Lara Perlstein: [00:00:00] And I had this moment of like, if I'm still sitting in the same cubicle on 20 years from now, I'm not going to be happy with my career choices. So I, I had a conversation with my manager. I was very close with her on a personal level. We had a really good relationship and I said, you know, Hey, I don't necessarily want to leave, but I want to do more.

David Fano: So thanks everyone for tuning in we're. Lara Pearlstein who I've got a long working relationship with, which I'm really excited about. And so I'm excited to have this conversation about some of the twists and turns in her career. And obviously some of the things she's doing at deal, but you'll, you can learn those in other ways.

So, uh, with that Leora, thanks so much for joining.

Lara Perlstein: No, of course, happy to be here and excited to.

David Fano: So, uh, I usually, I like to kick it off with the age old. Tell us a little bit about yourself. It's kind of like the interview question. Everyone has to answer, uh, extra pressure for you [00:01:00] because we teach people at teal how to do it.

So you gotta do like a really good one. Um, but no, just kidding. Uh, this let's kick us off with a little bit about yourself.

Lara Perlstein: Yeah, sure. So I live in Brooklyn with my husband and my dog who our office and our team tends to see a lot making an appearance. And I started my career with, I graduated during the recession with a psychology degree, really had no idea what I wanted to do and started kind of taking just more general entry level jobs, found myself working as an office manager and an administrative assistant for many years, kind of in the fashion and beauty world realize I wasn't super passionate about that and wanted to kind of find a company that matched my personal values a bit more.

I found my way to work, whereas how I met you. And obviously we're closely with Dave for several years, did a lot of different things there I can dive into later, but kind of was utilizing this kind of generalist [00:02:00] skillset that I had doing a lot of people, operations strategy, things like that. And then I found my way to teal and at teal, I'm also in a strategy and operations type role, kind of trying to oversee both our business offs, but then helping them.

The product and gross side as well.

David Fano: Awesome. What gives us a lot to pick from? So when, when was the first time you like, realistically thought about this is what I want to do, right? Not the, like when I was a kid, this is what I want to be when I grow up, unless it's relevant. Um, but when did you start to have like a little bit of an intentionality?

You know, I think generally for people it's like when they pick a major, but maybe not. So like, when do you feel like that?

Lara Perlstein: Yeah, I think I had like a couple different points. Um, it definitely was not in college or kind of in the college setting. I would say that was a time there. I was just like, these classes seem interesting, but I never really thought about how those might string together into a [00:03:00] career.

But one thing is I actually worked through high school and, um, on my summers in college and I spent many years working as a camp counselor and then programming director at, uh, an overnight camp up in the Berkshire. And I feel like that was the first time I was working, but it didn't feel like work. And I was like, this is so cool.

I'm, I'm helping kids have like the best summer of their lives. I'm helping staff members understand how to manage children for the first time. I'm going to be responsible for them for two months, you know, while they're literally in their, you know, bunks with them day to day. And I was able to kind of move up through the ranks and ended up in more of what they call like a senior staff position, where I was actually helping building the program of camp.

And I think that was the point where I was like, I don't know if I can go to camp forever. Like if there was a way to make this a job, that'd be really cool. But I was like, I'm really passionate about what I'm doing. And I also felt like I was earning like a gaining skills that I can actually translate outside of a camp.

So.

David Fano: I like [00:04:00] that as an evaluation criteria as like work, that doesn't feel like work. And I think a lot of people get hung up in that as language it's like, you know, if you'd love your work, you don't work another day in your life. Like, I think people are a little too extreme about that, but I liked that.

Just kind of like I can get lost in this. Um, and at the end of the day, like feel pretty charged up and happy with the work I was doing. And so I liked that as like, as a sort of general, like litmus.

Lara Perlstein: Yeah. And it was, it was also some of like the hardest work I've ever done because I was dealing with like parents when it came to their kids, behavioral issues.

Um, really like their wellbeing. And then I was also dealing with counselors who are in their, you know, like late teens, early twenties, who like, kind of thought this was more of an opportunity to party and less of a time to be a job. So it was definitely hard. And at times I was, I got very frustrated, but I went back at the end of the day and I said, you know, I'm make I'm changing.

These people's lives. I'm giving them a summer or summers. They can remember. So it feels, it felt worthwhile at the end.

David Fano: Oh, well, lots of memories made I'm sure. Um, all [00:05:00] right. So that sort of, um, introduced some activities and experiences that informed things you did later. You said school was not that, um, so let's say you're done with school now.

You already sort of ruled that out as something you wanted to do. What was like, what was the decision process there? Like what was like, all right. I got to get a job. I want to get a job. Like what was going.

