Caribbean American, Jesse Owens II (no relation to Jesse Owens the Olympian) – is a Product Enthusiast with a Love for Culture, History, and Education. He is also the Senior Product Manager of Digital Payments at MasterCard.
Resource mentioned in this episode: “Drive: The Surprising Truth About What Motivates Us” by Daniel Pink
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Hello everyone, welcome to another episode of the Carry on Friends Podcast. I’m so excited that you’re listening. Today’s guest is Jesse Owens II. Jesse is a senior product manager at MasterCard. I met Jesse a few months ago at a Caribbeans in Tech and Entrepreneurship meet up, and we got to talking and I thought he would be a great guest for the show. Now when I first decided to outline the podcast, I thought it was going to take a more inspirational angle and it does to a certain degree, but Jesse ended up giving so much information about his career and how he ended up being a senior product manager at MasterCard, that I instinctively knew that the topic of the show would be “The Importance of Being Strategic about Your Career”. I’m so excited about the episode and for you to listen to the episode because what Jesse ultimately says in the episode supports what I’ve been passionate about with Carrying on Friends, which is understanding your competitive advantage, leveraging that to be more successful either in the workplace or in the entrepreneurship ecosystem. I don’t want to give too much of the interview away. I do want to warn you though, we had a bit of a technical difficulty during the recording of the episode, and so the sound quality isn’t what it usually is, but I know you will still enjoy the episode. So I won’t keep you waiting any longer. Here’s my interview with Jesse.
Kerry-Ann Reid-Brown:Hello Jesse, welcome to the Carry on Friends Podcast. I’m so excited to have you on the show. How are you?
Jesse Owens II: I’m doing fantastic. Thank you for having me, Kerry.
Kerry-Ann Reid-Brown:Tell us a little bit about yourself, Jesse. Let the audience know who you are, which island you are representing and all that good stuff.
Jesse Owens II: Well, my name is Jesse Owens II, no relation to the runner, although I do have a sports – track, football background. My parents, well my mother’s side of the family is from Tortola, British Virgin Islands, and my father is from Munro, Louisiana. So as you can imagine, I have a bit of a Caribbean American background where I was raised in the United States, but I have strong ties to the Caribbean as well as the South. Also, I grew up in Virginia Beach, Virginia where my parents were stationed in the military. So I have a bit of a military brat experience, moving to different locations and meeting different people along the way. Fast-forward to present day, I’m residing in New York City, specifically Harlem. I’m a senior product manager at MasterCard.
Kerry-Ann Reid-Brown:That’s like a lot going on there. So you have the strictness of a Caribbean parent and a parent from the South, and you’ve been in the military. I can only imagine what it was like growing up. Tell me a little bit about what it means or what do you do as a senior product manager of digital payments at MasterCard. What is that job about?
Jesse Owens II: I would just encapsulate it with a product manager, has to research, validate and deliver products to market to enhance the consumer experience. And specifically with digital payments, we’re focused on a product that me and my team work on called MasterPass. MasterPass is a digital payment product that allows consumers to transact online, in-store, as well as through their mobile app. With addition to that, adding in some of the security features that you may see on chip cards and making that a part of the payment experience to further extend our brand as MasterCard is being the leader in payments, as well as securing consumer information.
Kerry-Ann Reid-Brown:That’s awesome. So tell us, how did you end up in this role? What was the path to being a senior product manager at MasterCard?
Jesse Owens II: That is an excellent question. It wasn’t a clearly defined path how I got into product, but I will just take you back to upon graduating from undergrad. So I received my undergrad at the Norfolk State University with a degree in computer science. Soon after that, I began working at J.P. Morgan as an engineer in their assets management line of business. So I spent some time as an engineer and it was a great experience, and you really appreciate how finance works globally, working on the tech side of things in supporting numerous trading desks globally. Then I started to – that was around 2007 and then 2008 happened and this was essentially a global collapse of the economy. So this was an interesting point in time where a lot of folks were displaced, a lot of downsizing was happening, but because I was very young, I felt like that wasn’t an incentive to keep me around because I was so young and that I felt like I was fairly proficient in the technologies, and so continued on my path as an engineer. So fast-forward, I transitioned into a role as a technical business analyst in the investment bank, where I was working in securities lending, working with our developers, our program managers, as well as our executives on defining requirements, how we want to rebuild our existing securities lending system, because we’re on a very old technology and we wanted to be on a platform that was a bit more scalable and something that was more maintainable for the sort of functionality that we want to build into the new product.
