Taking Leaps of Faith with Lauren Stoller (Podcast & Transcript)
“I encourage people to think about their development more holistically. It's not just about what is in front of you at work, but how do you keep your mind active? ” - Lauren Stoller
Lauren Stoller, VP of Data and Analytics at Brigit, is an experienced Data Product Manager known for full product lifecycle success, from ideation to iteration. A big-picture thinker, she uses analytics for competitive advantage and empowers teams to solve problems creatively. She has broad industry experience across retail, e-commerce, finance, semiconductors, and early-stage start-ups. Lauren holds an MBA in Strategic Management from The Wharton School. Earlier in her career, she worked in both law and finance before discovering her passion and skill for data and analytics.
In this episode, we discuss:
How Lauren went from law to finance to tech
The best way to leverage networking and career interviews
Her unconventional leadership style
The advice she’d give her younger self
Transcript has been edited for clarity.
Karen Ko: Hey there. Welcome to Engineer Your Career, a podcast brought to you by WEST, a learning community empowering women technologists through mentorship. Join us as we hear from inspiring women tech leaders who are challenging stereotypes and paving the way for future generations. We hope their career journeys inspire you with new ideas to engineer your career.
Let's get started.
Heidi Williams: Hello, and welcome to Engineer Your Career. I am super excited to have with me today Lauren Stoller, who is VP of Data and Analytics at Brigit. Welcome, Lauren.
Lauren Stoller: Thank you. I'm super excited to be here.
Heidi: Yeah, it's great to have you, and I would love for you to describe a little bit more about your current role in your company.
What is it you do at Brigit?
Lauren: Yeah. I am the head of data and analytics at Brigit, which means that I basically have three teams reporting in to me. I have data engineering, analytics, and data science, and we are sort of at the heart of all the decisions that we make as a company.
Heidi: Very exciting. And for folks who aren't familiar with Brigit, what is it you do?
Lauren: Brigit is a financial health app aimed at people who are living paycheck to paycheck. We are trying to help people make ends meet and help them break that cycle.
Heidi: I love that. What an amazing mission. That's really cool. And so, VP of Data Analytics, that's really, really cool. Is that something that you've always wanted to do?
Has it been a straight path, or what did you study in college?
Lauren: No, not at all. I had no idea that this existed. I don't think it existed when I was in college, actually. But anyway, I studied Government and thought that I wanted to be a lawyer.
Heidi: And did you end up exploring that at all?
Lauren: I did. So essentially, when I first moved out to San Francisco, I really did wanna pursue law. I worked at a law firm that was working in the public interest, and was starting to study for the LSATs, and did a bunch of career interviews. So I interviewed a bunch of lawyers, and they all said, "No. Don't do this."
Heidi: What was it that they were telling you to run from? Like, was it the work-life balance or was it something else? Do you know what was behind that?
Lauren: I was always very hopeful about being able to change the world or make the world a better place. And that's sort of what I went into these meetings with. And my ideal job was going to be working at one of these big law firms, but doing all the pro bono work.
Heidi: Nice.
Lauren: So that was a little bit of wishful thinking because, usually, it is partners that have been at the firm for many, many years, have built up a book of business, and then get the privilege of bringing on pro bono clients.
Heidi: Oh, wow.
Lauren: And so they, I think they kind of laughed at me. [laughs]
Heidi: Wow.
Lauren: And they were like, you're not gonna be fulfilled doing this if that's your goal.
Heidi: Wow.
Lauren: So it was good advice for me.
Heidi: Yeah. That's a bummer, though, to hear that the vision you have is a really, really far away from now, you know? I can imagine that's discouraging. But you know what? Honestly, I feel like sometimes figuring out what you do wanna do is a process of eliminating what you don't want. Between...did you actually work at a law firm for a little while?
Lauren: I did, so I was working at a law firm when I was doing all those interviews, and I was not, like, fully employed, I guess I was underemployed. I was reading newspapers and helping find articles on things, which is also very dated. From there, when they went to a contingency basis, I was kind of put in a position where I needed to find a job.