Lara Perlstein: Yeah, I definitely, I graduated and I definitely struggled because I had like about half of my friends who were just going back to school again on they're like, oh, you know, I want to go to law school.

I'm gonna apply to law school. I want to go to grad school for X, Y, or Z. And I, part of me was like, am I supposed to go to school more? Like, is that what I need in order to get a job? Because I didn't pick finance, you know, or a very specific route in college where I, I exited and there's like very specific jobs I should apply.

Yeah. I had a, I studied psychology, which I really enjoyed, and I think it [00:06:00] was a very useful degree now, looking back on it, but it wasn't a degree where you graduate and it was like, these are the five jobs you can go from here. It was like a question mark. And it was also a recession. So that question mark, you know, was even gloomy or scary.

So I, I started wondering if I should go back to school and I almost went to grad school. I submitted applications and I was actually going for a dance therapy, which is a very, very specific thing. I loved dancing growing up and I, I liked helping people in psychology and I wanted to put those two together, but financially I didn't have the funds to be able to do that.

So I was going to be putting myself in debt and I struggled with this idea of if I'm not really sure what I want to be doing, should I be putting myself in debt right now? So I ended up backing out, which I think was the right decision in the long-term. And I ended up just working retail and saying, Hey, I'll just work retail while I figure it out.

And what became like this very temporary job, I ended up really focusing on really investing in, worked my [00:07:00] way up through the ranks and ended up managing one of the flagship locations in New York city. So I think that I was kind of avoiding that question, but. I ended up by default. It's kind of finding a path within that,

David Fano: so right.

We've in previous episodes, talk about the kind of career cycle, um, the moment of kind of like searching for something, you know, transitioning into the role and then developing and what ends up happening is development hits a plateau and then you search again. So what was, that was kind of like your first real job in air quotes, um, after school, what, what was.

W w w what happened that resulted in change from that to what you did next?

Lara Perlstein: Yeah, so I think there were a couple of different kind of like plateau moments or revelations that I have. One was I had a rough schedule, right. So I worked weekends. I didn't feel like I had control over my schedule. I was working very, very late, because as far as [00:08:00] openly, and I was, you just didn't feel like I could make plans in advance or know what my schedule was going to be even like a week and a half.

Uh, so there, there was frustrations with that. Another thing was that I had kind of hit as far as I was going to hit in that setting. Right. So I was the store manager. There wasn't much room for growth from there. And I, I said, okay, like, I feel like I've, I've gained the skills and I've learned what I can possibly learn for this job.

And now I also feel like I have enough that I can put on my resume. So leave retail and actually try and get more, um, um, Monday through Friday type job, at least

David Fano: what'd you do then? So like what, what kind of like resulted in the change and just like, start looking, just have to like, get a little clear on what you wanted to do.

Did you want to keep in retail? Um, cause I think you kind of made a shift, so I'm kind of curious to learn a little bit

Lara Perlstein: about it. Yeah. So I knew I wanted to leave the. Retail side of like fashion. So I didn't want to be working in the stores themselves, [00:09:00] but I said, okay, I don't want to make like a total 180.

That might be challenging. So I said, okay, I can stick with fashion and just leave the store and go more to the corporate side. So I have a lot of learnings from the store and the day-to-day experience. And now I can take that back and say, okay, like what's happening behind the scenes there. So. Started applying to office manager and administrative assistant positions at fashion companies who had retail stores.

So I said, okay, maybe that's like a, a manageable pivot that I can write. And ended up getting hired for a beauty company. So not exactly the same industry, but a lot of similarities where they were selling their product in stores as well, but kind of working on the backend side. And I was, uh, an office manager for Moroccan oil, which is a hair care company.

David Fano: So, you know, I have that added benefit as an interviewer, having known you for awhile, um, and something that's always been really impressive to [00:10:00] me. How ego is just not part of your career. Decision-making I think to have a degree and be like, I'm going to go work retail. Right. I think it's obviously on the surface.

It's totally fine, but I think there'd be a lot of societal pressures to be like, that's a, that's a career regression. Why are you doing that? You have a degree, uh, And then this is, I think another really great example of that. Like, I'm going to go be an administrative assistant, you know, I was a manager and I think a lot of people get hung up on like title, title, progression, the idea that we go backwards.

But, you know, I always think about like, if we're going to jump really high, we squat first and we go down, right. We got to like build the energy. And I, you know, obviously I know what you're doing now. And you have a leadership position here at teal, but I feel like you've never been held. By that you can, can you talk a little bit about sort of how you do or don't think about that?

Lara Perlstein: Yeah, I don't, I don't think I thought about it earlier in my career. So in that, in that moment, I was just like so miserable working [00:11:00] in retail that I was like, you know, anything that gets me out of here. And I, I know my schedule and also I know what I'm going to be making. Part of the challenge of retail is I was being paid hourly.

So even in like a senior position. So I was like, I don't know what my pay. I. Not necessarily living paycheck to paycheck, but Patrik Patrik was a question, mark, what would that amount be? So, um, I think one of the other, the other pieces is I try not to get hung up. Right. Titles don't really matter. Titles don't necessarily say what you actually do.

And I tried to look at like, what is the experience I can get from this? So an administrative assistant to some people might seem like, okay, More of like a, a lower level job. You're not necessarily going to learn that much. You're just buying people lunch every day. But the reality of being like any kind of like really assistant from that standpoint is the exposure and access.

You get to information and to stakeholders. So sure. I had to run out and get lunch for my boss most days, but I also have [00:12:00] personal relationships with all the C-level executives of the company. And I. Got opportunities where I'd say, Hey, you know, can I sit in this meeting and help take notes? But it was also an opportunity for me to actually just like, learn about the business while being in that meeting.

And I don't think anyone else in the company could have said, Hey, can I just, you know, crash this meeting that was very much like something that's acceptable as an admin or getting to go on business trips or things like that. So I really looked at it like the experience and the exposure. And if I had taken a different type of role, that might've sounded better on paper to some people, there's no way.

Been able to see and hear and experience what I experienced.

David Fano: Yeah. I love that. And I, I, you know, it's a tricky thing to kind of communicate, to like focus on the intangibles. Cause obviously you gotta be able to do it. Um, But, you know, people figure out a way to prioritize things. And, um, I've just seen more often than not that sort of pays off.

It may not. It's taking a little bit more of a longer term view, you know, you'd probably tell me you weren't like [00:13:00] as deliberate about it, but there was just kind of like a belief that these experiences were beneficial, more so than like, kind of like what you needed at the moment and, and understanding that this was an investment in the long-term and not necessarily.

Clarity on what that was going to yield, but it just like, felt like a good investment.

Lara Perlstein: Yeah. I think the piece that I was aware of, like in the one that I chose intentionally was I'm now going to have experience working in an office. And I didn't have that in retail. I had experienced working in a store.

Sometimes I think even more powerful, but it's definitely different. So now I said, okay, I'm going to take this job. I don't know if I'll be able to grow there. I don't know if I'm going to need to leave soon after, but now I have experience working in an office and that that's going to show other employers, you know, potential job opportunities that at least that's something I can do.

And I've done before.

David Fano: Um, another thing that, you know, in retrospect now also doing the work that we've done at teal that I think was [00:14:00] smart. Yeah. Was you picked like how many things you could change? You're like, okay, so I know fashion, or, you know, the sort of broader industry. Um, but the, the one part I want to change is the context and I'll leverage all this other stuff.

And so, you know, did that actually play out, like when you were looking for that job, like, look, I understand retail, I understand your industry. Maybe I don't have experience in this particular kind of job. Like how were you able to talk about your transferability, uh, when you were in.

Lara Perlstein: Yeah, I think, I think the, one of the main ways I spoke about it was just like customer interaction, right?

Like I was on the floor every day, dealing with customers for better or for worse, but I was having a drug cause I knew what they liked. I knew what they didn't like, I know what they wanted, more of what they wanted, less of what frustrated them, what made them happy and right. You need all that information to make its way back to this, you know, backend corporate office type situation.

Okay. Usually the people [00:15:00] in that corporate side of it aren't necessarily getting out on the floor and talking to customers. So part of it was like, oh, you're a customer. Um, specifically with the hair care company, it's like, you are falling into our target demo. So like you're somebody who uses hair care products that can give us opinions on haircare products, but also you have all that customer experience.

So that was one of the ways I tried to pitch that. So I said, okay, customer experience. You know, is this is valuable from going from retail to corporate. And sure. Maybe fashion to beauty was a little different, but that customer experience was more valuable at the end of the day.

David Fano: Awesome. So let's talk about the next plateau.

Um, you were at Moroccan oil, you were there for a little bit, um, or kind of like maybe leading up to that next change, right? Cause then we'll get to that. We work where you were for a while. Um, and a lot of like interesting progressions there, but what was that like next moment, whether it was in Moroccan oil or, or like to the, you know, the next thing, but what was that, that next [00:16:00] moment in your career where you kind of hit a fork in the road?

