#113 – Matt Oppenheimer, from Founder to Public Company CEO of Remitly: Why Falling in Love with the Problem Builds Enduring Companies

I'm curious, I listen, I have a growth mindset. The shadow of that is it can come at the expense of like conviction, boldness, and decisiveness, because I really do respect people around me. And if folks come to me with a compelling argument, I'm like, "That's actually a really good point." So decisiveness, boldness may sound counterintuitive because I think we as an organization are very bold. We have a bold vision, but when it comes to my leadership style, I empower my teams. And there are some instances where I just need to be more decisive. Lead from the front as opposed to empowering and delegating to the team. So that's one that, again, towering strength, shadow, and I'll continue to work on growth.

Welcome back. This is From Startup to Grownup. My name is Alisa Cohn, and today I'm thrilled to welcome Matt Oppenheimer to the podcast. Matt is the co-founder and CEO of Remitly, the global money transfer company serving customers in over 170 countries. Matt founded Remitly after witnessing the challenges of sending money abroad while working in Kenya for Barclays. What started as a bold idea turned into a mission-driven company that went public in 2021, right before the IPO window slammed shut. In our conversation, Matt shares what it took to grow from first-time founder to public company CEO. We talked about the systems he put in place to scale, how he's learned to evolve his leadership style, and the unexpected ways he's built customer-centric culture at scale. He also opens up about imposter syndrome, the lessons he learned from hiring missteps, and how he stays grounded through it all. Please enjoy my fantastic conversation with Matt Oppenheimer, founder and CEO of Remitly. Matt, welcome to the show. I'm so excited to have you.

Thanks, Alisa. It's so great to be here.

I'm thrilled because I want to dig into all the ins and outs of, of Remitly and kind of you and your, your journey. You started Remitly as a way to send money overseas after seeing this was a problem when you worked in Kenya for Barclays. But my understanding is that not everybody thought this was a good idea as a starting point. And so I think that people gave you feedback and then, you know, I wanna know like how you dealt with naysayers and how you learned in your life productive ways to deal with feedback.

Oh, so many great questions within that question. It's great to be here. I'm excited about just the conversation. Yeah, so the, the most poignant origin story was when I was living in Nairobi, Kenya and I was running mobile and internet banking initiatives for Barclays Bank Kenya. Painful for me to send money abroad, painful for a lot of my friends to receive money from their loved ones in places like the US and Europe. And at the same time, there was this domestic mobile payment system that's continued to grow called M-Pesa that was transforming domestic financial services. And it seemed like the right time to actually improve the way that millions of people across the globe send money internationally. So that was the origin story. And I'd say that in the early days, there was a lot of feedback of why it was not a good idea. And one of the themes we may talk about in this conversation is I often think that there are two qualities that really form successful entrepreneurs. One is a grit, a tenacity, a perseverance that is directed towards a problem, not a solution, a problem. And then flexibility and curiosity around the solution. We can dive into that in a bit, but what I will say is in the early days, I actually sought out— I was really frustrated with how much it cost. So I was like, well, maybe we'll just build the search engine for international payments. And I asked a bunch of companies and people who had tried in that space and failed, and they were like, do not do that. And the reason for why not to do that is there wasn't a good business model. There's a lot of other things that we can unpack, but I pivoted towards the solution that we eventually built, which is being a heavily regulated money transmitter, building all the infrastructure structure. It was much harder. And there were a lot of folks who said, don't do that as well, which I can get into. But ultimately it was about falling in love with the problem. Problem was sending money internationally. Everybody knows it's broken, it's expensive. And then being flexible on the solution is a lot of folks said that's not the right way of solving it. And here's why. And I listened to them.

I may, I wanna get into all that, like literally everything you just said. Let's start with, I think this really important, what I sort of think of as nuance, but the way you just articulated it is so helpful. The idea of on the one hand, you've gotta have conviction. And on the other hand, you've gotta be like open and able to sort of adjust and adapt. So say more about how to know when to have conviction and how to know when to adapt.

Yeah, well that is exactly the gray area slash, so how to know when to have conviction. The first principle is fall in love with the problem one is trying to solve. For, again, for us it was sending money internationally. And using digital to do it and having it be more affordable and convenient. I think that what happens with a lot of entrepreneurs is they actually fall in love with the solution. And the most comical thing I hear at times, but also painful, is when entrepreneurs say, I've got this idea and I'm not going to tell anybody about it. And it's like, there's a level of like not having been in the entrepreneur's shoes and journey to recognize it's that grit, tenacity, and perseverance. Combined with a problem that someone is trying to solve. That is actually the hard part, right? And so the solution, I don't want to say is the easy part, because to your point, it takes that judgment of understanding, should I pivot and adjust? And I think the right entrepreneurs do pivot and adjust the solution, but stay maniacally focused on that problem. That's, I think, up to each entrepreneur to kind of understand where they have strengths and weaknesses. I think some entrepreneurs don't understand how much grit, tenacity, and perseverance is required to succeed as an entrepreneur. And I think some entrepreneurs fall in love too much or apply that too much to the solution as opposed to the problem. And it takes a lot of curiosity, a lot of listening, I think, to be successful in the, in the in-between of those two spaces. But what I will say is the idea, I don't wanna say is easy, but it's one of the easier parts. And anybody who thinks it's like the idea that's, that's the, the valuable thing, I really challenge, cuz I think it's grit, tenacity, and perseverance combined with understanding the problem and then pivoting the solution slash the idea to the right thing that solves that problem.

Yeah, that is very, very insightful actually. And then how would you say that you learned the ability to be curious, to stay open? Is that something you were just born with or is that something that you developed in your life?