And I wasn't ready to grow up. I wasn't ready to find a job, and I ended up looking on Craigslist and finding a role at a hedge fund. And the hedge fund liked me, and they hired me, and I really thought deeply about taking this role because I was so idealistic and hedge funds seemed like the opposite end of the spectrum, but I thought that it was a cool way to figure out, like.... I went to a liberal arts college, so I didn't really know much about business, and I wanted to use the opportunity to figure out how money worked, essentially.
Heidi: Amazing.
Lauren: So I did that, and the head of the hedge fund took me under his wing a little bit, gave me all these books, and gave me, really, an education on how the markets work.
The difference between value investing and growth investing, and that whole world that I never knew about.
Heidi: Wow, that is super fascinating. So that's sort of like fast forward, you end up in tech, but not just one pivot, to law, and then hedge funds and finance. That's fascinating. And what did you learn from that experience? How did that help you hone in on on what you wanted after that?
Lauren: So I loved how academic it was, where you were sort of measured by the quality of your decision-making, so the quality of the bets you were taking, essentially. And I wanted a chance to see if I could do that. So I ended up finding a role on Wall Street doing stock analysis, where I was giving other people recommendations on stocks.
Heidi: Oh, cool.
Lauren: Um, so I forgot what your question was exactly.
Heidi: How did it help you hone in on what you did wanna do?
Lauren: Yeah, so that was the next step for me. It helped me by opening up this world and showing me what was possible.
Heidi: That's really cool. So was that your first experience really with getting a toe into the analytics world?
Lauren: Yeah, that was my first experience where I actually got paid to think. [laughs]
Heidi: [laughs] Amazing. Amazing. That's so cool.
Lauren: Yeah.
Heidi: So each of those sound like pretty big leaps, but you did mention when we were prepping that it maybe wasn't the scariest or riskiest thing you ever did in your career. Tell me a little bit.... So Wall Street was not the next thing, right before getting into tech. What happened next?
Lauren: So essentially, I actually made a really hard decision to leave finance. I was at a point where the bank that I was working for, they were ready to, like, help me become the head of an analytics practice. And I just thought that it was such a big leap from where I was in my cushy position, where someone else was actually responsible for P&L of the little business that we were running. And it just, seemed so scary. But at the same time, my gut told me that I did not see myself making a career doing that.
Heidi: Hmm.
Lauren: Just like it was too far from my values, I think.
Heidi: Interesting.
Lauren: And it just didn't feel like totally integrated with who I was. It was more like a fun little thing that I did really early in the morning, every morning. 'Cause I was on the west coast, and wasn't my real life, even though it took up an extremely big period of time during the day. Anyway, the scariest thing was actually leaving that work, and I just left, and I didn't have anything lined up.
Heidi: Wow. Wow. Amazing.
Lauren: I was like, I need space. I need to figure out what my career and what my adulthood is gonna look like.
Heidi: Wow. What was that process like? Because I feel like on one hand you sort of take a break and wanna do nothing, but then maybe you also feel this pressure of like, but I gotta figure out something,
Lauren: But I gotta do something.
Heidi: What was that process of discovery like for you?
Lauren: It was a lot of career interviews. I worked for Tech for Obama.
Heidi: Oh, cool.
Lauren: I was in the Bay Area. I was, when I was a stock analyst, I was covering tech. So I was always around it, but I wasn't in it, and I really wanted to be in it, but couldn't quite put my finger on how to be in it. And so I worked at Tech for Obama. I was a program manager, and we did a bit of marketing too.
And so, through that, I also started to talk to startups and help them with, like, very early-stage startups, with marketing.
Heidi: Oh, cool.
Lauren: The real thing was when I was in finance, this was the age of when e-comm was becoming big.
Heidi: Mm-hmm.
Lauren: And so I would have to write up these reports and wait for someone to edit them. So I'd have to be in the office waiting for them to edit them and come back to me so that I could publish that night. So it'd be ready for the morning. And while I would wait, I would do a lot of online shopping, and so I was trying to think of a way that I could integrate some of the things that I enjoy doing with my work. Like shopping, and The Gap was big for me.
