Welcome to the Meet the Mentor series! In this series, we sit down with software engineers, data scientists, cybersecurity analysts, and more to uncover their unique career journeys, the challenges they’ve overcome, and the wisdom they’ve gained along the way.
Whether you’re just starting out or looking to level up, these stories are packed with practical advice, encouragement, and insights to help you navigate your own path in tech. Each article includes a mentor snapshot + links to follow their work, their video interview, and their Q&A transcript with links to any references.
Follow along and discover the people shaping the future of tech—one student at a time!
Meet Olivia Kasten
From actor to tennis coach to senior software engineer, Olivia has transformed her diverse experiences into a powerful journey of growth and resilience, and now handles internal operations at Betterment.
In her Meet the Mentor interview, she shares how pioneering her own path led her to discover a passion for software engineering and embrace new challenges with confidence. With determination and support from Flatiron School, Olivia embraced coding, secured her first job, and now thrives as a senior engineer. Her story offers encouragement to anyone facing career transitions, showing that persistence and openness to new opportunities can lead to success.
Snapshot
Current Job Title: Senior Software Engineer
Current Employer: Betterment
Past Employers: Colgate-Palmolive
Experience: 7+ years in Software Engineering
LinkedIn: https://www.linkedin.com/in/oliviadkasten/
Technical/Professional Skills: React, SQL, Front-End development, JavaScript, Python, Web Development
Teaching/Mentoring Experience: “I was a tennis coach for a while.”
Words of Wisdom: “Really trying to understand exactly what’s going on is going to get you way farther than just achieving some result.”
Favorite Part of Your Job: “Seeing the light bulb go off when we’re working through something—that is just like the coolest thing.”
Meet the Mentor Interview with Olivia Kasten
Q&A Transcript
Introduction: Who are you and what do you do now?
- Can you tell us a bit about yourself and what you’re working on these days?
- I am a software engineer, actually recently got promoted to senior software engineer at Betterment, which is a robo-advisor similar to Wealthfront. I have been there for coming up on 4 years now. I started at Flatiron in 2018. So I’ve had like 7 or so years of experience now. But now I live in New Jersey with my wife and my daughter and my dog.
- What’s your role at your company and what excites you most about what you’re working on?
- I am on our smart servicing team which basically handles all the internal operations kind of stuff. So, when you call into Betterment and you’re talking to CX, and they’re like, “Let me pull up your profile,” we’re the ones who build that profile for them. We’re also sending “locked out of your account” emails and things like that—we make the buttons to do that. We’ve also recently gotten into a bit more authentication-type thing. We just released 2FA in some of our advisor applications and our Betterment for business applications. So, we designed and pushed that. Currently, I’m working on some compliance stuff. We send checks, and they get returned and that’s an issue for the government, like, “Wait, you need to give people their money.” So, I’m working on figuring out how to find those people and comply with the laws.
Career Journey: How did you get here?
- Can you walk us through your career journey? Where you started, how did you end up in Software Engineering, and how did you end up at Flatiron School?
- Like I mentioned before, I went to Flatiron in the fall of 2018. Prior to that, I had moved to Brooklyn to try my hand at acting and living in the theater, which is incredibly difficult. So I learned that I am faint of heart and I cannot handle not having money or a job. My brother is actually a software engineer as well, and he reminded me that I took AP computer science in high school. And he was like, “Liv, you were pretty good at it.” And I was like, “Okay. Well, if I do this, I can probably have some flexibility and go on auditions and whatever.” So I found Flatiron. At the time, they had a cohort in-person bootcamp for low-income students. And basically, you pay back your tuition after you get your first job, which was perfect because I had no money at the time. So I went to that full time, I think it was fifteen weeks, graduated in late January of 2019, and immediately got a job. I was very lucky to immediately get a job, but I got a job with Colgate Palmolive, like the toothpaste. No one thinks of Colgate as like needing engineers, like software engineers, right? So my now wife, then girlfriend at the time, was from New Jersey, living in New Jersey. So I thought, whatever, I can take a job in New Jersey, Colgate’s down in Piscataway. So I took a job with them, which was really great. They had just formed a new team to build a brand new application in-house, kind of like similar—like it was still internal facing application. But previously, they had outsourced it and they’re like, “We can do it better.” So that was a really unique experience because I got to join a team and then build an application from the ground up. And obviously, having weeks of experience, like I had no idea what I was doing, but I kind of got to get my hands dirty and learn the hard fun way and make decisions that I probably shouldn’t have been making, but they gave me that power and I took it. First month there, they asked if we should use React or Angular for the front end of our application. And I had only learned React because of bootcamp. So I was like, “We should do React.” And they’re like, “Okay, great.” I was like, “Why am I making that choice? That is a really big decision to make.” So I hung out there for like two and a half years and then decided that I was ready for a new challenge, which is when I found Betterment. Colgate was great. I learned a lot, but I think I was more tuned for a smaller-size company, not so much red tape. I mean, obviously Colgate has to have red tape. They’re like worldwide everything, but I think I found a good fit with Betterment.
- What inspired you to pursue a career in tech?
- I feel like I was kind of pioneering my own path. A lot of my friends, especially in the city, were just like theater people. And so, they were taking odd jobs and making it, like doing the thing, which I couldn’t do. But no, it was really just like my brother being like, “You could probably do this.” And I’m like, “Okay.” And then like reading success stories online. It’s like, “Well, if they could do that, I could do that.” I think like my timing ended up being really good, especially right before COVID happened and then tech, like everyone leaving their jobs and everyone hiring people at the time that they did—that was just perfect timing for me and is probably not the same now. But, I just got super lucky.
- How did you land in your current role?
- I actually got a message from a recruiter via LinkedIn. I had literally just started using Betterment like 3 months prior to that message. And I was like, “Wait, I like Betterment. That would be really cool to like actually work for a company that I use.” I mean, I use toothpaste. So yeah, it was a message from a recruiter on LinkedIn that I decided to message back. I don’t always message them back, but that one I did because I recognized the name and then we just kind of took it from there.
Lessons Learned: What have you learned along the way?
- What’s one lesson or insight from your career that’s stuck with you and continues to guide you?
- The first one that popped into my head was never push code in the afternoon on a Friday. You’re stuck there till like at least six, so I I never merge code on a Friday afternoon. But more seriously, just asking questions. I learned that big time at Colgate. I would just take what people are telling me and be like, “Okay, I can do that.” And then I’d start coding and then realize like, “Wait, I don’t actually know what they want. Why am I coding? I don’t know what they want.” So just trying to ask questions and there’s no stupid question. If people are talking in a room and they’re throwing out an acronym that you’ve never heard of before, you can do a quick Google and try to figure it out, and if it contextually makes sense, it’s probably right. But otherwise, just asking, because I feel like companies have so many internal acronyms that no one could ever guess or Google or figure out on their own, so it’s just not expected that you would know that as someone coming into the company for the first time.
- Was there a moment where you faced a major challenge or failure, and how did you grow from it?
- I feel like a lot of the major challenges that I faced were early on in my career, understandably. But coming from a bootcamp and working with people who had degrees in computer science, I felt like I had to prove myself. Even though I was already hired and clearly I was doing something right, it was just like a lot of imposter syndrome. So like every time we would have a code review session, I never wanted to share my code because I was so afraid of the feedback that I would get and I would take it personally. It’s like, “Well I just went to bootcamp. I don’t know what I’m doing,” kind of thing. So there was a lot of defensiveness and trying to prove yourself and like write off what you don’t know. So I would say that was like definitely major challenge—it took me a long time to figure that out. And as soon as I just kind of stopped caring what other people thought, as long as I wasn’t going to get fired or put on a PIP program or something, then I was like, “I’m just learning. I’m here. I’m doing my best.” In terms of when I got my jobs, being a bootcamp grad, I was alone in that. But I did have another woman on my team who had graduated with a CS degree and was super smart. So it never felt like there was a gender battle or trying to fit in with the boys or anything. At Betterment, actually, there are a lot of bootcamp grads that I’ve met who’ve just ended up here—and like a couple Flatiron people, which is wild. My team now has another woman on it, but before that, I had spent like two or three years with all men. But all the men are super kind, super accepting—like, never felt like I had to try to fit in. I was like, “No, I’m just going to be who I am. And you guys can sit back and watch me go.” I’ve been really lucky to have good managers who have fostered a great team environment. And I think that is a big contributor to my success and my comfort asking questions and learning. Like, it’s okay to make a mistake and fail sometimes because I’ve had managers who are like, “Cool. Let’s figure it out. The whole team will help you.”
Mentorship: Why did you decide to become a mentor?
- Why did you decide to become a mentor, and what connected you with this at Flatiron School?
- I was just like looking up bootcamps online. I don’t think I knew anyone who had gone when I went. I’ve just really appreciated everything that Flatiron gave me. They’ve given me my whole career at this point. So I’ve always just like wanted to keep in touch and kind of give back and do these things. It had high reviews, which is always positive. I really appreciated the career support that you got throughout the process and then after the process, and also it worked perfectly for my situation at the time—being low income and like, “Okay, we’re gonna like give you the support that you need to succeed, and you can pay us back later,” and that’s like how we’re gonna work for you. So that was—I mean, it just fit all my needs at the time.
