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- [00:13]
A
It's Emily Peck from Huffington Post. I'm here with Felix Salmon of Axios and Anna Szymansky and Julia Turner, who is editor in chief of Slate. And Julia has some exciting news for us. She's going to tell us about her new podcast, which is called Women in Charge.
- [00:30]
B
Yes.
- [00:30]
C
I'm very excited to bring Women in Charge before the Slate Money panel.
- [00:34]
D
And you've chosen a new, especially special episode to do that with.
- [00:39]
C
Yes. Dropped into this feed for your listeners. Delectation is going to be an episode of this show. I'm doing a six episode run as a woman in charge, interviewing other women in charge about the state and tactics and strategies of being in charge. And the episode that your listeners will hear is an interview with Sukinder. Singh Cassidy, who is The President of StubHub, started on Wall street, came up through a variety of big and small companies in Silicon Valley, and has also recently founded a company called the Board List, whose goal is to make it impossible for people to say, I just can't find a woman to add to my board by sort of crowdsourcing a list of very qualified women for boards.
- [01:21]
A
Before we get to that, which I think is so fascinating because that is the number one excuse you hear when people talk about why there aren't women on boards, can we talk about this whole idea of focusing on, for lack of a better word, or focusing on lady bosses, which I always find as someone covering women in business to be a little offensive. Like, women in charge implies that to my mind, they're not typically in charge or they don't want to be in charge or they're not fit to be in charge. So do you think by doing this kind of podcast, you're sort of like, invigorating that stereotype or breaking it down?
- [01:55]
C
Well, I will say that the genesis of this podcast was my frustration at sometimes being asked, what's it like to be a woman in charge? What's it like to be a lady leader? How does it feel to be the first female editor of Slate? And it's like, I don't know, man. I'm just a journalist. I'm just trying to run a newsroom. It feels like me, I don't know any other way to be in charge. And in general, I have a real allergy to, you know, sort of gendered assumptions about anything about, oh, women's newsrooms are so much more nurturing. Women are such caring leaders. Wouldn't the world be better if women were in charge of everything? It's like, no, women Are have talent and flaws. They have skills and weaknesses like they are individuals. And the reason to want more women in charge, the reason to want more people of color, to want more historically disadvantaged groups to rise, is not about the fact that the true best type of human has been somehow disadvantaged through history. It's that society at large has incredibly, stupidly thwarted the potential talents and contributions of huge chunks of society by suggesting that only a small chunk of society can contribute. So I get asked these questions and I'm like, no, women wouldn't be better leaders. But then I look around and I'm like, you look at the numbers of women in leadership at the top of industries, and you can't ignore that the numbers are dismal. And they're. They're dismal in places you wouldn't expect. They're dismal in places you would expect. We have not remotely come close to achieving parity in women in leadership positions. So this show is kind of a Trojan horse for me to just ask other women bosses, just about bossing, just about management tactics. Like, it's really, for at least the first chunk of each episode, kind of a pure corner office. Like, how do you think about leadership and inspiration and management and vision and all those tactical questions which I find fascinating.
- [03:54]
D
Is there a difference in the way that women answer those questions?
- [03:59]
C
No, I don't think so. And that's kind of the point. It's not about female styles of leadership. It's just about offering examples and instances of women who have really fascinating jobs showing how they think about leadership. Yeah. Because I would say that most of the shows that are out there that are the kind of CEO shows, they may as well be called Men in Charge, because, I mean, that's pretty much what you have. I guess I'm kind of curious because I know one of the frustrations I often have with when media is targeted towards women in business, it always becomes like, work life balance. Like, it's. It's a very different conversation. And I'm just kind of curious, in terms of when you're talking to people, is it. Are the most of the questions focused on just kind of similar to what you would say if you had a man? Or are there also questions in terms of specifics of, like, being a woman in this world? I haven't been asking questions about work life balance or gender. I have, I. I've sort of spoken focused in the first chunk of each interview on, you know, how do you lead people? How do you drive good outcomes and avoid bad outcomes like Literally, what are the tactics? Just trying to push and get them down to kind of granular examples of specific instances. And then also just as someone who's, you know, been running or helping run slate for 10 years, but who has knows how to deploy a set of tactics, I've learned on the job in a newsroom, but the opportunity to talk to leaders of totally different scaled organizations. I mean, I just interviewed yesterday the Surgeon General of the army who literally has 130,000 people reporting up to her. Like, that's a different scale. So just getting to ask her, you know, okay, like, if I have a thing I want Slate to do, I have to tell like 70 people that, you know, how do you communicate across the thing? So just asking really tactical questions, that's been fun. And I've not been focused on like, and what about the kids? And you know, so it's like a.
- [05:45]
A
Stealth breaking down the stereotype, basically. Cause you're having this Women In Charge podcast, but you're not asking any of the questions that typically get asked of Women in Charge.
- [05:55]
C
Yeah, I mean, the place where it's come up is that in the second half of each conversation I do ask, how are things for women in your field? How do you think they're faring compared to when you started out? And most of the people I've spoken with for the show do end up talking about how some of the barriers to female advancement over time can center around those things. I mean, I interviewed Aline Brosh McKenna, who wrote the Devil Wears Prada, one of the most iconic female bosses ever in that movie, and runs the Crazy Ex Girlfriend room. She's the showrunner for that TV show. Just talking about how the culture of TV rooms was. A bunch of creative dudes show up at 2 and then they spend three hours arguing about whether to have pizza or Chinese. And then like they settle down to work at 6pm and then you're there till the showrunner says so. And so there were a bunch of people who cared about family life, men and women who were just like, ugh, TV writing. Like, that's not for me. And so she prides herself on running a room that's like, we show up at 10, we're done by 6. Like, this can be organized. It is possible to be creative within a predictable schedule. And we still fuck around and all watch YouTube sometimes. But this is a move I've made as a woman to try to increase the talent pool that we're working with.
- [07:06]
A
And should you tell us about the episode that we're going to put in the Slate money feed that you're about to hear, listeners.
- [07:11]
D
And specifically, can you tell us about this whole concept of board qualifications, which is what we were just talking about on the last episode, and what it is that qualifies someone to be on the board and whether that whole idea should be broadened out?
- [07:28]
C
Yeah, I mean, I think the argument that Sue Henderson Cassidy is making is that boards would be more effective if they had quicker turnovers, if they had more young people on them, more people who are connected with the forward looking trends in the industry. You know that just generally the kind of makeup of boards is the turnover is slow. They tend to be people, you know, kind of lions at the end of their careers. And that given the pace of transformation and change approaching boards broadly, even separate from the questions of just ethnicity and gender, could be really valuable for businesses who are trying to navigate this particular moment and then that women are amongst various groups of people, haven't typically been represented there and might have valuable perspectives. She has worked in a bunch of consumer facing businesses and also pointed to the fact that women as a consumer sector are driving the success or failure of these businesses. And so the value is there.
- [08:25]
A
How is she finding candidates? What is she doing that other recruiters don't do?
- [08:30]
C
Do you know, it is a crowdsourced network. So basically what she's doing is creating a network where people nominate people they know. And one thing that she talks about being proud of is having success with the, with the kinds of folks who say, I really want my board to be more diverse, I really need to find more women for this board. It's like, well, who do you know who could be on a board for something? Maybe they're not right for the board for your company. But like let's start every, everybody must know somebody who would be qualified, who would be interesting. And let's begin more explicitly making those.
- [09:06]
D
Okay, one other question. How rude are you to these women?
- [09:11]
C
I think what you're asking is, are CEO interviews bullshit?
- [09:14]
D
Yes, that's what I'm asking.
- [09:16]
C
Yeah, I mean I think there's like a broader challenge in management coverage where if you're, if you're ever trying to write about how to be a good boss, how to be a better employee, like the sort of kind of productivity mindset, Tim Ferriss type of business journalism, that there is a certain type of consumer who's like, everybody should not be focused on like self improvement and making themselves a more effective worker and then a more effective boss and then a more effective Leader like we need to look at systemically, you know, what the power dynamics are, how fucked up this all is, and individual self improvement and the Horatio Alger model as a mode of business coverage is fundamentally corrupt and lame.
- [09:57]
A
But how do you get these people to. I mean, the problem with interviewing CEOs and any top executives is that they, they just spew bullshit and talking points. They don't say anything remotely or real like, at least to start with. But I noticed, I listened to the interview you did with the university.
- [10:12]
C
Oh, Anna Marie Cauce.
- [10:13]
A
And it's sort of, it doesn't start out like bullshit, but it starts out and she's kind of just like. And it feels like she's said all the things before. But then as you go on with the podcast, I feel like she comes out of her shell a bit more and tells you some really interesting things. So how do you make that happen?
- [10:28]
C
Yeah, I mean, look, I'm fairly new at doing two way interviews for podcasts. Part of what was fun about this was that it was a learning experience for me. The way I approached these interviews was not trying to gotcha these folks about the state of their business. Like, what I was interested in was, is how do you drive the outcomes you're trying to drive? And not like, are those the right outcomes or are you fundamentally corrupt or whatever. I'm just trying to get to how do you think about moving a big organization of people to achieve an end? How do you think about that? And definitely for each of them, there's like the first few minutes and we've mostly tried to cut it back as possible. You can hear the talking points and the stories they've told before. And what I've been trying to do is get granular and get down to a level of insight and information that feels revealing and useful. And my bellwether for that has just been like, ooh, does this feel like something I could use when I think about running stuff?
- [11:21]
D
But you're a woman in charge. And I have to say, I mean, I'm not even a man in charge. I like, if I'm not in charge of anything, why should I care about this?
- [11:30]
C
I think that management is fundamentally psychology. It's like, how do you get people to do shit? And you cannot tell me you've never tried to get someone to do something, Felix, because I've been on the receiving end of that. And so even if you're not managing a company, you are constantly managing your own life. I find them psychologically fascinating. And to me, the psychology of it is the part that is interesting, and that's what I was chasing.
- [11:56]
D
And, Julia Turner, now that you are going off to the cultural wasteland of Los Angeles, which is a stereotype we need to break because there's lots of interesting stuff going on.
- [12:05]
C
Los Angeles is far from a cultural wasteland.
- [12:08]
D
There's lots of very awesome cultural stuff going on in Los Angeles. The question is, are you putting yourself forward? Are you gonna be on board? Because you should totally.
- [12:18]
A
Oh, yeah, you'd be perfect.
- [12:19]
D
Awesome leader.
- [12:20]
A
I'll put you forward.
- [12:23]
C
I'm gonna be fairly busy with my new job, I think, for the moment, but someday I aspire to be a lofty board member.
- [12:29]
A
It is the best job you could possibly get. Don't you agree? I mean, the pay is great. You show up, what, quarterly. You read a few things, pass judgment.
- [12:37]
D
How hard can it be?
- [12:38]
A
What's the big deal? I'm ready.
- [12:41]
D
Okay. So here is Julia Turner interviewing Sukinder.
- [12:45]
C
Singh Cassidy on Women in Charge. Women in Charge is brought to you by the Business Platinum card from American Express. Platinum enhances life's moments, both big and small, so that you can do business to the fullest. Don't do business without it. Welcome to Women in Charge, a podcast about women who are in charge of things and the things they are in charge of. This week, I'm speaking with Sukhinder Singh Cassidy, the president of StubHub, the online ticket marketplace. She's also the founder of the Board List, an organization that helps corporations find qualified women to join their boards. Today we talk about the importance of letting your employees see you be imperfect, what to do when you're told you're too aggressive, and why it's useful to have fresh voices on corporate boards. Hello, Sukinder. Welcome to the show.
- [13:29]
B
Thank you for having me.
- [13:30]
C
Let's start with your career. Tell us what you are currently in charge of.
- [13:35]
B
I currently run StubHub, which is the world's largest ticketing marketplace for fans to get access to live events.
- [13:41]
C
And how would you describe what you're trying to get the people you're in charge of to do every day? What's a good outcome and what's a bad one?
- [13:49]
B
I think a good outcome looks like the following. Number one, Waking up every day and making decisions based on a fan first mentality. So driving customer centricity. If I see people who kind of make spontaneous and sometimes high risk decisions, sometimes low risk, but in any case, all decisions with a customer orientation, I consider myself having had a successful day. Number two, I think My other job is to get people to value progress over perfection. I think as an entrepreneur and also somebody who's been at high growth, high scale companies like Google, I think the fine art between those two things is getting people to move and make material progress even if it's not perfect. And the larger an organization gets, the more I see a tendency towards perfection over rapid progress. So I feel like if I can get people to iterate faster towards a fan first journey, I'm having a successful outcome.
- [14:48]
C
So how do you tackle that? Suppose you've got an employee and they're working on some project or other and their approach, they're hung up on getting it exactly right. How do you try to break that mentality?
- [14:59]
B
It's a great question because it's easier said than done, right? So I try to lead by example. Meaning if I am trying to get something out in a month, I will do my best job or try to get something out at 80% and show it to our employees. When it's at 80% and I put it up in front of employees when it's not perfect. You know, at a recent town hall or something, I owe folks and I say, hey, this isn't perfect. But I chose to get it out quicker to get your reaction versus kind of laboring over my words. What do you think? And I try and do that a lot. I try and do that in large company events and I try and do it in small meetings where I'll throw out a hypothesis and say, do I have it right? If I don't have it right, tell me where I've got it wrong and you know, let's rapidly try and get to a decision. So I think one of my biggest strategies is sort of being pretty imperfect myself and trying to feel like there is always forward movement in my conversations with people and my own interactions with big groups and small and hoping that that is a big part of helping other people feel comfortable doing the same. Because to your point, I mean, to just say to somebody, hey, don't be perfect, progress imperfectly. Instead, when you're the CEO, I mean, who doesn't want to look perfect in front of the CEO? Most people want to look perfect.
- [16:22]
C
Yeah, that's such an interesting philosophy. Especially because I think one of the, you know, classic lines about how underrepresented groups can succeed in fields where they're not represented is sort of be twice as good. Right? Like that's the work twice as hard and be twice as good as the old saw. But sometimes leadership involves redefining what good is or being able to display and be comfortable with not being perfect and not getting everything exactly right? Have you ever experienced uncertainty about whether to show that vulnerability of not having it all totally nailed down? How did you find comfort with just showing what you've got at 80%, if that's what you've got by the time it's time to share?
- [17:05]
B
I think a couple things. Number one, just to go back one step, I always say to people, you don't need to be perfect, but you do need to be thoughtful and find the balance between thoughtfulness and speed. So really what I'm looking for at 80% is somebody has put together the bones for a compelling conversation and even a recommendation and then is sort of seeking feedback, whether that's through data, whether that's through experimentation, whether that's through a test to come back and inform the next decision. So I'm always looking for sort of people who are hypothesis builders willing and unafraid to put out an opinion that's only partially informed by data, with the desire to get feedback, you know, human feedback, verbal feedback, you know, data through a product iteration and then kind of inform their next set of decisions while operating still with a broad hypothesis. So when you think about that framing of it, I feel like having been an entrepreneur multiple times, you're forced to do that, you have no choice because by definition an entrepreneur is putting something out into the world that hasn't existed before. And particularly in tech, the trade off between being perfect in speed and may be the difference between you being late to a market and somebody else having gotten the lion's share of venture funding. And conversely, the problem with being early is you can be perfect and early and the consumer isn't having anything of what you're dishing out and you're going to have to pivot multiple times to get to something that is the kind of unlock with the consumer or a product that has product market fit. Either way, whether you're early, whether you're late, you're always iterating as a consumer entrepreneur and you're always, always iterating with at best partial data, often no data. And your job is to put something out into the universe in order to get data back.
- [18:49]
C
All right, so you encourage the approach that you hope to see through example. So with the other focus you mentioned on the fan first mentality, which is, I'm sure how you describe it at StepHub, but you've worked in many different consumer facing companies, thinking about the user first I think is maybe the Broader, more transferable way to describe it. How do you foster a workplace that's thinking about the user experience in a holistic way?
- [19:15]
B
So first and foremost, I think you've got to bring the customer near and you've got to make the customer kind of very tangible. Right? A perfect example. Right now at StubHub, we are doing the next level of our customer segmentation on who our customers really are.
- [19:30]
C
Right?
- [19:30]
B
And of course, we've been informed by data and research. But the most compelling things we ever do in terms of fostering customer centricity are when we do things like bring a panel of customers into the building and have everybody from engineers to product managers to people in corporate security listen to what a fan or user has to say about his or her experience. We have a quiz where you can identify what type of user you are. That's on the mobile phone that every one of our employees takes. You know, right now, on our management team at StubHub, what we do every week is listen to a customer journey and a call from the call center. And we just literally listen to 5 to 7 minute call as a customer's having a problem and customer service rep is trying to solve their problem. And many times you see the people in the room cringe because they just know it's not the experience it could be. But it's visceral. So I think part of what you have to do when you talk about customer centricity is make it very visceral. You know, we do things like giveaways at StubHub at any live event, we may be giving away an upgrade to an unsuspecting set of fans. By the way, posting those things on Slack and on Instagram do more for employee morale than any dozens and dozens and dozens of pages I can put up on a corporate website about our consumer strategy. So for me, I think again, when you think about fostering a fan first mentality, I always think that in most cases, proximity matters a lot. And bringing the customer closer to your users or your employees, sorry, and your employees closer to the customer. And creating, you know, I would just say as many, many interaction points as you can is probably one of the most compelling things you can do to get people to really be thinking about the customer all the time. Otherwise, as I said, I think it's very easy to get siloed and get distant from a customer pretty quickly. It's so obvious. But I don't think nearly well done enough. And I think the companies that do it best, that are large, for example, might Be, you know, people like retailers where every day they live and die by their merchandising decisions and have, you know, data from their online website or for their stores coming in and comping hourly, you know, and then are sort of rapidly kind of iterating on those decisions to make a new set of choices for the consumer. And they do that because they get real time data literally from store associates and from the website, you know, every moment. And they, and their job is to make that very literal and very real time and really, again, bring that customer choice proximate to your employees each and every day.
- [22:08]
C
You've been in leadership positions at many companies, from Amazon to Google to Joyous and now StubHub. How much of your management philosophy is consistent from place to place and how much do you tailor it to the particular problem set that you're facing or the scale of the organization that you're leading?
- [22:26]
B
So obviously I've been in companies big and small, having been an entrepreneur and then places like Google and Amazon as they were scaling rapidly. So kind of part of the journey to scale. StubHub certainly was at scale when I arrived. I think the parts of my management style that are consistent are probably not a surprise. Progress over perfection is a constant. Big company or small authenticity. Feeling like as a leader, my job is to show up imperfectly, but with people knowing I care deeply and I'm committed to transparency. That philosophy holds. The other philosophy that holds is I look for people, large companies are small, who have what I call a lot of operating range. And by operating range, I mean people who can go high and think about strategy and people who can get low and think about execution and people who are willing to fill in the gaps, you know, that exist outside of what is technically their corporate responsibility or their functional responsibility to just get it done. So I think that sort of bias for people who own totally bias for execution, authenticity, you know, kind of imperfect, imperfectly showing up, but progressing rapidly. Those are the things that are pretty constant across big companies.
- [23:35]
C
Small. Are there any things that change or that are different?
- [23:38]
B
Personally, I guess the big thing that changes is how you're working. Are you working through others, you know, or are you kind of working alone? Right. And obviously as a company gets bigger, you're working increasingly through others. Right. To influence rather than just directly do. But as we pointed out, even in, I think organizations that are pretty large, I try and be hands off and on enough that people can still see examples in action, if that makes sense. Right. Like, I don't really like the idea of, you know, somebody, you know, telling my story for me perfectly and then I, you know, come on at the end to like do something ceremonial. I'd rather be in it all the way. Even in kind of large company situations, I'd rather be hands on. And so I would say the biggest, the biggest thing for me is influence versus direct action. But I would say even at a large organization, I feel like my job as the CEO is really to be hands on enough to show people that I'm willing to walk my own walk.
- [24:32]
C
When you're working at a bigger institution and working indirectly through people, I mean, even the point you were making earlier about communication, right, Bringing the user experience to the center of whatever the company is that you're working on, it's one thing to probably do that on a team of 20 where you're working in a small slack group and communicating all the time, and another to create structures across a company of hundreds or thousands where everybody's getting the same inputs and experiences. How do you think about getting the results you want through managers who are reporting to you and working for you across a big team?
- [25:06]
B
Well, first of all, I think besides operating range, the one thing I look for in managers, particularly as I have gotten older, I'd like to think wiser, but certainly older, is I look for leaders who can do what I call managing me. So if you think about the scenario where you're trying to build scale and leverage, I think one of the flaws in management thinking is that the more people you put inside of an organization, the more you quote, unquote, manage, right? I happen to think that as an organization scales, your primary job is to surround yourself with people who manage you. And people are like, well, what do you mean people who manage you? And I'm like, well, you want people who walk into the room with solutions, not questions. You want people who walk into the room with an opinion. You want people who walk in the room having framed a problem with three options and are looking for your insight to get to a better outcome, but they're not looking for you to define the problem and define the outcome. And so I am best managed actually in this company. Scale. How do I scale and how do I scale my message? Because I, I try to surround myself with people who not only have great operating range, which is that ability to go high and low, but I look for people who effectively manage me. And that means that they can sort of take control in some ways of their own destiny by painting a picture and having a strong sense of their own narrative. And sense of direction and where they want to go, and then getting my buy in as opposed to walking into a room expecting me to outline the problem and the solution and how to get there.
- [26:35]
C
One thing that strikes me as challenging about coming into a leadership position at a new institution is you have to evaluate potentially huge group of new employees and assess what is their operating range, can they manage you? How do you approach that process of understanding the contours of the team that you're coming in to lead and assessing their strengths and their weaknesses and where they can contribute best?
- [27:01]
B
I definitely like to skip a couple levels and get exposure very quickly to multiple levels of an organization. So in the case of StubHub, obviously my ability to assess where my own leadership team is at is pretty high, given that I have high frequency interactions with them. Right. I'm seeing them every day and every week and multiple times a day, sometimes when we're talking or trying to figure something else. So the ability to assess somebody close in, as you pointed out, is not that hard if you have high frequency interactions and a lot to do together. The issue is, I think, how do you look at your senior manager talent and your director talent and your senior director talent and all of the levels right below, which, to your point, if you don't see it, you don't. You know, you may be relying on a group of people to manage you, but what happens if kind of the next level down, your leadership reports are spending all of their time managing others rather than themselves, getting leverage right from their direct reports, so. Or their kind of leadership ladder. So for me, I think the big thing that I attempted to do at StubHub and StubHub is really, to be honest, the only place I've ever arrived where the company's 15 years old and I arrived as a leader almost everywhere else I arrived and I built right at Google. I mean, I was there, relatively speaking, in the early years at Amazon. I was there, relatively speaking, in the early years and saw rapid growth. Certainly the culture was there, but it wasn't nearly as developed as a 15 year old company. And the rest of my time I've spent building my own company. So I think in a case where you're inheriting a culture, it's even more important, I think, to go very, very quickly to create situations where you get to see directly what levels the level two or three below you can do and obviously and then get very directly and immediately to hear the opinions and kind of get a pulse of the organization from people at every level. So for Leadership. I'm looking to create interactions pretty quickly with, as I said, two to three levels below kind of my leadership team.
- [28:59]
C
How do you do that just like actually tactically and not just be sort of the CEO or the president showing up in the call center to eavesdrop? How do you make that those encounters productive?
- [29:11]
B
A good example at StubHub, I don't know if everybody loved it, but I think in hindsight they loved it. When I arrived at StubHub, I think within a month we did what's called an H2 review of like the projects we wanted to undertake for H2. And I told my leadership team, I'm like, you cannot pitch these projects like I want to get. I want the kind of people who are managers, senior managers, directors, I don't care about title. The people who are doing the work should come in and pitch the projects and they should pitch them cross functionally. They should get together with a finance person, the business lead, the product person who's working it, and the engineers. And I want that group of, you know, subtem people to walk in and pitch their idea. And so, you know, H2, sorry, forgive.