At that point, I was about 5 1/2 years in my career and I really had a strong desire of being in a role or being in a culture where we were very scrappy, innovative, really moving with the market and really being on a product that was truly consumer facing, because a lot of the products that I was working on at J.P. Morgan, I was very internal and my customers were traders or program managers. And so, I really didn’t get a chance to really build products that I’m actually able to see in the market and consumers actually use it and getting some consumer sentiments on those products. So I started looking around, started looking at what sort of role would be conducive for the sort of experience I wanted to have, and I wanted – I definitely wanted to stay on the technical side and I wanted exposure from a business perspective. And then also, I had a desire to be in product design. So just doing my research online and I come across product management and clearly, I don’t have the experience right now to start interviewing for product management roles because I lack some of the business acumen as well as the product design. So what I did at that point, and this is around 2012 – so what I started to do was I self-taught myself iOS programming and UX design. I started taking some courses online, then there were also some courses offered through the Stanford school of – I believe it was entrepreneurship. Well it was courses offered at Stanford. So I started building up my product and my product was actually – it was a – this was pre-Instagram, pre-Snapchat. I was building a product that allowed users to take pictures and you’re able to view events based on proximity, and the app was called Piction*. It was myself and a couple other of my friends. We wanted to build an app where young professionals can get a preview of the event before actually committing to the event. You know how often times you get these invites to parties and then the party is going on and then you don’t really know what’s going on at the party until you actually get there. So this kind of gives you a sense of – it is a curate to the event experience into a single user interface that consumers or users of the app can get a view of the event without actually being there.
And so with that, I began using that as my way of pitching my skill sets of being a product manager to the point where I’m going to meet ups and I’m just talking to strangers, just hailing people on the street, just getting their feedback on the idea and the experience that we would want to build for this product. So we were going through the mechanics of building a product where we were building our prototypes, getting early validation, iterating over the feature set and then demoing the product at various forms, at meet ups or at events, and getting feedback from that perspective. So that allowed me to sort of hone in on some of the core skill sets that is required to be a product manager, which led me to a conversation that I was in at a meet up with a cofounder of an education tech startup, Imagine Easy Solutions. I spoke with the cofounder, the conversation went well and it was my thoughts that they were just interested in the product and just wanted to learn more about it. They invited me to their office and I presented a demo in front of the cofounders and as well as the engineering teams and sales marketing. They really loved the product and that ultimately led to a job offer on the spot. This was something that was totally unexpected because I was just going there just to demo what I had built up to that point. Then I was offered an opportunity, and because it really aligned on where I wanted to take my career, I definitely had to take advantage of that opportunity. That was my introduction to product management, as far as my first opportunity being in that role.
Kerry-Ann Reid-Brown:So you just said a whole lot and normally I’m like – I was busy writing because I love everything that you said. I just want to unpack it because I was like yes, yes, yes, yes. What made you realize that – because you know, I understand working for internal customers versus external clients who are going to use the products, is very different. So what was that one thing that you said you know what, I don’t want to do this anymore, I want to work on products that I can see people use in the market? What was that for you?
Jesse Owens II: So for me, it was really – I want to be able to tell a compelling story. For me, I’m very introspective so I’m always looking at – in every role that I’m in, I want to be able to understand what’s the story I want to be able to tell once I’m done with this experience. And also, I have to be honest that during 2008 and the years after, where there was a lot of financial distress and a lot of people being out of jobs, out of homes. It really made me start thinking about how else can I help, given my skill sets, and is it working in finance or is it really building products that actually delivers value to the everyday consumer, the everyday user. And so I wanted to really be able to tell a story. At that point, I was thinking about if I was to leave finance, what are three things or three sorts of problems that I want to have an impact on. At that point, it was education, music and healthcare. I think that’s very important when you’re thinking about making a transition, is identifying what sort of problems you want to solve once you leave a particular industry or company, and making sure that it aligns with your own personal goals because those are three sorts of avenues that I’m very passionate about. It just so happened that education happened to come up in my transition, where that’s how I was able to land the product management role at the education tech startup, because I truly feel that education is the key for longevity not only for professionals, but also for children, parents, just anyone that – if we’re existing, I feel like education is something that’s paramount. It just so happened and I was just blessed to have the opportunity to work in education and delivering solutions to help with the research and information literacy for high school and college students. That was essentially my role at Imagine Easy Solutions, was to build products and solutions to address those paying points in regards to research and information literacy.
