From Food Industry to Tech Ops: Theresa Freet on Building Around What Lights You Up

In this episode, I interview Theresa Freet, a Strategy & Operations leader with over 12 years of experience in the ed-tech field. Before her rise as an operator, she traveled internationally and immersed herself in the food industry, exploring the world and ruling out alternative career paths. Theresa emphasizes the importance of finding the right overlap between personal fulfillment and career growth, being comfortable with uncertainty, and effective delegation in management. Her experiences highlight the importance of recognizing what truly 'lights you up' and trusting the journey, even through transitions and unexpected shifts.

00:00 Introduction to the Push Pull Podcast
00:20 Meet Theresa Free: A Journey in Ed Tech
00:50 Early Career: Embracing Travel and Passion
03:29 The Madrid Experience: Unlocking Fearlessness
05:42 Teaching in Bogota: A Year in Colombia
06:52 AmeriCorps and the Path to Japan
09:25 JET Program: Life in Rural Japan
14:58 Discovering a Love for Cooking in Ireland
17:36 Exploring the Food Industry in New York and California
28:58 Transitioning to Tech and Volunteer Work
32:22 Joining IIN: A Return to Education
36:11 Incredible Team and Unmatched Benefits
37:06 Optimizing Systems and Project Management
38:04 Frustrations with Leadership
40:56 Transition to Thinkful
43:22 Growth and Challenges at Thinkful
46:45 Managing Remote Teams
58:07 Joining Polygence
01:04:55 Navigating Cultural Shifts
01:08:24 Exploring New Opportunities
01:13:50 Final Thoughts and Reflections

Transcript

0:06

Welcome to the Push Pull podcast. I'm Varun Raja, And in this podcast I interview professionals about their careers, specifically around the push and pull factors that informed the big decisions and transition points in their careers. Today I talk to one of my very good friends, Theresa Free. She and I worked together at an ed tech company called Thinkful, uh, and have remained friends for the better part of the last decade. She's a senior operations leader with over 12 years of experience in the ed tech field, and she's currently working on a fractional basis for a couple of different ed tech startups right now, What's super interesting is how diverse her experiences were before she actually got into being an operator at early stage startups. early in her career, she really focused on work being something that enabled the life that she wanted to live, namely travel new places and experiences. Um, the other thing was she also really exhausted. The idea of passions as a vocation. And so we talk about her time in the food industry and what she learned as a result of pursuing that whole hog. the other thing that Theresa emphasizes quite a bit is how to get. Really comfortable with discomfort and uncertainty. she has put herself in a position very early on to step into the unknown and Tackle life with a sense of fearlessness. Um, you'll see every few years when she's in a point of transition, she has to worry about does she have the transferable skills? Can she actually make it, into the next phase of her career? She leans into it and finds a way through, uh, in a way that re redos to not only her success, uh, but also to the benefit of everybody that she gets to work with. the last thing that comes up is a constant focus on. What lights her up. Uh, that phrase lights me up, came up time and time again. She found the things that actually made her get into a flow state, click, advance, and see progress over time. I think that there is so much that we can learn both from Theresa's, I, I would say second act, so far, which is really about the actual work in tech working as a strategy and ops leader. but there's also a ton of insights that can be gained from the early part of the conversation where we really talked about all of the risks that she took, and the wild rollercoaster, that brought her to where she is today. really excited to share this conversation with you and, hope you enjoy it.

varun_1_03-17-2025_141131 2:46

Hi, Theresa. Thanks for joining us today.

theresa--she-her-_1_03-17-2025_171131 2:48

Hey. Yeah, super excited to be here, excited to talk career and get the opportunity to chat with you for a little while.

varun_1_03-17-2025_141131 2:55

Awesome, awesome. I wanna turn it over to you, just a 30 to 62nd overview of who you are and what you do today.

theresa--she-her-_1_03-17-2025_171131 3:03

Yeah I am currently working fractionally for a couple companies after having spent the last decade plus building my skills as an operator across different ed tech spaces, and now getting the opportunity to really take what I learned, to drive forward some companies and cool ideas that I think are important that they exist in the world.

varun_1_03-17-2025_141131 3:25

Let's take it back to the beginning. where would you wanna start the story of Theresa's career?

theresa--she-her-_1_03-17-2025_171131 3:29

I think one of the most formative things that I did was actually decide to study abroad in Madrid in my junior year of college. I think it really unlocked like my sense of adventure, a love of travel that I didn't necessarily have prior, and I think important for me career wise, it unlocked a certain level of fearlessness and I think a comfort with risk taking that has informed a lot of the decisions that I've made in my career after that point.

varun_1_03-17-2025_141131 3:59

That's super cool. I would love to spend e even more time on that So Just a quick, a quick overview of like where you were coming from, where did you grow up and what were the alternatives? Right. sometimes when we think about the choices that we made, it's not just like, what's pushing you away from where you were before? But also like what are the trade offs and like opportunity costs for the other things that you might have pursued.

theresa--she-her-_1_03-17-2025_171131 4:22

Yeah. I grew up in Southern California and had through a series of decisions, studied Spanish in high school. Super fortunate I went to college on a full ride, which meant that I had money that my parents had been saving to pay for me to go to college. That was freed up for me to be able to consider doing other things. And so at that point, what stuck out to me most was this idea that I could study abroad and I could afford to do it for a full year. And for me then the question became where, and I had actually studied Japanese for a while when I was younger, but it wasn't really good enough for me to think about making that like a college language. but I had taken, AP Spanish, so it was an easier transition. It was a little bit like more of a smooth transition to consider. They had a program in Madrid at my school and it just made sense. to go to Spain and and then I knew I wanted to do the year long'cause I could afford to, and actually that ended up being what my major was, just because I spent so long in Madrid that I had built up a enough credits to graduate with a degree in that, which is a, another like formative career lesson In most cases it actually does not matter what your major is. Like I don't really use it. no one's ever been like, oh, that's super important that you studied Spanish. I guess actually having a Spanish degree did inform some of my later choices After my senior year of college, I actually moved to Bogota and worked in university in Columbia for a year, which I suppose I wouldn't have done if I hadn't had, like enough of a if I had a degree in Spanish.

varun_1_03-17-2025_141131 5:59

Yeah.

theresa--she-her-_1_03-17-2025_171131 5:59

again, to that focus point, it was really like the question was how do I get paid to be in other places, experience other cultures, get to travel, get to explore, and that was like the biggest pull for me in terms of what I decided to do across arguably the next five years.

varun_1_03-17-2025_141131 6:15

So what was it that you were doing in Bogota

theresa--she-her-_1_03-17-2025_171131 6:18

So I was working at a university in their English department and basically helping their, like full-time English teachers with like native style English speaking at a teacher's college. So people who wanted to become English teachers were studying English to, get their teaching degree. And so I supported and built out lessons and popped around to a bunch of different classes. So some degree, teaching English is one of the easiest ways that like a native English speaker can get paid to be in other places. And so that was a little bit of a through line. but it was much less about that type of what's next career wise and much more about what's next, travel placewise. So I went back to the US for a year and did a year of AmeriCorps. And again, this sort of this like crazy moment of do I have any real skills? Like how do I get a job? And AmeriCorps is, ha has been, and I think probably still is to the degree that it's got enough funding. this cool opportunity to do work at on a. Like for nonprofits, that really pushes forward community good. And so I worked in Austin, Texas for a college access nonprofit. And specifically my job was making sure that the students that we got into college stayed there. And I think that is also this interesting throughline to later in my career where I've worked with school students, college students trying to really drive forward, like career learning, education as economic mobility.

varun_1_03-17-2025_141131 7:51

Yeah.

theresa--she-her-_1_03-17-2025_171131 7:51

really became like the first place where I got to do that. But again, wasn't really the goal. It was much more focused on, all right, now I need a single year gap so that I can come back to the US and apply to go to Japan. but actually in hindsight was incredibly informative.