Lara Perlstein: Yeah. So as that, Moroccanoil, I want to say for about a year, year and a half, it feels like a lifetime ago. And I learned a ton. I got exposure to a ton. I got to travel to Israel and spend time there. So that was just like really cool from a personal experience. This was an interesting one. Cause the fork that I came about was not one I had planned for and I don't think I could have foreseen, but I had gotten promoted to the kind of, I was the executive assistant to the president and one of the co-owners of the company and where that started as a position that was very involved in the business.

He personally decided to take a step back from the business and focus a bit more on personal things and other things he wanted to do. And I didn't really see it at first, but he started to pull me away. So I was very much working for him. It was less, I was working for the company and more than I was working for this individual.

And I was very involved in, you know, aspects of his personal life and his home and [00:17:00] managing that. And so I kind of had this like wake up moment one day and I was like, I haven't even stepped foot in the office in a week and a half. I was like, I have not dealt with anything related to the business. And maybe two weeks, you know, even if I just showed up to the office, sometimes it was just to see friends and I see.

You know, if I want to be a personal assistant, if that's the route that I want to be going, this is great. I should stay, but it's not. And so I said, you know, I'm going to, I, and I asked, I didn't decide to leave right away. I had a conversation with my boss and I said, you know, I want to be more connected to the business.

Is there an opportunity to do that and kind of shift the scope of my role, or if not, I'll go take this executive experience and executive assistant experience. I'd find it at a company that does want it to be more business oriented. And unfortunately the, our kind of wants didn't line up at that moment.

Um, and we, I parted ways on very good terms, but I, I decided to find an executive assistant position. Not at all on the [00:18:00] personal side and a hundred percent on the business side. So I actually moved to another, I moved to a fashion company. So it kind of stayed in that similar realm who also have retail stores.

And one of the cool moments there was I, the amount of salary increase that I wasn't even like negotiating. I had a friend who was working at this new company and was like, Hey, this is the salary range for an executive assistant. Ms fashion company. And it was significantly more than I was currently making.

And I was like, oh wow. That's what my skill set should be valued at, which was like a wow moment for me. And that's a better opportunity. I'm going to take it.

David Fano: And so w that you got presented with that, or you, did you like, kinda like put feelers out to the world and say like, Hey, I'm open to opportunities.

Lara Perlstein: I put feelers out and I reached out to my network and I have. One of my employees who was with me at Moroccan oil had moved there ahead of time. And we had stayed in touch and she's like, Hey, they're looking for an EA. It's awesome here. It's very different from where [00:19:00] we were. And right. These are the reasons why, and these are the different experience you could get and I can put in a good word for you and kind of make that employee referral.

And so that worked out really well for me.

David Fano: I think there's going to be a recurring theme here. So we'll note this as relationship, job transition. Uh, all right. So you go to this company for a bit. And so here you were context, similar role, similar, um, back to business. So you were able to kind of like, but also comp went up because maybe the scope and, um, but in terms of like job, pretty similar, uh, which probably made it easy to interview for.

Um, all right. So you were there, how long were you there? Kind of, what, when did you hit that next.

Lara Perlstein: I was there for about a year. Um, it was very, so where I had come from was a less established company. It wasn't quite a startup, but it was less established. And where I went was very corporate and this was the first [00:20:00] time in my life.

I had worked in a very corporate office. Like I literally sat in a cubicle by myself and I didn't even know that cubicles still existed. It was the one and only time I will ever sit in a cubicle my career. I think I can confidently say that. Um, but I, I was working for. That had a merchandising. So it was a lot more actually looking at the business, running reports all the time, analyzing reports, sitting in business meetings, and I enjoyed it.

I learned a lot of skills and kind of a year later, I just kind of hit, I hit this point. I've learned everything. I can learn as an executive assistant in this box right now. And, and I was looking around and all the other EAs the organization were like lifetime EAs. And that's an amazing job. It's just not the one that I wanted.

So, you know, they had been there for like 20 plus. And I, I had this moment of like, if I'm still sitting in the same cubicle and 20 years from now, I'm not going to be happy with my career choices. So I, I had a conversation with my [00:21:00] manager. I was very close with her on a personal level. We had a really good relationship.

And I said, you know, Hey, I don't necessarily want to leave, but I want to do more. Um, and we had a really honest conversation that was like, you know, I don't necessarily need you to do more in this current role. Sure. And anytime you can get exposure to a few more things, you know, ask and I'm happy to give you those opportunities.

And we talked about, there were internal mobility options, but I would be going from an executive assistant to like an assistant buyer. And it was a different skill set. It could have been a cool opportunity, but comp wise it would have been a significant pay cut for where I was at. And so I was at a point in my life where that wasn't, that wasn't something I could afford to do.

