Marco Labs Episode 7: Culture in early-stage startups with Leslie Crowe

Hybrid and remote work have redefined in-person gathering.

In episode 7 of Marco Labs, we spoke with Leslie Crowe — Talent Partner at Bain Capital Ventures. With a portfolio of over 200 companies, Leslie has an excellent perspective on overarching trends in terms of culture in startups.

The rise of hubs

As a “back-to-office” strategy, many companies within Bain Capital Ventures’ portfolio have adopted the idea of geographical hubs — specific locations within a commutable distance that act as a gathering space. Teams can use these hubs for in-person collaboration and connection, rather than exclusively for working from full-time.


Key Takeaways

As Talent Partner at Bain Capital Ventures, the future of work and how to build culture in a meaningful way for startups is top-of-mind for Leslie. Below are a few takeaways to consider as companies think about culture in the hybrid and distributed teams. 


1. In-person experiences are growing in importance.

With more teams moving to a remote or hybrid model, in-person experiences can provide even more value than before as a dedicated time to connect.

“Companies will have, in a way that they didn’t before, really aggressive yet thoughtful planning around in-person experiences.”


2. The companies that are winning are leaning into flexibility.

Flexible work has so many opportunities that come with it, and the companies best poised to succeed are those that lean into these trends. That being said, it’s important to understand that a distributed company isn’t for everyone.

“Don’t build a company you’re not going to like. It’s really up to the founder.”


3. Culture can be used as a catch-all term.

Culture can sound like a nebulous term, and can be used to exclude others without understanding why. It’s important to clearly understand what you mean by culture, so you can make sure you’re using the term with the right intent.

“If you’re using blanket statements like ‘you’re not a culture fit,’ that can be the death of culture if you aren’t spending time to unwind them.”


Leslie's Pro Hybrid Tip

Even in a remote and hybrid environment, personal connections make the experience and result of working much stronger. Companies that set a high bar for managers and don’t underestimate the importance of this role here have even more potential to succeed. When people feel personally connected to whoever is managing them, they’re more likely to feel connected to their team and do good work.

Read the Full Case Study

Find Leslie's full case study (and half a dozen more) in our recently published Future of Workplace Culture Ebook.

Grab your copy here

Rather read than listen?

We've included a transcript of this episode below.


Hey everyone. I'm Suman, I'm the CEO and co-founder of Marco. Marco is an experience platform that connects amazing creators and hosts with companies to help bring their people together. And as part of that, we have launched Marco Labs, which is a podcast where we interview, both the creators, as well as the people leaders. Super excited to be chatting with Leslie this Friday, late afternoon evening.


The perfect time for a podcast.


It is the perfect time, you were making fun of me, cause I was, you know, we work with all these people watching me as I film this.


I feel like you have an audience as you're doing this. It's great. 


There's people, yeah, I wish. Yeah. I actually was super, I am very excited to chat with you because typically I like review people's backgrounds and you have such a broad background that ranges from, not only, I mean, in terms of function. So you've worked in strategy, you've worked in sales, you've worked in kind of leadership, on the people's side and you work at like tons of different types of companies that have, globally scaled and grown. And now you're at Bain Capital Ventures and you're working with like a ton of different portfolio companies.

So you probably have cool stuff to share about your experiences. So I’m obviously familiar with your background, but would love if you could just share with folks kind of your background, how you got to kind of lead the people team, be the VP of people.


Yeah, absolutely. So I think you set the bar a little high, so let's try to reevaluate it, put a little, a little bit lower, but we'll do our best.

Hopefully, there's something interesting to say, but it's lovely to spend some time with you, especially on a Friday afternoon, and for you, it's basically the evening happy hour podcast. So, yeah, you're right it's kind of the best way to think about it. As a salesperson turned people person, just by happenstance.

I was at a hyper-growth company. When, Dropbox, when we were growing fast, we had a lot of work to do. I like getting my hands on different things and learning new things. And so I ended up dabbling in people work. And then here I am many years later. So, I started my career at Google and ended up going to business school, joined Dropbox as a way to see a company that was a fraction of the size of Google when I joined. And see what it's like to be at a start-up. And I just got the bug. I love, I love the chaos. I love the ambiguity. I love trying to figure out how you put order to the madness. And I think most importantly, thinking through how you put together a really strong people function that scales and not saying that every single time I've done it, it's in perfect.

