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

What if the fastest way to grow your career isn’t a straight climb but a series of smart, sideways moves that sharpen your empathy and judgment?  In this episode, I had the pleasure of sitting down with Catherine Wong, COO and CPO at Entrata, to unpack how she scales products and people by shaping cultures where every voice is invited, and the best ideas surface early. From engineering during the dot-com downturn to leading global teams through acquisitions and hypergrowth, Catherine shares the habits that turn uncertainty into momentum: practice your voice, ask for real feedback, and reward behaviors that build trust.

We go deep on how product and operations intersect when you’re building an operating system for real estate. Catherine explains why diverse perspectives improve outcomes and how leaders can intentionally signal what matters by recognizing thoughtful execution, not just loud opinions. Her take on the future of work is refreshingly actionable: AI changes the “how,” not the “why.” Whether you specialize or stay broad, treat curiosity like a muscle. Run small experiments, unlearn out-of-date tactics, and stay anchored to clear business outcomes.

You’ll hear practical frameworks for deciding under ambiguity. widen inputs, seek data, welcome dissent, and iterate with agility. Catherine also breaks down visibility tactics for women who are competent but overlooked: volunteer for updates, lead slices of complex projects, and request precise post-meeting feedback. Her story of integrating a UK acquisition while battling imposter syndrome reveals a simple truth: courage plus clarity compounds into trust, scope, and impact.

If you care about culture design, product leadership, AI fluency, and building a resilient career in tech, this conversation is a blueprint you can use today. Follow along, share it with a friend who needs a nudge, and subscribe to get more candid, practical conversations. Loved this one? Leave a review and tell us the bold step you’re taking next.

Resources:
Catherine Wong on LinkedIn
Entrata

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Catherine Wong's Career Tips for Women Transcript

The 2B Bolder Podcast provides first-hand access to some amazing women. Guests will include women from leading enterprise companies to startups, women execs, coders, account execs, engineers, doctors, and innovators.

Transcript

Welcome And Guest Introduction

SPEAKER_00 0:00

Hi there, my name is Mary Killing. Welcome to the To Be Boulder Podcast, providing career insights for the next generation of women in business and tech. To Be Boulder 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 Intrata, 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 Omnature and Adobe, where she helped integrate teams following Adobe's 1.8 billion acquisition omnature. 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 have 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.

SPEAKER_01 1:56

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

SPEAKER_00 1:59

Awesome. Okay, so you currently serve as both the CEO 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?

SPEAKER_01 2:19

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 is we need diverse perspectives. We have the opportunity to really pull in a variety of um talent sets, experience levels to achieve these goals of delivering great product, creating fantastic experiences for our customers, right? And operationally being really hopefully excellent, right, in how we're doing all of this.

Career Origins And Early Lessons

SPEAKER_00 3:08

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 kind of that walk down memory lane kind of thing.

SPEAKER_01 3:25

Yeah. So the origins, you know, my origin story, I guess, is classic nerd. Um, started with a degree in computer science and worked as a software engineer. Um, graduated at exactly the wrong time in some sense, um, just as the bubble was bursting, uh, the internet bubble. And um it was, I'm so grateful for it, uh, to be honest, because it really helped me learn um very quickly what it was like to work very lean and to um pull together with a small team. So worked as a software engineer, then did architecture, um, got to wear a bunch of different hats because um I was at a small company and I and I loved that. I loved the opportunity to raise my hand and um say yes to things that I felt scared to do, um, 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 um, 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. Um, and there I really focused on leading engineering. And I will say I was a very reluctant um uh 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, um, really sponsor who pushed me into it and said, you can do this. I, you know, I promise. So got to, you know, do that at Adobe, which is a wonderful company. They they helped me learn so much about what it meant to lead it on a global scale. And then um I went to uh Domo where I got to run engineering and then product. Um we took it out of stealth mode. Um, so got to apply all the lessons that I learned in that first portion of my career, right? And um, and apply those lessons at Domo and work with just again a phenomenal team. Um, and then now most recently in Entrada. And I would say one of the through lines um through you know those experiences is the fantastic um people that I've gotten to work with. I really do, I cannot understate how important that is to surround yourself uh with people who make you better, who you know, support um and create an environment where you can really thrive and grow. And they those environments do exist out there. Um, and I'm just so grateful for that.