And so I said, okay, This isn't meant to be it's okay. And I'm going to now look for an opportunity where I, even if I have to step foot in the door as an EA EA with room to grow and expand from there, and it just didn't exist in that very corporate environment, unfortunately. [00:22:00]

David Fano: Right. So talk me through.

Lara Perlstein: So we're going to go back to relationships.

I I'm, you know, I had been talking to friends, colleagues, um, and have been chatting with one, um, one person in particular. I went to college with and they had started at this awesome little startup called WeWork and they were growing very, very quickly. He talked to me a lot about the culture. So one thing coming from super corporate cubicle.

I was like, I need, I need more, I need more people. I need more interaction. Like, I, I get energized by interacting with people. And by default sitting in my cubicle is just not good for me. So we talked, they were hiring a lot. They were growing a lot and it was like a startup. And I was like, okay, I don't really know what a startup is.

I had never really experienced startup life before my, my dad had actually worked for a lot of startups growing up. So like, I know he always worked at home. Remote was always on calls. It's always on video. Uh, some of them [00:23:00] worked out. Some of them didn't. So I was familiar with this as a concept, but I had never really thought about it.

So he referred me in, got my way kind of foot in the door. That way I went through a very chaotic interview process, which I'm sure anyone who interviewed that we were cause similar, but I, I probably interviewed at one point or another for like six different roles. They were all. Executive assistant coordinator, office manager type roles that the company was moving so quickly.

Like a week later that one would be filled, but there was this new one open. So I met with a lot of people. And the common theme I was saying is I was like, everyone I'm meeting with seems awesome. Um, you know, the offices seem awesome. It was fun to go there and interview. So I kind of got to like the last round of, I think it was called, I think it was a coordinator position technically.

Um, but very similar, similar salary to what I had been making. So it wasn't, it wasn't taking a pay cut necessarily. And I had a really, again, open, honest conversation with, with [00:24:00] the hiring manager and I said, Hey, like, I'll come on, I'll be an admin for you. I'm going to be like a kick-ass admin. I'm going to do an amazing job.

But I want to do more and if I can prove to you, I can do more. I want to know the opportunities there because I don't want to waste your time if it's not going to be there. And I'm just going to come for six months and then leave, I'm doing you a disservice. So we had this really honest conversation and as we dug into it more.

Uh, the scope he needed filled was actually less a traditional admin and more of like project management type things that I was seeing. And I was like, Ooh, this sounds really cool. So sure. If I have to get lunch as well, I'm happy to do it. If I get to actually like manage these cross-functional projects.

So it ended up sounding awesome. Agreed to make the move and add a wild four and a half years.

David Fano: So, um, what's interesting is like your time at WeWork was almost in aggregate the same as all the other places you had been working. Your first job was like a year and a half then a year and a half than a year.[00:25:00]

Um, which I also think, you know, you were proactive and intentional about it, right? I think a lot of people get worked up on the go, I need to be there at least two years. And it sounds like you had a real good sensibility of unlike. I don't feel like I'm progressing like this. Isn't fun. I'm not just going to like pack up and go and do like the stigma.

Job hopper thing, but I'm going to have an honest, balanced conversation of what's right. For the place I work at, I'm going to maintain relationships, but I'm also going to like put myself first and figure out what I want to do.

Lara Perlstein: Yeah. And I was really lucky that my boss at the time was like very comfortable with that level of transparent.

Nah, I was like, I'm going to, if, if we can't find something here, I'm going to start looking. I'm not going to leave you tomorrow. I'm not going to disappear. But also there was no worry about like retaliation and then being like, oh, you don't want to be here. And then leave tomorrow. It was like, no, we know you're going to leave.

We'll come up with a transition plan that works for both of us, but they were really supportive at the end of the day of, of me needing to do what was right for me and my career. [00:26:00]

David Fano: I don't think it's an accident that you've had that at almost every job up until the week. Um, every single one is like, I had a great relationship with my manager.

I had a very candid relationship with the hiring manager. This wasn't even someone, you know? Right. So I'm going to go ahead and give you credit and say there was something you were doing to have that consistently, uh, happen. Uh, like what advice would you have for people around, like how to foster that kind of rapport with, you know, this hierarchical relationship?

You know, maybe it's putting yourself out there being a little vulnerable, but ultimately it served you. And not that it always will for everyone, but like, if you had to look back on it now, and I didn't give you this question in advance, but like what, what do you feel like you were doing to enable that to happen time and time again?

Lara Perlstein: So the first thing that comes to mind is, is around like showing interest. So I think [00:27:00] something that I did again, whether it was intentional or not at the time. Is, I was interested in things that were outside of my job description. Let's say they weren't necessarily completely unrelated to what I was doing, but they were outside of my job description.

And so I asked questions, you know, I said, Hey, this is really interesting. Or I was sitting in a meeting and I heard the, I jotted down these terms. Like, I'd love to know more about what they mean and, and not even to necessarily my manager, but other people I had working with working relationships with.

And by doing that, I started coming up with ideas. I'm like an idea person. I know, you know that. And I said like, Hey, we're doing this reporting thing. And it feels like there's gotta be a better way to do this. And I started asking questions and coming up with suggestions and they weren't necessarily the problems weren't being given to me.

I was coming up with problems and trying to brainstorm potential solutions or opportunities to fix something. And I would be happy to be the person to do it, to kind of step out of my [00:28:00] scope and say, Hey. I have bandwidth or I'll make the bandwidth. This sounds interesting. And that really paid off for me.

I think people saw that I was interested in, they were willing to invest the time and energy back. And I found like, you know, sometimes the answer was no, but sometimes the answer was yes to green-lighting like these little projects that they had never thought of, but also they wouldn't be able to devote resources to outside of me.

And I said, okay, let me try, let me talk to people. And I think that's one thing that. Has paid off throughout my career so far,

David Fano: I like that be interested. Right. And I think it's, and it goes back to what you talked about earlier. It's the work, not feeling like work. Right. So to put those two together, maybe like if it's no longer interesting and it's not like sparking a curiosity, it's like, well then something's off here.

Um, but I think having that and being aware of that and being able to have those conversations, I think. One would invest in people that are interested, um, in the work they do and the things that they're doing. So, [00:29:00] um, I can vouch for you doing that, given that we've worked together. So, all right, so you take this job at, we work, um, and, uh, All right.

So I'm sure there was many moments of change there. So we won't just sort of jump over that one. Um, but I, I know personally, like a lot of the really cool experiences and things you got to do, so you, you know, let's get past the, kind of the EA thing, you know, like how did you start to get that? Not that being an EA is an awesome, and there's a lot of really interesting things that happened there and there's plenty of exposure to like really cool and interesting opportunities.

As an EA, we work were probably one of the best jobs there. Um, But how did you start to inch your way towards more like project management, operational things?

Lara Perlstein: So I have to say it happened like almost immediately to a certain extent. Like I think part of the problem was we worked didn't necessarily know what they needed.

It was just like, oh, I'm a senior person. I'm supposed to have an admin. That's a thing that's expected. That's the [00:30:00] thing that's like budgeted for. But in reality, My manager at the time, like didn't necessarily need help organizing their calendar. They didn't necessarily need help looking their own travel.

They needed help actually figuring out how to grow a team from scratch inside of WeWork. So at the time I was on, I think what we were calling the international development team and we were starting to build, we work locations outside of the U S for the first time. And so. Big part of that was they needed to hire a team, right?

Architects, interior designers, construction managers, engineers, and it probably made sense to start hiring people in some of these markets. Right. It was no longer realistic to job to jump on a plane every two days to go check in on a job site. When now you're going from New York to Shanghai or New York to London.

So part of it was like, how do we go about doing this? I started kind of talking to different departments. That was one of the coolest experiences. I [00:31:00] think I had, you know, I went to legal one day and it was like, Hey, I think we need to hire people in the UK and China, like, have we done that before? And the answer was almost always no.

And so I said, okay, like, I can look into what that looks like, but obviously I'm in a. Help from your team in order to support this, I'm not a lawyer by trade. And, and that happened with finance that had happened with HR and happened with legal. And one of the interesting things about WeWork is they had planned to hire people in these markets, but they plan to hire them for once the buildings were ready to be staffed and opened, no one had really thought about like, we need to build these buildings and we need resources to that.

So I was always the first one, the first one to figure out how we would pay people in China. And there's a lot of complications there. I won't get into. How we hire people and how we onboard them. Right. Are we flying them here? Are we going there? Some of these countries is actually hard to get a visa to the U S so I found myself actually needing to go to some of these countries and onboard them.

So very quickly, my [00:32:00] scope became very different from what I would assume is that of a traditional EA and really started to being almost as like special project manager on the side. Hiring and onboarding and figuring out how an organize again,

David Fano: like sort of seizing opportunities, which I think is, you know, that I think with career building and kind of thinking about our career paths, it's a really delicate balance between being strategic and opportunistic.

And I think some people will get a little too planned and too strategic around like this north star of like, this is what it needs to be and don't let themselves open to opportunities. And I think some people end up just kind of. But I've been made fun of before for calling like the career lazy river.

They just like go where it takes them because opera, you know, it's really cool opportunities, but at a certain point they wake up and they're like, wow, I don't feel like I had any say in where this took me, however good. The outcomes are not. And so just kind of like hearing this, it's been really cool to see you sort of manage that, that interact, that sort of like the tension between strategic and [00:33:00] opportunistic.

Um, so you did the international. Um, probably felt like a lifetime. Um, but you know, how long did you do that for, and then kind of like what came next? Oh

Lara Perlstein: boy, I feel like my it's hard to differentiate my time at WIWORK. Well, let's say I did it for like a year and a half to maybe two years in some respect or another.

And I, I continued to like gain scope along the way. I ended up creating a new position, hiring a team internationally to do that, managing that team. So. Did a lot of different things. I would say the next big shift was when I decided, I don't know if I decided, but I looked into the opportunity of moving, um, departments that we work.

So the whole time I had been there, whether or not, regardless of like the specific job I was doing, I was supporting our development team, which was like design, construction and real estate, which I by default had learned a ton of things. I probably never, would've learned about design construction and.

Some of which might [00:34:00] be useful if I decide to buy a home one day, some of my, some of which I might never use again. And I had gotten really good exposure. And this was an interesting one because I actually don't think I reached out. I think I was approached for this one. I was approached by, um, our head of sales at the time, and we've been chatting.

We had a rapport and relationship and he said, you know, I noticed what you have done for the other side of the org for design construction, real estate. I feel like we're missing. On more of like the sales and marketing side. What are your thoughts on maybe whether it was expanding scope or shifting and kind of focusing a little bit more on sales and marketing.

And I was like, that's interesting, but you know, I don't know anything about sales. I don't know anything about market. You as a really wonderful mentor that almost helped me create the story about like, how else? And he's like, well, you can say, look, you really focused on the supply side of the business, and now you get focused on demand.

And now you've seen both sides of the business. And I was like, I would've never come up with that on my own. But that, that does sound really cool. So [00:35:00] he was the head of sales and he does, did, and does make a good sale. So I, again, like, I, I was very lucky that we were putting. Options of like internal mobility.

And I, I kind of, I think I actually spoke to you about it. I came to you and I said, Hey, this opportunity presented itself at the time, your scope was both over design, construction, real estate and sales and marketing. So you're like, cool. You're still helping my people at the end of the day. So I decided to make a pivot.

And again, it was like, it wasn't this changing everything. It was taking the same type of role and responsibilities that I had, but just shifting who the audience was for who I was. So now I was going to be serving sales reps and marketers, which I've learned are very different personality wise than more of your design and construction people.

But it was a, it was a really cool opportunity and I I'm very glad that it was presented to me and I took advantage of it.

David Fano: And so what was, um, I feel like there, again, having the benefit of being there, [00:36:00] um, I got to see kind of certain projects that you took on and things that you did and. Almost bringing it full circle to where we are today.

What was your biggest project, um, in that role and like one of the ones that you like naturally gravitated towards and sort of started to feel, not like

Lara Perlstein: work. Yeah. So one thing that we were doing, which I thought was really cool as we, and I'm one of the, this is a revelation I had, like right before that.

So to kind of catch us up a tiny bit, I realized I was very passionate about people versus. Let's say business. So I thought the business was interesting, but at the end of the day, any project, I was doing that related to the people I got energized about. So in this kind of new role in sales and marketing, I said, okay, let me focus on the people.

And I didn't necessarily have a plan of like what this position would look like, what the team would look like again, because I didn't necessarily pitch it myself. And I went to our head of sales and I said, okay, what are your top three biggest [00:37:00] frustrations or biggest challenges right now when it comes to your.

Employees when it comes to the sales and marketing employees. Um, and so that was great because instead of like pitching some ideas, I had, I was like, let me go to the source and actually see what, what things I can potentially solve. I can't solve them all, but I can solve a few. And one of the ones that was brought up was career pathing.

Um, and he said, you know, we have all these sales reps and, and some of them are young coming from, you know, straight from undergrad or pretty soon after. And. They get here, they're hustling, you know, they're killing their sales goals, but they don't know how to grow here. So as there's this assumption, that's like, I'm going to get this in the same experience that we work.

It's going to look great on my resume. And then I have to move jobs and then I'll be able to grow and then I'll be able to make more money and then I'll be able to be a manager. So he's like, I don't want that to be the case. Like why don't we grow from within our own resources? So we under. Took a big project, which is not an easy thing to solve about like career [00:38:00] pathing as a whole.

And we ended up diving into little sections from there. First we looked at onboarding like, are we setting people up for success in this org? Right. Because if we're not setting them up for success, then they're never going to grow. And then starting to look at how do we. Show the different paths and the different optionality within the org.

