My guest today is Samantha Berg who is the Head of Design at Chime. In this episode, we discuss the following: - Samantha Berg recounts 12 years of hustle and grind to become the Head of Design - How to know as a designer if the leadership path is for you? - Role of a Design Manager - What does a Head of Design do - How to deal with bad hires as a design manager - Scheduling meetings for a remote design team - Promoting designers internally over hiring externally - Retaining design talent from getting poached by FAANG - How to ask your design manager for a salary raise - Challenges of being a woman design leader - Designing design organizations - How to keep a pulse on the team health as a design leader - Maintaining work life balance as a design leader For show notes, guest bio, and more, please visit: www.designmba.show
Samantha Berg is an award-winning design leader with nearly 15 years of experience envisioning, creating, and shipping next-generation consumer products. She leads and motivates teams with proven success across a variety of environments, including large-scale tech companies, mid-sized design consulting firms, and venture backed start-ups. She is passionate about building tight-knit high-performing teams and creating cultures of inclusion and equity. She's created and led women's groups at multiple organizations and regularly speaks at events in the design and fintech communities around how to design your career and how to create inclusive products that empower.
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Namaste and welcome. I am Jayneil Dalal and you are listening to the design MBA which is a real-life MBA program for designers. You will learn how to launch a side hustle and level up your design careers from the interviews rock star designers.
Jayneil Dalal: Today's awesome guest is Samantha Berg. Samantha is an award-winning design leader with nearly 15 years of experience envisioning, creating, and shipping next-generation consumer products. She leads and motivates teams with proven success across a variety of environments including large-scale tech companies, mid-sized design consulting firms, and venture-backed startups. She is passionate about building tight-knit high-performing teams and creating cultures of inclusion and equity. She's created and led women's groups at multiple organizations and regularly speaks at events in the design and fintech communities around how to design your career and how to create inclusive products that empower.
Welcome, to the show, Sam. Super excited to have you.
Samantha Berg: Thanks for having me. I’m super excited to be here.
Jayneil: I was just thinking about, as I was reading your bio, I sounded one of those insurance ad people really quickly zipping through it and I’m “What is wrong with you?”
Samantha: It happens to the best of us.
Jayneil: Oh my God! It's so awesome that I’m talking to you. You're the head of design at Chime and I’m just thinking about, from my perspective, you're on this other side and I’m on this other side, and it seems a super awesome job, it seems you've made it. And everyone wants to be head of design. These days when I talk to the designers, everyone's trying to work hard to get to that head of design level. So, is it that easy being the head of design?
Samantha: Oh gosh! It's funny. It's a very weird, I think, moment for me in my career because it's something I’ve always wanted to do and now I’m here. And I find that I’m still not satisfied maybe is the word and I have to sometimes remind myself “Hey, this is the thing you've always wanted to do. Let's maybe stop and enjoy it for a minute and really appreciate where you are and where you've come from.” I started my career about 12 years ago. And so, it's been a tremendous amount of hustle over the last 12 years to get here. And sadly, depending on how you look at it, or happily, there's still a lot of career left, there's still a lot of working years left in my lifetime. So, still a lot to do. Is it easy? I mean, no, but is anything ever easy? Plus, if it was easy, what fun would it be?
Jayneil: 12 years of non-stop hustle and grind. It just blew my mind away. So, it's insane 12 years ago when you were just all of us and you were starting out as a designer and now, you're here the head of design. In between that journey, when did you feel that “Oh, you know what? Leadership is something I’m interested or is something that could be for me like a path instead of just being an individual contributor.”
Samantha: Yeah, great question. I think, honestly, maybe in my first job. And I found this to be true of pretty much every job I’ve had but having a good manager is like having a good professor or good teacher when you're in school. You could be learning the most interesting topic like learning about the most interesting topic in the world and if you have somebody who just stands there and drones on and lectures at you, that thing that you thought was super interesting all of a sudden is just not interesting anymore and it puts you to sleep. And maybe in the opposite way, you could take something that on the surface seems really boring, if someone talks to you and they're really energized excited about it, you can tell it's getting them really jazzed up, it kind of gets you jazzed up too. I’ve found that managers in a job are really that. When you have someone who is excited and goes above and beyond and shows you different ways to do things and helps you think through problems and use different frameworks, it changes the job for you, it makes you really excited about what you're working, it makes you want to show up every day and you're learning and growing and becoming a better version of yourself. And when you don't have that, a job kind of sucks like It's boring, you don't feel you're growing, you're not really excited to go to work every day, maybe you feel undermined or disempowered depending on who the person is, and it's just it's really miserable. And so, I think it was pretty early in my career where I noticed that it really mattered who I was working with and who I was working for. And I’ve always been very ambitious with my career and I started thinking about “Okay, so much of my career development depends on my manager.” Certainly, I fully believe in owning your own career and owning your own development, right? So, there's a lot that I was taking responsibility for and owning but even the person who's owning their career the most, at the end of the day, a promotion, a raise, a title change, those things really come from your manager. And if your manager isn't excited about that stuff, isn't bought into it, doesn't want to help you with that, you're not going to get that career growth. And so, I decided really early on that this was important to me. And therefore, it's important to find and work for good managers and it's important to be a good manager and it was something that I thought “Hey, I’m passionate about this. I want there to be more good managers in the world. I think this is something that I can do and do really well.” So, I knew from very early on that I wanted to start managing and I started leaning into that whether that was thinking about “Okay, we have an internship program. Can I manage our intern?” or “Can I help mentor them,” looking for a lot of official and unofficial mentorship opportunities whether that was in organizations around me or at work or in other places. I spent a lot of time as a kid kind of teaching and coaching and mentoring. I taught Hebrew school for a number of years. I did a lot of babysitting. So, kind of nurturing and teaching others, I think, has come naturally to me. And so, I just kept looking for those opportunities until I could really take that on in a more official capacity.