- What inspired you to become a mentor?
- I’ve always enjoyed kind of like coaching and stuff. I was a tennis coach for a while, and that was my side gig while I was trying to act. My parents like to call me a late bloomer because I’ve changed what I wanted to do very late in life—just like compared to everyone else who knows what they’re doing. I’ve done a lot of things, but I just like coaching people. I like helping share what I know. I used to do a lot of coaching for high school girls, and like, high school is a hard time, especially for girls, so like just kind of being that constant support person and being able to model like “Hey, you’re gonna be okay after high school. I know it’s hard, but here’s an hour that we can work on tennis and get through it.” That’s just always something I’ve kind of been drawn to, and I’m trying to work my way into management. So I thought that like being a mentor would be a good opportunity to practice those skills and help other people out.
- Was there someone who influenced your career path and who (knowingly or unknowingly) mentored you?
- My manager right now is very much knowingly mentoring me. And then I would say unknowingly my tennis coach in high school was always just like a positive influence and kind of guided me on the paths that I’ve gone on.
- What has been the most rewarding part of mentoring students so far?
- Seeing the light bulb go off when we’re working through something—that is just like the coolest thing. It’s like, “All right, we can move. We can continue on. This is awesome.” It’s like, “I can show you, I can explain it, but now let’s let you code and let you figure out exactly what’s going on step by step.” And then you just see it in their eyes and it’s like, “Yeah, it’s cool, right?” You can copy and paste anything and it works or whatever, but once you really understand what’s happening behind the scenes, that is cool.
- If you could give one piece of advice to someone just starting out in tech, what would it be?
- I would go back to asking questions—really trying to understand the why of what you’re doing and not just kind of coasting with, “Here’s what they’re telling me in the course, and here’s the solution that they gave me, and I’m going to copy-paste and see that it works.” Really trying to understand exactly what’s going on is going to get you way further than just achieving some result.
Future Focus: Where do you want to go next?
- What’s something new you’re learning or exploring right now, and why does it excite you?
- I am reading leadership books currently right now—management and leadership books specifically in tech, which are very interesting. And I feel like a lot of it is inherent—like, it’s just kind of being a good person and showing empathy and caring about people and trying to foster their success. But the thing that is blowing my mind is that when I think about managers in a typical sense, that is absolutely not what the world has become. And like I think we’re shifting—we’re trying to shift toward empathy generally. I’m scared that when I become a manager, I will just fall back into the stereotype of “results, results, results” kind of thing, even though that’s consciously not how I want to be. So I’m doing a lot of internal exploration, I guess—trying to be super conscious of things that I do and things that I say to co-workers or in times when I can be a mentor or a leader. Like, how am I presenting myself, and how am I helping others.
- Are there any projects that you’re working on that you’re particularly passionate about?
- Currently, no. I mean, most of my side-of-desk time is spent with my daughter. So, my passion project is my daughter growing into a normal, good human being. She just turned one and she’s like starting to walk and stuff. The passion project actually should be like baby proofing the house. Right now, it’s just kind of moving everything out of the way where she can’t reach it and then figuring it out. But there’s not actually any baby proofing being done.
- Looking ahead, what’s a big dream or ambition you’re working toward in your career?
- In my career, I would say getting to management level and senior manager would be really cool. I did just think of a project that I would love to do if I had infinite time, which is: my wife is a elementary school teacher, and they have currently a terrible application that houses like all their grades, pictures, and immunizations. And I just know that I could make it so much faster and better. But there’s so much legal stuff and everything else that you’d have to get approval for to sell it to schools and whatever. But that, I think, if I could help the people who I care about do something and make their lives easier, that would be really cool.
Lightening Round Questions
- What’s something you’re listening to or reading right now? (It can be any genre and can be a book, audiobook, or podcast.)
- I am always listening to my favorite murder podcast, Catching Up. I am a big murderino. I love true crime anything.
- What’s one product or tool you’re into right now?
- GitHub Copilot has been a massive time saver especially like writing specs and stuff. I don’t know why specs are like really difficult for me to think about, but I like type in the title or like whatever make a new file and github copilot just kind of like makes all the specs for me and it’s amazing.
- What date does your next cohort start?
- I am starting course five of the software engineering program next week. So I think that’s like the second cohort set of sessions in one cohort.
- Where can listeners find you?
- What made you smile this week?
- Sesame Street, actually. I had just turned on Sesame Street for my daughter for the first time this week, and it is so funny. I have never realized how funny Sesame Street is. It’s like SNL with puppets. I feel like I didn’t watch it as a kid growing up but like I’m truly enjoying it. I just put it on and she’s like going to bed and I’m like “See ya.”