And so The Gap is in San Francisco. I wasn't ready to, I grew up in upstate New York. I always thought that I would live in New York. I wasn't ready to make the move to New York. I ended up finding a role in analytics at The Gap, and I basically pitched to them like, "I swear I can do analytics. Like I've been dealing with all types of data. I've heard about big data. I know you have lots of data, because I see that website, and I wanna help you figure out what to do with it all," and someone bought it. [laughs]
Heidi: I love that. I love that. That's so gutsy. I think that's really cool. I wanna go back to maybe two things you said, which I think our audience would be interested to hear about.
You mentioned twice doing career interviews. Tell me a little bit about what you mean by that. I think you mean just sort of like informational one-on-one sessions with folks but, how did you find them, and how did you set those up, and sort of frame what you were looking for from them?
Lauren: Yeah, so informational interviewing, I think, was something that I started to do in college. I think it must have been something that I learned about in college, but how did I set those up? How did I find those people? Honestly, some of it was LinkedIn.
Heidi: Mm-hmm.
Lauren: And a lot of, I still recommend people do this, and I wish that I would remember to do it too, 'cause I'm out of practice. But, you know, when you meet someone new, and they're doing something interesting, if you have a career conversation, a lot of times people will be interested in helping you. And an easy way that people can help you is by asking them, is there anyone else that you know, that I should talk to about this?
Heidi: Love that.
Lauren: And so that's sort of how I created a little bit of a flywheel of meeting more and more people.
Heidi: That's awesome. That's so smart. And it's something I encourage folks to do all the time. Like if you're looking at, especially doing a career switch of some kind, or trying to understand maybe about the culture of a company before you interview or something. It's a great way to get some information. And I love that second question of like, who else could I talk to? It's really, really smart.
Yeah, it can be intimidating, but I love that you put yourself out there and kept following those threads. That's cool.
Lauren: I mean, asking for help is intimidating sometimes.
Heidi: For sure, for sure. That's awesome. I know I said I had two things to ask you, but I can't remember what the other one was, so we'll just keep going to come back to, but, yeah, that's awesome.
And so you ended up going to The Gap. I love the fact that you just got the guts to say, I got this. I know I can do this. And then someone bought into it. How developed was their practice when you got there? Were the growth opportunities gonna be like self-learning, or were you joining a group that was fairly well developed already?
Lauren: No, it was a lot of self-learning. But that's only because, I mean, The Gap has all sorts of analytics, and a lot of it is, or was at the time, it's probably very different now, but was scattered throughout the company. Right? So there were real estate analytics, and I'm sure that there were marketers that were very analytical in looking at their campaigns.
And same with inventory and all of those things. I was on a specialized team that was started by the head of the online division to really look into strategic opportunities. And this team was like, the mandate kind of grew and changed over time. When I joined, our mandate was, or my mandate, actually, was to.... I was the head of digital analytics.
Heidi: Mm-hmm.
Lauren: Which was interesting, 'cause like I was the head of anything? [laughter] But I was responsible for making sure that we were tracking things appropriately online and also analyzing things in the right way. So we had a tool, we had to train lots of people on it, but I had to go to training for the tool.
Heidi: Yeah.
Lauren: So I had to become a subject matter expert very quickly.
Heidi: That's cool. That's cool. What a fun thing to have that ahead of you and to have those opportunities to just sort of open field, be like, I gotta go figure this out, and then I have to go train other people. That's pretty amazing.
Lauren: Yeah.
Heidi: That's awesome. That's awesome. And one of the other things that you had mentioned, so I love that you've had such a fascinating journey and sort of following things that are a combination of your passion, your values, and things that you're good at.
But you know, not all careers are super fast-paced the entire time. It did sound like you got to a head of a division very, very quickly, but I know sometimes your career can kind of slow down a bit, and maybe that's because the organization doesn't have resources or opportunities that they can give you to keep growing.
When those kinds of things happen, how did you stay motivated, or what did you do to sort of navigate sometimes potentially slower career growth moments?
Lauren: Yeah. So I think having some of your own goals of what you wanna accomplish in a certain role helps you maintain that sense of movement and development. One of the things that I did when I felt really stuck was, that's when I decided to go back to school.
