Breaking Through the Bamboo Ceiling as an Asian Female Leader

Michelle Tran, Head of Strategic Partnership, SVP at Vestwell

👋 Hello! This is Suzan. I write about leadership and interview leaders from tech companies like Etsy, Github, Google, Netflix and Spotify who share their insights on how they overcame a challenge.

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On to the interview with Michelle Tran, Head of Strategic Partnership, SVP at Vestwell about breaking through the bamboo ceiling as an Asian female leader. There are so many gems. Enjoy!

Michelle Tran, Head of Strategic Partnership, SVP at Vestwell and I have many people in common because of the Fintech women that Michelle created. Sharing intersections of being female and a person of color can make leadership more challenging. I was happy she came on the series to share her experiences. 

We talked about:

• Her first leadership role (in the fourth grade)

• How being first gen influenced her career in Fintech

• Why she started NYC Fintech Women 

• How perceptions of Asian Americans impacts how she leads

• How names impact perceptions of Asian Americans 

• Why she started Tiger Collective with Liang Zhao and their goals

Can you share a bit of background about yourself?

Yeah, absolutely. I am all things super passionate about women and Fintech access for folks through technology. It’s driven my story and what I do. I am the co-founder of NYC Fintech Women, which is a 12,000-plus member organization, primarily based in New York, but we're also in San Francisco, and Seattle, and just had an event in Chicago. I'd love to start something in Atlanta because it's becoming a really big fintech hub. And we recently had an event in London so we're going global. Our mission for NYC Fintech Women is to empower, connect, and promote women. Those three words: empower, connect, and promote drive our mission and what we do day to day. 

In my day job, I am the Head of  Strategic Partnerships for a retirement platform called Vestwell. That goes back to being passionate about providing access through technology. At Vestwell we help small businesses offer retirement solutions to their employees in a digital forward way. We know in the financial services, and retirement space that if you don’t make it super easy, people are not going to do it.

I'm a first gen in the U.S. I’ve seen the benefit of having retirement options available to me. So I was excited to join Vestwell a couple of years ago to help them supercharge the space of retirement.

What a great background. It sounds like being a first-generation that retirement plans were new or unexpected in your family. 

Oh, totally. My grandparents immigrated from China to Vietnam, and then my parents immigrated from Vietnam to the U S. My grandfather paid gold bars and put my dad on a boat, setting him off at age 17, not knowing where he was going or if he was going to see him again. I mean, that story is incredible. I can’t even imagine doing that to my kids. Like, “Go off and find something new” but they had to.

When they came over here, my parents started a restaurant. And as a restaurant, you typically, work really, really hard, but you don't have those more traditional saving vehicles available to you. I went through a more traditional career – I started Merrill Lynch, I went to BlackRock, and places like that. I was like, “Oh, what’s this 401k? What’s this savings account that you can save money for the future?” That was new and pretty cool. You set it out of your mind and it goes into a bank account. When I retire in the future, I’ll be able to live on it. My parents never thought about that because they were just trying to live day by day.

So being a first gen and having access to something like that, I want to make sure we get it into the hands of lots of others because there’s disparity when it comes to how much you’re saving for retirement as a female and as a minority. 

From a future in gold bars to retirement funds – what an incredible story. Was it the retirement aspect that got you into Fintech or something else?

Being a first-generation, Asian American, your parents tell you that you should be a doctor, a lawyer, work in finance, or something super stable – be an accountant, that’s the golden role. So I went into financial services. I started with Merrill Lynch in London.

Then I worked my way through BlackRock and the iShares business. It was more traditional financial services. I was fortunate to get an opportunity to work with robo advisors when they first came out in 2015. Everyone thought robo-advisers were going to take over the world, no more financial advisors, no humans involved, everything super automated. I got the opportunity to say, “Well, what’s our play here? How do we work with robo advisors?” We realized that what they’re doing is giving people who don’t have the same capital as those high net-worth individuals access to investing, so it makes investing really easy. So talking with all these robo advisors was how I got into Fintech. That was an a-ha moment. You’re using technology and making it so easy. 