Jayneil: So, you basically tried it in unofficial capacity, got a feel for it, then went in the official capacity. You also mentioned that you were noticing that who your manager was, was also impacting how you felt in the job. So, I’m kind of curious what are some of the things you took away that “If I ever become the manager, I would not do this,” like we all have had some managers where some things or some quirks, some were just outright “I’m never going to do this.” So, were there some of that laundry list of things that if you ever became the manager, you'll make sure that you did not do any of this?
Samantha: I don't know if I have a list of things I really don't want to do. I think I’ve actually been very lucky where I’ve had some not great managers in my lifetime, I don't know if there have been any that have destroyed my career or my sanity or anything like that but I think there are definitely things I’ve seen where I’ve been “I want to do that” or I’ve seen that have made me say “Okay, here's how I might approach it differently.” So, one of the things I think a lot about is how to empower people. At the end of the day, I’m not the smartest person in the room, I also don't want to be the smartest person in the room, it's a lot of responsibility and it's quite honestly not that fun, I get a lot of joy out of working with really smart people and collaborating and kind of plussing each other and adding on to things and innovating together. I don't get a lot of joy out of being the person in the room who I think has all the answers and telling everybody else what to do. It's not enjoyable. So, a lot of what I think about is how do you create the right environment for other people to feel creative, to feel they're doing their best work to get really excited. And sometimes the environment that someone needs to do their best work is not the same as what I need to do my best work. I think a lot about how do I hire people who I think are better at something than I am and then how do I get out of their way and let them do that thing. I’m not good at everything. In fact, I’m not good at most things. And I think a sign of a really good leader is somebody who's able to figure out what they're not good at and then hire great folks around them to do that. So, for me personally, I really love culture creating. I really like building teams and kind of being that person who says “Okay, let's do happy hour on this day and let's do Halloween and here's what we're going to dress up as” and that's where I to spend a lot of my energy. I don't to spend a lot of my energy on “What tools should we use?” Planning comes around I’m like “I don't care if we're using Asana or Trello. And in fact, I don't want to use any of that. I want you all to do your planning. I want you to come back to me tell me what you planned and you're good to go.” So, finding people who are really great and have complementary skills to mine and who are better at those things than I am, I’m not threatened by that. I want really great people. And then when they're here, I want to get out of their way. I want to let them do that thing that I hired them to do because they're better at it than I am. So, I don't want to tell them how to do that thing. I want to give them the space to do it and I want to help them think critically about what they're doing and how they might do it better but I don't want to tell them what to do or how to do it. I want them to go and run and come back and hopefully really surprise me, come back with something I’ve never thought of before that's going to be way better than what I would have come up with. So, that's a big one.
Jayneil: So, as head of design, how much time do you actually spend in actual Figma designing versus hiring, so to speak?
Samantha: Oh, zero.
Jayneil: What?!
Samantha: There's no time spent in Figma designing.
Jayneil: Well, how much time do you spend on hiring them?
Samantha: Oh, 100%, probably 100% of my time. So, look, maybe this isn't true at all places but Chime, the company that I work at, is very lucky to be in this hyper growth stage. I’ve been there for two and a half years and in the time I’ve been there, we've gone from, I don't know, I’d say 120-130 people to about 1100 people. So, really, really tremendous growth. And the only way you do that is by hiring. And you have to hire great people. Hiring takes a lot out of you and a lot of time and energy and onboarding and training people takes a lot of time and energy but then they're going to be amazing and they're going to do great things and there's nothing worse than hiring to put butts in seats and having someone work for you for a few months, who you have to then manage out and rehire for because you didn't make a good decision the first time. So, so much, I would say, almost all of my day every day is dedicated to hiring. Not necessarily the literal interviews, although there's a lot of that too but so much of it. I mean, this is the design work I do now, right? It's the org design. It's looking at the team and saying “Okay, what skills are we hitting it out of the park on? What skills are we missing? What skills do we need to get better?” And then “How do we want to get better at those things?” or “How do we want to fill those gaps that we're missing? Do we want to train people? Do we need to hire new people? Do we need to bring in new types of things?” So, one of the big things we added to our design team this last year was content design which I’m sure for a lot of people listening to this already get, no kidding, but at a startup, you start with a smaller team, you make do with what you've got, you add when you can. And we were at a point where really the designers were spending a lot of time on content, they were spending a lot of time litigating content with our compliance folks, with our product folks. Content is one of those things, kind of design work, that everybody has an opinion on because it's a language that everybody understands. And so, there's a lot of debate there. And a lot of the other types of design, the interaction design, the visual design, the motion design weren't getting done but also our designers who are really great at interaction and visual and emotion aren't necessarily great at content. They're not the same skill set. And so, that was a big thing that I kind of looked at, at the beginning of the year and said “Okay, this is a thing now that we're spending too much time and we're not efficient at. We really need people whose expertise this is who can come in and really do this for us.” So, that was kind of a piece of org design. So, identifying the problem is number one. Figuring out “Okay, we can fix this by adding new people of the content design flavor” was number two. Then number three, so “Okay, now let's go do the recruiting and the interviews,” you end up hiring a couple people getting them to accept the offer, great. And then there's onboarding and getting them up to speed. And so, that's really kind of what I do. It's a lot of rinse and repeat and thinking about “What does the company need from us as a team right now? How is that different than what the company needed from us six months ago? Who are the right people then that we need on the team now? What are the right places to find the kinds of people that we need? And what do we want this team to look like?” I think we've had … I think one of the silver linings of COVID is that it's forced us to reexamine our work spaces and how we want to build our teams. And so, previous to COVID, we had a pretty heavy “We hire in the Bay Area” policy and if you want to come work here, you're going to relocate to the Bay Area. That's kind of gone out the window. And I feel very strongly that if we want to make experiences that are great for our members, then the people making the experiences, designing the experiences have to resemble our members, they have to have similar backgrounds, they have to have similar education levels, they have to have a similar understanding of the ways that the world kind of does or does not work. And for Chime, most of our members spend more every month than they make. And that might be true in the Bay Area, I know it probably feels that way for all of us in the Bay Area but realistically, a lot of us in the Bay Area are not dealing with the same problems day to day that our members are. So, COVID’s been really great in that I’m hiring folks from all over the country. I would rather in fact hire folks not in the Bay Area than folks who are here. I’d rather hire folks who have never worked in fintech before, who have never worked in finance, who don't feel financially literate because those are our members. And that's something now that we can do.
Jayneil: And I’m glad you guys are doing it because a designer like me, whatever the reason might be, I’m just very happy staying put in Dallas and I’m sure there are people like me who are like … they're like “We don't want to move out of this home city. So, remote will be awesome but we don't want to move to the Bay Area” maybe because the expensive nature of the city or whatever the reason might be. So, that's really awesome. And something I was thinking about is it's like every shot that a sports person or say an athlete takes, they're not always going to make it. So, I’m kind of wondering does that analogy apply to you in your career as a manager, as a design leader that every hire you make is always going to turn out right. Maybe they don't turn out. Would that be true?
Samantha: No. I mean, there's no way. No one has 100% record on hiring but you try and you learn each time. I think sometimes this idea of failing fast gets a bad … I don't know, there's this idea that “It's great to fail. Everyone should fail.” Don't fail stupidly. If you make a mistake and you learn from it, you do it better the next time. I’ve made bad hires.
Jayneil: Was it hard for you to fire them afterwards?
Samantha: Yeah. That's tough for everybody, right? That's tough for them. It's tough for you. And usually, there's something that isn't gelling right. Either it's a different job description than maybe what the person thought they were signing up for or the company culture is different or the person's skill set is different than how it presented in an interview and they just aren't making it. And those are tough conversations to have but I honestly think almost every time it works out best for both parties at the end, right? If someone is struggling to keep up, they're not having a good time at work. Don't get me wrong. Work isn't always a party but you should enjoy what you do every day and want to be learning and growing and you shouldn't be trying to doggy paddle in the deep end just to keep your head above water. So, I do think there are always mistakes made. And I’ve also made mistakes in choosing jobs that maybe weren't great, right? It's not always about someone having made a bad hire. Sometimes you think a company is one thing until you get in there and it's something totally different but I think as we learn to hire more broadly, I think it's also about us and looking at our own teams and our own companies and saying what needs to be different. And so, this is the other piece of the org design that I do and this is why it's interesting now hiring all over the country is I have to change the way that my team works. If we want to be equitable and inclusive of all types of people, we have to work differently than we have to date. So, one example, and it's a very small one, is that within the design team, we kind of made a rule of there are no meetings before 10 a.m. Pacific and there are no meetings after 2 p.m. Pacific because 2 p.m. Pacific is 5 o'clock on the East Coast and 10 a.m. Pacific is 7 a.m. in Hawaii. And so, that covers all of our time zones in the US to have somewhat reasonable working hours. And so, if you're in Hawaii, you're going to have meetings from 7 until 11 but then hopefully, you have the afternoon to be heads down and do your work. If you're in New York, more broadly the East Coast, I’m a New Yorker, so I’m very New York centric over there, but more inclusively, if you're on the East Coast, you might not have meetings before 1 o'clock p.m. and then by 5, so you kind of get that heads down time in the morning. If you're on the West Coast, it's kind of in the middle. Same for Central and Mountain Time but that was a change we had to make. We were used to being able to go all day with our meetings and that's just not going to be the right thing now that we're in different places. I mean, these are the problems I’m constantly tackling as head of design is really how do you run a team that is equitable, that is inclusive, that is a great place that people want to work at when that means a million different things to a million different people. And that doesn't mean I want to go hire all the same people to make that easier. It means it's going to be a tough job because I want to have a bunch of different types of people on the team.
Jayneil: But what if you want to hire a candidate that you met at a design event and you're “Okay, I think we should hire this person” and you bring in the team to also interview them but the team is like “no” but then you are kind of like … still a little bit keen on the candidate. What happens then?
Samantha: I tell the team they're SOL and I bring the person in. No, I’m totally kidding. This goes back to the idea of hiring different types of people and hiring people who are better than I am. Hiring is not done in a silo nor should it be. And so, if there's someone that I’m really jazzed about, I still want the rest, not the whole team always, but I still want my leadership team to meet them, I want other folks on the team to meet them and I want to genuinely hear their perspective, maybe they see something that I didn't see or vice versa. I think we're all naturally drawn to people who are similar to us in some way whether that's we both grew up in New York or we both had dogs or, I don't know, our favorite color is blue, whatever it is. We like people who are us and sometimes that's good and sometimes that puts you in an echo chamber. And so, certainly, I don't want to be just bringing people onto the team because I them. I want to bring people into the team because they fill a gap that we have or they offer a new perspective that we don't have yet. And so, we try to be very objective about those things and that's why I’m constantly evaluating “Okay, where are we really hitting the mark and where are we missing the mark?” And when we're missing the mark, the answer is not always to go outside and hire new people. I think companies can be very quick to say “Hey, we need to go hire someone, we need to go hire someone.” One of the things I’m working really hard to do in my team, I want to develop the people that we have. So, when we need a new manager, I don't necessarily want to go outside and hire someone. I want to look at the folks who are leading my team and say “Which of them is ready for a bigger role?” And I think that's really important. I think, it's so incredibly important to company culture and to the signal you give other folks. For someone like me who's very ambitious in their career, I would way rather go work at a company where I see that they promote internally and people can stay there for five, six, seven years and get company growth than go work somewhere where I see people leaving after a year or two and I feel like “Okay, I might learn something but pretty soon I’m going to have to go somewhere else to keep learning.”
Jayneil: So, right there, let's say you have a star candidate on your team and Chimes is awesome hyper-growth startup but let's say Facebook, Apple, Google, Netflix, one of them comes in and gives just outrageous amount of money and let's say in this specific situation you cannot cross or you cannot maybe meet exactly that salary expectation. So, what is your take on trying to retain that talent from getting poached by other companies or some of these other ones that are just going to throw money?
Samantha: Yeah. Well, look, I mean, I know this is the same but money is not everything. At least for me and for some people money is not everything. And for some people, money is everything and that's 100% okay and those people should absolutely go work at a company that's going to throw money at them. there are a million times in your life when you need money, maybe you're about to have a kid or you're saving for a house or you're supporting a family member or whatever. Absolutely, there is nothing wrong with going and working for one of those companies.
Jayneil: So, you're not offended. If I came to you and said “Hey, Sam, I got to leave because Google's giving me this much money,” you're not going to be pissed or something.
Samantha: No. I mean, first it's a conversation, right? If someone says to me “Hey, I have an offer to go somewhere else,” there's a lot of things I want to know. First off, it’s like “Congratulations. Good for you. Getting an offer at any company is huge. It takes a lot of hard work. Good for you.” Second, I’d love to know why the person was looking, what is it about here that they're not totally happy with. And that's not necessarily an effort to save or rescue them but that's like “Hey, what are we doing wrong?” and I want to hear that because I want to think about that for the rest of the team. If you're unhappy with something, maybe somebody else is unhappy with that same thing or maybe it's not that they're unhappy. Maybe it's just that there's something else or something different in this other thing. And so, I want to understand “What's up? Is it about money? Is it that you don't feel you're growing as a person here? Is it that you no longer believe in the company or the leadership or is it that you don't like the mission or … what is that thing? And so, let's talk about it. And if there's a way to resolve that, absolutely, let's resolve it.” And if there's isn't a way to resolve that, if it's still like “Hey, they're just going to pay me 20,000 more a year and I really want that money right now,” “Okay, great. Good for you” and “How can I help? What do you need between now and then and how do we stay in touch?” It's really my intention with my team and my team members to make this a really great stop in their career but number one, I don't expect that it is the end-all be-all in their career. And two, my hope is that we stay in touch and we stay friends. The design community is very small. The design community in the Bay Area is even smaller but actually before you and I started recording, I had been up in San Francisco having lunch with one of my best friends who I met at my first job out here. My first week of my first job, I met her. That was 12 and a half years ago … 12 years ago and she's still one of my best friends, she was at my wedding a few months ago, I was at her wedding a few years ago. I say a few years generously. She now has two kids who are like 10 and 8. It's absolutely crazy at this point but those are the kinds of relationships that I want to have with people. And so, it's not about you should work for me or you should work for Chime or you shouldn't work for me. It's like “What do you need right now for your life, for your career? What's right for you or for your family? How do I help you get that?” because that's really what's important at the end of the day.
Jayneil: So, you believe that counter offers work? Because you know how the industry has their own take on it like you've got someone that's gotten a job from Google, that's coming to you and telling you about it and you feel you can remedy their situation. So, do you still believe that that counteroffer for them to stay at your current company will work or are you of the perspective that at this point, it's not a good idea probably?
Samantha: There's not … there isn't a yes or no answer to that.
Jayneil: Okay.
Samantha: The hot take is that I probably think most of the time counter offers don't work and they're not worth it. Look, I think if there's something that can legitimately be fixed, great. And sometimes that is the case. And, honestly, my hope is that any team that I’m leading, I hope we have a good enough culture and one of authenticity, one of transparency and honesty and one of really believing in each other and wanting the best for each other or if someone is unhappy, I really hope we find out before they have another offer in hand. I really, really hope so. And I think, for the most part, once somebody has another offer in hand, honestly, I think most of the time they've made up their minds already. And I think the counter offer is fine and if it's somebody that you really care about and want them to stick around and let's say it's just a like “Hey, I really want to stick around. I love this company. I love our mission. I love what we're working on but I’m getting this amount of money somewhere else and I really want to buy a house. And so, can you match that?” maybe, sure and you probably want to do what's right for that person. And, I don't know, that's not a conversation I want to have over an offer. That's a conversation I want my people to come to me and say “Hey, Sam, heads up. My family and I are looking to buy a house in the next few months. Is there anything you can do with my salary because I’m feeling a little bit stretched?” Absolutely. Then I want to have that conversation but I do think a lot of times when someone has another offer in hand, they've made their decision. And at that point, you're either succumbing to the bait of an offer … but I’m not going to say that's all the time. I will just say that that's my hot take on it.
Jayneil: No, I love that because literally … So, my counter perspective to this thing is if I’m the candidate and then you know I get this offer and I get a counter off from the company I’m working at, my perspective as a candidate is “Well, why did that offer not come like why did this raise not come without me having to present an offer?” What you're saying is that instead of us doing all this shenanigans and dance, I should just come directly to you and be like “All right, Sam, so XYZ reason but I’m here and I want to get here. Is there something we can do?” So, that will save me the trouble and you the trouble and we can have an honest conversation.
Samantha: Totally. And wouldn't you rather work somewhere and for a person where you can have those honest conversations? And I was coming at that, obviously, from the hiring manager standpoint. From the candidate standpoint, I totally agree with you, right? I shouldn't have to go interview and get an offer somewhere else for you to promote me. I shouldn't have to show you that somebody else values me for you to value me. With any manager I have, I want to be able to sit down with them and say “Here's what I think my value is. Here's what I think my worth is? Do you believe that that's my value and that's my worth? And if you don't, I want to know why and let's talk about it. And if you do, then you should be paying me or titling me or whatever it is at that worth.” And I think that that lets you have a really honest conversation – “Maybe I think I’m worth way more than my manager does. And they can tell me “Actually, here's why I’m not ready to promote you is because I don't see you doing enough of X, Y and Z.”” And then you know. And then you're like “Oh, okay, I didn't even realize that” like “Okay, I’m going to go work on those things now.” And so, I do really think having those development conversations, not even development conversations, but being able to have really candid conversations with your employees or with your manager about “Here's where I think I’m at. Here are the things I want next,” whether those are professional, whether they're personal … I’ve had employees come to me and say “Hey, I just want you to know my partner and I are thinking about having kids in the next year.” It's like “Oh okay, great. That's super helpful to know that that's the stage in life where you're at.” And that then helps me think through “Okay, what kinds of growth opportunities do they want? How much workload can they take on right now or do we need to tone some of that back?” or moving or this that or the other thing or they're like “I’m really gung-ho right now. Give me all the things to work on.” – “Great” but I think those conversations are just so important and so important to be candid. And I think, especially as a woman, I think it's sometimes scary to be candid in these conversations really. If you're an underrepresented party, I think you often feel like you can't show any kind of vulnerability, you can't be candid, you can't talk about things. And I think that's really important. I’ve met so many people who leave a job thinking “They're not paying me enough” or “I don't get enough vacation days” or whatever it is but they actually never go ask for those things. And they're afraid to ask because they think that if they ask, they'll get told no or they think they'll get fired or whatever it is but instead, then they go find a job somewhere else. It's like “But you were happy there. Maybe you were learning and you were growing. Why not ask for those things?” So, I do think it's really, really important.
Jayneil: I told my brother to renegotiate his offer and he's “Oh no, I can't do that.” I’m like “Why?” And his answer just made me laugh, he's like “Oh, if I ask for more, they'll take back the offer.” I’m like “What!? What if they take back the offer?”
Samantha: So, I’ve had offers rescinded on me before. I literally have gone to negotiate offers and they've rescinded the offer and said like “If you're negotiating with us, you're clearly not bought into our mission and we don't no longer want you to come work for us.” And you know what? Great, great because if I can't have a candid conversation with you and say “Here's how much I think … here's how much I value myself and I think you should value me at that amount too” and if they're not going to entertain that conversation, I’d way rather find that out now then sign that offer and then get into a culture like that. For me, personally, that's not a culture I want. So, actually, it's kind of a fun test, negotiating an offer, because it tells you a lot about a company before you go to work there but I think it's very scary to hear the word “no”. It's also, I think, scarier to anticipate hearing the word “no”. And I’ve done all of the leadership books and all the leadership training and a lot of the how to be a female leader in a male-dominated industry and the word “no” tends to be one of these things that as humans we're very scared of, we're scared to tell people, we're scared to hear ourselves. And one of the pieces of advice I heard at one point was “Just get used to hearing no” like go put yourself in situations where you're going to hear the word no so you stop being afraid of it. And so, I’ve started doing things like any time I fly, I’ll walk up to the ticket desk before I get on the plane and I’ll be “Hey, can you upgrade me?” and they’re like “No.”
Jayneil: Oh my God!
Samantha: And I’m like “Okay, cool” or if I’m at a restaurant, I’ll be “Hey, you want to give me an extra glass of wine for free?” And what is surprising, I think, more than anything is how many times someone's like “Oh sure. Oh, yeah, first class is full. We’ll upgrade you.” I mean, it happens rarely in the airplane scenario; hotels, same thing, but a lot of times I can get the free glass of wine at a restaurant or a bar. It helps if I kind of bat my eyelashes a little but it's really interesting this idea of getting comfortable and the idea that there's nothing attached to it like if I ask for an upgrade and I don't get it, the world goes on. And so, this idea your self-worth is not tied to these negotiations, that you can value yourself and you can hear the word “no” and you can figure out is that thing important to you or not and kind of go on with your life. Anyway, a little bit of a tangent but …
Jayneil: Oh, I love that because it's a perfect segue to my next thing I was just thinking about as you said this. As a female design leader, as a woman design leader, what are some of the unique challenges you had to face that maybe if you were a male in a parallel universe, you wouldn't have had to face?
Samantha: Oh, I could talk about this for hours and hours. How long did you say we were going to record? Just kidding. There's so much. I mean, there's a lot to unpack there. I can talk about my own personal challenges that I faced. A big one, honestly, just being … I’m from New York. I’m very type A. I am a very candid straightforward person, if that hasn't come across already. That can be very threatening to people in a lot of environments. I think there's definitely this expectation, even still today, that women are quiet and accommodating and nurturing and I am not a lot of those things. I’m certainly not quiet, occasionally accommodating, nurturing for the right people when I want to be but that is the expectation. And when I show up with a strong opinion and I’m not afraid to really sit at a table and lean in and see something, have definitely … had that be intimidating to people. And I’ve had … I’ve been told before that the reason I wasn't getting promoted was because not enough people liked me. And it's always couched in something so it doesn't sound ever that blatant of a … what's the word I’m looking for? It's not that blatantly biased but it's usually though like “Well, we want to make sure that if we announce this promotion that everybody would be genuinely excited about it,” which is kind of the same thing as “Well, you're not winning the popularity contest right now.” So, that's been a big one. A big thing that I’ve been taking on recently is deciding what matters to me and deciding what I want to own and what I’m going to let other people own. And so, I have learned over the course of my career that when I get very excited about something, I can act very intense and my tone of voice can get very intense. And so, there are a few things I’ve learned about this. One is that it happens. Two is I’ve learned to catch it in the moment. And then I’ve learned how I want to handle it. And so, if it's something that I’m actually not that mad about … Sometimes it sounds mad. Oftentimes it sounds mad when I’m not mad, that's really what this comes down to, right? And so, if it's not something I’m mad about, I’ve learned to like kind of catch myself and say “I think I’m sounding I’m really mad right now. I’m totally not mad. I just feel really strongly about this.” That's something that I can own, right? And so, I’m not going to pull my punches, I’m not going to soften my words and not say the things I’m saying but I will try to soften my tone and externally communicate that I’m aware and that I’m self-aware, I know what's going on but the other piece of that are the things I’m not going to own, which is if you're intimidated by me, that does not make me intimidating. That makes you intimidated and that is an emotion for you to own. That's not necessarily something for me to fix about myself. And so, I’m going to own my intensity. That is how my passion comes through. And passion is important. And people who like the passion, the intensity are going to want to work with me and hang out with me and people who aren't are not and that's okay. I don't have to be for everybody. So, that's been really important. And I think it is very easy as a woman especially we are very often taught to be nurturing and accommodating, taught to take care of others. And so, we don't always take care of ourselves. We don't always think about “What do I need right now?” We think about “How do I change myself so everybody else can like me? How do I be nicer here but a little bit stronger here and how do I give you my chair at the table instead of taking my seat where I deserve a seat at the table?” And so, there's a lot to unpack there but I think maybe the most important thing that I have learned as a woman in any industry but especially the male-dominated one is to turn around and pull other people with you. I think way too often there's unfair pressured competition between women like it feels if there's a table of 10 people, only one woman gets to sit at the table. And so, all the women are competing for that one seat instead of one woman sitting at the table and then offering the chair next to them to another woman, right? And I think that's so, so important. And so, there's a lot of fighting to get the seat at the table but once you're there, you have to be inviting others, you have to be turning around and helping other people get there too. It's the only way that we're going to change things.
Jayneil: Oh my God! A lot of things are coming to my mind as I was just processing everything you were saying. It just made me aware of so many things that probably I don't have to think about and I was like “Wow! I never thought about it from that perspective.” Oh my God!
Samantha: I was having a conversation with someone at work the other day and we were talking about this because we were talking about going back to the office and how it's very weird being at office after all this time and seeing different people's energy in the room and how that's different than their energy on Zoom. And we were talking about how in some ways Zoom is really great for gender bias specifically and then in other ways it's not but there's this idea of physical space. And I don't know if you've ever noticed this, and obviously this is generalization, but typically, you walk into a conference room, let's say there's a table and there are chairs around the table and then there are kind of chairs around the perimeter. For the most part, men are going to walk in, take a seat at the table. For the most part, women tend to sit around the perimeter kind of thing and “Let somebody else have a seat before I take a seat” but then you end up, again generalized, but with a table with men sitting around it, women tend to be around the perimeter. And then as you're getting into conversation, again generalized, men tend to interrupt and talk over and women tend to kind of raise their hand or wait. And if you're on the perimeter, people can't see you necessarily raising your hand, they don't see you trying to get into the conversation. And the people at the table are speaking over each other and the decision is getting made there. And so, Zoom is very interesting in that everybody is kind of equally at the table when you're looking at a screen. And in terms of physical space, women tend to also in a room cross their legs and kind of arms here and take up as little space as possible again in this nurturing accommodating way like “There are so many people around me. I don't want to take up space.” Men kind of come in, legs are spread, doing their thing and taking up more physical space.” And, again, you can't do that on Zoom, right? Everybody gets the same size box. So, it's just very interesting to think about all these behaviors and characteristics that you become aware of and that as a woman I’m constantly, when I walk into a room, it's not as easy as just walking and saying “Hi, how are you?” and sitting down. I’m constantly thinking “Okay, I want to sit at the table. So, I’m going to go and sit at the table so that I can have my seat” but then I also look around the room and I look for my team members and I’m like “Actually, I’m the head of design. I don't need the glory. I want to give my seat to one of my team members to elevate them.” And so, all of this is going. And then I’m thinking like “How do I not sit with my legs crossed?” and trying to be as teeny as possible but “How do I really take up more space?” And these are the things that go through my head when I walk into a conference room and sit down and the meeting hasn't even started yet, right?
Jayneil: Oh my God!
Samantha: Absolutely, these are all the things one has to think about. I’ll stop. I’m going off on …
Jayneil: No, it's there's like a Sam microprocessor that's already running even before the meeting started, figuring out all the algorithm and all these things happening. I was like “Oh my God! The amount of planning and stuff and … oh my God!”
Samantha: And I was going to say there are a million ways in which I have been very lucky and very blessed and very fortunate. I’m a white woman in America. This is probably not that hard for me but there's a lot to think about if you're in any kind of underrepresented class beyond just the day-to-day of the work. And then people wonder why we're all exhausted at the end of the day. It's like I haven't looked at Figma in six months but I’m exhausted at the end of every day.
Jayneil: Speak to me a little bit about that. You said, let's say as head of design, you haven't looked at Figma in a little bit. See, as an individual contributor, for me, a lot of that confidence comes from the fact that I know how to use my tools, I know how to do this and that's how I battle my imposter syndrome. So, do heads of design actually have imposter syndrome? Is that even a thing that's even valid for them?