Heidi: Oh, wow.
Lauren: So I had a little bit of space at work. And I had always wanted to get my MBA, but it was just never the right time. It was never the right time, or felt like the right time, for me to step out of the workforce, forego an income, and spend a bunch of money on an education. And I was able to do the Wharton Executive Program while I was at The Gap.
Heidi: Oh, cool.
Lauren: And that really, it kept me motivated also because I was learning new tools and new ways of looking at the business.
Heidi: Mm-hmm.
Lauren: And it gave me a reason to go and talk to new people at the company and ask them about their work, or use the MBA as an excuse to go and knock on doors, essentially. So that definitely helped. And I encourage people to think about their development more holistically. It's not just about what is in front of you at work, but how do you keep your mind active?
Heidi: Yeah. I love that. I love that. And I think it's so interesting. I know it's, I mean, kudos to doing school and work at the same time. That's definitely a lot. And I see people who do it, and I'm like, oh my goodness, that seems amazing. But I can also imagine that value of being able to immediately apply what you're learning to work. And so it sounds like you even not just sort of passively applied it, but proactively applied it by going out and talking to folks.
And did they know when they made space for you to be able to do the MBA, did they know and expect that they were gonna get those benefits of the learnings coming back and being applied at work?
Lauren: I mean, that is what I wrote in my letter to them, [laughter] whether or not they believed it was another thing. I'm not really sure. Yeah, but it definitely affected the way that I showed up.
Heidi: Let's take a quick break to hear from our sponsor.
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Heidi: And now, back to our discussion.
That's cool. I don't know if it's actually true, but I've heard that a lot of MBA programs don't want folks who have never worked anywhere yet, because I think they want you to have that sense of how would you apply this, as opposed to just theoretical learning and things like that.
But that's really cool. Do you feel like you got more out of the program then, by doing it at the same time that you were working?
Lauren: It's interesting because I think that there are trade-offs.
Heidi: Mm-hmm.
Lauren: There's trade-offs with everything that you, every decision that you make, but particularly with this one. Yes, there's a huge benefit that you can go and start to experiment and apply these things, and then come back to the classroom and ask questions about mistakes that you made or trouble that you're having.
On the flip side of that trade-off is that you don't get to go quite as deep. Like there were topics that I would've loved to read every single case study that they gave us, but I ended up having to read like the first sentence of every paragraph.
Heidi: Yeah.
Lauren: That's kind of a bummer. And I kept them all to go back to read, and they are in a box in my storage space.
Heidi: That's awesome, though. I'm sure if a moment came where you're like, oh, I remember there was a case study about that. You could go and dig it out if you needed it. I love it. I love it.
I actually had a chance to do, it was a mini version, like a 12-day version at Stanford, and I still recall those case studies too, but you're right that the 12-day where you're living on campus and actually doing all the homework and working through it and have the space away from family to actually do it, you know, that was pretty cool.
And, now I look at the way companies work, and I'm like, Ooh, they're gonna write a business case study about that one sometime, you know? And I just, it's really funny to think about it that way.
Lauren: Yeah, totally.
Heidi: So you did your MBA, you were still at Gap. How did you eventually make your way to Brigit?
Lauren: Yeah, so when I wrote my essay for the MBA, it was about being able to apply my current skills, the skills that I had at the time, the skills that I was going to gain, to make the world a little bit of a better place.
So I was still sort of trying to figure out how to do that. I knew that I wanted to be in an environment that moved more quickly than a big, big company like The Gap. I still knew that tech was a place that would be a cool place to apply some of the skills that I had gained. And I figured out that I really like working in a direct-to-consumer space because it's usually a product that resonates with me.
But also from a data perspective, the consumer is fascinating. Like, we are so fickle, we are not consistent. There's behavioral economic things, there's user experience things, all of these things that come into play that make it super fascinating. So I knew that I wanted to be in direct-to-consumer, but I also thought that I wanted to be able to be a little bit closer to finance, which is where I came from, essentially, and sort of like putting those things together.
FinTech was growing. It was also a place where there were a bunch of companies trying to make the world better by improving people's lives. And so I started to look in that space, and that's how I found Brigit. Brigit found me.