SPEAKER_00 6:05

Uh 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.

Embracing Difference As An Advantage

SPEAKER_01 6:24

And I think part of, you know, what I 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 um what it meant uh to be in business or, you know, um in aspects of this world. Um, I'm the daughter of immigrants and I'm so grateful for the lessons that um they they helped instill in me around, you know, hard work and um taking every opportunity that you can and 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. Um, and I think, you know, what I love about um this podcast and 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 and it really helps to expand um kind of my mind as to what is out there and and what the opportunities are.

SPEAKER_00 7:24

I love that because I I agree with you completely. I think we can continue to learn from each other and inspire each other. Yes. Um, you've advanced in senior leadership, obviously, in industries and environments that historically might have been more male-dominated. Uh, what do you attribute your mobility upwards and mindset and habits? Like you you got where you were today because of obviously hard work. Um, but what else was a driving factor for you in a world where there weren't many women?

SPEAKER_01 7:59

Yeah, I think um some of it was really coming to embrace and understand um that me being different was actually more than okay, that it was pretty great. Um, but I will say I didn't start off thinking that way. I thought because I I felt different, I looked different, you know, um, sounded different. Um, at first, I I'll say I I probably tried to kind of mask that. And I tried to fit in. And um, luckily I was surrounded um by folks and had some mentors who really tried to help um 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 the business outcome is stronger when we have different voices. It can be different generations, it can be different, you know, um, backgrounds, um, different walks of life, um, different disciplines that we each studied in college. Um, 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 um embrace that my voice was going to be different and that it was actually helpful um to vocalize that instead of trying to dampen it down, right? Um, to do that. I think the other thing that really helps, um, and I see this with up-and-coming leaders as well, is um 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 um a culture and an environment that you promote where people feel like they can be open, they can be transparent, they can be vulnerable. Um, 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.

Cross-Discipline Empathy And Lateral Moves

SPEAKER_00 9:57

I I absolutely 100% agree with you. I think diversity just makes business better, makes people better, makes you know the community better. Um, 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?

SPEAKER_01 10:26

I love this question because I think, you know, so much of it is um, you know, reflected in a lot of what we use as a product philosophy, which is um 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 um, you know, getting requirement documents from the product manager and thinking, well, you know, I 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 that's hard. We're sitting here and you know, now I've got to um, you know, kind of look at it from this perspective. And I think when we're able to do that, um, it really helps strengthen us. Um, 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 um, 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 um 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 um skill sets are are just so foundational to it. Um, and so I think that, you know, I've been grateful for um just the opportunity to sit in so many different seats.

SPEAKER_00 12:13

I I love that perspective because uh I remember uh in my corporate career, I did make a couple couple pivots where it seemed lateral, but and and I struggled with that. Like, am I 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.

SPEAKER_01 12:34

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.

Designing High-Trust Team Cultures

SPEAKER_00 12:52

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

SPEAKER_01 13:09

Yeah, I think there's so much that goes to this. You know, we could talk for hours, but I I think a couple of things that I've learned is that um what we reward or what we recognize is going to be a strong signal to folks, you know. And then um 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 um 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. Um, and it it requires a mindfulness and a thoughtfulness. But I um I've been fortunate to, you know, learn from folks like Adam Edmonds and others who um they do that, they exercise that. And um that creates a culture where everyone wants to be excellent because there's transparency and there's accountability, um, and there's also high trust because folks know that you know they they can be vulnerable and it's okay to make a mistake and to to move forward. Um and they can really um bring their whole selves, right, to the opportunity and the task at hand or the project, uh, whatever that may be.

