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Product Hero is our bi-weekly series that highlights outstanding members of the product management community. These industry leaders share tips on processes, team building, how to be a better product manager, and who they are outside of their careers. This week our product heroes are Ryan Frere, VP of Global Payments at Flywire and Jason Moens, VP of Product.

C. Todd: I’m here with two product heroes from Flywire here in Boston. I’ll let you two introduce yourselves and tell us how you got into product. Jason, do you want to start?

Jason: Hi I’m Jason Moens, VP of product at Flywire. I’ve been here for about seven years. I joined Flywire when it was just an interesting idea, but had no customers, revenue, or product. It seemed like a compelling idea – to help change the way people around the world move money, especially for big purchases like medical care and tuition payments. My history before Flywire was in the payments and software space at a few startups and larger companies.

I was a software developer for about 10 years, but the intersection of technology and business was always my focus, so product always seemed like the best home for me. Now I’ve spent the last 15 years in product.

C. Todd: Awesome. Thank you. Ryan, how about you? Tell us a little about your background. How did you get into product and design?

Ryan: Sure, I’m Ryan Frere, VP of global payments at Flywire. It’s funny hearing Jason’s story because I came from the business path to product. Originally I was at a larger, enterprise software company in an inside sales role. I have a bit of a technical background and the more I dug into that product, the more I knew there was a better way to build it. At the time, I didn’t know about product management as a function. Working closely with the product manager at the time, he thought I could be a good fit for a product role. So in 2006 I moved over to product.

Fast forward eight years, Mike Massaro, the CEO of Flywire, (it was called peerTransfer at the time) called me about a product job here. He saw my experience in education and international payments and here I am now.

It complimented very nicely to where Jason was coming from on that side of domestic payments first. And now, we both jointly run product here from the two different perspectives.

C. Todd: Can you describe your relationship a bit more? How do you deal with being two heads of product? What does the division of work look like?

Jason: When Flywire began, we had really fundamental questions we kept asking ourselves. We needed to validate that people were having difficulties moving money internationally, and that we could create a sustainable company to provide that solution. What is interesting is that our core area of business is in something we didn’t expect: education payments. We were expanding the use cases for our product. As we’re trying to uncover different ways to apply our solution, we have a sort of laboratory function where we do a lot of experimentation. Right now, Ryan has been driving the established product lines, focused on the stuff we’ve proved to work. I’m on the other side figuring out what will be valuable or not but uncovering new learnings and then driving through ideas.

Ryan: What’s funny is I came from a 30-year-old technology company that was relatively stagnant with innovation. They wouldn’t want to invest in an idea if they didn’t know it that it was going to result in a lot of revenue. But, how would we know that yet without actually getting something going and learning along the way? So it was a lot of fun to start working with Jason, where we can experiment.

Where we are as a business, one of the smartest investments we can make is drawing a line between what is known that works and what we don’t know. We can cause a lot of disruption by experimenting in the realm of what we don’t know.

C. Todd: Can you explain what Flywire does?

Jason: Most people were using their local banks to send money to another country. Almost entirely, those payments were sent by international bank wires. They’re very expensive when you take fees and foreign exchange markups in the cost. For example, if you live in Spain and you want to attend MIT, you would end up paying an additional 5% because of transfer fees. We process payments for 200 countries and territories.

Under the traditional model, while the money disappears from your account right away, there’s a delay for MIT to recognize the payment. Two weeks after you send the payment, MIT can finally credit your account. Our intention was to provide a solution to improve the experience on the payer’s side and streamline the process on the recipient’s side.

We partner with the world’s biggest billers: universities, colleges, hospitals, and businesses that are trying to receive funds from any country. We localize the experience of the payers. Instead of a student or parent in China having to visit their bank for a transfer, they can use their UnionPay, WeChat Pay, or Alipay for example.

We can cause a lot of disruption by experimenting in the realm of what we don’t know.

Jason Moens

VP of Product at Flywire

C. Todd: So this isn’t to transfer $20 to my friends in Spain for dinner. This is for bigger ticket spends.

Jason: Exactly. A number of companies help with small balance transfers. Our goal was to help streamline on the receiver side. These big billers have challenges with traditional bank transfers like money showing up and all the fees were missing so the balance was short of the actual bill. Or, they didn’t know who the payment belonged to because the message was lost in the transfer.

C. Todd: What are some of the challenges that keep you up at night?

Ryan: The nature of running an international payments company is stressful. Regulations, currency fluctuation and all the fun stuff that comes with it are all involved. We have teams all dedicated to those aspects of the business. Thinking about products specifically, wondering if we’re growing fast enough is one of the big concerns. I also think about if we’re learning fast enough, not just from what we’re releasing, but with getting better from a process perspective.

C. Todd: Is there any specific thing around process that you’re looking at and trying to solve right now?

Jason: I’m quick to say that running a very small, efficient team is one of the easiest things you can do. The question is how you scale that up.

Ryan: How can I forget scaling?

C. Todd: Scale breaks everything.

Jason: Exactly.

Ryan: Which is good. I mean it’s actually okay if it breaks it. You’ve just got to learn and iterate on it fast enough.

Jason: What’s the expression, that growth brings complexity and complexity kills growth?