Yeah. Oh, that's such a good question, Alisa. I think that honestly, I think my parents really modeled what it means to be curious. And there's so many examples of, of I think my parents really having that curious growth mindset. And I can tell a story or two there, but yeah.

Can you share some examples?

Yeah, sure. I think there was a time that, as we all are and can relate to, I was getting frustrated with my dad. And I talked to my wife and I was like, and it was kind of a stressful time in life. And she was like, well, you should apologize to him. And I was like, that's a novel idea. I will do that. And so I went and I said, Dad, I'm really sorry. I've kind of been just a little bit, you know, short with you, a little bit rude. Here's the deal. Like, my parents are incredible human beings. They're two of my largest role models in life. And also, like, any of us can relate with our parents because we're so similar to our parents. There's like that 10% we're trying to grow, and that's the part that actually annoys us at times, or annoys me at least. And so those were the things. And I told my dad, I just wanted to apologize. It's like, not about you, it's about me. It's about this 10%. Like, he knows how much I respect and love him and adore him. And I said, it's just that 10% of things that I'm trying to grow in. And, you know, it's just, it's why I get short-tempered, but that's about me, not you. And so I apologize. And he said at that moment, he goes, Buddy, I would love to learn about the 10% of things you're growing in. And I was like, that is why I have a growth mindset. And my mom is a therapist. So she, I think, has always been very, very introspective. She's an art therapist. So it's about like learning about thyself and growing. And so honestly, I think my parents are the biggest individuals to credit in terms of just having a curious growth mindset and a lot of tenacity and grit and resilience as well. I think that they modeled that really well as well.

Yeah, that's incredible. By the way, who gets that response from their father?

I know, right? I will never forget where we were sitting. I've told him that story a few times, and the fact that it wasn't exceptional for him, I think, says a lot too, in the sense that he just is always really curious and looking to grow.

Yeah. Wow. Well, speaking of your parents, your parents traveled with you all over the world when you were growing up. Is that right?

Yeah. When I was little, I, um, my parents really valued travel. Back earlier in like the '60s, my mom was a flight attendant. And so she always really valued travel. She wasn't a flight attendant when I was growing up, but both that and then my dad and even my grandparents always traveled a lot internationally. It was kind of a family value. And so, and I think it was important in terms of just getting to know different people, different cultures. I think that when you apply curiosity to that, I think it's very powerful and very defining for who I am. So yeah, throughout life I've been to close to 100 countries. The first trip internationally was when I was 6 years old, which again, thanks to my parents for taking a 6-year-old to— we went to China and Japan in the '80s, and that is a lot of work. I remember like getting an ear infection. I remember like all the kid stuff that happens with traveling with a 6-year-old, but I'm so thankful they did because I think it really formed who I am and gave me a much more like global perspective. And so, yeah.

Well, I mean, it's so funny when you say 6-year-old get an ear infection, of course that's what a 6-year-old does. But also I think I might think The 6-year-old's not gonna remember that trip. Like, why are we wasting this trip on a 6-year-old? But apparently it did. Could you say more about what, how that impacted your kind of like, I don't know, your blossoming maybe as an entrepreneur or how you lead today? How does that kind of live, that early travel experience live through you?

I think the most poignant thing that's relevant to Remitly is the fact that I think it gave me a much more global perspective. And ultimately, if you go back to that principle of like, find a problem that you wanna, you know, commit a big part of your life to solving, I think honestly, often we're surrounded by problems that are marginally accretive because there's a lot of people that see those problems that have the resources and ability to solve them. Right. And so I would say that the most poignant thing was just not being afraid and in fact embracing and really enjoying putting myself in different countries, cultures, situations. And what that enabled me to do was find a problem that I think I had the unique ability and resources to be able to solve. So I think it was foundational for why I eventually moved to London and moved to Kenya. And I think it's been foundational once I started the company in terms of just like being able to authentically and truly connect with our customers and the people that we serve. There's a— the tangent that I was thinking of was one of my personal heroes who I actually mentioned at this Remitly launch event. I quoted him at this Remitly Reimagined launch event was Desmond Tutu. And it was It's kind of bold in my view to quote Desmond Tutu in a product launch event, but I had the privilege of meeting Desmond Tutu in 2002, I think, when I was in college. He came and did a little seminar and there were like 25 of us and I wrote him a handwritten thank you note to say just how much of an inspiration he was to me. And about 2 weeks later, I got a note back from Desmond Tutu, handwritten note that's hanging on my desk in my home office. And I told him about some of the volunteer work I had done then in Africa and just various, and it was like a very thoughtful note. And the tangent but relevant part to your question earlier is one of the things that, one of the reasons Desmond Tutu was one of my absolute heroes is because he treated everybody that he met with the same level of dignity, respect, presence, connection. And obviously that was true in his work in South Africa, but it was amazing that this random college kid at a college in the US, he took the time to write me a note back. And I felt like he had the same level of respect and presence for anybody he interacted with, whether it was the president of a nation versus some random college kid. And there's this element of humanity binding us together that I talked about in the Remittly Reimagined event. But I think that that's the reason I mentioned that is because I think traveling at a young age instilled a sense that we are all so different in some ways. But when you get under the veneer and the surface, we're actually all like very similar in terms of wanting to provide for our families, in terms of wanting safety, security, in terms of just basic things. And that's always what I've been drawn to is like finding that thread of connectivity amongst anybody that I meet across the globe. And I think that helps because then you can actually get— going back to remotely— get a sense of what are the problems that whatever segment of customers a business is trying to solve, what are the problems that are really there? And then I think it's incumbent upon the entrepreneur to solve those problems, not ask the customer to solve them, but really understand them on a deep level. And then it's the business or entrepreneur's job to say, well, what is the solution to that problem?

