gym. And I think there's strength in that. And, that also helped me change my mindset around and instead of thinking of this as, you know, going to move up and up and up, really embracing breath and a, you know, different experiences, which give you the empathy to be able to then connect. And then as a leader, you start to realize over time, it's really about hearts and minds and connecting with people and helping, you know, align on a vision and listening and synthesizing, right? So all of these skill sets are just so foundational to it. And so I think that, you know, I've been grateful for just the opportunity to sit in so many different seats.

Mary Killelea: I love that perspective because I remember in my corporate career, I did make a couple couple pivots where it seemed lateral, but I struggled with that. Like, am I sabotaging my career? But at the end of the day, the knowledge I gained from that and I could apply that to my next position made me more valuable to the company.

Catherine Wong: 100%. And I think that's kind of a misconception sometimes that we may have, or we may to your point, I've had that moment too where I felt, wait, am I doing something kind of wrong? Or, you know, am I taking a step back? But in the end, it actually, you know, wound up strengthening perspective. So I love hearing that.

Mary Killelea: You've spoken a lot about the cultures and high-performing cultures. How do you intentionally build cultures? What advice do you have for other women out there who have teams and are looking to foster a really healthy, productive culture?

Catherine Wong: Yeah, I think there's so much that goes to this. You know, we could talk for hours, but I think a couple of things that I've learned is that what we reward or what we recognize is going to be a strong signal to folks, you know. And then I think the other aspect of culture that I've learned just from watching being, you know, managed by a lot of great folks as well is when we pull from the voices that maybe we don't always hear from, maybe they're not the loudest in the room, maybe they're not the most, you know, kind of vocal or forward. I think that also influences the dynamic of the team and the culture that you're setting. And it requires mindfulness and thoughtfulness. But I've been fortunate to, you know, learn from folks like Adam Edmonds and others who do that, they exercise that. And that creates a culture where everyone wants to be excellent because there's transparency and there's accountability, and there's also high trust because folks know that you know they can be vulnerable and it's okay to make a mistake and to to move forward. And they can really bring their whole selves, right, to the opportunity and the task at hand or the project, whatever that may be.

Mary Killelea: Yeah, I know I love that perspective, and especially coming from you as a leader, because I there's a lot of people who are introverts in business who, you know, unless they're called upon or feel like there's a safety net, they will not contribute, even though they have such intelligent thoughts and additions that could help the business grow. So I love the fact that you call that out.

Catherine Wong: Well, and I got to benefit from that, right? Like I had a mentor whose main feedback to me was louder. Because I was quiet, right? And I would just kind of hang back and think, well, everyone's probably already thinking this. So, you know, I or I don't want to kind of disrupt the flow. And I appreciated that he said it louder.

Mary Killelea: Yeah, I love that. Okay, so there's a lot of anxiety right now in the world. But let's talk about careers and mid-career professionals, especially women with layoffs, restructuring, fast-moving technology shifts. Where do you see the job market going and how can women future-proof themselves when it feels like everyone is literally replaceable right now?

Catherine Wong: There's a lot of change, right, in the air, for sure. One of the things that I love is I do think, you know, AI and all of the new techniques and tooling is something to embrace. And I think that when we're willing to reimagine what we can do with the technology and with the tooling, you know, I think that's going to enable a lot of, you know, ongoing success because that's part of what we're using. But the core principles of what we do as leaders are still the same, right? The core, the core principles are still we are trying to achieve this goal as a team or a group. We have to have clarity around what that is. I think it's more than that, you know, particularly in tech, we're re-evaluating, right? We may have new tools at our disposal and new techniques that we can employ with those tools and technology. But I think really as leaders, staying focused on what's a value, what's the business outcome that we're trying to drive to, and then really embracing the new technologies is something that I'm hoping that you know everyone's leaning into and not afraid of. I think if you lean into it, that's a strong posture to take.

Mary Killelea: Yeah, no, I totally agree with you on like the woman out there listening who's saying, what's one skill that I could focus on to make me more marketable to a company like yours? Would it be AI-like proficiency? Proficiency. Yeah. So would it be best to select something in AI and be proficient in that? Or would it be better to get kind of smart, like a wide range of what's happening in the world in AI?

Catherine Wong: And I know that's broad, but yeah, I mean, I think a lot of it depends on what kind of what you want, you know, from a career perspective. So I think it's a great question that you're asking. I think, you know, if you have a certain role or domain that you're really passionate about, then I think, you know, making sure that you understand and have that proficiency and aid AI there. If you're more open to and you're looking at just general leadership strengthening, you know, then I think maybe broad could work too. But I would just say having curiosity about it and not being afraid of it, but just being curious and asking the question and kind of leaning into it is probably the biggest, and curiosity is a skill, you know, it is exercising that. And in some cases, I know, I've had to unlearn how I've done part of my role and learn a new way to do it. And it's okay, you know, it's actually kind of fun, it's invigorating.

Mary Killelea: I love that you called curiosity a skill because not many people call that out like that. And I think when you put it in that perspective, it instantly is like, okay, that makes sense to me. Let me build that muscle.

Catherine Wong: Yes. And it can feel a little bit, you know, you're kind of venturing into the unknown. And there's things where you're not maybe the expert right now in it. That's why I think it is a bit of a skill set that we have to practice sometimes.

Nary Killelea: Many of our listeners struggle with being seen, even when they're very highly competent. What advice do you have for women who want to be more visible, more respected, and more confident in their leadership voice?

Catherine Wong: Practice. I think just as many at bats as you can get on various aspects of that. And, you know, whether it is raising your hand on a different project or, you know, seeing if you can be the one to share the update or, you know, whatever it may be for your role or environment. But I think the more practice we get naturally, the, you know, of course, the better we're gonna get at it. And, I think the other thing to do is be open to asking for feedback. Feedback. And you know, I think it's hard sometimes to really push. Sometimes in my career, I would ask someone for feedback after a meeting, let's say a big meeting, and say, hey, how do you think that went? And you know, they might say, Oh, it's great. But to actually say, wait, pause. No, give me real feedback. What did I do well and what could I have done better? And I think if you really do, you know, kindly open yourself up to that, it's really helpful because sometimes we just, you know, we need that that sponsor, that mentor, or that person on the side to give us the perspective that we just, you know, need in order to amplify our voice.

Mary Killelea: Yeah, I know that's great advice. When you're operating at scale, decisions are obviously at much higher stakes. How do you make decisions where the answers aren't super clear? How do you build confidence in ambiguity, which the world is living in ambiguity right now? So I think that's important for a lot of the women out there to feel confident in making decisions and ambiguity related to business. What's your advice on that?

Catherine Wong: So I think, you know, definitely I rely very heavily on my team, and it can be my peers, it could be the, you know, folks within the organization. Because I think if you take it on as like, hey, I'm gonna make this in a vacuum, that's hard, that is lonely, and that feels probably pretty anxiety inducing. But really making sure that you have the data and then you're enlisting actively, you know, feedback and input on, you know, what am I not seeing? Where are the corners that I'm not necessarily looking at or looking around? I think that really can help in times of ambiguity. The other thing that I think is helpful is if you promote a culture of agility. Because, right, in some cases, you because of the ambiguity in our world today, what we may have thought was the plan a year ago is different, right? We have to adjust and we have to adapt. And so if we are kind of comfortable as a culture in being agile and quick, and you know, then I think it also really facilitates that speed balanced with, hey, with more information comes, you know, better decisions. So as we're constantly getting that signal and that input and we're actively listening, then we can adjust.

Mary Killelea: I love that. You've mentioned in our conversation that you had mentors and sponsors throughout your career. How did you build those relationships?

Catherine Wong: I think I have been fortunate to work with a lot of them, you know, and that is really helpful because they get to see you in action and they get to kind of, you know, watch along the way as you're leading various projects or as roles become available. And then in other cases, I think, you know, as your network expands, you get to, I think, pick up on a lot of folks who can be sounding boards for you. I always say I learn from everyone. It doesn't matter where in the org they are or, you know, kind of when they joined. I think there's just always a mindset of, you know, let me learn. And it's pretty magical when you interact with everyone that way.

Mary Killelea: I love talking to leaders like you who actually believe that and have that work ethic because I think that's so invaluable today to the people coming up, to your peers. I mean, it's just so invaluable for the business in general. So thank you for that.