Kerry-Ann Reid-Brown:So what I heard was the first thing you did – which is kind of something that everyone really needs to understand. In a changing economy, especially you were in finance, you needed to figure out how to diversify your skill set because if you were creating products for internal teams and a financial company and the economy is going kaput, there’s not much to ensure that you still have a job versus where if the product is consumer facing, you have a better chance of maintaining a role because consumers will still buy things that they like, enjoy or will need to use in their everyday life. So that was so key and that’s what I picked up in that. I tell people all the time, diversify your skill sets. You were strategic in identifying the areas that you really enjoyed. You did the research to figure out where your deficiencies were and try to fill that gap by doing the research and doing all the work. So you are like answering questions that I had like way down in the interview. It’s really amazing how you can plan your career. I think the challenge people have is that in the direction you took, it doesn’t mean that it’s in months. I don’t know how long it took, maybe you could tell me that. What was the time between okay hey, I don’t want to do – I want to work on consumer products, to actually building your app, getting the job at the tech startup to know that you are at MasterCard. That’s about what like five, six years?
Jesse Owens II: Yes.
Kerry-Ann Reid-Brown:Yeah. And so, it’s understanding that the journey to the career path that you are going for, it’s not an overnight thing. It’s going to take intention, planning, some continuing Ed certificate course. The other thing you talked about here is making those connections. So going back a little bit, you mentioned at the very top of the conversation, your mix of the Caribbean background. Your parents are from the South, you are an Army brat. In all of this navigating through your different roles, what role did culture play? The culture in terms of your Caribbean culture, how you were brought up, just how being in the military, how did that affect you in terms of settling in or how did that help you approach your career transitions?
Jesse Owens II: So my culture background is one of hard work and perseverance. Both my parents did not come from wealthy families, so hard work was definitely something that was amplified in my family because nothing is given to us as my parents liked to – they were adamant on if it’s something that you truly want, you have to work hard for it and really knowing what you want and then just being very steadfast in your pursuit to achieve that. With my family, like they were very blue-collar, where my grandfather, even though he’s a well-known fisherman on the island and my father’s side of the family, they used to work out in the fields, picking cotton. So that’s very humbling just knowing like where my family is from and the sort of work that they had to put in to achieve the monetary success that they are able to experience.
So for me, how that resonated to me as a child growing up, is that I don’t want to disappoint my family or my culture because of my lack of hard work. That was something that – you can tell me that I probably need to improve, I may probably be the most articulate, I may not be the brightest so to speak, but one thing that I would make sure that I was the hardest worker. And with that, renders a lot of value as well because you’re able to outwork your peers, you are able to identify opportunities for yourself that you can ultimately improve. So for me, I had a mentality of I always want to feel like I’m in a mode of constant improvement. I’m always self-reflecting on myself on what can I improve on. It all correlates to the hard work that was infused in me growing up as a child, and that’s evident now. Even the stage that I’m at now in my career, I’m always trying to identify areas of improvement and doing self reflection and always trying to collect feedback from people that I work with, even my friends, family, on things that I can do better because I always feel like you’re always in a mode of constant refinement.
Kerry-Ann Reid-Brown:Love that. You said something earlier which I think a lot of Caribbean children – I’m still a child, I have a mom so you’ll always be a child even if you’re an adult. It’s never wanting to disappoint them because you really know what they had to go through, where they are coming from and you know that their hopes and dreams and all the hard work was put into you. And so, instinctively, we are working not just for ourselves and to survive, but I think – at least for myself, for a very long time, I never did anything for myself. I did it for them first and I considered myself after. I was just like alright, I’m doing this because… It’s a double-edged sword because after a while, you tended to – at some point, you have to say well I kind of have to do things for myself, but the fact that we do it for them first is our drive for excellence regardless of what we do. So I am really glad you said that because sometimes I feel it’s just me, but you saying that just reminds me that we might come from different islands, but we all have that thing where it’s like we’re doing this for our parents, because we know how far they are coming from, so really, really amazing. Jesse, I’m going to go back a little bit because oh my God, you said so many amazing things. I need to go back and unpack that a little bit. So I’m going back to the story where you transitioned and how you mapped everything out and the three things you identified. Let’s talk about Piction. How long did it take you to develop the app, build it and are you still building apps? Tell us a little bit about that.