Right. And one of your values at Remitly is customer centricity, which I really feel like, I mean, I looked at your web, your website, and I saw a whole bunch of values. We can talk about that later. But like specifically, I've heard you talk a lot about customer centricity and it feels like, you know, you were shaped in many ways about really seeing firsthand what's going on with people. And the connection with people, and that brought you to customer centricity. Is that right? Or could you speak about that?

Yeah, yeah, we have a longer list of values, which I'm, which I'm happy to talk about later and give context on why, but there's only one at the top, and that's customer centricity. And I think that, you know, at some level, any and every company, if they're not serving their customers and putting their customers first, then they won't be successful in the long run. I do think there are some businesses and some companies that just are so deeply rooted in purpose and mission and serving an absolutely incredible and inspiring customer base as defined by the employees that serve those customers. And I think Remitly is one of those companies, and I think it gives us an ability to recruit, motivate, deliver for our customers that is incredible.

I can imagine that. And I guess I'm just curious, how does that feed into, for example, recruiting? Like, you know, because you think about culture, culture is all these different things and culture is like kind of the leverage you use day to day and how you, what you reward and what, right? But first and foremost, I think it's who you bring in. So what are some of the ways that you really embed customer centricity in the hiring process and then inside of your operating system?

Yeah. So yeah, I think culture, my definition of culture is how people interact and how people get things done. And it is different at every company. As you know, you've been part of a lot of companies, you've interviewed so many leaders and You know, if you walk the virtual or real halls of a company, any person listening to this podcast, like your first few weeks on a new job, it's like, this place is like this and like that, not like this and like that. So what we try to do is define it with our cultural values and our cultural values are how people interact and how people get things done. And you'll see in our values, you'll see things like customer centricity, but you'll also see other values like bias for action, continuously improve, lead authentically. And it's a longer list because human interaction is complex. And I think it's hard to capture in like 5 catchy memorable words. So what I often say to Remitly employees is you'll never be required to memorize these. And companies that I respect, not in terms of the content of the values, but in terms of the construct, like Amazon's leadership principles, again, content of the values, you'll see values in our cultural values, like lead authentically, be a compassionate partner, things that are unique to Remitly. But I think companies that have scaled their culture for decades have a longer list, not shorter list. So I think that is a common misconception. And then you integrate that into the interview process, the performance review process. Those are what I call the bookends and then everything in between. So it's not just what is being accomplished, but it's how it's being accomplished. And then you refresh those values every year or two because there's different strategic needs of the business. Companies evolve and change. And so those have evolved every year or two where we do a very deep refresh. And by deep, I mean I spend a lot of direct time and energy thinking about what are the things that we need to change in terms of how we work and how we do things. What are the things that we need to add, remove? And one example of that from two refreshes ago was Lead Authentically, which is very remittent and very true. Another value that we added in this most recent refresh, and we removed some others, was Reimagine What's Possible, which has been just You can tell it's the right value to add because people are just using it organically all the time.

How, like, how, what, what are they doing that they may even use it organically?

I'd say there's two things. One is, you know, I think while there's a lot of hype around AI, I think AI is incredibly exciting. And for companies like us, it is really important that we are thinking with an AI-first mentality. And so I see the team really reimagining what's possible in terms of everything they do, leveraging the latest AI technology and tools, which is really important because the next startup is, you know, building their company with completely AI-first mentality. So that would be one example. But also, we've been around 14 years. Most of that growth has come in the last 5. You bring in world-class experts at what they do, and they might have come from a bigger company and think like, oh, they've been doing this forever. But I encourage them, like, reimagine, help us like reinvent what the way we're doing things, because we're at this place where if you continue to refine and improve and rethink things as opposed to just let momentum carry you, that's how we'll deliver for the decades to come. But going back to your question on customer centricity, I think that ultimately the way that we judge customer centricity is grading, you know, our team, celebrating and providing coaching based on how much they're working back from the customer. And that's easier in some functions like product or business management or marketing, But I think that if you were to look at our risk teams, they are absolutely customer-centric in, in ways that I think help propel our business forward. But then we also try to provide tools for our team to be able to get close to our customers because we operate in 170 countries. And so not all of our employees can use our product every day. And if they can use our product, they almost by definition can't use it across 170 countries. And so what we do there is we do things like we have a travel benefit that if you travel to one of the countries that we serve, which is most of the countries on the globe now, and then you come back and share your experience sending money with Remitly and what it was like and what we can improve, we reimburse that employee $1,000 of their, of their trip. Another is we have having like a centralized, what we call Remitly Scholars Program, where we help folks. We set this up 5 or 10 years ago in the Philippines, where we help folks at 2 universities with scholarships to pay for school in the Philippines. Instead of paying for that centrally, we pair new employees with recipients in the Philippines, and we call that Remitly Scholars. We reimburse that Remitly employee. They're using our product, sending money, not in a test environment, but to a university student in the Philippines, and then giving us a ton of feedback on things that we can do better. So those are some of the ways we try to support that customer centricity as well. Wow.

Those are very, So I just wanna reflect for a second. Those are very innovative, first of all. Like, I, you know, I've interviewed over 100 founders. I've talked to many other leaders. I've never heard of those two specific, you know, ideas. They're very specific, right? Also, I feel like they really emanate genuinely from you and your love of travel and like wanting to encourage people to travel. And then also to say the obvious, they're in some way, if I can put it this way, like kind of giving back to the community without being quote unquote charity. Or something. So, do you feel like, is that sort of shadow of a leader? Like, yep, that's me.