There's always like every time you do this, you make different mistakes. But it's a ton of learning and I think it's probably the most critical thing you do when you're growing. Figure out the people you choose and the infrastructure you put in place to actually support them and help them grow. So I ended up at Bain Capital Ventures, about a year ago after being the chief people officer at TripActions.

And I spend my time with our portfolio of talking about all the things that we've talked about and that we'll probably be talking about today.

Suman: Yeah, totally. So as a kind of first-time founder, I could certainly not agree more with that kind of, convincing people to join you on what is kind of, especially at the very earliest stages, a crazy journey. It’s certainly one of the most challenging things and also of the most important things that at least I spend my time on, but I'd love to hear, obviously this is a crazy time that we're hopefully kind of emerging from, but what do you see as an you private pretty advantaged point?

Cause, you know, I think Bain Capital Ventures has, you know, 200 plus portfolio companies, like what are the biggest challenges you think that you see as a kind of a people leader right now? 


Yeah. I mean, I think from like an all type, it's mostly to like trends and what's happening today. I think, you know, every single year, it feels like every few years we kind of have this dialogue in talent where it's like, it's the hardest it's ever been. The war for talent is so great. I think the challenge in the last year or two for founders, and for any company that's growing is not only is the war for talent gotten greater, but the game has changed. It's no longer the same game that we all were playing a few years ago, we're telling was concentrated in certain areas and, you know, hiring, uh, everything from an engineer to an operations manager in Topeka, Kansas wouldn't have been the thing, something that people would have thought about doing, but today it's very.

I think the game is totally changed. So you think about that, it makes recruiting even harder, more complex than it was a few years ago. Just a huge challenge as a people leader. I think, I mean, one of the things that I'm sure you think about all the time is because of that, you're building very different companies.

You know, if you've leaned into those trends and you really believe that you want to find the best talent, that that talent is not necessarily all in San Francisco, New York… how do you do that? You have a very different type of culture and company you have to build. There's just a whole slew of, I don't call them problems, but like real challenges that come up when you can do what I feel like was trendy.

When I started in the tech world, which is like, your office is the center of your world. And like, everything is about your office. And like there's so much money poured into your office. And not that offices will go away. I think they'll be here in some way, shape or form, but it's not the same as it was maybe 10 or 15 years ago.


And I asked that question first to then. Kind of your, your past, cause I'd love to then talk about that, uh, in terms of your kind of career. So by the way, I've been to the Dropbox office, which now obviously it has changed, but it is amazing. I guess even before Dropbox though. Right. So just even rewind so we get the full picture. So you're at Google, and then you were working in a sales role. Right? And then you went to, so just like, I'd love to hear, even before we get to your, kind of like Dropbox and then the rest of TripActions, kind of like what drew you to, well, first of all, why did you get the MBA?

And then how can you, I know that you wanted to work at a smaller startup, but kind of like what dreams are kind of like the strategy role and what you do at Dropbox?


Yeah. So at Google I started off in a very traditional inside sales role. So like mid-market cold call to close. I didn't even know what sales really was, I was pre-med in college. So for any of you out there that resonate with that? Where you ended up being something totally different. I'm definitely in that camp. So I ended up taking this job. My last job at Google was a huge flyer.

Like it was a manager who happened to take a huge bet on me. I was the least experienced person on my team. I was the only person on the team and got an MBA. Um, and they hired me because I had sales experience, which they didn't have. And we were designed to be this like, Incubator at Google for new ad products for like the long tail.

So I got this kind of like startup within Google experience, which was really interesting, especially because we used to joke, we were like the best funded startup in Silicon Valley. Cause you're at Google. And so which is probably, and you know, I just got a chance to work with everybody on my team had an MBA.

I always thought I'd go to grad school. I think I spent my whole college career thinking about sciences, which I never used again afterwards. Unfortunately, I thought it would be an experience to be able to learn and grow. And, my manager at the time was a really huge advocate. He had an incredible experience.

So I went really because I wanted to do it. And be able to sit in an executive room boardroom at one point and actually know what a balance sheet was, you know, like some of those basics around business that I just didn't ever get exposure to because I spent all of my time in college, focused on the sciences.

And so I went just to be, hopefully become a more well-rounded leader. Not that I remember if you asked me to put together a balance sheet, would I be able to do it, the answers? But at least I, you know, let's cover that part. We're gonna have to cut that part out, real embarrassing. But yeah, I just kind of wanted to be a little bit more well-rounded and have some working knowledge of the rest of the components of running a business.

And it was all that. I think, and you asked about the Dropbox connection purely cause I got this like startup bug at Google. I figured Google would always be there. I can go back, like, why not give it a shot? And I interned there over the summer. There's 75 people back in the day. It was awesome.

And I just like, I loved it. It was like super smart people, really passionate about the product. And you got to really do stuff like that was the biggest difference. And like, I felt like I was doing things at Google. That company was so big. I was, you know, my impact was basically a drop in the bucket.

You've been at a startup like Dropbox at the time. Like you really could have impact in those school. So I started out as like a jack of all trades for our head of sales. It was purely like really an ambiguous role didn't have I like, we've made it the title on the spot. It was just like, come and help me build.


And then, but then you transitioned to, you were working in like a strategy role and then you basically got into people somehow. So then how did that kind of…


Yeah. So I ended up doing a lot of work, in my role in the sales team, working for the head of sales around, sales hiring. So we had to go hire about a hundred salespeople in a year, opened up a few new offices.

And, my boss at the time had actually managed, run recruiting at Salesforce in a previous life. He was a sales leader. So he ended up saying, Hey, if you ever want to think about leading a team or leading a function. Yeah. Well, I had already led teams, but like small teams, like really small ones.

This was not like, this is like multiple hundreds of people and he's like, you're gonna have to figure out hiring. So like take on the hiring project. So I ended up coordinating how we really thought about the hiring profiles, where we hired what we were looking for, how we assessed, like, and ended up just really getting into the recruiting stuff.

So I dabbled there, ended up working on our first leadership development program because we didn't have anything in place. Despite the fact that we were growing so fast. So just happened to get my hands. I read the rotation program for a while, which is our new grad program. Our CFO, it was the one who started it. He was like, okay, would you be open to running it for a bit? So I did. So I just kind of got all these, but just, it was kind of like an L and D plus program management. So I kind of got like bits and pieces of all the different or not all, but some of the different functions in people and, in the end, just like really found the work to be impactful. You know, it could be a salesperson. I can go, you know, close to $10 million of revenue in business, but I could also just go hire 10 people, making close to a hundred million dollars revenue business. That's the impact of that is so great. So yeah, that's kind of, I just, I think I just got sucked in and then they kept being decision after decision of jobs that kind of got me further and further into that world.


Yeah. Big growth story IPO. Any part of that, and then TripActions, where you at TripActions during, like I forget what, what time you left TripActions and headed to bank implementers? Were you there during kind of the, some of the pain that can that? 


Yup. I was there, in March of 2020. September of 2020, so that's six months after the pandemic started.


Okay. So that must have been like a super interesting experience. Just like responded very well is my understanding.


Yeah. I mean we moved quickly, right? So we ended up having to, we did a layoff, which was a hundred percent of the right thing to do. We'd hired about almost a thousand people in a year.

And you know, you're when your revenue drops to zero. And it wasn't a day, but it felt like a day and you have to make quick decisions. So huge kudos to our board and to our CEO for really making a quick decision. But it was a time when no one was doing it was like we were one of the first companies to do a layoff.

So it was a little abrupt and it wasn't perfect. There are a million things looking back on it that I’d do differently. Yeah, it was a really, it was a hard time, but you know, the truth is it's an incredible product. And I think that's why, you know, whenever I talk to people that making decisions on joining a company yeah.

It's like, it is all about the people work for amazing people, work for people that you'll learn from and you'll grow. But like the product really matters, right? Like, is it something that you connect with and is it something that is really meaningful and like, and I think TripActions is both of those things.

I love to travel. I think business travel is broken. I think that, you know, the company is obviously doing a great job, weathering, weathering the storm. And I think that like, You come out of this, like the company is going to kill it because it's like, there are no other [products in this space that are nearly as good.

It's just so it's incredible. And I think so what will kind of originally attracted me to TripActions? I think in the end, we'll, you know, yeah, it's a gruff couple of years, but the team's executing. They're doing really cool things to like, make, move the product forward in the meantime. And then I think on the other side it would be great.