And it might be going sure from sales rep to sales manager, to sales director, to VP of sales, but also it might be going from sales rep to sales ops to, you know, business development. So we also wanted to like kind of break that stereotype of like careers being like a ladder and more of this idea of a lattice.

And different pathways and different options. So that, that's the big thing that I was working on. I would say the last, you know, year and a half or so that I was there.

David Fano: So then you're almost like in this like hybrid HR position,

Lara Perlstein: a hundred percent, I should have like an in a different company. I would have been living in the HR org in, we work it, it actually made my life a lot easier to not [00:39:00] be in the HR world, just cause I didn't have.

Follow as many, quite as many rules and regulations, but I worked very closely with HR and I said, Hey, like, we don't want to build something that you're just going to say, no, what is this? Let's not use it, but let's build something together. You have resources and expertise. I have resources and expertise and how can we make something that kind of solves what the company needs, but also solves what this sales org needs.

David Fano: So I think that speaks a little bit to like being in. And we don't have to get too deep into what you're doing at teal because people can cover that in other ways. And, but I think let's, let's end on this, on this kind of idea of being in a startup, because to your point, right. And another company like that may have been an HR, um, but at a startup, even though it's fairly big at the time when we were, when this was happening, there was still very much a, I think startups do a good job of focusing on outcomes more than me.

Well, I think big [00:40:00] companies start to focus on means for repetition and consistency, uh, which, you know, the funny thing is I think they end up affecting outcomes in an unfortunate way. Um, but what did being in a startup mean for your career and your ability to kind of like navigate that and, and try things and test and learn and gain exposure to experiences.

Lara Perlstein: So, Big self-actualization moments I had towards the end of my time that we work with this idea of like being a specialist versus being a generalist. And I think I was flat out having a conversation with somebody about this, and they're like, you're at a point in your career where you need to become a specialist and you need to pick that specialty and you need to focus on that specialty, or you're not going to be able to do.

And I really struggled with that because like, just by definition, I'm a generalist. I love learning new things. I love trying new [00:41:00] things. I like expanding my scope to different projects. I'm working with different people. So the idea of like picking one thing and saying, this is what I want to do the rest of my career.

It was like terrifying, frankly. And I really, really struggled with it. And I, I tried here and there, but I, and nothing ever felt quite right. I don't know if it was when I was talking to you, Dave, or just other people in general about, you know, what I wanted to do next after we work. And I said like, I'm a really good generalist.

Why am I trying to become something that I'm not? And I don't want to be. And at a company that we work size at the time, they don't need generalists in these senior positions. Right. They need more specialists. But if you go to a smaller company, like a startup, generalists are a lot more valuable, right.

They can't afford to hire. 10 different specialists roles. So they're looking for someone who can cover three until they can grow, grow those people, and then their cover shifts or their coverage expands or whatever it might be. So I wanted to go early, [00:42:00] early startup, which I hadn't done before we work with still a startup when I joined, but it was already 300 people.

And as everyone probably knows, grew very, very quickly. I don't know, 10,000, 13,000. Does that even sound right? Well,

David Fano: actually it probably was, but that was probably on the downward, uh, cause you the after that's what I think let's maybe a better rate at its peak. I think it was like 15,

Lara Perlstein: 16,300 to 16,000. So obviously the general skillset that I had at 300 looked very different and its value to accompany of 16.

David Fano: Um, that's awesome. Um, the generalist specialist, I think is a really good one. It's funny. You're, you're a specialist at being a generalist. Um, but, uh, it's, you know, it's an interesting tension and I think it's, none of them are good or bad. Right. I think it's like, what's right for you. For some people, the idea of being a generalist is like nails on a chalkboard and the other way around.

I think it's a really important thing to kind of come, come to terms with, [00:43:00] and there's supporting evidence for both there's books written on both, you know, and how both of them, and really it's about knowing yourself and like where you're energizing. It's also not static. Maybe there's a time in your life where you want to be a generalist.

Maybe you want to be a specialist, but you want to try being a generalist. But I think having that language and that clarity around that is super.

Lara Perlstein: Yeah, and it was a big unlock for me, cause I was like, Hey, I can be a generalist. I just need to be it in a different context. And the context here was, you know, stage and the size of company.

David Fano: Awesome. Well, thanks so much for sharing your career path with us. Uh, there was a lot of really great insightful moments and uh, I think we're going to have to do this again.

Lara Perlstein: Awesome.

David Fano: And that's it for this episode of Non Linear. If you enjoyed today's conversation, make sure to subscribe, share, and rate us wherever you listen to podcasts.

You can learn more about Teal in our website tealhq.com, or follow us on social media @teal_hq. Thanks again, and please join us again to keep hearing about how we make decisions that shape our careers.