Since then I look for how technology provides access to those who don’t typically have it. It’s either the underbanked or those who don’t know how to invest but want to start investing. It’s cool what’s been happening over the last 10 years. Technology has supercharged the way people can get into capital markets.

I don’t think people outside the industry realize how much Fintech gives access to those who don’t have it.

Yeah. What was really cool about the company I joined after Apex Clearing was that you could open an investment account in like five seconds and start investing within minutes. Before that, you have to go to a firm to fill out PDFs on paper. You have to send in a copy of your ID. You have to send a check over or wait for the wire. But with this you can pick up your phone and you're like, all right, cool.

Think about those who want to continue to build wealth, the fact that they have access to these markets is cool. It changes the landscape.

That’s so great. Was being a leader something you saw for yourself?

When I was in fourth grade, I started a babysitter's club in our neighborhood. I don't think we actually ever babysat anyone cause we were too young, but for me, it was “Okay, how do you drive a team? How do you have an impact? Where, how can you drive strategy?” It’s determined where I've gone in my career. I was at BlackRock for many years. Going to smaller firms, I love rolling up my sleeves. I love helping others see how they can have a big impact on the firm. So it’s definitely in me and in a future state I will probably run my own company. 

How did you get that first professional leadership role? Were you tapped or promoted into it?

Yeah, I was tapped. A lot of it is digging in, showing that you’re doing good work and having impact but you also have to ask for it. A lot of people don’t ask for it because we’re afraid to ask for it. I say down with my manager and said, “Hey, let's talk about our three-year track or our five-year track. I want to build a team. I want to manage a team. That's important to me as a next step. So tell me the things that I need to do to get there.” 

Of course, you have to show your impact. But the first thing is asking, making sure it's known that you want to head in that direction. So that was the first role for me. It was a small team. A lot of it was thinking about how to drive this strategy. How do we impact the market? It was about making sure I had the business case to tackle the market and build the team for it. 

Asian Americans have been tagged as the model minority, a little bit more submissive, a little bit quieter, and self-sacrificing. People tend to think of Asians as good workers, not as good leaders.  I'm not very quiet generally but I realized as an Asian American female leader, I need to speak up more. 

What were those early leadership roles like for you? Exciting? Scary? 

I think both, right? It’s super exciting because you're taking on a new challenge, but it's also scary. Am I doing this right? Am I helping the people out? And I think that's ongoing. Making sure that you drive, and you have the business bottom line is your number one goal. I've been in sales roles, so it's always numbers-based, right? How have we hit a specific number?

There are great people who all help underneath it. You have to think about how you’re helping each of those people achieve 100% of what they can and helping make sure they’re thinking about that next step. 

That’s the scary part – how do you help extract the best of them? That's also the fun part – you develop these great relationships with folks who are happy to have you guiding them, being a sounding board, or helping clear the air with stakeholders. That’s the job of a manager and of a leader to take on some of these difficult conversations and make sure we have the buy-in from everybody. Those are hard things to do. We have great people. And then sometimes you don't have great people, right? I think that's hard is making sure you, like when you take action on someone that isn’t living up to what they're supposed to do. You don’t want to cause long-term harm but it’s also just not a right fit now or the right team. Those are the hard parts too. 

But I think it's been a lot of fun. You get to set strategy, have a seat at the table, and have a voice on how the business is progressing. When thinking about leadership roles you must be super vocal. That visibility and being heard is really important as a leader. And taking ownership and having an opinion. 

I love that. Don't be afraid to speak it out loud. It's okay to share what you're doing, share the impact you're having.

Yeah, put aside the fear of bragging, especially females, especially minorities, you have to promote yourself all the time. It's hard for a lot of us. Even I have these days too. I was writing a LinkedIn post about something where I got recognized. It took me two months to write it when it should have taken me five minutes because I didn't want to come off as too braggy, but I wanted to showcase people who have helped me along the way. I was tagging 20 people, you know, all those things. It got erased so I had to redo it and did it in a few minutes. 

