(Women on Top in Tech is a series about Women Founders, CEOs, and Leaders in technology. It aims to amplify and bring to the fore diversity in leadership in technology.)

Here is my interview with Jessica Chen Riolfi, the Head of Asia at TransferWise, an alternative to banks and brokers that allows people to transfer money across borders at a lower cost than ever before. She is responsible for 15 countries in Asia, including India and China, doubling the volume every six months.

What makes you do what you do? 
Growing up in a Chinese-American household, my family always had one eye to the East. As a result, I have seen firsthand the types of change brought about by globalization. Traveling to Shanghai for the first time in the early 1990s, I recall the unpaved roads and lack of infrastructure. Returning just ten years later, I barely recognized the city: construction everywhere, a general increase in standard of living, and my aunt’s pride as she showed us her newly constructed house.

Since that time, the power of technology and business to make meaningful change has been a persistent interest of mine. I’ve spent my career building global products and currently work to accelerate TransferWise’s mission of money without borders throughout Asia. My enduring belief is that when there’s a new invention or new product in one part of the world that can meaningfully improve people’s lives, then it’s worth accelerating that access to people all over the world.

How did you rise in the industry you are in? 
I took the initiative. In my career, I’ve worked for progressively smaller companies. As you can imagine, the smaller/the younger the company, the less structure there is. That means there’s more opportunity to take initiative and more responsibility. I remembered joining TransferWise about three years ago… I felt like a kid in a candy shop. So many things to work on and not enough people to work on them! In such an environment, it’s about raising your hand and just doing it. Your learning curve and your level of responsibility is accelerated. Obviously there’s risk, but I would encourage others to take as much risk as they’re comfortable with. You won’t learn and you won’t grow if you’re too comfortable.

Why did you take on this role/start this startup especially since this is perhaps a stretch or challenge for you (or viewed as one since you are not the usual leadership demographics)?
When taking this role, it didn’t even cross my mind that I was different from the typical applicant. It was a challenging opportunity that was a good match for my skill set; there’s no reason on this planet why I wouldn’t go for it and push ahead.

Not being part of the usual leadership demographic is what motivates me even more. Since I was a little girl, I’ve been inspired by the strong women who came before me. Sandra Day O’Connor as the first woman in the US Supreme Court, more recently Sheryl Sandberg as the COO of Facebook, and pushing the cause of women in the tech industry.

Do you have a mentor that you look up to in your industries or did you look for one or how did that work? How did you make a match if you and how did you end up being mentored by him/her? 
I have lots of mentors – people I’ve met throughout my career, former managers and teammates. Different people define mentorship differently. For me, a mentor is someone I look up to professionally and who I’d feel comfortable going to for advice. From that perspective, my network of mentors is as wide as my entire professional network. I’ve always found incredible support when I’ve asked mentors for help or advice… it’s just a matter of having the courage to reach out in the first place.

Now as a leader how do you spot, develop, keep, grow and support your talent? 
That’s an incredibly tough question – it’s something I will likely spend a lifetime continually improving. There’s one main principle that I stick to, however, both on the hiring side and the supporting side. I try to hire people who are self-motivated, who are excited by the opportunity to learn and grow in the role. Then, following on, is the understanding that those people most likely won’t be on your team or your company forever, therefore your role is to help them get to where they want to go. If a teammate wants to eventually start her own start-up, how do you give her the opportunities to be entrepreneurial in the current role? It’s about, to the best of my ability, building their confidence and giving them the skills and honest feedback they need to grow.

Do you consciously or unconsciously support diversity and why? 
I very consciously support changing the professional workplace so that we remove hidden biases and ensure more equal footing for those of us in it. One thing I’m super proud of is that in TransferWise Singapore, we give new parents 16 weeks of parental leave, no matter if you’re a new mom or a new dad. So many companies give unequal maternity and paternity leave, or even none at all, and it constrains parents into family structures that may not work for them. There are so many more adjustments we can and should make… it’s how we’ll get the best out of our workforce of all types.

What is your take on what it takes to be a great leader in your industry and as a general rule of thumb?
What I’ve seen differentiate really great leaders is vision. It’s a personal conviction that rallies other smart people. I joined TransferWise in part because of Kristo and Taavet, our founders – they passionately believe in a world of money without borders. It’s incredibly powerful because (1) the world would be a better place if this vision came to be, and (2) the vision is actually possible. People can tell that it’s genuine.

Advice for others?
I’ve now worked at different companies and in different roles and have the realization that, try as I might to force this thing, my career, in a certain direction… whether it’s to get a specific title, or to get a specific role, it doesn’t always work exactly the way you plan. Both opportunities and roadblocks can’t be fully anticipated and planned for. Therefore, my advice is to focus on what you can control — work at the intersection of what you’re good at and what you like. If you keep pushing in that direction, and if you always stick to your values, then you’ll end up in a good place.


If you’d like to get in touch with Jessica Chen Riolfi, please feel free to reach out to her on LinkedIn: https://www.linkedin.com/in/jessicachenriolfi/


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