Samantha: Yes. I mean, I can only speak for myself. And I wouldn't call it imposter syndrome, at least not for me, but there are definitely … I mean, it's funny. I do use Figma. I’m in Figma probably every day but very rarely to do design work. I draw org charts on Figma. It's just like I prefer that to doing it somewhere else. I was working with our recruiting team the other day putting together a really cool file and book that we could send to candidates. So, I designed that. Again, it goes back to hiring but I was doing something and I was trying to change the color or something and I could not get it to work. And it's like “This is ridiculous. I’m the head of design. I don't even know how auto layouts work in Figma.” You throw a file at me these days and I am lost. And in some ways that feels … in some ways that builds a little bit of insecurity, right? It's like “Hey, I’m the head of design. I should be the best designer on the team.” And so, sometimes I’m like “Oh my gosh, I’m not the best designer on the team. What am I doing?” and then a lot of times I’m like “No, I should not be the best designer on the team.” If your head of design is sitting in Figma doing design work, they're doing the wrong thing. That's not what the company needs from them. There are very talented ICs probably like yourself out there who are on top of market trends who are in Figma every day who can and should be doing great design work. That is not what Chime or any company needs from the head of design. What Chime needs for me right now is to grow our team to keep up with all of the amazing things that we're going to do for our members next year. I mean, I’ve hired … I think I’ve hired 20 people this year, 21 people this year, hopefully with another six or seven before the year is out. That's what Chime needs from me. And so, I don't need to be in Figma. I don't need to be good at design. It kind of goes back to how we started this conversation. I want to hire people who are really good at design, who are on top of the trends who can do that but that's not the role I’m supposed to play anymore. And so, Chime needs me to grow the team. Chime needs me to make sure that the work the team is putting out is really good. So, it's my job to give the team things like principles of “Okay. Hey, here's how we should operate as a team and here's what every experience should feel like. And have you done these things? Have you gotten it in front of your partners early and often? And is it scalable? Does it work today and when we add these 10 other things later?” That's what Chime needs for me but I don't really feel bad about not designing stuff in Figma every day. That's not the highest impact thing that I can be doing with my time right now.
Jayneil: But then how do you keep the pulse of the culture like the things you should be focusing on? Because somebody could be not performing, somebody could be rude to me because I am lower in the totem pole but they could be very nice, they could say all the sweet stuff to you and everybody is going to paint a very rosy picture to you. So, how do you figure out “Oh my God, there's really this issue going on in the team and nobody's telling me the real stuff.”
Samantha: Yeah. So, this changes all the time because as the team gets bigger and has different types of people on it and we just need different things. When the team was small, I used to have a weekly one-on-one with every single person on the team. And then as we got bigger, they became bi-weekly. And then for a while I was doing monthly one-on-ones with every single person on the team. And now my team is 35 people. I can't do it. I really want to, I can't but that was a great way to kind of just check in with every person regularly and see like “Hey, what's going on?” and “Tell me what you want the next step in your career to be and what kinds of opportunities should we be putting in front of you?” and “How's your dog?” and How's your spouse?” or whatever. Now I’ve gotten to a place where I kind of do office hours and I hope folks come in and hang out with me. I get sad when they don't. It's a lot … And, again, this is over Zoom, right? If we were in-person, it'd be the happy hours and the coffees and the having lunch together and stuff like that. I find that's really hard to keep up over Zoom like when I’m on my lunch break, I actually want to walk away from my computer for 30 minutes and refresh my eyeballs. And when I’m done with the day, I really don't want to be drinking beers over Zoom. I want to be sitting at a bar drinking and talking to somebody, not their computer screen but I do find ways to do that. And so, it's a lot of just checking in with people but it's also a lot of trusting the leaders I’ve hired beneath me and checking in with them like “Hey, how's your team? How are your employees? What's going on? What are you hearing? What should we be doing better? What should I specifically?” because there's a difference between “What should we as a team do better?” and “What can I, Sandberg, head of design, do better?”, right? I mean, obviously, nothing's perfect but I do try really hard to have one-on-one relationships with everybody on the team to make myself very visible and as approachable as I can be while knowing that sometimes I intimidate people and really letting people know that I have an open door and that I want us to have the candid conversations. I’ve told my team, I’ve told every team who I’ve ever worked with, every person who's ever worked for me that I will not lie to them, that they can ask me anything at any point in time. I will always answer openly and honestly. And if there's something I can't tell them, I will be very clear about what I can't tell them like “Hey …
Jayneil: “Am I getting fired, Sam?”
Samantha: Yeah like “Do you know why so and so left this team?” – “I do. I can't talk about the details” is a way to say like “Hey, I know something that I can't tell you” or it's “I don't know” Reading between the lines here's kind of what I saw” and “How are you thinking about it?” And that's just one example but I want the team to know that I’m really here for them, period, end of story. And it goes back to like “Someone wants to leave. Great, if that's what they need to be successful.” I want to see people be successful. Chime, earmuffs on the company, I don't want them to hear me say this but I love Chime, it's a great company. Obviously, I want to keep great employees there for as long as possible but at the end of the day, it's so much more important to me that somebody is happy and getting something … getting what they want out of their career. If that can't happen at Chime, I want to help them find that next thing, I want to help them find what that is. So, I feel we kind of went full circle there but …
Jayneil: I know. And I’m just thinking that you're the head of design and a lot of responsibilities are in the shoulder and now you've got a family too, you've got your family life, you've got your friends and all these things. So, it could be very easy to just like destroy the boundaries between your personal Sam’s time when Sam is with family and friends and Sam is at Chime or any other company she works at. So, how do you maintain a healthy work-life balance or there's just no thing as work-life balance if you're the head of design then, the weekends you got to be hustling and grinding too? And then if you do that, the employees think that “Oh, this is what we got to do to survive in this kind of culture.”