Just a really rough time, you know, you can't predict it. Like we just came out of an e-staff meeting, like the week before that was like, okay, let's go hire, you know, a thousand plus people this year, revenue related, just nuts. And then, you know, global pandemic, but whose who could have predicted this.


The, the whipsaw is, must be, must be well, especially if we believe our guys and then go do that. Right. 


You're like, I mean, I had to lay off half my team, many of which were from my network and people that I had managed before in my career, like it was a heartbreaking, like the hardest career experience I've had to date by far.


I remember, hearing Stewart Butterfield talk about Slack and how the scariest part was when they were like running out of money. And he was like, I convinced people to like, come live in a different city and move their family and, and which I'm sure you did. Cause at this point, people were coming to probably San Francisco, right?


Yeah. And like you put your reputation on the line, you put people's lives on the line. Like you think it takes that if you're a good leader, I think it takes so much heart to build this. You know, and I, I'm not that I'm a great leader, but I think it's like, that's for me, has been like, I think it's probably a strength and a weakness, you know? Cause it's really hard to separate that sometimes. 


The reason I asked, like what are the challenges now? And then I went to, to rewind to the beginning. It was like, I'm curious, as you were telling your story that I was just curious to hear whether those challenges are. And it sounds like they're kind of different, right? Which is that the challenge is you mentioned at the beginning were kind of like, Hey, the game has changed and also as part of that, perhaps this whole notion of the office, which, you know, a lot of the places that you worked, which is kind of Google, a multiplex of works. And then Dropbox, the cafeteria Dropbox is probably my favorite restaurant in San Francisco. 


Oh goodness. I mean, we can't, that was the problem. And you never wanted to leave the office because you're like every meal I buy outside, the opposite is going to be worse than the meal I'm eating right now.


Totally. Totally, exactly. And so, so then how you think about where we are now, um, and how are your, so now you're at Dropbox, right? So we are starting to think PCB fast forward and you're, you know, overseeing my understanding is you work a lot with kind of the portfolio companies. There's some internal side, but even, so you probably see a lot of lead people.

And how are they, what are they doing? Like what is their plan, you know, for some of the challenges, which is like, Hey, so we obviously, as Marco, you know, we're some places to be emphasized. We're going to have office space, but also people are distributed. How we're, we're curious to hear how your kind of portfolio companies you thinking about.


Yeah. So on the office topic, I think the most common approach, across the portfolio seems to be this concept of creating hubs, where they have a sizable amount of talent within commuting distance and using those hubs for collaborate patient space, like. Not necessarily like rows and rows of desks, but Hey, you know, maybe you want to come in a couple of times a week and this is a space that you, you use and you kind of use it as a gathering point.

So there have been spilled model tends to be the most common as companies still have distributed talent. So then, then it comes into like, how do you connect those people? And that's actually where I think it actually ties the TripActions to. I think that's where a lot of, I think people will be back traveling people already starting to travel and people are excited for the after.

I just think travel will look probably different. Like, I don't think you'll see as a lot of like, as much like, Hey, I'm getting on a plane for an hour meeting that we've learned today that you can do on zoom. I think you'll have a lot more of the. Hey, our team is meeting quarterly because we're not all in the same place anymore.

Quarterly we come together, we do a big offsite and we like, you know, work on our strategy and we stay connected and we build our relationships. And then we go back to our homes and whether we're in Topeka, Kansas, or we're in LA or San Francisco or New York or whatever it is like we have that level of connectivity.

So I think that's, that seems to be the main trend from an office perspective is like trying to figure out how you plan for. That hub and spoke model. And then how you, how you think about, and you, I'm sure you're thinking about this all the time too, but it's like, how do you think about what the cadence is and what the like set of processes you put in place are to ensure that people can still stay connected?

Despite the fact they're not, you know, all in the same room or building anything. 


Yeah. I mean, we were just in Napa for our quarterly geometry, which you can do, and we were trying to link up, but then you were in Hawaii, which is the benefit of remote work, because by the way, I was in Hawaii with a colleague. Right. And so, yeah, I feel like the concept of the vacation has changed because now instead of going somewhere for a week, Like if I go see my sister who just had a kid, like I would stay there for two weeks. I'm not going to, I'm not going to leave. 