The promotion piece is hard for folks. That's something we talk about a lot at NYC Fintech Women and that's in our mission for a very specific reason. You need to brand yourself, you need to promote yourself and others need to help you in that as well. The amplification effect of promotion is huge. I tell everyone to try to amplify someone at least once a week. It is easy to share what Suzan is doing, and what her podcast is doing. And hey, she had Edwina on, so you're doing a double amplification there. Just getting that out to my network and then getting your names out there will just have this waterfall effect. We have to do that work.

Amplifying one person a week is such great advice. Not just amplifying ourselves but what we can do together. How does being an Asian female influence how you lead and also if being first-gen influences how you lead?

I think it does. 

Asian Americans have been tagged as the model minority, a little bit more submissive, a little bit quieter, and self-sacrificing. People tend to think of Asians as good workers, not as good leaders.  I'm not very quiet generally but I realized as an Asian American female leader, I need to speak up more. 

So there are a lot of issues when it comes to showing equality and Asian leaders in the space. Asset management has something like 7 to 19% of Asians in executive roles, while we make up close to 30% of the total industry. It’s across everything, law, tech, you name it. And it's because Asians aren’t necessarily seen as leaders. So I’ve had to learn to be vocal. People don't expect me to speak up, I need to speak up more. Right now, through my work at Vestwell, I work specifically within the retirement industry and I have met two other Asian female sales leaders and that's it.

So out of the full retirement industry, I've only met two others. So again, it's driving, how do people perceive Asian Americans? And what do I need to make sure people can hear me to combat a lot of those stereotypes? 

I remember my parents sending me to school with Asian food. I was like, nope, I want peanut butter and jelly. I want turkey sandwiches. I want to be like everybody else. Now as I look back on it, I'm like, you should embrace the cultural differences. That's the only way that not only are you going to embrace it yourself but to share and expose others to cultural differences. 

What other challenges do you face as an Asian female leader? 

Diversity itself in financial services and the retirement industry in general is tough. There are a lot of firms that are trying to be very intentional about hiring and getting the right leader makeup, but it's difficult because it goes back to, okay, who's going to school? Who's starting in these industries? I recently just was looking to hire a pretty senior role on my team. I told the people I wanted a strong, diverse pipeline, to make sure I’m talking to everyone across the board. Unfortunately, because I wanted to get very specific within the retirement industry I couldn’t get very diverse. That means that started way back when, we don't have the right people who are just getting the ability to come into the industry. So my job is to see how we can get diversity in and that’s a challenge. How do we be super-intentional about getting folks in? 

The other challenge, going back to how people see Asian leaders. I recently read that Asians tend to get tapped into CEO roles when companies are going through distress or they're going through a decline. The reason they think is that Asians are more self-sacrificing. So they will go into these roles and do everything they can do. It goes back to this long perception about Asians. The model minority concept is not new. That came out years and years, decades ago. But it sticks with us, Like even through to college admissions, Asian Americans kind of have fit into this model minority. And we kind of play both cards. Either we're not considered a minority and we're considered, you know, good workers and good students, or we fit into the minority bucket with everyone else. And so we have to bridge both and for some people, it's a fungible minority class for us. I think that's sometimes a bit difficult when it comes to thinking about Asian leaders.

It's fascinating, but not surprising that Asian leaders get tapped as CEOs when they're going through a turnaround because of those beliefs about self-sacrifice. “This is a really hard thing. We need somebody who will take it on the chin and pull us through.” 

Yeah, it's really interesting. There are usually single-digit numbers of the percentage of Asian Americans who are in leadership positions. That's in tech, in law it's like 5%. 

In all these different industries, Asian Americans are just not being tapped to be leaders because of perceptions. I keep thinking about how we become cognizant of this. How can we combat those stereotypes? 