Jesse Owens II: So Piction came intofruition… It was myself and two other friends of mine. We were just talking about the idea and we felt like it would just be a cool app for not only young professionals in New York City, but we felt like this would be applicable to any metropolitan area that has a vibrant event, social scene. So we were thinking about the idea, and I’m in my process of attempting to make a transition. This was something that we were working on over weekends, sometimes late nights. And so, I guess the time that it took – just to preface this, the app never made it to the app store, but what we did, we had a prototype that we were in refinement to bring to market. What was apparent was when we were demoing the product, one of the main questions is – and I think the issue is, is that this product, being that we are in New York and New York is a very, in terms of startups, New York is very stringent on funding startups that doesn’t have a clear revenue stream, whereas in other locations in the US, you hear of startups getting these evaluations and you’re still trying to figure out what’s the business model. So we were constantly trying to figure out like what’s the business driver of Piction.
As far as what the use cases, we had valid use cases for the product. It came to a point where we were unable to sort of determine what would be the revenue drivers for an application like this. Given that we are basically on the heels of the Instagrams. It was hard to really drive preference to this application when you have Instagram in the market. At that point, we all felt it was a great idea, but we also had other interests as well. And so, we just decided just to put the project or the product on pause, but we had basically used an entire year to go through that whole process of developing the product, getting the validation, putting together our pitches and showing up at different events and collecting feedback. Ultimately what occurred is that essentially, we were able to understand where this product had fit and where our product sort of lacked in terms of what are some of the business viability of this product. And so, at the end of the day, we all realized that and it was just the situation where we definitely enjoyed the experience because it was something that was very impactful for all of us, just going through that whole process, then just getting that validation. Sometimes you need failures to really help refine your way of thinking on building products and how you approach developing products. That was something that definitely resonated to me. Then at the end of the day, we just decided not to pursue the product anymore, but through that experience, we were all able to build out those mechanics of developing products.
Kerry-Ann Reid-Brown:I can imagine that this experience was really a foundation for you in terms of your current role and understanding, going through that year of building out the program, understanding use cases and how people interact with it. So like you said, this one year, while it never made it to the app, you failed up because you used that experience to springboard you into giving you more insight as a senior product manager. The other thing though, I think the previous site, meeting site, the Caribbeans in Tech and Entrepreneurship meeting, there was a group of gentlemen – I can’t remember their names. They have an app, is not a picture*, but it’s called the Whim app and the concept is so similar. You are able to see into parties and all that good stuff. They did a pretty decent demo and that might be getting a little traction. So you were really a pioneer, it’s just that I think now, I think we might be maturing in terms of different revenue streams or how you could generate that. That’s also part of it because when you probably did this, people were looking to more traditional revenue models versus a mixture of rewards or sponsorship or – not sponsorship, ads. Again, I’m sure this experience was just like really an insight because, because of this experience, you ended up landing the role that the Ed Tech startup. So that was exciting. Tell me, did you have any obstacles that you had to overcome in the workplace culturally, academically? What were some of the things you had to deal with?
Jesse Owens II: I would just start with my transition from undergrad to J.P. Morgan. There was a bit of culture shock for me, a) just being from Virginia and moving to New York. Then it’s also like meeting the analyst class at J.P. Morgan and just really having a moment where while we have all these kids from all these prestigious universities, and then I’m the only one from an HBCU. And so that, for me, it motivated me and it sort of challenged me to make sure that a) the hire wasn’t in vain and I’m just not like the diversity mark that the institution made, but I’m also a person that is delivering value and I wanted to outperform my peers. So that in itself allowed me to try to understand what are some differentiations that I can display on a consistent basis from my peers that makes it very evident that they made a great decision on me. So that was just my perception going in. And then actually working, there was a bit of a culture shock with the lack of diversity in my group because essentially, I was the only African-American in the entire organization, or in that particular division. That presented some social issues where I was trying to identify either like mentors or either try to connect with my peers, and trying to just connect on a personal level.