Heidi: That's awesome. And how big was Brigit when you joined?
Lauren: 30 people.
Heidi: Oh my goodness. And how big is it now?
Lauren: 140.
Heidi: Whoa. Whoa. And so what was your role? What were you hired to do at Brigit?
Lauren: I was the head of data and analytics. Data and analytics was two people.
Heidi: Excellent.
Lauren: So I was there for two or three months, and then they gave me data engineering. Data engineering was one person.
Heidi: Yep.
Lauren: And I had the mandate to hire, and I realized that a lot of startup life, if you're in a leadership role, is about hiring people.
Heidi: Yeah.
Lauren: So my team is a bit bigger. I think we're more like 15, 16, and I probably have five open roles.
Heidi: Wow. Excellent.
Lauren: So if anyone's looking for a job, happy to chat.
Heidi: Good shout-out for sure.
That's awesome. And in the beginning, were you doing stuff hands-on? I'm curious about your path to leadership and leading a bigger group, and actually, maybe even had you already managed people before you joined Brigit?
Lauren: Yeah, I managed people at The Gap. It was not consistent throughout my time there, but I had managed people.
I think this was exciting because right away, I was presenting to the leadership team. I was included on the leadership team. So right away, I got exactly what I was looking for in terms of feeling like, I didn't mention this before, but one of the main things that I was really looking for was I wanted to make an impact, and building a company, you make an impact. When you're at a 30-person company, everyone has an impact. So that was all very exciting to me.
Your question about leadership or development and leadership? Is that what your question was?
Heidi: Yeah, I'm curious a little bit, yeah, about the sort of, I imagine when you started, you might've even been pretty hands-on with a team of two, and sort of doing stuff yourself. But as you grow your team, you have to develop different leadership skills and different, I don't know, ways of knowing what's going on without being hands-on and things like that.
So I'm sort of curious, is it true you started hands-on, and what's your path been from, you know, director to VP? How has your leadership evolved along the road?
Lauren:
Yeah, so that's a really good question because I feel like I am learning every day, and there's always more to do, but most of the leaders of Brigit are pretty hands-on.
Heidi: Mm-hmm.
Lauren: So I would say that I'm still hands-on to a large extent, although I'm not necessarily sitting here coding.
Heidi: Mm-hmm.
Lauren: The ways of working, I think.... I tend to be sort of more on the side of waiting for things to happen organically, mainly because I wanna see how people fill the space that is available.
Heidi: Mm-hmm.
Lauren: And then see if we need to course correct. Maybe that's not the best way of doing things, but I like doing that because I feel like then people have a little bit more ownership over what's going on around them.
Heidi: Yep.
Lauren: So what I try to do is encourage people to be problem solvers as well as problem spotters. So, how I've stayed plugged in is I try to develop relationships with everyone who reports in to me.
Heidi: Mm-hmm.
Lauren: Which, I wanna be honest, is super time-consuming.
Heidi: Yeah.
Lauren: We have had a pretty flat team thus far, meaning I have a lot of people that report directly in to me. And that's not sustainable. I don't recommend people stretch themselves that much, but it has kept me plugged in.
Heidi: Yeah, I think it's always, I know it takes a lot of time. I'm someone who does a lot of skip levels, and so I totally hear you. I feel like relationships and that sort of, sometimes the casual conversation.... Maybe specifically working remotely, like you don't get the water cooler gossip otherwise. And I don't even mean gossip, but just sort of like, what's going well, what's been frustrating, what's happening? What are patterns that you might spot?
So I always feel like it's a good investment, but you're right, it is very time consuming to both hear it all, not be immediately reactive, synthesize, you know, all of those things. But yeah, it always feels like a good investment.
Lauren: Does feel like a good investment. I would also say that one of the things that I find very rewarding is knowing all these people at a level that's a little bit deeper than, give me the update on your Jira tickets.
Heidi: Yeah. Yeah. A hundred percent. A hundred percent. And I know a lot of people have read the Radical Candor book, but the piece that resonates with me is that if people know you care, it's so much easier to give feedback.