- [29:51]
C
Me for the less, the less business savvy. H2 is like second half of the year, right?
- [29:55]
B
Second half of the year, yes, exactly. So as I arrived, I had to figure out, where are we going to spend our time for the second half of the year? So I could have turned to my direct reports and said, hey, cascade me down a plan of what we do next. And instead I said, okay guys, pause. I don't want to hear from you. I want, I want to hear from, you know, your direct reports and in some, you know, two or three levels down. I want the people who are doing the work to come in and pitch and feel like they're empowered to pitch. But that also brings with it an accountability. And for me, I got insight, I don't know, very quickly into the next 100 people in the organization. And it turns out at a company StubHub size, I mean, you know, we're 2,000 people. But you know, you go to kind of employees, kind of 10 to 200 or 300, you get it. You know, you're getting pretty far deep in an organization. And then separately, I went directly onto Slack and set up office hours one on one and just let anybody from the company come in every week and set up kind of 10 minute conversation with me and tell me whatever they wanted. So I continue to run one on ones that are direct with any employee who wants to sign up Women in.
- [30:59]
C
Charge is brought to you by the Business Platinum Card from American Express. With the Business Platinum Card, you'll earn membership rewards points on virtually all business expenses, and you can turn those points into anything from new supplies to flights, one perk access to over 1,000 airport lounges worldwide. That will give you a calm space to get in the right headspace. Or Platinum can help you find that hidden gem for the best working lunch in town or get a few hours of me time after Facetime with clients with guaranteed 4pm late checkout at over 1000 fine hotels and resorts worldwide. That's the powerful backing of the Business Platinum Card from American Express. Don't do business without it. Terms apply to all benefits. Visit americanexpress.comexploreplatinum for more info. You've spoken in the past about, I think got your start or early in your career, spent time at Merrill lynch, and you've spoken about having been perceived differently as a woman in finance in New York versus when you first arrived in Silicon Valley and began working in entrepreneurial tech ventures. Do you think that those industries treat women differently?
- [32:00]
B
I think in general, one could say finance went through what tech is going through now, like kind of the reckoning of how they treat women. I'm not saying it's rectified, but if you were to look at the 80s and 90s right in wall street, you know, you would see the same articles posted about Wall street that are now being posted about entertainment and tech. So I think finance might have had its many me too moments. Not that they're over by any stretch, but certainly the crisis of where are all the women? You know was something that was talked about 20 years ago, I think, in entertainment and tech, that's a conversation of the last three to four years, and we would probably agree the last 12 months in particular. So that's a macro lens. My specific experience is actually weirdly the opposite, which is I arrived on Wall street kind of, you know, wet behind the ears, from St. Catharines, Ontario, Canada, where I grew up and went to college at the University of Western Ontario and arrived in New York, relatively speaking, not knowing what to expect in green. And I had a phenomenal experience in finance. I ended up working for a managing director on a potential IPO was one of my first projects, and he loved working with me enough and I loved working with him enough that he sort of bypassed the regular staffing rituals and would staff me directly on projects with him instead of putting a lot of layers between us. So in finance, interestingly, at Merrill I got a lot of exposure to senior people and senior projects early on from virtually the day I arrived. And so interestingly, by the time I arrived in Silicon Valley, having worked at Merrill lynch and then at News Bsky B, where I had similarly got a lot of exposure, I arrived in the Valley at year five or year six of my career pretty confident that, you know, I was really good at my job and people would trust me with a lot of responsibility and having been treated, relatively speaking, well. And then my first job in the Valley on day two, my boss told me I was scaring the secretaries, I think because he sort of perceived me as being too aggressive, which was kind of shocking for tech. And by month six, I'd quit my first job because I just felt systematically that something was off and I was constantly getting more junior assignments and being told I was, quote, unquote, the rookie on the team, while I saw a more volatile male colleague being constantly rewarded for his behavior. And I did nothing wrong. But I guess just by showing up and seeming overly aggressive, I was sort of not feeling a lot of love at my first job in the Valley and I quit. So ironically, my micro experience has been the reverse, but at the macro levels, yes, I think there are parallels.