So those are some challenges, but I feel like I’m able to adapt to well, just given my military background and having to adapt to different environments and cities and making new friends. So this was a very common place that I’ve been in, so that was a challenge, but I was able to overcome it just because I was able to apply those same skills that I had to hone in on as I was moving as a kid, moving to different cities and making new friends at different schools. So it was a similar situation. I would just say from a tech perspective, I feel that the technology itself was a transition because we’re going from undergrad where we are building small projects to now where you are working on enterprise applications and people’s jobs are on the line if things go wrong. And so, it’s that sort of pressure that goes into as well. There was a period of time where I was super, super paranoid of doing something wrong and it being a reflection of where I went to school. And so, I felt like I was not only representing myself, but representing my university and anyone, African-American that they even think about hiring. So I wanted to put on my best self as I walked through the doors of J.P. Morgan.
Kerry-Ann Reid-Brown:Awesome. What key lesson you learned about success or managing your career? What was the key thing that you learned that you feel has contributed to your success?
Jesse Owens II: There is a book that I would highly recommend, it’s called Drivewritten by Daniel Pink. One of the key tenets around the book is identified what drives people and what motivates people. It’s a great book not only for individual contributors but also people in leadership. One of the key tenets it focuses on is having autonomy of your work and being able to make decisions. Purpose, like working on things that’s very purposeful and that you can actually see value in. Then there is mastery of skills, and it’s basically just honing in on the things that you care about and working on projects and products that allow you to refine your toolkit. I really feel like wherever I went – I feel like I was at my best when I was able to operate at a high level across those three facets. That’s how I’m able to determine success at a company, but just generally speaking, I value success also in the relationships that you build along the way because it goes beyond just doing a great job. It goes beyond like “oh I wrote this awesome code”, but you need to be able to understand the psychology that goes into building relationships and understanding what motivates others and what’s driving other people within the organization. Especially if you’re in a customer care role where you are managing expectations across different constituencies, understanding what’s driving their metrics, what’s driving their performance and how you play an intricate part in that I think is very important.
Finally, I’ll just say that success always comes with a price. So I would say with success, you have to be prepared with the responsibility that comes with your success. Point being is that – like the saying goes, it’s always appreciate where you are at, but never lose sight of where you want to be. And so, that being said, you want to be able to be appreciative of the space that you are in but also have the clarity that once you do ascend in your career, there’s going to come with more responsibilities. So that’s definitely things to take into account once you obtain different levels of success, is that much is going to be expected of you and you have to be prepared for that and know how to navigate those conversations – sorry, manage those relationships with the people that are invested with what you’re doing.
Kerry-Ann Reid-Brown:The thing that I’m going to highlight here which I think is a challenge, is one of the things I talked about at the last site meeting and you just touched on it, the psychology of the relationships that you build at work, because typically, we are loners. We stand by ourselves. Caribbean people, they don’t talk that much, not all of us, but generally. Understanding the value of those relationships and why you want to have those relationships and understanding that those relationships don’t mean oh we’re best friends, but is important that if you’re working with those people at least eight hours a day, 40 hours a week, cultivating a relationship because there is a certain level of success you want to attain and understanding that your co-workers will be part of you being able to attain that success, you can’t do it alone. So I really, really like that. The name of the book isDriveby Daniel… what was the last name? Pink?
Jesse Owens II: Yes.
Kerry-Ann Reid-Brown:Okay. Definitely add that to my list. I love the other thing that you said, be prepared for the responsibility of success and appreciating where you are but never losing sight of where you want to go. I just love that. It is really key for us to be very strategic about our career, the direction it has to go and understanding that when you are strategic and you do plan, it’s going to take some time. Part of that, when you do plan, you have to have a little sway room and that plan because different things might come up. That’s such an amazing less and thank you for this book. I love reading books, so thank you. I’m going to add it to my phone in a few minutes. What’s the best piece of advice you’ve ever received when it came to your career or personal life?