So if you know that they know it comes from a good place and that you know and believe in them, and there's just something that needs to, like you said, course correct along the way. So I love that. Yeah. I also love what you said about ownership and empowering people and becoming problem solvers and not just problem spotters.
I think that's a great way to scale your team and help them grow, by giving them those opportunities. I think sometimes for folks who are like, well, I know how I want it to be done, it's very easy to come in and do it and become a crutch for people, and then they end up becoming a little sort of helpless or disempowered, or they don't know that you actually wish they were doing it instead of you.
So I love that, it sounds like you've got a good formula, a good recipe for your team. That's really cool.
Lauren: Awesome. Thanks.
Heidi: So, one question, maybe looking back, you said your career path wasn't super intentional from the start that you were… it was putting pieces together, solving a puzzle.
What advice would you give to women in tech who are maybe worried their path isn't linear enough or strategic enough?
Lauren: So a piece of advice that I received when I was doing all these career interviews that has stuck with me to this day, and this was like when I was fresh out of college. Someone just told me to, really just follow your nose. And they meant like, follow your interest.
Heidi: Mm-hmm.
Lauren: And try not to think so hard about what is this, what is the next step? Where am I going? This is true for life too, right? You don't know where you're going to end up. No one really does. So you can set the compass, but I think you need to follow your nose, follow your interest in order to develop that compass.
So that's the advice that I would give.
Heidi: I love that. That definitely resonates. That's definitely how I have also followed my career, that now, looking at it, you might think it was super linear, but it was never intentional from the beginning. And I always think about, I remember talking to someone once where they had all the steps planned out, and I thought, oh, that's so brittle. If one thing happens to disrupt that, the whole rest of your trajectory is screwed. You know? And so it does feel brittle to have every step planned ahead of time.
Lauren: It does, it does.
Heidi: Or at least scary to me that I would be terrified if everything got blown up when I had this perfect plan in place, you know? [laughs]
Amazing. Amazing. And so looking back on your career, you had so many different experiences, and I love that you followed your nose, but I also can see you probably picked up something from each along the way that you still apply or influence you somehow. Is there anything that stands out from being a stock analyst to covering semiconductors, or you know, all of those experiences that you feel like still influences you, or that, yeah, I don't know, how you think about business or data today?
Lauren: Interesting. There's so many little things. The main thing that really, I don't know if this is a learned thing, though, but the main thing that I think is interesting in looking back is that this whole concept of trying to make the world a little bit of a better place was with me from the time I was like four.
Heidi: Oh, wow.
Lauren: So I think it's kind of interesting that now, like 40 years later, I'm still trying to figure out how to do that. It seems like kind of a big problem to solve and many ways to go about it. So I don't know if that really answers your question, but I think in reflecting through doing this interview with you, that is striking to me.
Heidi: I love that. And it does feel like a piece that has been your compass, and that has, in whatever role you had, you were able to find purpose and impact in that role in some way. And, I think that can be really motivating, at least as a learning experience, even if it's just as a learning experience to get to the next piece of impact that you might have in the next role.
Yeah. That's super cool. That's super cool. Well, I have loved hearing your stories. I think they have been amazing. Was wondering if we could maybe wrap with a piece of advice you might give to your younger self, or a recommendation of a book or an article or a resource that you have found super helpful that might be helpful for others.
Lauren: I guess piece of advice, two pieces. One, it is a little bit trite, but don't be afraid to make mistakes.
Heidi: Love that.
Lauren: It's okay to make mistakes. It's okay to make the wrong decision as long as you learn from it. And I think the other thing is stay curious. Definitely stay curious all the time. Yeah. It'll lead to bigger and brighter things.
Heidi: I love that. And I can see how curiosity definitely was a through line for you as well. And back to the point of, you know, being curious about like, what do you do? What is that job like? What is this industry like? That's a great way to use that curiosity to figure out maybe what you want more of or what you want less of in your next step.
So that's awesome. Yeah.
Very cool. Well, thank you so much. I really appreciate it, and hope you have a great rest of your day.
Lauren: Heidi, thank you so much. It was nice talking to you.
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