Yeah. I think the danger is though. And I don't know about, I found myself trying to like, do both really well. And I think you just kind of have to realize it's like, During their working remotely or like, if you're good to go on vacation, like take, actually take the time off. Like I was at the end, I finally was like, I had to go to a wedding. So like I'm taking the Friday off, maybe even Thursday. I don't remember, but like I, cause I tried to be like sort of on vacation in the afternoons, like late afternoons once it was past specific to working time, but the mornings and I was like, I'm not doing this very well. So I feel like get to like lead into the remote work thing, but then also like not try to do it all, like enjoy, actually take some time and.


I'm the wrong person. Yeah. Yeah, exactly. Right. I'm the wrong data point. But so I guess on that note, so we're talking about challenges. What about. What about the opportunities? Right. So we're emerging, uh, like I said, hopefully what you're describing is flexibility, right? Which is, which is embedded because regardless of how nice the Dropbox offices were, as you, as you kind of mentioned, right.

You know, it was an enticing kind of thing to get people to spend more time co-located in one place. What are you seeing? Do you believe that there is kind of some options? Are you optimistic about kind of the future of work and how people are going to kind of get together and that. 


Yeah. I mean, I think we've, we've learned a lot from being at home. I think we've learned that we can do our job. Many of us can do our jobs at home. Obviously not every job in the us can be done at home. And there's a lot of people who can't, but we're sitting here and we're on opposite coast of the country and we're having a conversation and getting stepped on or like that can happen.

Right. So we've learned a lot. Yeah. Being productive at home. But I think we also learned a lot about, you know, the other things in life that are important that are very early, even just like a reprioritization. Right. You know, I used to commute down to Palo Alto every single day. And I'm from San Francisco, which doesn't sound very far, but if you've ever been on one-on-one traffic, you would know that it's very far.

And I, you know, I'm sure everyone has a version of the story, but you did things that you didn't even realize as you did. The grownup, it seemed fine, but then it's like, okay, that was two plus hours a day. Like, what did I need to do that everyday of the week? Does that make me more productive, you know, questioning those types of things.

And I think, I think what will, what I'm optimistic about is I think that there's an opportunity for companies to really come out of this. With a much more loyal employee base. Should you really lean into the good things that have come out of? COVID like, think about it. I was talking to someone earlier today who runs talent for a tech startup and she was, or people for Techstar, but she was like, you know, we had, he's a top performer asked to move to Montana and I was like, you know what? I would bet you that top, cause you will be what the person is. I would bet you that top performer is now way more loyal to your company. And they ever would have been before because they were able to do something for their life that was good for them. And they still feel like they can be successful.

And that you have these mechanisms for them to stay connected. Like that's a level of loyalty. I feel like no offense, like no one really had in tech. Like the problem with tech is it's just like every 18 months someone's changing jobs. And like recruiting is hard because you'd actually don't know whether or not.

Good or not because people just like take new jobs every 18 months when there's like a new shiny object. And so actually think that like the benefit of this, if you. Handle it well can be a new type of employee loyalty that I feel like only existed in like the past generations and has not existed for the current working ones.


That is really interesting. So because, okay, so of course you've heard of like the great attrition and you have so many people kind of leaving. Uh, and I think, I don't know if you read the McKinsey, kind of study and that there's a few interesting things there. One is, um, at least it said that tech company has experienced this perhaps even more acutely, which is that to your point, people in tech tend to move jobs at a fairly high rate.

So perhaps some people are more loyal, but do you see, do you see the attrition? Do you see people leaving tech jobs? Like well-paying, high growth tech companies. Is that affecting your portfolio companies or is it more so they just can't, it's difficult to win the talent?


Yeah, I don't, I don't see. I'm not having as many, like we're having crazy amounts of attrition conversations. Not that it doesn't exist. I just don't think it's maybe as widespread as it may feel. Cause I also think that think about those articles. They're really. Across all tech companies across all industries, it's not just tech.

So then that might be part of the difference. I think talent is moving faster. So like attrition is, it tends doesn't tend to be like, everyone's just leaving because they decided they wanted to. So the other beach somewhere and not work anymore. It's just, there's so much more competition because there's so many more great jobs.

But I think it's almost like we're kind of already used to that in this world, if that makes sense, like that's kind of existed for a while. So I don't think it's as dramatic as my opinion. It doesn't feel as dramatic in tech as it may feel for other industries. 


Well, one thing you said resonated, it seems kind of consistent with what the article talked about, how there is this, basically all employers think that the reason employees leave their jobs is perhaps because of pay. I mean, obviously very important, but a lot of it is actually human connection 


And feeling recognized and rewarded 


Totally. Which I thought was really interesting. How are you, you have ACV or companies that you see that are doing this well?

Like how are they actively getting ahead of. 'cause one of the things is we do get together because it is hard to, you know, we, we now have 15 people and growing, and it is, I think what struck me was they're talking about being transactional at work versus actually having relationships. And I've noticed that if you don't know someone and it's purely transactional, like, Hey, can you do this for me? It isn't, you don't have to work. Isn't as good as, as someone who actually has empathy and B how do you solve. 


Yeah, totally. I mean, I think you're absolutely right. Like those personal connections make the work product and work relationships so much more effective and stronger. I think it's been the hardest thing in the last couple of years.

It's like, you're, it's not even like. You're forced to be. Everyone's forced to be remote. And there's some ways to build those connections that are in-person. It's been really hard. I mean, it's not until the last several months that I feel like people actually started potentially dipping into an office.

Like you're in a WeWork now. I'm pretty sure like a year ago that wasn't really happening. So it's, it's a lot has changed, which is good and we're trending in the right direction. But I think it's hard. I just don't know if there's a replacement for. Those in-person connections. Um, but I think to answer your question on like companies that are doing it well, or keeping people connected, honestly, I think the companies that are doing the best are the ones that spend a lot of time and energy enabling their managers.

Like they put their managers get a ton of support. They have a very high hiring bar and like high scrutiny in their interview process for managers. Like they don't just like anyone let anyone walk in and manage people because the reality is. You're connected to your manager, that person's going to be fostering connections within your team.

You're going to feel more connected to the company. Especially for large, I mean, you're obviously in your environment, you're doing a lot of that work and your co-founder is too. And like, but you scale that up. It's really going to come down to whoever the line managers are. It's not really about the executives anymore.


Yeah. That makes, that makes a lot of sense. So I guess one kind of different question is. You have 200 companies and just, we talk about the word culture. What does culture, what do you, how do you define culture and does it, does that definition, like, is there a consistent definition, do you think companies should think about the word culture in o?


It's not gonna be an elegant definition, but I think it's kind of the intersection between your values and how those translate to behaviors. It's like how you. How, like what, what you decide, how you treat each other, um, and how people interact. Is like, I think you can put all that kind of together and that's what you ended up.

That's what defines culture. But I think the hardest thing about culture is actually to that point, it's like defining what it is. Like you hear a lot of buzz word, especially in the valley. It's like, if your culture is like hardworking and driven by our hyper-growth. Whatever. It's just like all this stuff, all the buzzwords and stuff.

So I think it's like, it comes down to like, how do people actually treat each other? And like, what do you actually value as a business? And that, that meant. As your, as your culture. And I think that it's such a personal thing and it's one of the, I'm sure you've been interviewed processes to your words.

I don't think there are a culture fit and like, that's actually, I think be like the beginning of the death of the culture, if you start just using blanket statements like that and not actually, I mean, the times like unwind, what does that mean? Like you said, someone doesn't fit in the culture, but is it because, you know, You know, aren't collaborative and we believe in collaboration here, like, okay, cool.

Like that, that makes sense. Right. But I think the danger of culture is like, it becomes like an ingroup and outgroup. Right. And versus something that's inclusive. And a lot of, obviously a lot of talk about this, we think about building inclusive cultures. It's part of the emphasis on D and I. I think that like, that's, it's a great word, it's a nebulous word, pitstop word, because the reality is it also can be these like weird weapon that it's like, you're kind of like, oh, you're not in it. So you're out. But like, what is it? Right. 


Like do you, when you talk, is it, do you encourage your founders or your portfolio companies or whoever you enter, to invest and build culture, understanding that it is different for each one of them. Are those conversations that you, that you have? 


I mean, I think, I think the good news is these days of your founding a company. You've probably gotten enough input from whether it's your investors or your peers around how important people in culture are.

I think it's just about how you do that. Right? So a lot of my conversations, when a founder will ask about how do I build culture, it starts with like me trying to understand, like, what is your culture? And like, what are you trying to build? Like, what is it today? How do people operate? What do you value?

What type of company you're trying to build? And then what's missing or what are you trying to enhance as you think about evolving the company and it's, it's never a one size fits all thing, you know, like people will ask, like how do you build a great culture? And, you know, maybe there's some like high level platitudes that you can, like, you can share that role, like kind of get some of the basics off, but it's a really custom type of thought process.

It's not a one size fits all type solution. 


Cool. It's yeah, we will. We, we actively work. We've done kind of like recently mission and vision and values sessions and all that sort of stuff. It's very fun, but it is also very difficult to define how we're trying to build our culture. It's quite difficult. I guess like a broad question, to just to get to where that towards the end is, like, what do you think over the next couple of years? Do you, you know, how do you think they'll look like, and obviously, you know, no one has an answer, but optimistically, like how do you think the future of work will evolve. And I know you mentioned kind of hubs, if you could paint a picture of like, oh, now this is how the nest next TripActions is being built. Right? Like it's a hub it's, you know, how, how does, how does, how do the most successful companies use? 


Yeah, I think, I think the distributed workforce piece is, is a huge piece.

I think it's company companies will have in a way that they didn't before really. Aggressive, but yet thoughtful, um, planning around in-person experiences. Like I think because you have a distributed workforce. Um, I mean, I remember when we were MuleSoft, we had an annual conference that we held up until we got acquired the, I think the last time it was like 1500 people or something like that.

And people thought you were crazy for doing it, but it was a really is a hallmark of our culture was so important. I think stuff like that. It's surprising anymore. And it may not all be big stuff, but it may be like smaller, regular gatherings. But I think it's like putting my mindset in TripActions. It's like group travel versus individual travel in terms of being a much more important component of how people interact.

Yeah. I think the companies that will win are going to be the ones that like not necessarily go soft and let their employees do anything. But the ones that really start to lean into flexibility and allowing people like the autonomy to do their jobs well within whatever confines are comfortable. And I'm not sitting here saying that everybody needs to have a distributed company.

I tell founders all the time, if you believe that you need to be successful, you need to have every single person in an office every day. Do it, like do not build a company that you're not going to like, cause you're not going to, you're just going to end up giving up and it's not going to be what you envisioned, like, do what you need to do.

So it really is up to the founder. But I think from a trend perspective, especially as you get, get into larger companies, I think talent just going to keep moving. I don't think the hubs are going to go away. I don't think I asked, said for New York is going to be like, oh, there's no talent here left anymore.


I just don't think it's going to be only those because my twin brother lives in SF and I now live in New York. And so we basically switched places because he was in New York with his wife. If it's, I'm still have a fond place in my heart for SF. 

But so. The last question is what is the most, interesting quickfire. Just what is the most interesting cultural ritual you've seen a company do? Or like weirdest, cultural ritual?


Weirdest. Oh man, that's a good one. I'm sure I've seen something weird. I actually, I'm trying to think back to. I'm sure we had some weird stuff at MuleSoft.

We were really into art. Like the culture, there was like very, very intense. Someone's, drop-off actually in a very different way. I think Dropbox had more overt culture, you know, like it was like very people knew what it was then, because it was a consumer company originally. I'm trying to think. We did some funny stuff, like all hands on Friday at Dropbox.

Like there were some interesting rituals there, there used to be at the happy hour on Friday after all hands and like drew would go in and we had a music room and he would play like, that was a pretty cool. And if it qualifies as weird, but like cool or different rituals that we had. But I'm sure there's something weirder, I'll just have to think about that one. 


That’s a good one. Yeah. Fair enough. We'll get you next time. And then what is your favorite thing about being a people leader?


I think there, the fact that there's nothing that doesn't really touch people, right? Like you're in a business, everything touches your people. And so the fact it keeps just love. It keeps me like you can't get bored. There's always something that's going on. Always something that people are involved in and the company is people.

So in the end you get a real chance to not only have impact, but again, can't ever get bored, which is great. Keeps me on my toes. 


Excellent. And with that, I will let you enjoy the rest of your Friday afternoon. Uh, and this was an amazing conversation. I appreciate the time, Leslie.


So great to spend time with you. Have a great night.


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