I think so. I think so. And then I think as any company, as it continues to scale, it's not only a shadow of me, but it's a shadow of so many people that join our company that like either have family abroad, like traveling themselves. Like there's somebody who sits right out here who doesn't necessarily have family abroad, but I know that, part of her defining journey was traveling herself and so is drawn to join a company like Remitly that offers those kind of benefits and, and values kind of that global perspective. So yeah, I'm proud of benefits like that and I think it recruits the right team.

Yeah, for sure. Now you talked about how just vast your network is and what you said, 170 countries. I mean, it's just a lot of countries. It just is, right? With a lot of currencies. How do you keep everyone— it's a regulated industry, as you said. It's very vast. And everyone's got different rules and regulations, different currencies. How do you keep your team aligned in such an environment like this?

Yeah. Yeah, it's a great question. I think that when I hear the word aligned, I think of two areas. I think one is making sure that we are— we have the right strategy and strategic objectives. We start with our vision, which is transform lives with trusted financial services that transcend borders. There's 3 parts of that. Transform lives. We don't have a separate mission because it's too many constructs. That's the mission and purpose. Trusted gives us the North Star that trust is hard to build and easy to lose. And it is incredibly important to trust. Start and ends with our customers, but it's in an ecosystem of banking partners, of regulators, of investors. And so trust is the second. And then financial services that transcend borders. It's not— we're not doing domestic financial services. We are specifically trying to solve the problem of individuals, 300 million to be specific, that live and work outside the country they're born. And then millions of small businesses that don't have the ability to not only send money internationally as easily and affordably as they could, but also have other financial services needs met, trying to solve things like the gap between credit access and creditworthiness, trying to give customers the ability to hold multi-currency accounts. And so I give that construct of the vision because there is a lot of depth and thought that went into that vision. We've only changed it once over the last 14 years. Then what we do is we operationalize that vision into our integrated product strategy and then into annual OKRs. And like any company, we can continue to improve that. There's a long list of things that are on my mind that we can continue to— that's one of our values, continuously improve. But I think that construct of starting with vision, then 3-year strategies, then annual goals, and then we review those on a quarterly basis is how we try to stay as aligned as we can when it comes to our strategy and what we're doing. And then how we're doing it is culture. And that's equally important to stay aligned. And that is the cultural values that I mentioned that we defined and then try to communicate and integrate into interview process, performance review, and everything in between.

Wow. That is very tight. Very well said. Very articulate. And it just feels like, ta-da, that's how Matt does it. Were you just born that way? Like, oh yeah, that's how we do it. Or like, how did you iterate your way into figuring out that as you grew?

Yeah. Great team is that. Great team, great board, great advisors. And it may sound crystal clear and perfect. But as anybody working in any company knows, there's tons we can improve within that construct. And so, but yeah, it's been amazing. Like team members, I often think people, when people talk about advisors and mentors, I think they often look, they think externally. And I do have a lot of those, including our board. But like some of my best advisors in terms of how we've learned everything I just said were my team, were my team members. And it doesn't mean I wasn't managing them and coaching them and developing them, but I intentionally bring on team members with the attitude, if I'm the smartest person in the room, I'm in the wrong room. And what can I learn from this individual? Because so many team members over the last 14 years, especially my direct reports that I've worked the closest with, taught me so much over the years. So that's the main answer.

Yeah. Talk about that journey because when you were— talk about who you had around you when you were starting the company And then let's say 5 years in and now 14 years in as a public company. I've checked out your management team and it feels like your management team now has kind of been with you 2-ish years-ish, maybe some 4 years, but that obviously there were folks who kind of— it's like always like a process of bringing the right executives in for the right level. So talk about how you thought about that. What was hard about that? What was sort of obvious to you about that, about bringing new executives throughout the growth?

Yeah. Oh, it's such a good question, especially for founders, entrepreneurs, leaders of growing businesses that are listening to this. I would say that I'll start with just getting to know me a little bit better. I think about towering strengths, meaning what is that towering strength that an individual has? One of my towering strengths is I think that I get to know people, I connect with people, and therefore I'm pretty loyal to individuals. And I often see and find what's best in them. The shadow of that is I can be too loyal and I cannot make team changes fast enough and things like that. And where I think I've improved over the years is two things. One, recognizing what is needed for a certain stage that is coming or is already here. I used to be way too late at that. And that's where I do ask my board, ask advisors, ask, you know, my network for especially when we were going from Series A to B to C to D to E, like, what does a Series E chief fill-in-your-blank officer look like? And I would get to know those individuals. Sometimes what I would do is I would pair those individuals with the current executive and they would help them continue to grow. Sometimes with those individuals, it would just be like, aha, this is what is needed at this stage, and I need to start building towards that transition to get to that. And sometimes what it would do is actually establish a relationship with somebody that I would eventually hire. But the important thing, and this is how I've bridged the gap with the loyalty and the deep care I have for people, and this is, I think, really important for any CEO or executive that is on. Some individuals really have the desire and the skills and the you-name-it to go from Series A to public company. Most individuals, it is a completely different job. And it's like putting a square peg in a round hole. And the challenge that we have as a society, as leaders, as you name it, is getting past the judgment or stigma that somehow, like, the skill of a larger company is more important than the skill of a startup. It's just different skills. It's just different skills.

Or like, oh, you couldn't, you couldn't make it, right? So you couldn't do it, right? You couldn't scale, right?