Samantha: Yeah. No, I very firmly believe in work-life balance. I very firmly believe in vacation. I very firmly believe in nights and weekends. So, I’ll start with me and what I do for myself. Because I’m very type A, my brain is always spinning like always hustling somewhere and I need a break from that. And I found for me that the only time my brain stops moving is if my body is physically moving. So, I work out almost every day. It's not because I necessarily love it. It's not because I think it's going to keep me skinny, I eat way too much for that, but it is literally to give myself a mental break every day. And I really to work out over lunch in particular. For me, personally, it is the most gratifying time to work out because I get a break from the day. And so, whatever problems I was ruminating on from the morning, I put out in my mind for a little bit, whatever I’m nervous about in the evening or the afternoon, I can get the stress out. And so, working out over lunch is my thing. And so, that's just what I do. My calendar is blocked off every day for an hour. If I don't work out for whatever reason, I go for a walk. When we were in the office, there was a yoga studio that was kind of down the street, I would go there over lunch and people just knew I was not in the office. From 12 to 1, I went to Yoga, I always came back after showering and people are “Oh, how was your workout?” but that was really … it still is … that's really, really important to me. Early mornings and nights are my time. I’m grumpy in the morning. So, you don't want me in the office or on Zoom anyway in the morning when I first wake up but I have my time to have my coffee and get my head working right. And really for the most part in the evenings like after 6 o'clock, I’m shutting it down. It's dinner time. I’m spending time with my husband or I’m spending time with friends. And it really, to me, makes me think of the classic airlines like put your mask on first before helping your child like you need to be your best self to help other people be their best self. And if I am tired or stressed out or burning out, I can't help other people be better. And so, I really need to take care of myself. So, that's kind of where I start. That's the Sam boundaries. And those are just my boundaries, right? I know other people who are super productive from 6 to 9 p.m. but then they're going to sleep until noon. And so, if that's the boundary you want to set, great. So, that's kind of me. And then I also think a lot now … as the head of design, I think a lot about what my actions signal to other people, which you don't have to do early in your career. You kind of just do your thing and you don't think too much about it. And now, it's like everything I do, I’m thinking about how are other people going to read it and what does it say to them. And so, I am pretty public about the fact that I work out over lunch and I’m not ashamed to show up with my wet hair for all my 1 o'clock meetings because I want it to signal to my team and to other people “You should absolutely take time for yourself.” There's nothing worse than walking out of the office at 5 o'clock and especially this time of year when it's dark outside and you're like “I have no idea what the weather was like today I never left.” That's not the kind of balance I want my team members to have. I want to encourage them go out for lunch, go take a walk or workout, do whatever you need to do. I always take a big vacation over New Year's. Last year I was gone for two whole weeks. This year I’ll be gone for three weeks but it's not quite over New Year's, it's a little bit earlier and it's our honeymoon. So, it's a little different but I’m also very vocal with the team like last year I was “I’m going away for two weeks. You will not see me on email. You will not see me on Slack. See you in two weeks. I’m out.” And I want them to see that from me because I want them to take two weeks of vacation every year. I came back … Oh my gosh! I came back a brand-new person, right? I was re-energized. I was excited about what we were working on. I was missing my team. I hadn't seen them in two weeks. I was excited to start 2021. I want people that all the time. And so, if that means long weekends, if that means taking vacation, please go do it. And the thing I’m really, really loving these days is that in both email and Slack you can schedule send. So, it used to be Slack somebody at … for me it would be 6 o'clock on a Saturday and be “Please don't read this till Monday but I was out to dinner with a friend and I was thinking about this and it made me remember that I need to talk to you about this. And so, I’m leaving this here so that we can talk about it before I forget but don't read it right now” but then people see it and they read it and whatever. And now, I’m like “Oh, great, I can go put that in Slack and schedule send it for Monday morning.” And so, I try very, very hard not to send Slacks any time before 10 a.m., anytime after 5 p.m., anytime … it doesn't mean I always do it well but I try really hard to schedule that stuff and send it later because I also don't know what boundaries other people have just because I don't want to … or just because maybe I am working at 5 o'clock on a Monday, again, my colleague on the East Coast probably is not working at 5 o'clock. And so, if I schedule send, it's safe. They'll see it in the morning. Email being the same thing like getting those weekend emails is the worst since now it's like “Send first thing Monday morning” or sometimes …
Jayneil: And it’s from you. So, people are probably going to reply even if they don't want to.
Samantha: Exactly, yeah. And I know when it's me like if I get a thing from my boss or from our CEO, I’m “Oh my God” like instantly “Am I in trouble?” And then my second thought is “Okay, what is it they need then? How do I go do it right now and make sure they're not waiting?” I don't want people feeling that for me. I don't want them feeling like they're in trouble. I don't want them feeling they have to respond to stuff because … I think you have to work smarter and not harder. So, I want people to work fewer hours but I want them to be smarter when they do work like what are the things that are highest impact, where should they put their time today, how are we going to get the most out of them and do that in those fewer hours. And so, I don't want my team to think that they have to work 13, 14, 15-hour days just to be successful. I would way rather see someone getting all that work done in like three hours and pat them on the back and be “Great. Go off the rest of your day if you're that productive” like amazing “and teach us … teach the rest of us how to do that too.”
Jayneil: That's awesome. Oh my God! How can people find you or get in touch with you?
Samantha: I mean, all these usual suspects. There's always LinkedIn. I have a personal website SamanthaEBerg.com. You can check that out. I’ve got some things up there, some of the talks I’ve given, some articles I’ve written if you want to go hear a little bit more from me but otherwise, I think LinkedIn is probably the best way to get in touch.
Jayneil: Got it. Thank you so much, Samantha, for coming on the show. It's been a blast.
Samantha: Yeah, thanks so much for having me. This has been an absolute pleasure.
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