SPEAKER_00 14:35

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.

SPEAKER_01 15:00

Well, and I got to benefit from that, right? Like I had a mentor who his 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 and I appreciated that he said louder.

AI, Skills, And Future-Proof Careers

SPEAKER_00 15:18

Yeah, I love that. Um, okay, so there's a lot of anxiety right now in the world. Um, 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?

SPEAKER_01 15:40

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

SPEAKER_00 17:13

Yeah, no, I 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 would it be best to like select something in AI and be proficient in that? Or would it be better to get kind of smart on like a wide range of what's happening in the world in AI?

Finding Your Voice And Getting Feedback

SPEAKER_01 17:44

And I know that's like broad, but yeah, I mean, I think a lot of it depends on 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 um, you know, if you have a certain role or domain that you're really passionate about, then I think, you know, um making sure that you understand um 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, um, then I think maybe broad uh 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 um kind of leaning into it is probably the biggest, and curiosity is a skill, you know, it is exercising that. And um in some cases, I you know, I've had to unlearn maybe how I've done part of my role and learn a new way to do it. And it's okay, you know, it's it's actually kind of fun, it's invigorating.

SPEAKER_00 18:43

I love that you called curiosity a skill because um 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 like build that muscle.

SPEAKER_01 18:56

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

SPEAKER_00 19:09

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

SPEAKER_01 19:23

Um, practice. I think um just as many at bats as you can get um on various aspects of that. And um, you know, whether it is raising your hand on a different project or, you know, seeing if you can um 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 um, I think the other thing to do is um be open to asking for feedback. Feedback. And you know, I think it's that'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 um open yourself up to that, um, 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.

Deciding With Ambiguity And Agility

SPEAKER_00 20:44

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

Mentors, Sponsors, And Continuous Learning

SPEAKER_01 21:15

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

SPEAKER_00 22:45

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

SPEAKER_01 22:54

I think um I have been fortunate to work with a lot of them, you know, and and that is really helpful because um they get to see you in action and and they get to kind of, you know, watch along the way as you're leading various projects or as roles become available. Um and then in in other cases, I think, you know, as your network expands, you get to, I think, pick up on a lot of folks who um can be sounding boards for you. I 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 um, it's it's pretty magical when you interact with everyone that way.

SPEAKER_00 23:40

I love talking to leaders like you who actually believe that and and 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.

Stretch Moments And Imposter Syndrome

SPEAKER_01 23:57

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

SPEAKER_00 24:27

Um obviously, leadership requires resilience and reinvention. That's kind of we've touched on a little bit. Do you have a specific moment that maybe required you to stretch or learn quickly? I have so many.

What Lights Catherine Up At Work

SPEAKER_01 24:44

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

To Be Bolder: Final Reflections

SPEAKER_00 27:09

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

SPEAKER_01 27:45

Right now, what I love the most is when we have um a group working together on, you know, building product or, you know, making design decisions, or that group element um I love. And it's 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, uh, they're absolutely getting the at bats that they need, you know, um, 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. Um, and you know, that is really, really fun. That's true leadership.

SPEAKER_00 28:39

Um, all right, last question. What does to be bolder mean to you?

Closing And Listener CTA

SPEAKER_01 28:45

To be bolder to me means really embracing you, embracing who you are. Um, and as you know, different as that may be, as um, you know, um unique as that may be, and uh 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, um, you know, what it is that you value and um what your contribution can be. I think it it may seem small, but I really do believe like that embracing of yourself is what it means to be bold because we need that. We need um that diversity and that perspective. It absolutely improves the outcome. Awesome.

SPEAKER_00 29:44

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

SPEAKER_01 29:49

Thank you so much for having me.

SPEAKER_00 29:51

I have enjoyed this. All right. Well, I uh I will put your company's website um down below in the show notes. And is it okay if I put your LinkedIn profile so people can connect with you? Absolutely. Please connect. 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 twobeebolder.com. That's the number two, the little beboulder.com.