And some of our early executives, I mean, first they've done very well as the company has done well, right? Because they were early employees. But second, I think that they've, they've, they've learned about themselves. Some have learned they like to continue to grow and taking on larger teams and larger organizations and different challenges. Some have learned like, this is my sweet spot, and have become serial entrepreneurs with that executive role within that stage of companies. And that's just awesome. So I think that's a really hard thing for CEOs because I think most CEOs, it's all the spectrum, but they care deeply about their team. They have loyalty and The reality is like the company would not have gotten from A to B, B to C, C to D without Executive X. What people forget is that the executive for whatever the later stages actually wouldn't have been that good in the early stage. That's why they wouldn't even interview for those jobs because it's just a different skillset. So approaching that without judgment, but with a lot of thoughtfulness, care, and then making sure as a CEO, if it's your first time, you're making sure you are understanding at least what that skillset looks like, which I didn't until, and I learned the hard way, 'Cause that's the worst thing as a CEO and manager is if you don't know what that looks like a couple years out, 'cause then you can't guide and lead thoughtfully towards that. And so, a lot of lessons learned, a lot of mistakes made on my part, but I think I've grown in that area to be both, you know, loyal, care deeply about people, but also have honest conversations about what skills are needed at various stages.

Yeah, oh, so important, though, and so hard, so challenging. When you say you learned the hard way, can you give us an example of, like what happened, how you learned the hard way?

Yeah, I would. I mean, the most poignant example, and this is where I say when I learned the hard way and I made mistakes, is when I didn't— when I ignored the signs that somebody was outgrowing this certain, like, stage and scale that they were at. And I had to have the board or others come in and say, you're not moving fast enough and you have a blind spot. And getting defensive in those moments to be like, you're not seeing the skill in this person as opposed to being reflective. And the out on that I found over time was like, hey, show me what you're seeing in terms of talent. And sometimes, honestly, advisors, board members, all of that were maybe too soon. But the mistakes I made, it's the worst mistake as a manager. It's not knowing what success looks like at that stage or period of the business. And then it results in more rapid transitions because you don't have time to kind of have those like thoughtful conversations that I think I, as a manager, owe any employee, and in a rapidly growing company, things change quickly. And so, it's when I didn't know what success looked like 2 years out, therefore, I didn't provide as clear and continuous and ongoing coaching and feedback, and therefore, it was a faster transition. That's on me as a manager, and that's where I've learned.

Yeah, I hear you. What does the conversation look like? Like, let's say I'm the employee, I'm the executive that— Yes. And by the way, to your point, not good, not bad, but genuinely not right now the right fit for this role, or you can see in a year not gonna be the right fit. What was the conversation you would have with me?

I think it's so dependent. I believe on situational leadership. Honestly, I think that one of our values, lead authentically, hires people who know themselves. And I think that you'd be surprised more often than not, I have, conversations with team members that are like, I'm not enjoying this as much. Like, you know, you brought me in to do this and this, and I've done that and it's been awesome. But, you know, I'm ready for my next chapter and let's talk about having an organized, thoughtful transition. And sometimes that comes via very clear, direct feedback I'm giving them, which kind of forces the issue. But oftentimes I've really, throughout the journey, so many members of the team have exhibited self-awareness and opted out when they've felt like it's just time to hand the baton in a very positive way because they crushed that lap racing and it's now time to hand the baton to somebody who can take the next lap. Yeah.

Wow. I think that that is very— that does sound like you have people with self-awareness and also one way or the other, they were, as you said, like they were, they were kind of coming to an understanding. And back to your point about lead authentically, how do you make sure you hire self-aware people? Because as a coach, let me tell you this, when someone tells me I'm self-aware, I'm like, great. Yeah. I'm sure you are. When they keep telling me they're very self-aware, what I know for sure is they are not self-aware. So how do you really test for that as you bring people on board?

I would say that I tend to get to know people through their whole journey in terms of just like understanding their journey and, and understanding why they went through various career transitions more so than what they did. And I get into more depth on the more recent experiences, but the why of various career transitions is, is, is sometimes telling. I then do ask that towering strength and shadow question, which is interesting to kind of see the level of both self-awareness and authenticity that comes in an interview. I ask about failures and areas where folks have grown through failures and seeing how authentic and deep that is. One of my favorite questions is I ask, what are 5 words that you would use to describe yourself? And I say, don't overthink it. Just 5 words. Like, what, what comes to mind? Helps me kind of get to know just kind of more of that stream of consciousness, how they do view themselves. But to your point, yeah, I don't respond well to like, I'm super self-aware, I'm super self-aware, because it's the most self-aware people recognize it's a journey. I am so humbled so often when I'm like in my 40s now and there's a like area of myself that I just did not see. For 40 years. I'm like, how did I not see that for 40 years?

Yeah.

And so, yeah, anyway, to your point, those are some of the ways that I interview and ask those questions though.

Yeah. By the way, you're just making me think like, and I'm a coach, right? So I will come across again areas that I'm like, goddammit, I'm still working on that. You gotta be kidding me, right? Yeah. It's the hard stuff is hard.

Yeah, totally. And on that, I try to model— I think the combination of lead authentically and continuously improve to our values kind of ladders up to, you know, what folks kind of call a growth mindset. And I try to ladder here areas where I have failed, here areas where I have huge strengths. I think sometimes like we need to, like, it takes confidence to actually be like, here's where I'm strong. But then I also put together a development plan I do an annual 360 in-depth review that my board leads, different board member each time. I can talk about that process. But then what I do is I take that and I put together a development plan. And then I share either all or parts of that development plan with the entire team. And I think that also is something that just kind of sends a signal. This is less about interviewing, but once folks are part of Remitly, kind of sends a signal like we're all growing. And to your point about growing in different ways, I must say it's a little demotivating when— no joke, there were some things where I would have that on my development plan for like 3 years. Be like, still, it's still there. And then honestly, when I take it off, I'm like, even like thinking right now, I'm like, I should probably put that one back on. So it's a journey.