Catherine Wong: Well, it is, you know, and I think we're seeing a newer, a new generation, right, of workers come up. And so I'm highly curious because, and I have to ask questions, I have to understand. You know, what do you see? How do you see, you know, the opportunity? Our customers, right? And all of us, if we're building some sort of product, you know, there are new people coming online using what we built. So it's ever changing. It's what I think is so fun about tech. Yeah.

Mary Killelea: Obviously, leadership requires resilience and reinvention. That's kind of what we've touched on a little bit. Do you have a specific moment that may require you to stretch or learn quickly?

Catherine Wong: I have so many. I wish I could say, you know, that it's just been really smooth sailing. But what I would say is there's just been a series of moments and experiences where I've had to stretch and you know, from the very beginning of my career. And in some sense, I think that's been helpful because I've never been able to become complacent. I've had to at every turn say, well, okay, this is a new opportunity, it's slightly different. You know, how can I think creatively about the problem? And, you know, how do I need to stretch or maybe challenge old ways of thinking or, you know, adapt to what the scenario is. And then part of that is because tech is constantly changing, right? And then part of that is just, you know, different career moves that I've made and different roles I've had the opportunity to fill. But I think, you know, it's a pretty constant thing. One that I'll share is, you know, earlier in my career, we acquired a company that was based in the UK and we were trying to integrate it. And it's hard, you know. This was certainly my first time really doing that. And so we needed someone to kind of spend more time over there. And so I raised my hand and I remember sitting on that plane, headed out there thinking, I've never done this before, you know, full-blown imposter syndrome. I've not done it, I don't know. But you know, I believe in the company, I believe in what we're doing, and I really like the team out there. And so it turned out great. But I think you, you know, you definitely have those moments where you just jump in. And I think as long as you're clear on the problem and the outcome, like what is the outcome that the business needs? Which isn't, I think sometimes we fall into the trap of the problem that we think should be fixed. But you know, if you can align with leadership, like what's the real meaningful outcome here, and then you know, you do excellent work and you work well with others, you know, it's kind of like what we learned in kindergarten. Like, can you work well with others and really enlist the best out of everyone? It'll turn out great.

Mary Killelea: And that is so inspiring because I think so many people see leadership without the sense of self-doubt or you know, feeling senses of imposter syndrome. So you sharing that really is invaluable to listeners. So I appreciate that. And I think courage, courage of you pushing through that and again aligning to the business outcomes. Great advice for women listening. What part of your work right now lights you up and brings you the most fulfillment?

Catherine Wong: Right now, what I love the most is when we have a group working together on, you know, building products or, you know, making design decisions, or that group element I love. And it's not necessarily the project itself, but it is that I see so many faces around the table where they are better than me in, you know, aspects of what they're doing. They are growing their careers, they're absolutely getting the at bats that they need, you know, to achieve their goals. And we're working on something that we just know our customers absolutely want, you know, and are gonna love using. And you know, that is really, really fun. That's true leadership.

Mary Killelea: All right, last question. What does to be bolder mean to you?

Catherine Wong: To be bolder to me means really embracing you, embracing who you are. And as you know, different as that may be, as you know, unique as that may be, and really you know, bringing your whole self to the opportunity. And that means really being in line and in tune with what is important to you in your life, you know, what it is that you value and what your contribution can be. I think it may seem small, but I really do believe that embracing yourself is what it means to be bold because we need that. We need that diversity and that perspective. It absolutely improves the outcome. Awesome.

Mary Killelea: You're amazing. Thank you so much for being here. It has been such a pleasure getting to know you.

Catherine Wong: Thank you so much for having me. I have enjoyed this.

Mary Killelea: I have enjoyed this. All right. Well, I will put your company's website down below in the show notes. And is it okay if I put your LinkedIn profile so people can connect with you?

Catherine Wong: Absolutely. Please connect.

Mary Killelea: All right, awesome. Thank you so much. Thanks for listening to the episode today. It was really fun chatting with my guests. If you liked our show, please like it and share it with your friends. If you want to learn what we're up to, please go check out our website at 2bbolder.com. That's the number 2, the little bbolder.com.