It's a hard challenge to battle. There's a lot of inherent perceptions. Part of it is just talking about it. With COVID happening a couple of years ago, it coming from China, we saw a lot of racism happening against Asian Americans, a lot of crime. Asians were targeted because there was this belief that we brought Covid over which is not true. So that's what spurred me. 

I meet other Asian leaders in the space. We just need more community around each other to have these conversations, normalize them, and have more vocal conversations about it. There are a lot of really cool groups now like Gold House, Asian Hustle Network, and Hyphen Capital that focus on Asian founders. All these different mechanisms are starting to bring up the conversation. We just need more of it.

I understand that you are starting or have started an initiative called Tiger Collective, which is a platform to share Asian female leader stories. Can you tell me more about the impetus for starting it and what you hope to accomplish?

Tiger Collective started to share stories. Eventually, we also want to help these leaders in other ways, either by investing in capital or connecting them with the right firms. As for the name, when we think about Asian culture, what does a tiger represent? We wanted to make sure that we're very loud and strong – that's why we named it Tiger Collective. It’s an initiative started by Liang Zhao and me. Liang is the CEO of Vansery, a fintech PR company. She was born in China and came over to the U.S. We're kicking off a couple of things. One is a podcast called Her Name Is because a lot of women who come from Asia tend to change their names.

Their Asian name won't resonate as well in the U.S. where it's hard for people to pronounce. So they change it to Mary or something that people can understand. Why have people changed their name? It’s because they wanted to assimilate. My parents named me Michelle for a very specific reason. It's because I was first gen. They love the song Michelle from the Beatles and they wanted an easy name for folks in the U.S. to pronounce. My aunts who came over from Vietnam (I have seven of them). They all had Asian names and they all changed them. We have Eileen, Shannon, and Tiffany...they came over in the 80s. They changed their names over here to make it just super easy. 

The podcast is meant to tell the story of your name, your journey, and your story as an Asian leader. It’s kicking off this year. We’re really excited. 

I think it’s easy to forget how much names impact people from other countries who are trying to assimilate. 

Yeah, and as a parent too, right, when they came over, that you wanna set your child up for success. They're going to go into schools and they want to make sure that they blend in because that's what assimilation is. 

I remember my parents sending me to school with Asian food. I was like, nope, I want peanut butter and jelly. I want turkey sandwiches. I want to be like everybody else. Now as I look back on it, I'm like, you should embrace the cultural differences. That's the only way that not only are you going to embrace it yourself but to share and expose others to cultural differences. 

We live in a very culturally diverse world. We learn so much from each other and from our differences. So the naming perspective is really important because if you're not exposed to all these different names, then you expect everyone to be Mary, John, and Mark.

I can’t wait to listen to the Her Name Is podcast. I believe we’re better when we embrace, and acknowledge our differences rather than trying to all be the same. There’s so much research that shows results from diverse teams.

Yep. The numbers show themselves. The more diverse you are, the more successful companies are. In the past couple of years, we've seen a lot of focus on DEI and bringing leaders to focus on DEI. It needs to be done more. It's been a hard road for DEI. I recently read that a lot of those head of diversity, and head of inclusion roles are being restructured because it's hard to get that big change, to get all those stakeholders to change the way they think. It's been a hard road, but we need to continue to focus on it. We need to continue to talk about it and make sure that people are intentional in all parts of the business when it comes to diversity.

Vocalize what you want and do it often. Make the ask and continue to ask for what you want. Don't wait. 

I recently read an article that showed that when you invest in DEI work at the highest leadership levels there are massive results. Besides the podcast, what are other things you hope to accomplish with Tiger Collective?

We want to tell stories in print and digital formats. Our long-term goal is to raise capital and help female founders and Asian founders take that next step to get into the market as an entrepreneur. There’s a founder conundrum. As Asian Americans, we've been taught to be risk averse. Starting a new company is a very risky thing. “Is it going to succeed? How am I gonna get money in? How long will it take?” We're supposed to be doctors and lawyers and all things stable. So we want to help de-risk that journey and get more Asian founders in the market. 

On the female side, you know, the stat for institutional investing in female founders is 2%. It's ridiculously low. For female minorities, who are founders, the number getting VC money is even lower. We'd love for Tiget Collective to be a big change mechanism in that space to say, why don't let's invest in more Asian founders? Hyphen Capital run by Dave Liu is a great example. He’s tapped into a number of great Asian leaders to fund his portfolio, fund his funds, and look for Asian leaders.

That’s just one example. We need to do more of that. Similar to how there are a lot of new VCs focused on female founders. We need to do that for the Asian community – bring them more into the fold, build some structure and process to get them into the bigger names like Sequoia and the Kleiner Perkins. 

I love that. One of my missions is to change how we see leadership and who gets to lead. When you started your career was identifying as a female and Asian something you thought about in how you presented yourself in the world? 

I didn't think of myself as, okay, how do I think about my cultural differences? What are the challenges I need to think about? Being intentional, I think that comes after years of being in this space. I wish I had been a bit more aware of it when I started my career. And that's also the goal, right? I love what you're doing with your podcast. You're getting different faces and different voices out there.

If I heard this podcast when I was, you know, 22 and starting my career, I might have a different perspective. How do I need to drive my career? How do I need to behave in the workplace? So no, I definitely didn’t. I will say though, that I've always joined women's networks at work and driven a lot of initiatives at women's networks. That's always been the core of what I've believed in – getting the female voice out there. So I’ve been fortunate to be at firms where there were opportunities to be part of the Women's Initiative Network or the Women's Group at Vestwell. We started the female ERG program and it's called Women at Vestwell Elevated. It’s really important to say, how do we come together? To give a lot of information, make sure that you are set up for success, that we give you exposure, that you're speaking, and that you have people to talk to. It's really important to have those communities and networks and another reason why I started NYC Fintech Women.

Building out your network is really important – everything is through the people that you know. Finding your next job, sales, making sure that your team is running well, it’s all about networks. These are people who become your personal board, people who can give you a little bit of advice. 

Was there a moment when you recognized that you need to consider both of these intersections – woman and Asian? Or was it more of a slow burn? 

I think it's a slow burn, especially as you go through a career and you become more senior. Sometimes you lose out on opportunities, sometimes you win opportunities. I think particularly when you lose out, you're like, why? Who else is in that pool? Right? Why am I losing? Some things become very obvious as an Asian and as a female. There was a very particular moment when I started NYC Fintech Women.

A while back I was in a meeting and was interrupted, the pitch taken over, and those kinds of things. I wanted to find a community of women in Fintech who I could commiserate with, and who could help me with that conversation. 

It’s beautiful to hear about the fourth grade you to now. It’s clear that you want to lead not just for your betterment but for the community. (tears up)

What advice might you give to Asian females who want to get into leadership?

Vocalize what you want and do it often. Make the ask and continue to ask for what you want. Don't wait. 

Early in my career, I waited a couple of times. I thought, I do good work, it’ll show for itself. They’ll tap me and move me up. That doesn’t happen very often. You have to put a stake in the ground and make the ask. 

The second thing is to tap into your community. Earlier in my career, I wasn't thinking about how do I build relationships with the firm? How do I network? Networking is scary. It’s hard, especially for those who are not extroverted. At our NYC FIntech Women events, we tell everyone to meet five women. We say that very specifically because it gives people a number to hit and gives them an excuse to meet other people. Like, that woman on stage there told me I have to meet five people so I feel more comfortable just walking up to someone and saying hi, my name is. 

Building out your network is really important – everything is through the people that you know. Finding your next job, sales, making sure that your team is running well, it’s all about networks. These are people who become your personal board, people who can give you a little bit of advice. 

I call Edwina Johnson, Michelle O’Connor, and Filippa Noghani on things. We talk about our careers, our companies, and the challenges we’re having. We have a-ha moments when we talk. Having a tight group of folks (really helps when in leadership) and you get that by meeting people and networking.