I was going to say, what are you actually— what was that thing that you were thinking? I should put that back on or what? What are some of the areas right now that are on your development plan? Or that— or that—

yeah, I think that I can be more— I think that I can be more decisive, assertive. I think that, again, towering strength and shadow. The towering strength is I'm curious, I listen, I have a growth mindset. The shadow of that is it can come at the expense of, like, conviction, boldness, and decisiveness, because I really do respect people around me. Folks come to me with a compelling argument, I'm like, "That's actually a really good point." So, decisiveness, boldness may sound counterintuitive because I think we as an organization are very bold. We have a bold vision. But when it comes to my leadership style, I empower my teams. And there are some instances where I just need to be more decisive, lead from the front, as opposed to empowering and delegating the team to the team. So, that's one that, yeah, again, towering strength, shadow, and I'll continue to work on growth.

Yeah, yeah, the journey continues. I want to talk about your journey as co-founder CEO of a startup to a larger company to an IPO, right? So maybe first talk a little bit about how you would think that you've grown, and then I really want to talk about, you know, like, when did you— how did you come to understand— how did you come to the decision to IPO and what was that like? But first, just talk about your overall how you see yourself having grown in that, in those stages.

Yeah. Oh, that's— there's so many areas. I think what comes to mind first is, you know, in the, in the early days, I was in my like mid to late 20s when I started Remitly. And part of this is being a first-time founder and CEO, but there's just a lot of doing. Like it's direct. Action to contribute towards building a great product that has product-market fit and good unit economics that then can start to scale. There's a lot of doing, right? Like, and so I co-founded the business with two amazing co-founders. One was a co-founding engineer named Shavas, and the other was co-founding product. He was the CEO of his previous business, actually. Speaking of self-awareness, he was like, I don't want to be CEO of the next business. I want to find a strong CEO. And he was our mentor in Techstars. And so, he joined—

He was your mentor in Techstars. Fascinating. Okay.

Yeah.

Yeah.

He was our mentor in Techstars and he had built and sold a successful company in Amazon. And so, he was at Amazon at the time. And our first office was in South Lake Union in Seattle as part of the Techstars office. And he would walk across the street because he worked at Amazon and I think he missed the growth stage and the startup stage. But he, Josh is his name, Josh, product. He was like, it was such a gift in those early days. Because if you think about most first-time CEOs and they get their first term sheet, and they'd be like, what does this mean? And what legal counsel do I go to? And what blah, blah, blah, blah, blah. Josh had done all that, not to the scale that we had gotten, that we have obviously now gotten to, but Series A, B, C. And so like, I had my, like, to the point of team members being the best mentors. I was like, well, you've been CEO before. And so, but a lot of those early days was about doing. And I felt my job, especially as a highly regulated fintech, was to get the licensing, get the banking partners, take out the trash, get the office set up. And then as the company has grown, the biggest shift is now it's 100% about leading and managing a team and setting the right culture. And so anytime I'm not doing that, I need to ask myself, you know, why am I digging too much into this area? But there have been a lot of other ways that have grown too. But that, that's, that's the biggest. It went from like pure doing— sometimes I say from doing to directing. Like when you're 50 people, I think that, that good judgment, which quite frankly Josh and Shavas have better judgment in some ways than I did in the early days, like they are right a lot. But it's directing, telling the team what to do still. And now it's much more setting the right goals and culture and driving the right outcomes and accountability, less so than telling people what to do in terms of being more directive. And the other last thing I'll say is that hasn't changed is our commitment to mission and purpose for sure has been there from the very start. And the second is our like intentional approach to culture. Again, does not mean we have a perfect culture, But guess what we did before we had a single licensed product or transaction? Josh, Shivas, and I did a little offsite where we whiteboarded the kind of cultural— our first set of cultural values, which had good intent, weren't actually very good in practice because I can go through an example of how it's evolved to be better. But I think that culture, that intentional approach to culture, I think has been there from the start. Again, far from perfect, but trying to take an intentional approach, I think, has been there from the start too.

Right. What was the example when it could have been better?

So if you— I still have a photo of the— oh gosh, this is my handwriting, which is so bad. My handwriting is so bad. But I still have this photo. It's— oh my gosh. And I'm not, I'm not being self-deprecating there. In elementary school, my mom saved all these things, like, my— and so I have an elementary school, like, whatever grades, and like, It was like, it was like not satisfactory for penmanship. So I'm not, that's a fact. My handwriting sucks. But the, but the, the thing is, but it was my handwriting is we whiteboarded our values and customer centricity was there. It's always been there. It's never changed. It never will change. And I don't say that broadly, by the way. I mean, I don't say that lightly saying it never will change, but other values, like we had a value relationships that I still can picture the whiteboard. And then we had what relationships means. Think about relationships in the context of an interview process or a performance review process. It's way too big. It's way too broad. And this is why I think you need a longer set of values because what I found myself in interview debrief is like, this person's like strong at relationships or not strong at relationships. No, like that's no. So we've evolved it into things like lead authentically, like folks who have authentic leadership styles, I think can naturally have stronger working relationships, things like be a compassionate partner, and things like constructively direct. And those are the things that actually form healthy working relationships. But it evolved from the intent to much more nuanced and specific behaviors that drive the outcome of strong relationships. That's the example.

I got it.

There are many though. That's not the only one.

Well, that's, I mean, it sounds like it's just a company that's been evolving and that you actually had, you had a lot of intentionality around your culture. And so, you take a look at it every every year, and so that you then kind of continue to refine it.

Yeah, for sure.

Yeah, for sure.

And culture should also— one last thing is culture should match the strategy and the vision of the organization. And I think folks like, there's no right or wrong culture in my view. There's just cultures that do a better job being intentional about aligning for what the organization needs. So if I think about reimagining what's possible, that's very applicable to today with AI, but it's also very applicable when you think about our broader vision as we're expanding from a payments company to financial services that transcend borders. That takes a lot of reimagining and rethinking. And that is a cultural value that's in service of a company strategy. And I think that's also something that a lot of companies get wrong is they think that every culture should somehow, there's like a right or wrong culture. Now, I think there's just more and less intentionality in certain cultures. And there's more with the ones that are more intentional, some align it with what the business needs are, and, and some are less intentional on that front too.

Yeah. It's not just a set of words, not just a set of pretty words. It's actually gotta, gotta amount to something. I love that. So you IPO'd in 2021. And I'm just curious, what was the process like internally to get, as we say, IPO ready? And then what was it like for you to learn now to be a public company CEO? How's that different?

Yeah. Every company that wants to go public takes a slightly different path in terms of readiness for us. And I'll break down readiness into the nuts and bolts of readiness from the how to kind of prepare and think about the team and how to engage the team in that IPO process. So nuts and bolts of readiness, I think we had slightly better because we're a highly regulated institution. But we also, unlike a bank that can buy like a core banking system, we've had to build a lot of our own technology. And so getting a lot of the controls and other things like that set up without onerously slowing down our velocity and speed was something that we had to, had to just get more maturity around. And there were a lot of other things that you just have to get in place, you know, to be a public company in terms of processes, forecasting, compliance to Sarbanes-Oxley, security, privacy, all of those things. So there was a lot of nuts and bolts that needed to go into it. And it was, you know, a process. I don't know if you could say a year or 2 years, but it was a process. That we did with the team members that needed to be involved in those work streams, okay? And we tried to take a first principles approach to prioritizing the work that had to be done anyway, that was good for our business as well as helping us, you know, go public. We did not engage the broader team that much. And that's something that I see some companies get wrong, which is that they set the IPO as this like north star of like, let's all rally towards like getting public. And that's like the goal. And the problem with that is twofold. One, it's not especially customer-centric. And two, companies can't control when they go public. Markets are markets and they have IPO windows and they open and close. In fact, when we went public in September of 2021, within weeks, I mean like a week or two or three, it was somewhere in that, the market completely shifted and the IPO window closed. And had we rallied, and now we got lucky getting out before the market closed because that wasn't our intention, But had we not, I just think it would have been a big demotivator for the team had we engaged everybody as opposed to keeping the group involved that needs to do all the nuts and bolts of getting ready. And then the team, of course, knows you're thinking about it in terms of like you have to do like various filings and things. But ultimately, the IPO wasn't the goal. It was continuing a journey of which the IPO is a very important like gas refueling station in terms of accomplishing a bigger and bolder vision. And so therefore not highlighting it too much with the team is I think something that I recommend other folks thinking about it.

Yeah, that's very insightful. I mean, there is so much, I mean, to say the obvious, when you went out then, I mean, the IPO window kind of closed for almost like 2 years. Like, if everyone had been like, what am I going to do now? So this idea of like, we need to keep this as a tight team and navigate as we need to is a very, I think, very insightful point. And obviously all the readiness factors. I mean, you guys had a real burden because of your regulation and whatnot. So it's very interesting. So you were really, it sounds like you were marching towards that for, you know, a year or more. It doesn't just happen overnight. And I think that companies don't always recognize that. So what was that like for you to make that shift, right? From, from '21 to now '25, you've had to grow in terms of, you know, being more visible and reporting to Wall Street and all this stuff. What, what changes have you made and what that's been like? What's that been like for you?

Yeah, I think it's felt like a continuation of a journey, and that's maybe more specific to us because we had raised several private financing rounds over a lot of years. And so there was still— and I took a pretty proactive approach to investor relations, even though private companies don't call it investor relations. In the early, early days, I sent a monthly— this was way too frequent, maybe it was quarterly, but I think it was monthly at one point— update to our, like, angel investors on how we were doing. Maybe that was a little too much overhead, but I've always felt like it's important to communicate to investors in the right way and ask investors for advice and help in areas that they might be able to help. What changes in a public company that is undoubtedly true is that it's public, so it's way more individuals, and there are a lot of guardrails, which have both positives and negatives around that, meaning like there's Earnings, there's a period where you can talk to investors and then that window closes and you can't talk to investors for a period of time. So it can be pretty intense in earnings in that post-earnings period. There's also the need to set expectations with public investors. And that's why I think companies are very wise to understand their business and forecasting and things like that before thinking about going public, because that kind of forecasting and predictability of the business is very important and really important to think through, which I do with a very talented CFO and IR our team who have been through that a bunch of times. So there are definitely differences. I need to be even more intentional with my words. I need to be even more intentional about what I say. But overall, it's been a— a lot of public company CEOs don't say this, but it's been a positive experience in the sense that it's a continuation, I feel like, of having many private company investors to now just being in the public context.

Well, it feels like you really just have been building muscle for years. I mean, without necessarily knowing it, but that like you're again You talked about your towering strengths. It feels like your towering strength is also just engaging other people. And so it would be the most normal thing in the world for you to kind of engage your investors and engage your kind of stakeholders. And that pool expands, that circle expands, but you're continuing to do the work of engaging people. So it doesn't feel like it's that different for you.