varun_1_03-17-2025_141131 8:07

You were definitely a woman on a mission at that point, right? Like To go to a bunch of different places, and it wasn't like you necessarily got tired of one place or one job. It sounds like you knew that everything that you were exploring was going to be meaningful, but temporary. That's what it sounds like to me. Let me, let me know if I'm getting you right. Yeah.

theresa--she-her-_1_03-17-2025_171131 8:28

think that is right. Like I knew there, I just knew there was more, like more to see, more to do, and I wanted to get to see that next thing, do that next thing, at least at that point in time. This is all my early twenties. And like advice for anybody who's like very early in their career, i, I honestly think it's the best thing that you could do. Like you don't actually lose that much in terms of trajectory towards your peers. And if you can afford to do it, like the, that period of time, I just had no ties, no, I had very little stuff. I had I had nothing that was like holding me back from doing that type of exploration, that type of travel. And I do think like that is the perfect opportunity to do it for anybody who can and was, like I'm so glad that I took advantage of it

varun_1_03-17-2025_141131 9:16

So you did AmeriCorps AmeriCorps was like something to tide you over while you figured out your next international trip. So what came next after,

theresa--she-her-_1_03-17-2025_171131 9:26

AmeriCorps actually did then make it to Japan. So I used that year I applied to do the jet program again, having and Japanese

varun_1_03-17-2025_141131 9:35

what, what is the JET program?

theresa--she-her-_1_03-17-2025_171131 9:37

it's the Japanese exchange and teaching program. And so Oh, okay. that the Japanese government runs and they will you apply for it, and then they place you for a year and you can renew for up to five years. They place you for a year in a school district. And then if you are accepted into the program, the school actually chooses you and you don't get a choice. you know, maybe of relevance because I knew I liked traveling internationally, but I also, had built up a level of confidence that like where I thrived was in larger cities, so I knew I didn't wanna be somewhere super rural. I got my placement and it was in a little town that was connected to the main island of Shu, which is for anybody who's not super familiar with Japan, like main part of it, Shu looks like California, but flipped backwards. And then underneath is like a round blob shu. And so it was like shu about an hour and a half outside of Nagasaki connected by a bridge and a bridge like very rurally o on this little island with 17, with 1700 people.

varun_1_03-17-2025_141131 10:42

Wow.

theresa--she-her-_1_03-17-2025_171131 10:43

small, primarily anybody who lived there worked. Either they were a fisherman or they worked at a salt factory. And one town over there was a ship building factory. a very rural definitely the only white person for miles. And I had 30 people in the middle school class and about 60 people in the elementary school class. And then I worked two days a week on different islands that I actually had to commute to by boat. I would go by boat one to an island that had two students total and yet a full school, like a full staff for those two students of 13. And then the other had five students. I'm pretty sure I remember at the time it being because it wasn't legal to homeschool. So like they had to figure out a way to school kids on some of these smaller islands.

varun_1_03-17-2025_141131 11:33

This is insane. How long was your daily boat commute?

theresa--she-her-_1_03-17-2025_171131 11:39

let's say I wanna say it was probably like a half an hour. It wasn't that long when the seas were rough, it was not great because it wasn't like a fairy, it was a 12, 16 person little speedboat And the guy who was the boat captain was actually the father of two of the students. And then he would take everybody where they needed to go and then he would just like fish during the day and then pick everybody up and take them home. so sometimes, like especially towards the end of the year when people were more familiar with me, he would offer me a plate of sashimi of what he had caught on the boat like at the end of the day when I was leaving.

varun_1_03-17-2025_141131 12:13

That's amazing. Wow. Um.

theresa--she-her-_1_03-17-2025_171131 12:19

de again, an a hugely different life experience than being in big cities. And I think I learned how to function, but I do also think that was even more, proof for me in terms of where I actually really derived joy and where I thrived it turned out not large cities or like in large cities. Not in very small spaces.

varun_1_03-17-2025_141131 12:41

yeah, te tell me about that. You end up getting assigned to a very rural, not big enough for you to be in one classroom with everybody that's been in other classes together. Like it's a very unique situation. What were the things that stood out to you to reinforce like, I need to be in a bigger, more bustling place.

theresa--she-her-_1_03-17-2025_171131 12:58

I think the amount of time that I spent like on my own or wandering around the island, or like I used to drive an hour and a half to go have dinner with a friend and then drive an hour and a half home, which in retrospect is like an insane commute to have dinner for maybe an hour and a half. like that sort of missing like communal piece. And I had the opportunity to make some amount of friends, but I think there was a level of isolation and also I was missing like the like bustle of being in a city space. Like when I would go into Nagasaki or into Fukuoka, which was the largest city and on Shu. And I really loved being in it. Like I could just feel the energy of the city impacting me differently than being in the like quieter, more, and it was a beautiful place. Like the island was beautiful, like vegetation, Costa Rica, like gorgeous space. But just the way that like, I could feel myself interpreting energy just felt very different than when I got the opportunity to be in a city.

varun_1_03-17-2025_141131 14:01

Yeah, totally. Then, you know what came next was this one of those things with the JET program where like you could have stayed on for longer or stayed in Japan broadly For longer. Yeah.

theresa--she-her-_1_03-17-2025_171131 14:13

You could stay on it's actually, they tell you this'cause they know it's gonna be a problematic period of time to make you make a decision, but they, you have to decide in February if you're going to stay on for another year, because if you're not, then basically they need to reassign your role to somebody else who would needs the time to decide if they're coming. So you have to decide in February and it's the coldest and darkest period of time. they're like, you will be

varun_1_03-17-2025_141131 14:37

Wow.

theresa--she-her-_1_03-17-2025_171131 14:37

Don't take that moment, take like the entirety of your experience and decide if you wanna stay. And I don't think I could really see past that point. And also knowing that I was like, I feeling a little isolated. I

varun_1_03-17-2025_141131 14:50

Yeah.

theresa--she-her-_1_03-17-2025_171131 14:51

on a, as you'd expect, by the time that I left, it was July. It was gorgeous. Like beaches were open and I was like, oh, maybe this would've been fine. But but from there, actually one of the things that I noticed about myself while I was working is I got really into like cooking blogs and food. And a lot of times I spent of my time thinking about what I wanted to make after work. And some of that was traditional stuff. Some of that was like. American things that I missed. And I also saved a lot of money'cause I lived in the middle of nowhere and there wasn't a lot to spend money on. And you get this sort of a standard stipend of what you get paid regardless of where you're located. So I saved a ton of money up and I decided what I wanted to do was go to a, sustainable farm to table cooking program in Ireland based on ba based on, a blog that I had read by a guy who I really liked his work. And so I had decided I was gonna go home for the summer, and then in the fall I was gonna go to Ireland for three months and learn how to cook.

varun_1_03-17-2025_141131 15:55

Whoa.

theresa--she-her-_1_03-17-2025_171131 15:55

formally learn how to cook.

varun_1_03-17-2025_141131 15:59

Okay. And so how was that experience and what came out of it?

theresa--she-her-_1_03-17-2025_171131 16:04

Yeah great. Also, hilariously stressful in the silliest ways. it's a program called Ballet Malo and it's it's just outside of Cork in like Southwestern Ireland. a house that you can stay at that's a hotel and then they have a cooking school run by a woman called Doina Allen who is lovely still running the program. And she's I think you know the Alice Waters of Irish cooking. So you learn everything. You learn everything is seasonal. Like they grow a lot of the stuff, they source a lot of the stuff locally and you learn how to do everything from like knife skills and basics all the way through like French pastry. I have this very hilarious memory of into tears as like a, this meticulously made pastry just oozed out the side in the oven.

varun_1_03-17-2025_141131 16:48

Oh.