Jesse Owens II: As you are going through life, I would say look how you can add value to others’ lives because that’s where you start seeing the success and recognition coming to fruition when basically you’re being a servant, not necessarily like you are submissive, but being able to look up around and below you to see how you can add value in someone else’s life. And so, I take that from a personal perspective because I’m very adamant about mentoring, mentorship and just giving my time and energy to people who inspire to get into tech. If we’re talking about in the workplace, if I’m walking around and I see someone working on a particular project and I’ve identified a way of how they can better optimize their productivity, or increase their productivity rather, I would want to share that information with them so that they can do their job better so that we can all come up together. With that, it’s an incentive for them to sustain that relationship with you because you’ve done something for their life or you’ve done something in their role or their job to allow them to be more proficient. And so, I would point to that as – that was one of the key advices that I’ve got early in my career and it’s proven to do very well. I think it can apply to your personal and your professional life.
Kerry-Ann Reid-Brown:That’s an amazing advice because it’s not so much what you can get, it’s what you can give and in the process of giving, you’re also receiving. There’s this amazing thing that happens when you help other people, you also benefit just by the behavior. I feel excited when I help other people. It’s just like wow, not for me but the feeling is just, I can’t explain it. It’s like seeing someone else happy or they have joy, or I’ve helped them with a situation, seeing how much better they feel or how much – like you said, more productive or more successful. That brings me joy. So in church, they call it – that’s where I hear it most, it’s called servant leadership. You are in a leadership role, but you are serving others in their pursuits if you are able to give them resources to help them advance in their pursuits. So I do agree with that and I do enjoy that. Thank you for sharing that because it doesn’t apply to jobs that people think are like around social work, or people even in the tech industry, any industry, it doesn’t matter. Helping people, putting their needs before yours and ultimately just doing it just because you really want to goes a long way in helping each other grow. So very, very excited you said that. What’s the final take away that you would like the audience to know about Jesse Owens and just anything that you want to share? What’s the one take away that people should have from this interview and from managing or navigating their careers?
Jesse Owens II: It didn’t come easy for me. I came from humble beginnings and I had to be humble in order to come to some of these realizations that I mentioned earlier in this interview. I didn’t have the most humility growing up as a kid. I would just say from a humility perspective, I definitely needed some work around it. I definitely had a great foundation with my family, but I definitely needed some life lessons to experience, in order to really appreciate some of the lessons that my parents were conveying to me. I had some of those just dating back to high school, where going into my senior year, I had a 1.7 GPA and still thinking that schools were trying to pursue me even though I was a fairly decent athlete. I had to go through that humbling experience, just going through that constant stream of rejections from college institutions and then given an opportunity to attend a four-year institution but being in remedial classes. It was very inspiring for me, and also it was a very reflective moment that there needs to be some changes in my life and I need to do it now because they’re going to be some consequences if I don’t apply myself.
So just to give that sort of background, but just a little bit about me, I’m a very – I think my journey is a journey that speaks about perseverance and it’s also one that I want to share my story with others. Also, I want to help bring others up, because getting into tech and sort of navigating through your careers and understanding some of the social dichotomies that goes on in the workplace, it’s not easy. So I want to be able to share some of my stories and some of my opportunities and failures throughout my career, but ultimately, just providing some insight of someone who has been through those experiences and just want to be that person to help uplift my community.
Kerry-Ann Reid-Brown:Jesse, thank you so much. The vulnerability of that story and the college GPA and the remedial classes and where you are now, reminds me that people should remember that while our failures can give us insecurities or situations like that can give us insecurities, it’s not who we are now and we can always rise to be better. Those experiences have value and you got that value, or lesson really early and made that pivot really early to get to where you are. So thank you for sharing that story. Wow, success, we often think it’s this really clear root from go to high school, get to college and then we get the big job. You’ve just demonstrated in a very authentic way that it’s never that. It’s about the early failures, learning from those early failures, making adjustments along the way and then being strategic about what you want to accomplish in your life or in your career. So Jesse, I want to thank you for being on the show. I know I’m going to have you back because there is a whole bunch of other topics swimming in my head, but thank you so much for being on the show. I really appreciate your time.
Jesse Owens II:I really appreciate you giving me an opportunity to share my story.
Kerry-Ann Reid-Brown:Cool. And so folks, that’s it. Until next time, walk good.