Yeah. Yeah. And engaging. And there's also an element of like teaching and Again, towering strength and then shadow. My towering strength is like my brother's an elementary school teacher. I like telling the story over and over again. I like curiously listening to feedback, not just being like this investor, whoever doesn't know what they're talking about. Like I filter feedback sometimes, but I think that that can lack some intellectual stimulation for some CEOs at times. But I go back to a story during our actual IPO roadshow where we were, you know, saying literally the same story over and over and over again. And it was during COVID So we were— I was doing it from home and my wife was like, I think you've said the same thing 200 times. And I'm like, but isn't it awesome? Because I'm like so passionate about our vision and our mission and like telling people about it. And maybe it's not the most intellectually engaging at times, but it's like teaching people about what we do, why we do it. And I love that. So again, it's about knowing thyself. And I think a lot of founder entrepreneurs are more drawn to problem solving. Some of the things that I've surrounded myself with my team members that have those as towering strengths. So I think to your point about it being a journey, yeah, it's been a journey and I've had amazing coaches to help me improve and I still am improving in terms of my communications and my ability to educate and tell a story.

Yeah, I love that your wife said that and you're like, yes, I wear that as a badge of honor. It's a good thing, not a bad thing.

She said it as a compliment too.

Okay, that's good.

That's good. She said, you said it like 200 times and every time it seems like you're saying it for the very first time.

There you go. That's good. It's good. Just a few more questions. Have you ever experienced imposter syndrome or severe self-doubt?

Absolutely. Many times. Many times. And it was really good to have advisors and mentors and co-founders that I could go to at that point to kind of help me get out of my head. But there were many times, especially, I mean, most founder CEOs early to mid in the journey get fired by their board, which the board could have done at any point. And so because I relinquished control of the business pretty early, and so those are the ones that come to mind the most is like me going to my co-founder and being like, I think they're going to fire me. And he's like, what? And I'm like, no, I think they might. And then, and then we can talk through some of those like insecurities. So imposter syndrome has definitely existed. It's a human emotion, especially when one is being stretched and it's really important to have trusted people that can give you real feedback. My co-founder was not— and he's still on the board— he's not a, oh, you did a great job and everything's great. But he was like, they're not going to fire you, but he's like, here are the 12 things you actually messed up in that meeting and that you need to do better.

So is that your advice for other founders and how to handle imposter syndrome, to sort of have people around you to help?

I think so. I think, I think sometimes it's hard to have an objective view of oneself, at least for me, I'll talk about myself. In those instances, it was hard to like, I didn't know if I was in the spectrum of like going to get fired versus whatever it was. And I think that what we can do and what I've done in those instances, and that's why I mentioned Josh, my co-founder, as an example here, is it's hard to get objective good advice. And so I love surrounding myself with like people that are not afraid to be very direct and very clear. It does not mean it's like, you did a great job. Sometimes we need to hear that. And I feel like there are more people that you can reach out to to just get a like great job. But I think finding those individuals that are in the room that can give you honest and direct feedback of, hey, listen, imposter syndrome, let's get off the table. You shouldn't be in the room. You should be in the room. Okay. Here are things in the room that you did of why I say that. And here are things that you've got to continue to grow on to be able to continue to stay in that same room. And that I think is surrounding oneself with those individuals, I think is like gold. But it's hard because it takes a lot of trust. Like most people, if you're honest, like don't want to give that tough, direct feedback because they're afraid you're going to get upset. So creating that psychologically safe environment, I think, is also really important.

Totally. Yeah, I think that's such an important element. People will not tell you the truth unless you give them incentive to tell you the truth.

Exactly. That's true with investors, by the way. If they're early founders on this, investors, they will not tell you. They don't have any incentive to piss you off because they want to stay in touch for the next round. So you got to create a lot of psychological safety. For them not to just be like, it's timing, you need to look at a show, a little more traction. And some of the best investors gave us the best feedback. And then guess what? Those investors led our next round. Almost every single round was led by an investor that passed on the previous round. And we didn't listen to a lot of investor feedback because it wasn't very good. But the really good ones, we created this psychologically safe environment to say, what don't you like about the business and why? And what can we learn from you? And then we solved some of those things and then they came back and led future rounds.

Gold. That's amazing. That's amazing. That's a masterclass, by the way, just a masterclass in so many things. Psychological safety, listening to feedback, not reacting and responding. There's so much there, right? Matt, what do you wish you had known earlier on your journey?

My towering strengths and shadows. I think it's hard to know those until getting some years of experience and feedback and things professionally under one's belt. So had I known those earlier, I think I could have even directed things even more effectively. And I'm still learning those things. Like there's still a bunch of my towering strengths and shadows that I either haven't crystallized or haven't found out about myself. And I think the earlier one does that, the more they can craft their career, craft who they surround themselves with to complement some of those things, and then craft their development plans to the right direction. So that's what I would say.

Love it. And last question, what advice do you have for other founders as they embark on their journeys to grow into leaders?

I mean, my advice to founders in general, maybe it's not them developing into leaders, is fall in love with the problem, not the solution. And then have grit, tenacity, and perseverance, but apply it to solving the problem. Don't apply it to hardheadedness around the solution. That would probably— I'd probably reinforce that point.

I love it. Matt, what can I tell you? It has been like this hour has gone like a minute. And I just want to say thank you so much for this great conversation. A lot of people are going to benefit from it.

Thank you so much. This was so fun to see you. I always love our conversations, so thank you.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.