theresa--she-her-_1_03-17-2025_171131 16:50

even though like obviously didn't matter at all. And you do this three month long program and then towards the end of it, there's a final, you like propose a menu and you have to make it inside a time period, and then they grade you on it. And that's how they decide if you've passed out of this program or not. And the other thing that Darina will do is you can meet with her and she'll talk to you about what you wanna do after. And what I learned when I was there is I, loved bread. I was fascinated by Hmm. It was one of the things we learned how to do and I would do in my spare time while I was there. And obviously her network is much more in Europe than in the us but she had an introduction for me to a woman who worked, at a wholesale bakery in just outside of New York City. I actually went and stayed with my cousin in New York for maybe a month and did a stage at this bakery, which is actually in Inglewood, New Jersey, which is not New York City it's like a train and a bus away. And then that woman actually entered, and that was actually Bazars Wholesale Bakery for people who, know New York City, breads like a pretty large New York City institution. And she actually recommended that I reach out to this other guy who had just started a bakery in Brooklyn called Qui. And so I walked in with my resume, which is like a hilarious resume for trying to like, do anything with food. It's I've done like a bunch of English teaching in other countries and here's my Spanish degree. And he was like, yeah, sure. If so the thing about working in food is like you can get your food in the door by just working for free in what's called Asta. And I spent two weeks working with him and I would work

varun_1_03-17-2025_141131 18:34

What What is a sta? Is it just unpaid internship? is that

theresa--she-her-_1_03-17-2025_171131 18:38

of saying

varun_1_03-17-2025_141131 18:40

I,

theresa--she-her-_1_03-17-2025_171131 18:40

unpaid labor.

varun_1_03-17-2025_141131 18:41

Okay.

theresa--she-her-_1_03-17-2025_171131 18:43

so it's a fancy way of saying we're not gonna pay you to learn how to do these things.

varun_1_03-17-2025_141131 18:47

Okay. Gotcha.

theresa--she-her-_1_03-17-2025_171131 18:47

common. And so I worked with him for about two weeks in these 10 hour shifts. And again, I was staying with my cousin who lived by the Columbia campus, and I would wake up at 1, 1 30 in the morning and I would take the, a train local all the way from Columbia all the way down to

varun_1_03-17-2025_141131 19:07

Wow.

theresa--she-her-_1_03-17-2025_171131 19:07

to like Hoyt Skimmer horn which is a very long local ride for anyone who's familiar. And then I would work 10 hours and then pop out from the restaurant or like from the bakery at 3:00 PM and it was a very strange period of time, but at the same time, I had also gotten in agreement to go work at a farm in Northern California for a season. And so I knew I was leaving from there, from New York City in these two STAs to go spend from like March. And at this point in time, I think it was like January, February. And so I was gonna go.

varun_1_03-17-2025_141131 19:41

Huh.

theresa--she-her-_1_03-17-2025_171131 19:42

from like March through end of summer, maybe like August, September, work on a farm in Northern California that was in the spring and in an environmental ed camp for alternative schools, like Montessori

varun_1_03-17-2025_141131 19:56

That's so cool. Okay.

theresa--she-her-_1_03-17-2025_171131 19:58

in the summer it became a family camp where families would come and pay to stay by the week. And so worked in the kitchen there. And then in the spring I also taught kids how to make bread and like cinnamon rolls and cheesy biscuits and things like that. I knew I wanted to explore being in food a little bit more. I had, I. quite sure I wanted to work in an actual restaurant at that point. And so I was trying to find alternative ways to be in the food industry and let that felt a little bit like lower stakes than trying to go be a line cook. And also that, had some kind of like finite period of time for me to figure it out. And so that, that ended up being one of it, it was a little farm called Im Andal and again, another great experience for me in validating like what types of spaces bring me energy. Because it was about like 45 minutes down a mostly unpaved road outside of Willits in Northern California. So like very rural space. Gorgeous, beautiful along the E River. But there were 16 of us that lived there, including the woman who owned it and her son and his family, and the degree to which all 16 people were just like, so in each other's business I was like, oh, like I need the anonymity of a city so badly.

varun_1_03-17-2025_141131 21:23

what was it about food that really attracted you? as we've told the story of I was in Japan, I started reading a bunch of stuff. I started cooking a bunch of things and then I got, I like went to Ireland, I got really into bread. It would be curious about what are the through lines there or like what do you find really valuable about food

theresa--she-her-_1_03-17-2025_171131 21:38

I think there was some component if of it being a way of connecting. So all this time while I was away, it was a means of connecting with my brother and my sister. while I was in Columbia at Bogota we started actually this like food challenge where one of us would pick an ingredient and then all three of us had to find a recipe and make something with that ingredient. And

varun_1_03-17-2025_141131 21:59

That's awesome.

theresa--she-her-_1_03-17-2025_171131 22:00

a point of connection, which I think probably helped foster it. But more for me it was this really fascinating and to this day, I still just love getting to try new recipes, explore things like I love finding a food or something I haven't seen before and getting to figure out like what it takes, like how I use it. So it was much more about this like love of food that I wanted to see if I could figure out how to. that into work and yeah, and so unlocking that with, by going to a cooking school to actually then get a bit more training, get a bit more clarity on what it looks like to actually cook professionally, like what the skill level looks like to be able to bring some of that in.

varun_1_03-17-2025_141131 22:43

Yeah. That that's really great. Where did that end up? Or at least continue on from, from we left off.

theresa--she-her-_1_03-17-2025_171131 22:49

there's a continuum on, and then there's a cautionary tale at the end of it because I'm not in the food industry today but so I I left Mondal, and again, at the end of that period of time, I started to figure out what I wanted to do next. And so I had. Both in and out of food. I had talked to some people in San Francisco, talked to some people in Denver, and I also reached back out to the guy at B and Qui who, the founder of B and Qui, who I had worked with. And he offered to let me come back and work as a full-time employee, come back and work as a baker in his kitchen. That ended up being what I decided to do and actually in part thinking about that like push pull factor of like how to decide San Francisco,

varun_1_03-17-2025_141131 23:34

Hmm.

theresa--she-her-_1_03-17-2025_171131 23:34

of time in California. I grew up in California and I remember thinking at the time like, I'm 25 if I don't move to New York now. don't think I'm gonna move to New York. This

varun_1_03-17-2025_141131 23:47

Yeah.

theresa--she-her-_1_03-17-2025_171131 23:47

just like the point to try to go live in that city knowing what I know about cities. And so it was less like the job was the dream job and it was more like the job was an opportunity again to move to a city that I wanted to be in and, incredibly grateful that somebody was willing to let me, Because for Zach who had started B que, this was like, his like child and he's yeah, sure you can come work in this kitchen. So I moved to New York and then worked for about six months at b and qui mixing and shaping bread dough. So spent a lot of time with bread and I think the biggest thing I learned there is. One, like I, my body was just not made for that type of work. I was developing carpal tunnel in my right wrist. But also it just completely diminished like my joy for bread because having to do it like on that type of cadence, like every day, that number of days a week, just really shifted my relationship to it. It became less something that like, there was like joy and novelty to, and more of something that became like a must do. And that, that I think is actually probably the bigger lesson for me around like trying to right size what like am passionate about and what's a hobby versus what's a career like the number of times that people are like, oh, this thing that you love. Or if you're good at something, like you should do that for a living. And I'm always a little bit cautious around but actually sometimes things should just be stuff we do because we love it. Like

varun_1_03-17-2025_141131 25:20

Yeah, that makes sense, right? Because it's not. It, and it doesn't necessarily mean you can't be successful or have a successful career with something that you're truly passionate about, but it's that when you make something that you're passionate about work, it becomes work and all of the things that we associate with the things that we don't like about work, that is the things that are the necessary friction of keeping jobs going and the paperwork and the bureau rocketry or whatever, right? Like you, you have certain mandatory inputs that you have to put into your work. When, like for bread, like you, you're not gonna give yourself like a early morning marathon where you're shaping bread all day every single day. That's not the thing that you would choose to do. But like, when it becomes work, then that's your job.

theresa--she-her-_1_03-17-2025_171131 26:07

Uh. to choose what you wanna do. You don't get to wake up and say I feel like making this today. It's you've got orders, you've got commitments, Tavern is waiting for this type of role. You have to do the same thing every day. And there are some people who really, you know, find joy in it. Like I ha I have some lifelong friends that I made at that period of time who truly love like the nuance of day-to-day, seeing what's different and getting to do that routine and that cycle on a day to day. And I just found that was not quite what lit me up. find that kind of like meditative joy of being like, today it's slightly different. I wonder why, let's think through this instead it became like more of a chore.

varun_1_03-17-2025_141131 26:45

this is really great and a really helpful lesson for a lot of people. I also feel like we were part of a generation that was like, do the thing you love. And there's always truth and value to that message, but there are always truth and value to like the flip side of but then it becomes work and you had a lot of other. Priorities, I think. And that's the other thing that's really amazing about all of your early twenties story is that you followed, not necessarily the work itself. it doesn't sound to me that you were purely strategic or even transactional about this is gonna be good for my career. You were kind of like, this is the life that I wanna live. And Whether it's traveling to different places or actually cooking and baking, right? You're like these are the things that I love and I'm going to find the opportunities that allow me to live that life.

theresa--she-her-_1_03-17-2025_171131 27:34

yeah. I think that's exactly right. A lot of focus on what I wanted what lit me up, and then I. To be fair, at a certain point I had to come to terms with, actually at some point in time, I guess I gotta figure out was like a quote unquote real career. Versus hopping around from thing to thing. But that exposure and I think what I learned from all of that was incredibly important. that lesson in getting the opportunity to do something that I thought I really love doing and make it into work, and then getting to see how that felt was really different.'cause I think there are lots of people that still have this dream of oh, I don't really like my job, but I wish I could one day like run a, be like a bed and breakfast or do, an art studio. Like I started doing ceramics recently and people would be like, you should just sell your ceramics as a living. And I'm like no. Like I don't actually wanna have to make 300 of the same mug. What I wanna do is make one mug that I like and then. So it just was such a good formative lesson. And like sometimes hobbies and things you're good at, like you're allowed to just let them be expressions of joy and then you can do other things that you love doing or that light you up or that you know you care about, but that are actually more transactionally about funding the rest of the lifestyle that brings you joy.

varun_1_03-17-2025_141131 28:55

Beautiful. That's awesome. Cool. What came next?

theresa--she-her-_1_03-17-2025_171131 28:58

Yeah, so from there I ended up leaving again. And so I had a really good friend of mine, Vanessa, who had a startup at the time. And she couldn't afford to pay me, but she could afford to like, take me on board, give me the experience, and also The cover in my resume to, to be able to start to transition into something that might look like a more traditional career. And so I worked with her for a little bit and then started, doing a bunch of volunteer work and figuring out what I wanted to do next. What I was doing for my friend, so she, her tech startup actually conceptually what it was is basically developers need to keep so like software engineers, developers need to keep learning new and practicing their programming skills in order to keep fresh. And so she wanted to marry that with a push for more open source software and nonprofits. So help nonprofits open source their platform code in a way that like developers could build practicing rather than build another calculator app or like

varun_1_03-17-2025_141131 30:00

Okay.

theresa--she-her-_1_03-17-2025_171131 30:01

tool, help basically like

varun_1_03-17-2025_141131 30:03

Right.

theresa--she-her-_1_03-17-2025_171131 30:03

fund this virtual cycle. And so I helped her just random. of all trades. She was trying to get that off the ground she also ran a meetup called Developers for Good that was trying to do a very similar thing. So I helped her run that. then I also was doing some work with a with a company that was trying to basically build out like food and nutrition and culinary skills as like a little food truck for high school students in the Brooklyn area. So it was basically trying to bring like food and nutrition and cooking education to schools via

varun_1_03-17-2025_141131 30:41

So cool. Yeah. Wow.

theresa--she-her-_1_03-17-2025_171131 30:45

And so that actually did tie in a little bit more of the food component. And yeah, I actually don't remember how I got connected to that, but that I would like, I would go work for them for a day a week work for my friend for a little bit. I was doing a little bit of odds and ends and different like food jobs to make some amount of money while I was doing it. And then also applying for things that say, gave me healthcare,

varun_1_03-17-2025_141131 31:08

Tell me about this time, like how long was the period between, quitting the job that you had and starting the next one? what were the, pro pros and cons? I wanna know, obviously there's this, like I gotta put food on the table and get healthcare eventually. That's obviously a huge drag What else was notable to you about this time?

theresa--she-her-_1_03-17-2025_171131 31:28

Yeah. So it was probably a four or five month long period where I was trying to figure out what I wanted to do next. And there is like a huge amount of stress not quite knowing what comes next and being in that job seeking phase. We mentioned this earlier, but I think that through line of the moment of panic where you think, have I built any transferable skills that like I can cobble together into a reasonable flexibly of a. Job skill match but also it was cool in the sense that it was maybe my first taste of being fractional in the sense that I was doing a bunch of different things and getting to like weave between different opportunities and get to focus on more than one thing that I was excited about or that was a priority.

varun_1_03-17-2025_141131 32:15

All right. Let's get to the IIIN We're finally at the most recent 12 years of your career,

theresa--she-her-_1_03-17-2025_171131 32:22

in this point, right as I'm starting to think about joining Institute for Integrative Nutrition which I'll from here on out call IIN'cause it's just I was actually the first point where I thought, am I gonna stay in this place? So that up to this point I had been moving basically like once a year for the prior eight years. And I actually at the time, remember looking at a job in Philadelphia and thinking I'm not quite ready to leave yet. New York has a certain type of energy. That's what I've been looking for. I'm like building an A community and a network here. And I don't think I wanna move again. I ended up at at IAN and it was this nice marriage of, I'd been working for my friends tech startup for a little bit. And so I had some of this management, which also I think I had from being at, doing the volunteer work that I was doing. And then what IN does is they basically run a year long program for people trying to get into health and wellness coaching and run their own businesses. So it was a year long program with these three. Core pillars of nutrition and food and wellness and coaching experience, and then entrepreneurial experience. And that was really my return to education. So I think I, after panicking that I had no viable skillset, I actually could pull together this narrative of I have a ton of education background, I have food background, I have this tech component. I actually am a good bet for this role. started there doing like more project management, some like more entry level set up things, owning some different kind of programs. And yeah, I spent three years there had, the first of many incredible bosses. Actually both of my bosses when I worked at IN were just like. I still think about like how incredible my first boss was in terms of, I never asked for raise the entire time I was there. She like proactively fought for raises and promotions for me in a way

varun_1_03-17-2025_141131 34:29

That's awesome.

theresa--she-her-_1_03-17-2025_171131 34:30

informs how I try to operate myself now. I actually can't express enough how much she impacted my later career trajectory just in those three years, she probably single-handedly caught me back up to what somebody might have been at, like having spent, all of their twenties working somewhere. was pretty cool. Like she more than doubled my salary in the three years that I was at that company, which is no mean feat

varun_1_03-17-2025_141131 34:57

Yep.

theresa--she-her-_1_03-17-2025_171131 34:57

somebody who has been a manager and worked to fight for promotions for and raises for my team, it's not easy to do. It's actually hard and constant. And the degree to which she, an advocate for me without me even having to like, go ask for things was, just a gift.

varun_1_03-17-2025_141131 35:18

Yeah.

theresa--she-her-_1_03-17-2025_171131 35:19

is something that maybe I didn't quite recognize at the time, but I definitely recognize now.

varun_1_03-17-2025_141131 35:24

That's awesome.

theresa--she-her-_1_03-17-2025_171131 35:25

And then I think inside that also recognizing potential was able to give me opportunities to grow, my skills and my career and grow myself as like a project manager, as a as a technical leader. It's where I got to advocate for a bunch of different trainings that I took that helped me level up, skills wise.

varun_1_03-17-2025_141131 35:47

Awesome. What what were the things that you liked about working at IAN and what were the things that you didn't like as much? And get curious what, what eventually led to you leaving there?

theresa--she-her-_1_03-17-2025_171131 35:58

Yeah. I loved the people that I worked with and I think this is broadly a through line for me. The the wi it was all women actually, I think the entire time I was there who worked on the education and the content and operation side. Team was incredible. They were like so generous, incredibly caring super smart. And just a, it was fun to be at work with them. And it was also the job with the most bananas benefits that I have had across my entire career,

varun_1_03-17-2025_141131 36:29

Oh really?

theresa--she-her-_1_03-17-2025_171131 36:30

lunch catered every day, every two weeks. There was like a 15 minute massage that you could

varun_1_03-17-2025_141131 36:36

Oh my God.

theresa--she-her-_1_03-17-2025_171131 36:38

There was yoga classes three days a week after work in the building. Every Monday they put a fresh flower on your desk, like once a month. You

varun_1_03-17-2025_141131 36:46

Oh.

theresa--she-her-_1_03-17-2025_171131 36:46

a chocolate bar. It was like and there are more I'm not even exhausting the list of options, but, just a real deep dive after having worked in very non-tech spaces for what some of that benefit culture looked like. Which I loved at the time. But I think the other thing I really enjoyed is it was the first time that I really got to flex project management and also, this through line for my career of getting to really find an optimized system. So a lot of what I did while I was there is different programs or systems or features that we offered and get to figure out how to run them better. Make them work better for the end user. Figure out, why we were doing what we were doing, if it was actually the, most useful way we could run, say like a coaching program or a website offering.

varun_1_03-17-2025_141131 37:47

Who.

theresa--she-her-_1_03-17-2025_171131 37:47

like that.

varun_1_03-17-2025_141131 37:48

Gotcha. Okay. So you're at this place, this is the, you're optimizing systems for the first time. You're finding a lot of you're deriving some like value and fulfillment from that, obviously. What what leads you to feel like it's time to wrap up your time there?

theresa--she-her-_1_03-17-2025_171131 38:03

Yeah. So maybe about two years in even I started to feel some level of like friction or frustration with decisions, more at the top of the company. Like I really, again, I really like my managers, but I. Wasn't always bought into the decisions that were coming from the founder or like from the head, like lead of the company.

varun_1_03-17-2025_141131 38:26

Hmm.

theresa--she-her-_1_03-17-2025_171131 38:26

for me, that began to feel like this point of, again, did I want to do this work? Did I wanna have show up and be in this space if I found myself, like unexcited by directionally what the company was doing or what we were like pushing towards. And I, I think just as I found more and more decisions where I thought I don't think this is the right thing. Do I wanna have to show up every day and actually have to do this thing?

varun_1_03-17-2025_141131 38:51

Yeah. Well, and, and, And how did that um, I, I think like a lot of people can resonate with that Sentiment. I'm curious about how that showed up for you Did that result in additional tasks or work that you had to do, that you were just this is a waste of time? Or was it more like. If I'm showing up, even if the work itself is like bearable and I like it, if we're moving in a direction strategically, that's gonna actually shift the nature of my, like what was it kind How did your place in the company change as a result of strategic decisions being set at the top?

theresa--she-her-_1_03-17-2025_171131 39:25

So I think for me, I'd grown a lot, I'd learned a lot over those three years in terms of project management, agile development taking a scrum course. And as a result was getting the opportunity to lead these larger projects like an LMS migration. And what I found frustrating was having built that skillset it happened in tandem with sort of new leadership coming in that was coming from a less tech background, more of a traditional corporate background, didn't have that same experience and was really bullish on doing things the way that they thought they should be done rather than deferring to what myself or other, like some of the product managers on the team under understood to be doable, possible. The best course of action based on. Our learned experience as well as, what agile or best practices are. And so I found myself just on a constant basis feeling like I was hitting my head up against this wall of a misalignment of skills and expectations that found that just led to it being very frustrating.

varun_1_03-17-2025_141131 40:36

Yeah. No that, that makes a lot of sense. did you start looking at that point?

theresa--she-her-_1_03-17-2025_171131 40:40

At that point I started to look and again the constant through line will be had that, ever present panic of what did I do here for the last three years? Can I make this into a soluble resume that someone else will hire for something that's different? And actually the friend who I had worked for at her tech startup originally, I. Came through in a hugely impactful way, and she actually connected me with it, someone in her network who was hiring. And that happened to be Daryl, who was the head of a company thankful which is where I landed next. And so she sent me, an email saying Hey, this guy's hiring. He reached out asking for recommendations. Do you want me to recommend you? And so I said, yes absolutely as much as it was a, I was frustrated and trying to leave, I think the other thing I was looking for at the time was like given that kind of juxtaposition of feeling like the leadership necessarily aligned with what we were trying to build or how we were, how the company. At IAN probably should operate as a tech company that has, that and dies by an online app that, that people use. company thankful. I really liked the founders. I liked the way that they talked about the work they were trying to do. And that had been like a very important piece for me of I wanted to go somewhere where I trusted what the leadership was trying to do, and that they like, knew what they were doing at that time.

varun_1_03-17-2025_141131 42:10

Yeah. Yeah. I obviously don't need a whole primer on what Ful was, but te tell us, Tell the audience this is where we met, obviously.

theresa--she-her-_1_03-17-2025_171131 42:19

so thankful was a somewhere in the more traditional technical bootcamp. So at the time that I joined, we just had software engineering programs, so we had a full-time and part-time program for people. Who wanted to transfer into software engineering as a career. And so it was this interesting through line for me. I didn't have experience with engineering, but I had experience with people who were career switching into new careers via an online program. And the, the job they were hiring for was basically to run a full-time online program for people who were learning full stack JavaScript and wanted to become developers at the end of it. And so it ended up being this more logical transition than you otherwise might think.

varun_1_03-17-2025_141131 43:08

Obviously a long tenure in that job so tell us a little bit about what was it like when you got there? How did it change over time? What were the kind of trade offs? Were there any points at which you thought, I don't know if this is for me anymore?

theresa--she-her-_1_03-17-2025_171131 43:22

I was there for about six years through a lot of change in growth. And I think one of the, again, one of the coolest things was my ability to learn and grow alongside the company. And especially towards the start, I think. I was maybe employee 24. So it was this all hands on deck in various spaces. And most of the team worked out of an office in in Brooklyn. interestingly for me now, I prefer to work remote, but I think being in person with the majority of the company and with both co-founders, it when I was more junior in my career, was just a huge, made a huge difference in terms of trust and their ability to take chances on giving me things to do that maybe I don't need any more in my career, but made a huge difference at the time as we think about like remote work and when to be remote and in person. But. The work itself I think was super interesting. I learned a lot about software engineering just by default, by almost by osmosis. And that actually we didn't touch on it, but I got my first management experience at I and, and it

varun_1_03-17-2025_141131 44:37

Oh,

theresa--she-her-_1_03-17-2025_171131 44:38

Because most of the time when you're a manager, you get like thrown in and they say good luck. Hope this works.

varun_1_03-17-2025_141131 44:44

right.

theresa--she-her-_1_03-17-2025_171131 44:46

But actually this was the first time that I managed and managed, I think more intentionally.

varun_1_03-17-2025_141131 44:52

Yeah.

theresa--she-her-_1_03-17-2025_171131 44:52

in my first couple years, I got the opportunity to start managing the team of instructors that I, that led students through our full-time program. And then over time slowly built my team up to take over. of the support functions for what, across all 15 programs and two different career tracks.

varun_1_03-17-2025_141131 45:16

So you came in first, Program managing, finding efficiencies, making sure things are running. Managing, uh, and you start growing it. That's like Of you are taking on more and more responsibility and seems like exponentially. So over time, which is like really amazing.'cause it sounds like there was a lot of trust being placed in you at what point in time. Are you making these affirmative decisions and like having these conversations like with your managers versus like how this stuff just unfolding in front of you.

theresa--she-her-_1_03-17-2025_171131 45:46

I think a mix of both. So to some degree. There were points across, especially the first four years where I would say I can take that on. And again, because it's a smaller startup and things are a little more fluid, you have the opportunity to raise your hand for more work or more responsibility. And I had a lot of manager switches across my time at Thinkful, which I think is also pretty common for smaller startups that like org changes and things switch around. I, yeah, I think for me there was, it was a mix of both. Some of me advocating to my manager and some of them saying who can take this on? Let's have Theresa take on this new program. Or like this for example. Yeah.

varun_1_03-17-2025_141131 46:32

Yeah. And then and part of this obviously is just inside knowledge knowing, having worked at Thinkful for many years. But, you did talk about the kind of the value that you had gotten out of being co-located. but over time, Thinkful became a far more distributed company. Everyone that was like reporting to you, the first people that started reporting to you at the very least, right? Were remote. Did you see any sort of like tension or transition or anything notable about the kind of transition to an in-person with a co-located office in Brooklyn to be like a largely distributed company?

theresa--she-her-_1_03-17-2025_171131 47:03

Yeah. So I think actually I'm sure people that we worked with would disagree with me, but I think actually thankful did a pretty good job of building a sort of hybrid workforce. Put a lot of work into like how meetings should run in a way that felt inclusive for both. office and remote folks? Yeah, almost, I think exclusively across my six years at Thinkful, my entire team I think there were maybe two people, over time that worked out of the out of the in-person office, but most of my team was remote. And I think experiencing that kind of shift and trying to do my best to balance out, in person versus remote probably made a, it made me definitely more thoughtful about trying to build in like that community piece or like some amount of collaboration. Like it made me much better about thinking through transparency and

varun_1_03-17-2025_141131 48:01

Hmm.

theresa--she-her-_1_03-17-2025_171131 48:01

teams needed to know if they weren't in person in offices.

varun_1_03-17-2025_141131 48:06

Yeah. How many people did you end up managing?

theresa--she-her-_1_03-17-2025_171131 48:09

Started with it, when in my first year I was just a I was an individual contributor. And then in my second year I started managing a team of three. And over time that grew to be think probably like 30 ish people who are full-time across both the US and Delhi in India. And then also about 150, 170 part-time employees, and then a network of about 400 contractors. That all rolled up into my area of the business.

varun_1_03-17-2025_141131 48:42

Wow. That's a lot. What, I would want to know.

theresa--she-her-_1_03-17-2025_171131 48:45

Yeah.

varun_1_03-17-2025_141131 48:46

I think a lot of people would wanna know, like going from an individual contributor to a manager role in the first place, I think is something that, like people, I've heard people like agonize over and try to figure out okay, is this actually right for me? Et cetera. Was that a natural progression for you? And then from going to hey, I've got three, maybe four, like people under my employee who I'm like responsible for their success in a lot of different ways, delivering feedback, going to bat for them. That growing to 30 FTEs and like Like there, there's a lot there. And so I'm not even sure where to start in asking like, what were the friction points? What were the points at which you like, maybe thought that hey, I'm really good at this. Or what were the points where you were like, I need help with this. Did that help come in? What did that whole uh, you journey look like?

theresa--she-her-_1_03-17-2025_171131 49:30

yeah. Definitely points of friction. I think one of the things that I learned to do over time, and, we'll find out in, in, in the comments section from people I used to manage. But I think I became better at delegating

varun_1_03-17-2025_141131 49:44

Mm.

theresa--she-her-_1_03-17-2025_171131 49:44

of that period of time, which I think is one of the most important things you can do, both as a manager and as a manager of large teams and understanding that there are like, levels of delegation. So one of the things I think that I really struggled with at IAN and that I became better with at Thinkful was there's different types of delegation you can do based on the person's level and how much you trust them. And so getting to the point of understanding my team their strengths, what they're good at, and how to drive good performance from them, as well as knowing who I can task with, what level of complexity and who I need to Work with more tightly or who needs much more structure in the asks that I make and who needs not a lot of structure and can run with things was one of the biggest ways in which I I managed that, that large team and managed that transition. I think to that point of that earlier conversation of the excellent manager who always advocated for promotions for me, the bigger the team, harder it is to keep everyone happy.

varun_1_03-17-2025_141131 50:50

Yeah.

theresa--she-her-_1_03-17-2025_171131 50:51

And for me, I think being afraid of hard conversations is probably the other thing that I really worked on as a manager was I didn't want anybody to feel blindsided ever by a decision or by what was gonna happen or whe whether or not they were doing a good job getting a promotion. And so I really tried. To one, have constant touch points, whether it was weekly or biweekly check-ins with all these various folks to be able to keep in the loop, but also make sure that they didn't have any kind of open question marks around how they were doing what they should expect, like what was expected of them and that I think is the other thing that I thought a lot about as I was managing that team. I did very little to actually out any of the programs. A lot of what I did was figure out the containers and how we actually would run things and how we'd make sure that they were successful. So one of the things that I loved doing and was proud of doing was building out kind of our QA system of what does good look like? How do we tell, like what are the KPIs we need to measure? What are the, service level indicators of like how fast we need to get back to students. We need to measure to know that all of these complex systems we've built are on track and working so that we can respond more quickly or we know the right number of staff to task against any assignment. And that was this complex system that took a ton of time to build, but definitely wasn't something I was building alone. It was like in tandem with. whole team of folks who were like tasked against individual pieces of it. Again, that piece of delegating, like how I had to think at this higher level and then be able to parse out work amongst a team to be able to drive through what it actually looked like on the ground.

varun_1_03-17-2025_141131 52:46

Yeah. And it sounds like you felt like empowered to do that in a lot of ways. So it's like, you I hear this kind of through line a little bit starting with IAN and where you're oh, I get to really focus on operational efficiency And now you're in a place where over time, not only are you doing that, what your purview is maybe gets split a little bit across people and like making sure that they're effective at doing the things that you were doing Were largely responsible for not a one-to-one as to like exactly what your role was, but you're delegating your hiring, you're delegating, you're managing, there's the people aspect, and then when it comes to the actual operational aspect, you're also like a little bit more removed from the implementation of all of those things. And like all of those specifics and the job itself gets like abstracted a little bit more. Um, I mean that, that's What in an ops role feels like to me. Yeah.

theresa--she-her-_1_03-17-2025_171131 53:34

absolutely what it looks like. It's and you have to be really intentional about pulling yourself out from doing individual work at some of those points, like answering the email, implementing the individual thing, because you are trying to basically have that 10,000 foot view and then be able to give the right guidance, direction feedback, ask the right questions so that everybody who is actually then doing that next layer of work knows what they need to do, is getting the right. Inputs is actually like getting unblocked in the right ways. I think one of the things I learned at Thinkful was part of being a good manager is just figuring out how to unblock your team. Whether it looks like getting other stakeholders in the room that they need input from, whether it looks like helping them with skills training, if there's something missing that they need, like that's just a huge piece of how to be an effective manager is figure out what your team needs and then like how do you advocate for getting it for them?

varun_1_03-17-2025_141131 54:31

You're managing more people, you're achieving more in terms of what your team is actually able to deliver on, and it's measurable. It's fantastic. What comes next? What's, what's Up for you?

theresa--she-her-_1_03-17-2025_171131 54:40

Thinkful gets acquired by a company called Chegg which is a larger player in the ed tech space. And that became in and of itself its own transition. Min the many hours of stories and what it's like to be acquired and going through that process. But that moved us from a company of about, I think 180 or so to being a part of a 2000 person, publicly traded company. And so I learned a lot also in those two years post acquisition of getting to work with bigger teams, like getting to work with really robust legal teams as I worked with contractors and did workforce management, getting to work with really strong people ops and like HR teams in a much more structured environment. But it also came with a lot more constraints and top-down pressure around and margins and thinking through what it looked like to scale this company at the next level. had, really great opportunities and great managers and got to do a lot that was cool inside that larger structure. But at a certain point started to feel this friction of wondering if my own career growth and like trajectory wasn't quite in sync with the company's growth. And so was I able to take that next step into more senior leadership or was I stuck slightly more in now a like middle management role at this much larger company. And there became a point in those two years where even though I was well compensated, the work was interesting. I loved my team. I had this friction point of saying actually, I think I wanna be someone who has more of a like stake in the strategic decisions we're making in the larger picture thinking. Is that possible at a company this size with my experience level, or do I wanna move into something a little bit smaller where I can have that more like senior level strategic role? I had, experienced a lot of like promotion and growth, but there wa there felt to me like a disconnect in terms of my ability to move like that higher level picture strategy. And that

varun_1_03-17-2025_141131 56:55

Yep.

theresa--she-her-_1_03-17-2025_171131 56:55

that I wanted to be able to, that was a skill I felt like I was missing and I wanted to build if I wanted to be if I wanted to actually like. Level up myself as a, as an operator, as somebody who might someday be like a COO of something. that kind of level of strategic influence felt missing and I didn't see a path towards getting to practice that at Chegg.

varun_1_03-17-2025_141131 57:19

Yeah. So if we're thinking about the push factor Chegg, it's it's not like you were capped on your compensation or your titles and all Right? It's very much about the level of responsibility that you could have that actually has influence and impact over the organization. Yeah totally makes sense. So what so push, pull factors. What was pulling you to your next gig?

theresa--she-her-_1_03-17-2025_171131 57:41

So actually, interestingly, at the time, this is the. first and only point in time in my career so far where I didn't have that moment of, oh my God, do I have functional, useful skills? I had the good fortune of a couple people who I had worked with in the past reaching out to me about two different opportunities. So I was, in conversation with two different teams that we're looking to do. Things very similar to what I was doing at Chegg. And so I ended up at a company called Poly Gens. And what Poly Gens does is they run research mentorship programs for mostly high school students, but students who want to explore something that's outside what they can access in their K 12 education. And we would pair them with a mentor who is a near peer, so like a grad student, a PhD holder, but younger who could talk them through both how to do research as well as the actual subject matter expertise for things like quantum physics and, like

varun_1_03-17-2025_141131 58:42

Wow.

theresa--she-her-_1_03-17-2025_171131 58:42

printing and the diplomacy of, the Arctic regions and cool things like that. then they would build, they would basically build some sort of research project together, whether it was like a physical prototype of something. I remember there was one kid who was like exploring basically wind shape in air tunnels and doing it via design system. So sometimes it might be a prototype, sometimes it might just be a research paper that they're writing together as they learn the process. And the thing that I thought was really cool about what they were doing was I'd spent a lot of time helping people switch careers if they decided, at some point in time in their career that they had made the wrong choice and wanted to do something else, whether it was health and wellness coaching or software engineering or design. And there's something very cool about working with high school students to validate what they're interested in before they start college, before they start their career. trying to help them like. Make a decision that they were excited about and validate that it's something they actually wanna do before they get into it. And then also, I just remember meeting like the head of product and the head of marketing from those teams and like just like loving the conversations we had, the way they thought about their work and thinking Yeah. These are people I want to be my peers.

varun_1_03-17-2025_141131 1:00:00

Yeah. That's awesome. So what, Did they hire you for? What were the analogies between the role that you had at Thankful and Chegg? Like similarities and differences? Did you feel like the thing that you weren't getting at Chegg was something that you were getting more of at Poly Gen?

theresa--she-her-_1_03-17-2025_171131 1:00:14

Yeah, they hired me basically to lead customer operations. And so that was both the more traditional customer support roles, which is something I had taken over at a certain point in time at Thinkful, as well as starting to run through at the start mentor operations, but also the admissions flow. And eventually what I took over as well was some of the earlier product launch as we expanded what our offerings were. And there was a ton of overlap. They obviously had a huge pool of mentors, which was something I had experienced managing for my time at Thankful. As well as just managing the operations of running remote programs, like online remote programs. And in terms of thinking through like that, what was missing and what felt right is there was, so it was two first time co-founders and I think what I was excited to be able to bring to the table was a lot of what I had learned across, the previous nine years at both IAN and at Thinkful in terms of what are the, like how do operations scale, what works, what doesn't, almost like pattern recognition. Because this was a company at an earlier stage and it was and I could see and help drive things into a more useful scalable direction.

varun_1_03-17-2025_141131 1:01:35

Yeah. And what were the kinds of things that you maybe thought were gonna be like easier, um, coming into a role with a bunch of pattern recognition? I've done this stuff before, I've seen these, I've seen this movie before. Did, it sounds like maybe you encountered a lot of that at poly gens. I, I'd be curious to know a, if that's accurate, and B if it wasn't quite as simple as as Theresa is coming in as a soothsayer. Yeah.

theresa--she-her-_1_03-17-2025_171131 1:02:01

Yeah, so I think there were two pieces to that. So one, I was surprised how much I could recognize from having been in, other slightly more mature processes of what was going to work and not I remember early on looking through some of the workflows for the admissions team and the, and the broader sales team and saying actually, this should probably shift. And, you know, it took time to actually prove out why that was, but I could take that and do that pattern matching. And then the more challenging part was having not had six years of all of the trust that I'd built up at, thankful with leaders and with peers, I had to rebuild all of that or come with really robust data to be able to prove out why they should take, like what I was seeing at face value or why we should act on what my instincts were because wasn't used to, having to come with like that level of receipts,

varun_1_03-17-2025_141131 1:03:00

Yeah.

theresa--she-her-_1_03-17-2025_171131 1:03:00

And so that was definitely one piece of learning curve.

varun_1_03-17-2025_141131 1:03:03

What was the kind of like realization of when you get to, when you got to having to bring receipts? Was it like you had encountered friction and then you brought some receipts just because you were being so frustrated and then you were like, oh, I should have done this the whole time, or.

theresa--she-her-_1_03-17-2025_171131 1:03:17

So I remember one piece of there was a process that we had with win the deadline for students and win the deadline for the internal sales team. Commissions were and it was the same day. And I remember saying actually that doesn't feel right. They should surely be further apart. And getting told no, it's fine. And then finally, two months later, we actually then got the data from our incredible data analyst who said actually when we put these two things together, like via all of the behavioral consequences of this deadline and that, and how the team acts, like we're converting much slower. And then it was like we changed it a week later. Like it was a no brainer, but what we needed was basically someone to say, here's the data that shows why this isn't working.

varun_1_03-17-2025_141131 1:04:01

Right,

theresa--she-her-_1_03-17-2025_171131 1:04:02

say I I've seen how this type of team operates, like this can't be the right approach,

varun_1_03-17-2025_141131 1:04:09

right.

theresa--she-her-_1_03-17-2025_171131 1:04:10

to say quantifiably the team is slower at making those switches. And so that actually was really interesting point for me to say, oh, I see this is actually how I need to think about coming in. Like one, the data is what will tell the better story? it shifted how I think about wanting to find and come in with the data as a piece of the argument. And then I think it also for me was that point of realizing I actually need to build my cases for things differently here than how I've had to in the past.

varun_1_03-17-2025_141131 1:04:39

Now what I'm curious about as someone who started as an individual contributor and gained a lot of direct reports, what was it like going into a role as a leader as opposed to the role that you were in before, which you established yourself and grew into a leadership position over time,

theresa--she-her-_1_03-17-2025_171131 1:04:55

Yeah. I underestimated how much I would need to shift to fit inside the new culture. And so it was almost less about in as a manager. I think a lot of how I thought about managing a team, I could articulate well to this new team and try to I. Tell them how I wanted to operate, try to understand how they wanted to operate. But biggest shift for me was actually culturally moving from one company that operated in a very specific way and where you had to operate in a very specific way to get heard, to get things done to a company with a very different communication style, collaboration style. And one of the things that my manager at Poly Gens did, that I'm super grateful for is actually this 90 days into my job there. She did a 360 round of feedback with my peers and my direct reports. And I got a ton of very critical feedback around how I collaborated, how I communicated with my team in meetings. And I was honestly quite shook. It was, communication is something I think I'm pretty good at. I think my is pretty high. And so one, it was like. An exercise in absolutely removing ego from the tail nobody likes to hear, actually, everybody thinks you're doing a pretty bad job. So sorry. But it was honestly one of the most valuable piece, it's one of the most valuable things she could have done because it gave me the opportunity still relatively early to get to course correct and also to understand what I was doing. So like the next time that I move into a different team and system, be more thoughtful to how I wanna adapt to how they communicate and collaborate. Because a lot of the, maybe more like brusque very forward like to the point types of communications that got me where I was going at. Thankful and at Chegg then didn't work in the more academic setting where there was more of a focus on collaboration and everybody participating in the conversation, everybody deciding together. And so I think I just hadn't quite come to understand what it would look like to shift from some, all of the habits and routines that I had built over the past six years into a different system. And I couldn't just move myself into it and assume it would work.

varun_1_03-17-2025_141131 1:07:24

Yeah. Yep. Totally. That is that's really insightful. So let's talk a little bit about What happened at the end of your time at Poly Gents.

theresa--she-her-_1_03-17-2025_171131 1:07:33

So unfortunately over, it's a it's a very common tale across most of the tech industry and ed tech specifically just didn't necessarily end up being the year of growth that the company was anticipating. And so we ran a round of layoffs in May of 2024, and then with the size cut that we were making, it just didn't make sense for. role to still be there, at my level of seniority. And so up not being the, that, that was much more of say like a, I guess a push than a pull in terms of how we're thinking about it. But also has been this really great way for me to get back to that comfort with discomfort, comfort with unknown. So nearly immediately after finding out that I wasn't gonna be at Poly agents anymore, I bought a ticket to travel in Asia for a little bit and decided to embrace what are the things that I haven't been doing?'cause I've been in more of a, like nine to five structured job that I can get back to doing and give myself the sort of the luxury because I could of being able to return a little bit more to that like exploratory roots.

varun_1_03-17-2025_141131 1:08:51

Yeah, that's really nice. How long have you been doing that for, and like, how are you living that out today?

theresa--she-her-_1_03-17-2025_171131 1:08:57

I did that for maybe or five, six months, and then I started to try to figure out what I actually looked like to do, like what I wanted to do next. Because I still live in New York. It's not the cheapest place to live. Eventually I have to figure out what comes next. And so my ideal goal was figure out do I wanna be fractional? Do I wanna return to something full time and spend some time exploring that, talking to companies. And then where I've landed is being in a couple different fractional roles, using, again, the experience that I have that, and getting to do that kind of cool like pattern matching. And having been now through three different companies with very different experiences, but through line through each to be able to help drive forward some operations at smaller startups that are maybe on the earlier stage of some of what I've seen through my time at other companies. interestingly, like both of the two things that I'm working on currently came in through unexpected roots. So I'm actually working with a former colleague of ours um, who was my first manager at Thinkful. And he has built a company called Atrium Academy, which is basically like a boutique training program for right now folks in the crypto space. And it's really about helping drive talent a so basically finding talented developers who can build in these ecosystems and then giving them the tools and the training to be able to contribute to different. Crypto protocols and ecosystems and, be able to contribute to those companies and like what they're building. And knew nothing about crypto, still don't know that much about crypto, but what I do know about is like building education programs and how to scale operations at tiny Systems. And it's been cool to get to put that in practice, work with BOIC again, and also get to once again kinda learn about this new space that I knew nothing about prior, but is obviously a very much in demand talent market. then the other thing that I've been working on is actually something called real education. And that again, in the ed tech space, but what it's focused on is basically I. Trying to fill a skills gap, need for Gen Z or, younger folks coming into the workforce of, learn all the hard skills and they maybe have some of the social emotional learning, but what they don't have is like these practical skills of understanding how to basically flourish as individuals, as parts of a company, as like in their future career. So helping to build in some skills in the practice of understanding what gives them energy, to fold back to like our earlier conversation of figuring out

varun_1_03-17-2025_141131 1:11:55

Yeah.

theresa--she-her-_1_03-17-2025_171131 1:11:55

you up. Just the practicalities of what does it look like to get enough sleep and moderate, like your intake of various things and make sure that you're doing like the exercise and whatever, so that your body feels right. Like how do you build in, the anti fragility of taking on hard challenges and not letting them depress your motivation or your confidence levels, or like how do you use those to like, keep building, how do you like, remove the self-imposed blocks for what you decide you can and can't do. And so it's a very cool program that we're working to embed with colleges, with other schools, and help build this as a core piece of an individual needs in order to be able to like fully flourish and come into themselves and live a meaningful life that they derive a ton of value from.

varun_1_03-17-2025_141131 1:12:47

I really love how many of the through lines, like throughout your career, including what started at the beginning of just like essentially putting yourself in a position to live the life that you want to, and then still finding the things that kind of like light you up. you know, over time finding operational efficiency, being in like the early spots of finding like new educational models and things that are missing in the world. And doing it in a fractional way also. Right now, it sounds like that is maybe could be a longer term thing for you. Maybe could not. It sounds like you're

theresa--she-her-_1_03-17-2025_171131 1:13:15

I think if you asked me like 10 months ago what I was gonna be doing now, I don't think I had an idea. If you asked me 12 years ago, 20 years ago what I was gonna be doing at this point I am a firm believer in not necessarily trying to like, decide the exact thing in advance. So

varun_1_03-17-2025_141131 1:13:33

Yeah.

theresa--she-her-_1_03-17-2025_171131 1:13:34

like these are two things that I really care about driving forward and that have been incredibly fun to get to work with the folks that they're, that are building them and excited to see what they turn into as we build them out and launch them.

varun_1_03-17-2025_141131 1:13:48

This is awesome. All right, thank you, Theresa. thank you so much for taking the time. This is super fun. And I I.

theresa--she-her-_1_03-17-2025_171131 1:13:58

You're welcome for the monumental editing task that I have set upon you, but

varun_1_03-17-2025_141131 1:14:02

great. I asked for it.

theresa--she-her-_1_03-17-2025_171131 1:14:05

What, what comes out of this is useful to other people that maybe people see a little bit of themselves or like where, what they've shifted through what's worked or not for themselves. And if it inspires just one person to go travel instead of be at their laptop, then I think that's in and of itself a success.

varun_1_03-17-2025_141131 1:14:24

I love that. Oh, that's wonderful. Awesome. Thanks, Theresa. I'm gonna

1:14:35

there you have it. Uh, that was my conversation with Theresa. Uh, we had recorded for about two hours, and so whittling that down to an hour, 15 ish was actually really difficult. Uh, I really loved everything that we were able to talk about and, um, yeah, I, I, I still think that the early parts of her career are super instructive and really inspiring. I find there's. Courage, truly admirable. But I also think her approach to her traditional career is also incredibly instructive. she's very clear-eyed about what it takes to advance professionally, Her insights into what it actually takes to get into a management role and continue to advance, Is a really laser in focus on delegation. I wish I actually spent more time with her on that It sounds like she was really effective at understanding a bit of complexity, making sense out of it, and then hammering out the inefficiencies of it, and then as she built trust within an organization, I. Uh, and was able to hire or manage people under her in order to take care of some of those smaller problems. She was able to solve more systemic problems at a higher level, and being able to implement that by delegating. and that's how you become an effective operations leader over time. And it's funny because everything I've learned about management and everything I've seen from people who are really effective leaders, reflects. Exactly the kind of thing Theresa shared with me today, but I haven't heard it articulated as well as Theresa was able to articulate it today with the examples that she had given throughout her career. So, hope you found this inspiring and, yeah, if you are a little bit earlier in your career or if you're a little bit stuck and don't know what to do, maybe close your laptop and, buy a ticket to somewhere in Southeast Asia. But otherwise, I had a real blast. And, if you can, you know, hit me up with a, with a follow or a subscribe or a like, on, whatever medium that you're listening to this or watching this on, Leave me a review or a comment and, uh, let me know what you think. Thank you so much.