C. Todd: How do you work with the broader team like marketing and sales? How do you ship products out the door?

Ryan: My team consists of product management, design, and product marketing functions when it is needed. We need to make sure that all of those people are informed and aligned as to what’s going on.

If we look to the experimental lab side of the business, analytics actually sits there. So much of the decision-making for the future is data-driven.

We incorporate the collective experiences of all the people who work here into our product.

Ryan Frere

VP of Global Payments at Flywire

Jason: Just to elaborate, the analytics team is actually embedded within each of those teams. We pretty much follow the Spotify model: Autonomous squads that consist of a product lead, an engineering lead, additional engineers, and a design lead where it makes sense. Some of the internal payment processing doesn’t have much of a design need.

Each squad is given a mission. The mission starts with guardrails and guidance from people from all levels and functions of the company. These people could be on the global payments team, or marketing, or sales. They’re pulled into the conversations but are not embedded within the squads themselves. We want to tap into their brains while also letting them know what’s being worked on. Squads are pretty autonomous and use their best judgement to get stuff out the door.

The makeup of each squad takes into account the mission. It’s a very scalable approach. With this model we’re poised to commit to investing in an idea that works to become a permanent part of the company. That idea would then transition from my side of the business to Ryan’s.

C. Todd: Could you describe the Spotify model you referenced in terms of your squad?

Jason: Sure. We haven’t had enough people to get into the tribe and alliance guilds like Spotify. We’ll keep an eye on our squads to see if we can flesh it out further. The concept is people from different functions, who work on wildly different things, coming together as a cross-functional team.

The program here is called Fly Stronger, which is the ability for anyone to raise their hand and express interest in something. If there are enough people interested, the company will provide money, time, and space to explore that idea. We’re a global company, which leads to interesting challenges. We do an all-company gathering somewhere around the world and it gives tremendous opportunities for people to travel. It gives us the experience of learning about a different culture where we might struggle to pay for something and understand how currency may be different.

Ryan: It’s cool. One of our product guys who’s based in Singapore does a lot of work in China. Last week, on his own, he planned a trip to China and vowed not use any cash to see how far he could get. He only ran into one challenge with a taxi, but that was about it.

Jason: The way I framed it is – this is an international payments company, I’m the least international person here. So if the ideas that we are going to pursue are limited by what’s in my head, we’re definitely going to fail. Every single person on the development team has lived, studied, and traveled immensely. We incorporate the collective experiences of all the people who work here into our product.

We support the ability for people to get out of their comfort zone in a whole bunch of different ways. And that feeds back into us making better product decisions. So I think the travel aspect of our jobs is immensely important. We’re really fortunate to have gotten to this stage of the company where we can give people those opportunities. At the same time it feeds the product and yields a ton of return for us.

Regardless of the size of the company you work for, small or big, whether you like it or not, you are at war.

Jason Moens

VP of Product at Flywire

C. Todd: What problems are product people not talking enough about? What’s missing from the conversation?

Ryan: People are definitely talking about how to hire a product manager. You can find many conversations about whether you should hire an internal person and train them or hire a seasoned product manager externally.

What I don’t see is enough talk about the personality traits you need to do the job. It’s not always about experience. I don’t necessarily look for people with 10 plus years of experience in product. In some ways, that experience takes you back to a very old way of doing things, neglecting more modern approaches.

We need to stress the ability for people to break down a problem. Also, everyone does product a bit differently. There are some consistencies, but as a whole, we need to see that person has the ability to influence without authority, which is a key piece of product roles. Assessing that ability is hard when you need to see if they fit with the culture, that they love to learn, they’re curious, can problem solve, and so on. All of those pieces are part skill-based but also behavioral.

C. Todd: What are some products that you really admire?

Jason: I’ll say, within the payment space, I think Stripe has done a great job. They’ve continuously added more functionality, almost as though from the beginning they knew these functions would be coming. Everything is seamlessly integrated.

Then with the expansion into Atlas, I love the way that they’ve seamlessly stretched that into a legal aspect, and a global presence, and a whole bunch of things which I think are probably anything beyond what their original focus was.

Ryan: I’m going to put my own personal consumer hat on – if I can pick a product that saves me and solves the problem for me every day – it’s Waze. I commute into the city from the North Shore. Route 1 is a blast but there’s a lot of ways around it. So I don’t start my car without lighting up Waze to get to work.

C. Todd: What advice would you offer anyone who is new to product?

Ryan: Put a focus on understanding your customer and the problem. Get out of the building and spend some time in the world. I always use Jane Goodall as my analogy. She didn’t read books, she didn’t “study,” she lived in the jungle to understand chimpanzees. Even if the problem is on the outskirts of our product, you don’t know the exact customer problems you can solve until you’re actually in their environment.

Jason: Regardless of the size of the company you work for, small or big, whether you like it or not, you are at war. I love the concept of insurgency and guerilla tactics. And at the end of the day, clawing, scratching, kicking, and finding a way to be able to uncover new learning and to do it better and faster than anybody else.

A few years ago someone asked me since we didn’t have any patents: What would stop someone else from doing the same thing we did? My only response was that if they could understand the customer, their pain points, and build something that is better than our product, then they deserved the business.

Interview notes: