In this episode, Vibe Check’s host Brett Martin sits down with Maia Josebachvili, a member of the Leadership Team at Stripe, who imparts wisdom to managers of distributed teams. Maia begins by taking listeners through the evolution of her career journey that’s full of big jumps and even bigger opportunities, an experience that makes Maia a well-rounded and trusted leader.
When the pandemic drastically changed daily operations at Stripe, Maia kicked it into high gear to successfully lead her newly remote team. She is a shining example of flexibility and strong leadership for other remote managers. To be a better leader, Maia urges managers to consider tradeoffs and opportunities, understand that there’s no one-size-fits-all solution, fill their team’s “trust cup”, and to embrace the magical moments of remote work. Maia also offers wisdom into handling disagreements, especially when communicating asynchronously. Maia concludes the episode by painting a picture of what the future of work may hold.
Having served in multiple leadership positions across departments, Maia Josebachvili is a member of the Leadership Team at Stripe. Maia’s leadership roles included Head of Strategic Operations, Head of Corporate Development and Investments, Head of People, and Vice President of Startegy, Marketing, and People.
Brett Martin: Howdy, y'all and welcome to Vibecheck. It's a human-centered discussion about the struggles and opportunities of remote work life with the folks that are defining the future of work. I'm Brett Martin. I'm the co-founder of Kumospace, and I'm going to be your host. Today I'll be speaking with old friend and classmate of mine, Maia Josebachvili. She's head of Corp. Dev and investments at Stripe. You know, Maia has a, shall we say, a very unorthodox career journey, but rather than me butchering it, why don't I welcome Maia to the floor and, Maia, why don't you just give us a start about your background and how you got here today?
Maia Josebachvili: Hey, Brett, thank you so much for having me. I am super excited to have this conversation with you. Yeah, I think unorthodox is probably a good way to describe it. I have definitely had a lot of jumps, both little and figurative in my career. I'd say the through line has really been building. Whether it's building companies, building functions, or building teams. I'm just drawn to the big opportunity, big problem space. How do we come together as humans to create something where the whole is greater than the sum of its parts? So, you know, after college, I did a quick…ended up founding an e-commerce local adventures company pre Stripe interestingly, so had to go through the pain and struggle of degrading a payments provider during that time, ran that business for a few years, ended up selling it to Living Social, which was part of, you know, that daily deals rise and unfortunately, pseudo fall and Living Social was 300 hundred people when they acquired my company. It grew to 5000 over the course of two years. And that's when I really saw firsthand the challenges, but also opportunities of hyper growth and growing companies.
So when I met the Greenhouse founders, for folks that don't know Greenhouse it's a HR technology and recruiting software. I was super sold on the concept of treating, recruiting and hiring and people generally as a very first class problem at companies, which today feels very obvious and intuitive. At the time it really wasn't thought that way. And so I joined Greenhouse pre-revenue through about 400 employees and wore a few different hats there. I was VP of new initiatives, then VP of People, and ultimately CMO, which then logically or not logically brought me over to Stripe almost 4 years ago. First, as our Head of People, we were about a 1000 people at the time. Now we're 7000, so you can kind of get a sense for the scale and growth we've seen there. And then for the last one and a half years, I've been leading our Corp Dev, which is our M&A and investing team.
Brett Martin: So clearly you've covered a number of hats between trader and head of people to head of M&A. I mean, that in particular, I think, is kind of a crazy transition that I've certainly never heard of. Can you walk us through the sort of thinking there?
Maia Josebachvili: Yeah, I get those question a lot, and maybe sometimes the jump isn't nearly as intuitive, but if you think about the people function as helping to build the organization and translate that to M&A, it's actually quite similar. You're helping to build what the product and what the business and the company will be for years to come. And rather than doing it through hiring individuals who are building, you're doing it through acquiring full products and full teams who can integrate with the company and create the broader suite for our users. For what I think, it's actually a very, very natural transition and then it also just helps that, you know, because I wore so many different hats and been a founder and sat on all sides of the table it gives you a pretty holistic perspective for how to identify, evaluate, and very importantly, integrate these companies into the organization.
Brett Martin: You know, as you mentioned, you sort of helped take stripe from a 1000 to 7000 people, and your tenure obviously started pre-COVID. And then everything changed in March 2020, how has that changed to integrating folks into the company and what are sort of the biggest lessons you've learned of managing that transition to remote and now, hopefully optimizing it?
Maia Josebachvili: Yeah. I'll speak from the perspective of being a manager and leading my team through it. Impart because I think that's actually where a lot of the big decisions and a lot of the big impact is. It really is on the managers and the team leaders and the folks on the team to help navigate and get to the best kind of working and operating cadence for their team. I think there's no right answer about what is the right way? What is the best way to do remote, hybrid, distributed? My perspective is there's no one size fits all. And whatever you do choose to do for your team and for your organization will come with tradeoffs. And it's about being very clear-eyed about what benefits and tradeoffs make sense for your team and the work that you all have to get done within the broader context of your organization.
Brett Martin: Yep. This one size fits all, makes sense. There are several more dimensions. What are some examples, the tradeoffs you're seeing out there and then how managers can and should evaluate them?
Maia Josebachvili: Yeah. You know, I've been going into the office about once a week, and I went in yesterday and I hadn't been in in a little while, and it was just wonderful, wonderful day. The richness of the conversations I was able to have with folks, you know, kind of standing up, going to the whiteboard. It was just really fantastic. I walked away feeling a lot of appreciation for in-office time, but having to go into the office every day also has tradeoffs and just, you know, again, very concretely thinking about the team I work with and lead. I think it just depends on the person. For me, we actually couldn't, because not all jobs are conducive to working remotely, like my husband is an anesthesiologist, and they have not cracked the code on remote anesthesia yet. If I think about myself, pre-kids and pre-marriage, I mean, this would have been my dream situation. And I watched some of the folks on my team who have slightly more flexibility in their life because for whatever reason, you know, they don't have young kids who are tied to a certain school. They don't have a partner who's tied, you know, to an office, you know, like, again, we don't have that flexibility, but I watch folks on my team do the kind of month-to-month hopping across cities, working out of Tahoe for a month or deciding to try living in Santa Fe, New Mexico, for a little bit, just to see what it's like there and then coming back, that's very tied to a kind of life stage. So that's kind of one axis. And then the other axis I would think about is just the nature of the team. If you happen to have a small working team and they're all in the same city, some folks might not want to move in that moment in time because of the sort of fun, collaborative nature they have with their team. I don't know how many people are so driven by that, but I do think that is an interesting perspective as well. And so, on a personal level, it's great to collaborate with them in the office when we're all together. But for their own personal lives, this flexibility has just been fantastic. That's the other benefit of more remote work is that you can go and live a life that is more flexible and more attuned to what you wanted to do.
Brett Martin: Yeah, that's interesting, right? You know, that this team member of yours is living in these places. Is that something that you had to think about before? And if not, you know, how is a manager, do you think about that, should you just sort of try to turn a blind eye to it? Like, how do you think about your part in sort of facilitating or not your employees' personal lives?
Maia Josebachvili: It's such an interesting point because not to say that this was true for everybody, but when you were sort of bound to your location and office, when an employee was debating a move that was often not a collaborative conversation with their manager, right? That was a very personal conversation they were having in their private life because the outcome of that could lead to I have to quit, or you might not give me the opportunity to keep working this job, whatever it might be, right? Whereas if I just take those folks on my team that I was just describing, it's just been part of our conversation for a while, you know, the first time was like, are you comfortable with this? And then after a while, it was just kind of like they have a new background every month, and I was so curious to learn more about where they were. And so I do think it has probably sort of opened up the opportunity to have more of these conversations than you would have otherwise. I think the other sort of philosophical cultural shift I've been seeing is we are all getting more glimpses into each other's life, and that's just become more normal. You know, there's, like the meme of the kids running behind the screen and the dog in the background, even just kind of, I've watched people move around their house, right? And I remember the first time I saw my manager's kitchen, I was like, oh, cool. That's your kitchen. What a glimpse into your personal life. And so I do think we've all just had to open up our worlds a little bit more to each other in a really nice way.
Brett Martin: And, you know, this is kind of a hot topic, right? Everyone's talking about the breakdown of work-life boundaries and what I see most often is people saying, okay, you have to recreate boundaries between work and life. We need to set timers. And after this certain time, we close the laptop and we have rituals to transition. You know, now that we're working from home, there's less boundaries. You're sort of looking at it from a slightly different angle that maybe the integration of work in life, it's not all bad. How do you feel about integration of work-life versus creating boundaries between the two?
Maia Josebachvili: It's such an interesting question, and I'll go back to the first point we were talking about, which is, I don't think there's one size fits all. And so this is not to say this is the right way to do it, but I will say I have at a personal level, been leaning more to this sort of blurrier lines. Recently, I was having my first in person meeting with someone that I've worked with from time to time, and we decided that we'd go for a walk. He mentioned that he lives next to this park. I really like in San Francisco. I haven't been to in a while. It's got a little hill. And I said, Oh, great why don't I just come over there and we'll walk there. And so I went to his house and we went and climbed up this hill and, let me not get too personal, but before I went to my next meeting, I was like, oh, can I jump in to use your restroom as I walk into his house and I saw all his kids artwork everywhere and just to kind of set the stage. This is not a work acquaintance where before times I would have ever considered meeting at their home, but it was just a logical thing to do at the time, and I feel like it just brought us so much closer because, again, seeing someone's kids artwork on the wall, I just saw who he was as a person, and it was really, really lovely. And so I've been having this thought of what are the magical moments that are unlocking because of this new situation, and how do we lean into that more, which is a little bit of these blurrier lines, right? One of my kids comes home from preschool every day at 12:30, and usually I remember to lock the door, but I don't always. Right now it is 12 is we're recording this, but it's making me think I should probably remember if you have a meeting with me sometime in the 12 to 1 period, there's probably a 50:50 chance my kid pops in. I don't know. I don't really mind that. I think it's kind of nice for people to be able to see. This is who I am. This is a big part of my life.
Brett Martin: Interesting. Yeah. So you're sort of embracing that. And I think what's interesting is that if you talk about the problems that people discuss about remote work right where they feel like they've fallen short is around that sense of creating camaraderie or sense of belonging or culture. And so are you saying that the actionable way of working around that is to find other opportunities to share your personality with your co-workers?
Maia Josebachvili: Yeah, I probably hadn't articulated it that intentionally, but I do think that is really, really important. I talk about the Trust Cup a lot. You know, the Trust Cup on your team, the Trust Cup between your team and other teams across the organization. And there are many interactions that deplete the Trust Cup. We've all experienced them, right? We have a disagreement on an approach we should take, we don't know each other that well. I might experience your feedback as personal criticism as opposed to collaboratively, you know, working on the project, whatever it is, it is natural to be depleting the Trust Cup through interactions. Pre sort of this very common, remote world I think we had a lot more opportunities to fill the Trust Cup in that sort of casual conversation in the hallway. The meeting ends, and we can kind of keep talking. The meeting hasn't started yet, and you can have more one-on-one conversations, which I just find happens last when you're all in one big zoom. I do think we have to be very intentional about filling our Trust Cup, and that can look like a few different things. Like I said, it could be just being okay with having a kid pop into the screen or working in different parts of your home. So people see different parts of your home.
Brett Martin: It feels like everyone's trying to figure it out. I don't know anyone who's trying to get everyone back into the office 5 days a week, 50 weeks a year. But some people are talking about hybrid fixed or hybrid flex. So hybrid flex, meaning anyone can come in 3 days a week. They pick the 3 days or hybrid fix, saying, okay, everyone comes in Monday, Tuesday and Thursday. You know, I think the problem with the former is that, oddly, you have people coming to the office three days. They're not in the same three days, and then they end up kind of alone in the office zooming with everyone else. Hybrid fixed, of course, it doesn't have the flexibility which people crave, right? Like part of the beauty of working remote is being able to do your work from anywhere. Do you have an opinion on how to structure time there? And, you know, maybe even like tricks or tools that you use to bridge the gap?
Maia Josebachvili: Yeah. I mean, the first, I'll say, is just to acknowledge it is really, really hard, and especially from a top-down sort of edict to the whole company, is very, very challenging, even just in terms of planning office space. How big does your office need to be? What kind of capacity do you need on any given day? What if everyone wants to come in the same days? What do you do on the day that no one comes in? If you remember back to March 2020, when offices first started shutting down and people were shutting down the office for 2 weeks, 3 weeks as the initial sort of decision making point. Now we're two years later, COVID has shown us we're particularly bad at predicting the future of what will happen. When I was head of people, and I was kind of making these scenarios of, okay, what happens if we're back in the office in a few weeks? What happens if this goes on to the end of the year? And then I made my extreme scenario, which is what happens if this goes on for a year and a half and everyone kind of looked at it, and every time we looked at it, we would chuckle and say no way, but let's just plan. And sure enough, here we are 2 years later. All that is to say, these are really complicated questions. And I actually think most organizations don't have enough data of human behavior in this world, and most people can't really predict how they'll want to do it. To be able to really say this is exactly how it should be.
Brett Martin: So it's almost like flexibility on the organizational side is required in terms of the organization needs to be flexible and kind of adapting as its people are.
Maia Josebachvili: We will never know less than we know today, right? About how we all interact in this new world and so my personal philosophy as a manager and as a leader of my team has been to be flexible, listen, adapt and learn and, you know, lean into the benefits, acknowledge what our tradeoffs are in the current situation and try to kind of buttressed those. So just kind of very, practically speaking Pre COVID the team was all San Francisco based. And so we had sort of norms and certain ways of operating. Over the course of two years between the individuals who have moved and knew hires who've joined the team we now don't have those in-person collaborative opportunities anymore. So the pilot we're doing, we've talked to every single person and said, “How frequently do you feel comfortable traveling for, you know, a variety of reasons?” And right now, the sort of lowest common denominator was quarterly. And so we've said great. So for the next two quarters, we're going to pilot quarterly. The onsite is the new offsite, right? Quarterly, quote, unquote, offsite. It's where we just meet in one of our offices for a few days. And so we're doing that. Then we just kicked off this kind of bi-weekly 3-hour Zoom or Kumospace where we're going to kind of try to mimic, you know, whiteboard collaborative conversations and see if we can do it. Yes, we're being flexible, but adaptable to try to say, okay, if we're trending in one direction, what else do we need to do to counteract any of the tradeoffs that this way of working is creating for us?
Brett Martin: Got it. And obviously, I think you've already talked about these are great benefits of being in person, the feeling of connection. But how do you think about building culture while remote? How do you reinforce culture and build culture the other 46 weeks of the year when you're not doing your, you know, your on-site off-site?
Maia Josebachvili: Yeah, for sure. I mean, culture has so many layers and so many facets to it. Culture is the connection you create when you're in them every day. But culture is also the behaviors and the norms of how you interact with each other, and that is not limited to in person. Culture is what do you celebrate? How do you react to bad news? I do think back to this concept of, like, the Trust Cup gets depleted more quickly in this world, and it is harder to fill it. I think in some ways we need to be that much more conscious and intentional of the tough moments and how we handle those, because I think those are pretty big shapers, right? I've been rereading the five dysfunctions of team recently. This concept of absence of disagreement and absence of conflict as a dysfunction of a team and it's been fun to reflect on that a little bit. Conflict, I think, has a lot of negative stereotypes. Conflict as the disagreement of, like, basic, fundamental ideas in non-personal ways. In my world, it's kind of like should the product strategy go in this direction or that direction and which is better? And it would be weird if we all had the exact same perspective. And so how do you bring out the different perspectives and argue and debate and get to a shared sense of perspective on it and then move forward? I think those are actually really, really important cultural moments. And so how do we create safety and the opportunity to have debates is one thing I think a lot about in this new world, especially for new folks who are coming in and you can't read the body language. And so you don't know, is it okay to disagree? Is it okay to have conversations like this?
Brett Martin: And so to get kind of even more tactical with that disagreement happens in a meeting on a Zoom. And, you know, whereas historically it might have happened in a meeting, in an office, you might have been more comfortable to hash it out right there. And even if not, you probably break off into small groups, and then you kind of have an opportunity to digest instead, you know, all of a sudden the meeting ends. Everyone's sitting alone in their home offices. Yeah. How do you think about that? Like, is it certain channels for certain types of information? Do you try to avoid certain conversations on Slack and make sure you do them on video? Do you use the phone for different types of conversations, just wondering how you tactically handle different types of content, and if you use different tools for different messages?
Maia Josebachvili: Yeah, two things. One, I'd say that disagreement doesn't have to be contentious. And so one is just sort of, what's the tone you're setting in all these conversations? And what are you encouraging? And so I'll speak about zoom meetings very tactically. We have a norm, and I don't know if most companies have this or not, or if this is just like a very common thing. But folks generally stay on mute and then when you have something to say, you on mute and it's sort of a signal for everyone that you have something to share. So I think that's been actually a very inclusive norm, whereas in person, sometimes it's just harder to get in a word, or if you have, like, a half-distributed team, it was harder. So just kind of norms around how people can contribute. I think the other thing I think a lot about as a leader is what role are you playing and facilitating the conversation? And so if someone is talking a lot, giving others the opportunity to speak. So something I find myself saying a lot in meetings is, you know, Brett, haven't heard from you in a little while. Really curious what you think about this and your perspective on this, and so kind of facilitating the various perspectives feels important. I think the challenge with slack or any kind of written and ascent communication, as we all know, is tone, can be hard to read. We were having a competition yesterday about just using more emojis because, again, if you're, you know, in person and someone says something with a smile, you interpret it a certain way versus if they say it more frowning. How do you bring that into your async communication as well or written communication?
Brett Martin: Yeah. So there's almost like an additional level of sensitivity I think, as in person, you're kind of piggybacking on millions of years of evolution and nonverbal cues. And in this new kind of world mediated by technology, you have to be extra intentional about the message and the medium through which you propagate it. And so how do you make sure that your team is using best practices there? Is that something that you coach your managers on- just wondering how that knowledge is being spread?
Maia Josebachvili: I think if just talking about it as making me reflect that it feels more intuitive than intentional. Well, at least for myself, I feel like I'm intuiting it more than being super intentional. It's a good thing to think about even funny things. Like there's one guy I work with who is so good at communicating in slack. And as I reflect on why he's got a great use of italics and just the way he talks, you can kind of hear him talking through his Slack. I don't know what to make of that other than how you come across in written for matters a lot more than it ever used to.
Brett Martin: Absolutely. I mean, something we find even building Kumospace, people will get into heated debates on Slack, and then things can spiral out of control. It's like, oh, just hop in Kumospace just to remember. And so we've actually started. We all now live in the office, and that's been great because there's a sense of immediacy. And so if we find ourselves chatting for more than two or three back and forth, it's instantly and frictionless for us to start actually just communicating face to face, because the bandwidth is there, and the verbal and the nonverbal cues are there, but that actually takes some practice remembering what is the right channel to have a particular communication in?
Maia Josebachvili: Well, and maybe to take us back to the beginning, there is no one size fits all. It depends on the type of conversation and the type of back and forth that it depends on the relationship between the people who are having it and their history. I do find myself saying often this might be better live, right? I write that a fair bit. In some cases, that is true. And in other cases, like there are people that I've just had such a long working history with, and sometimes it's just faster and easier to do it on Slack weirdly enough.
Brett Martin: Where you have that trust, where you have that communication, where you perhaps are better at interpreting. There's less ambiguity for you in interpreting what the other person's saying.
Maia Josebachvili: I do think it is a big part of it. With certain people if we're having a disagreement on Slack, I don't think of it as, oh, do they not think I'm smart or kind of taking this personally? And to be clear, a lot of other times, if I'm disagreeing with someone on Slack, I definitely get the impostor syndrome of maybe I don't know what I'm talking about. And so you just have to. I wish there was a formula of if this, then go do that, right? The engineer IN me loves that concept, but I think it's really about what's your relationship with the person? What's the dynamic of the conversation? What's the broader context of where you all are, you know, in the org and how's your trust cup filling in that moment?
Brett Martin: Well, we talked about all these new complexities of managing interaction, right? As we've gone from the controlled environment to the office, to the kind of wild west of remote work, what do you think the future looks like? In 5-10 years, do you think that we're going to be slacking and zooming, or do you think that there's a totally different kind of paradigm that we'll use to do work? What does the future of work look like Maia?
Maia Josebachvili: That is a big, big question. I want to go back to something I said earlier. Well, two things I said earlier, one is, gosh, we are bad at predicting this whole thing. I don't know is the answer. I was trying so hard to predict what this would look like two years ago. And, you know, I was pretty far off, and I felt like part of my job was to try to do that. So my honest answer is, I don't know, but it's the same concept of there won't be one size fits all. And I think different companies will end up doing it slightly differently. And what stage of company are you, a small startup? Are you a massive enterprise with multiple global offices, you know, serving multiple segments? What kind of people do you attract? And then even just as individuals, will we be more drawn to certain types of companies and certain working environments. I mean, that's always been the case anyway. And so I think that will all just continue. And so what does the future work look like? I think it really depends on the person and the company ultimately. Office culture has changed in the last 30 years without this push took more remote. And so there will be more factors that change how we work together beyond this push to remote, and we will just keep adopting and evolving to them. And we'll make some mistakes along the way. But I think we'll also discover some magic and some benefits throughout it as well. And I'm optimistic that this leads to better work experiences for people over time if we all collectively try to make that happen.
Brett Martin: Well, Maia I'm very grateful to have you here to share your most up-to-date thinking with me and our audience. And I just want to say thank you. It's been amazing to have you here on our chat today and wishing you and your team the best. I hope wherever you are, you're having a lovely day.
Maia Josebachvili: Thank you. This was the blast. Really appreciate it.
Brett Martin: All right. Thanks, Maia. Talk to you soon. Bye.