- [34:30]
C
Interesting. So tell us about the board list and what the impulse was behind it.
- [34:34]
B
Well, I think it continues on that narrative of sort of what's going on for women in tech. So I think I identified that my first experience in the Valley wasn't great. But then I quit that job and went on to join a startup that was subsequently acquired by Amazon. I went from there to starting my first company, Yodlee, which was an amazing experience. I went from there to Google and the rest of my career unfolded ironically. Kind of textbook style meritocracy, where the better I did, the more opportunity I got. So despite that first interaction in the Valley, my next 16, 17 years were largely ones where I felt like I found my tribe. My aggressiveness was more often than not welcome. Now keep in mind, my functional background was business development and sales, so you can imagine that that's probably a job area where aggressiveness is welcome. That's how I grew into a general manager. Right, was through that path. So nobody was ever scorning me, right, for being overly aggressive. After that first job, kind of flop. But I think it was 2015. I remember continuing to see the headlines about how terrible tech was for women. At the time. I was an entrepreneur running a company called Joyous and I really felt increasingly that a I had an opportunity and Responsibility to tell women that in fact tech was not such a terrible place to be. And if you want to control your destiny, all things being equal, being an entrepreneur is one of the best ways to do it. And number two, recognizing and remembering that awful first experience I had where somebody just judged me to be too aggressive, right? And that sort of shut out opportunity for me. And hearing the horror stories from younger female entrepreneurs who were trying to get and raise money at the same time that I was an entrepreneur. And while I had it easy, relatively speaking, the stories I would hear and encounter were so appalling that I felt like I was facing this duality, which is I wanted to encourage women to come into the field. And number two, I wanted to acknowledge that something is broken and needs to be fixed. And I think that combination, along with feeling like I had an opportunity to give back, led me to want to create some solutions to the problem of women's advancement in tech. And the board list was really born of that frustration. Plus the desire to see us change the system from the top, from corridors of power, not just acting like every problem with women in tech is a function of us not having enough girls entering engineering, which is another problem. But it's certainly not the reason or the excuse that people can use for the lack of women in leadership positions in tech.
- [37:10]
C
So describe how the board list works.
- [37:12]
B
Sure. The board list is a curated platform. Think of it as a LinkedIn for boards where CEOs and senior executives with board experience nominate great women they know for board opportunities. And companies early stage, mid stage, late stage private public who are looking for female board members can log in and find an amazing, highly curated set of diverse talent for their boards. That kind of hopefully shuts down the question once and for all, where are all the great women? It sort of seeks to solve the problem of, or the perceived problem of lack of supply by making available outstanding, curated a diverse talent for boards in an easily accessible place by crowdsourcing it.
- [37:54]
C
Right. So you, you shut down the, the pipeline problem defense for people who have a board with no women on it and say, well, they're just, it's, you know, there just aren't that many women you could find, say, well, here's a list.
- [38:07]
B
Well, we're only two and a half years old, but we're on our way to shutting it down. Let's say, let's put it that way. We definitely do hear the board list quoted increasingly as a solution when people say, I don't know, I don't know any great women from My board, we definitely. I do hear folks referring them to us.
- [38:21]
C
Well, I first learned about it a few months ago, and then someone was complaining about they were trying to find a woman for their board. And I said, I just heard about an institution that you should consult.
- [38:30]
B
There you go.
- [38:31]
C
I am not on a corporate board. I suspect most of our listeners are not on corporate boards. What happens on a corporate board and why is it important for women to be on them?
- [38:38]
B
I would say it's important for any leader to be on them, interestingly. Right. I wouldn't. To your point, I wouldn't classify that only as sort of something women should consider. Men should consider it, too. So corporate board is obviously a body or group of people who are there to look out for the interests of shareholders of public and private companies and advise effectively the company and the CEO on strategy and execution by bringing a diverse set of perspectives into that room. If you think about why you should sit on a corporate board, if you have expertise in a specific area or overall as a leader and a, want to give back, and B, feel like you are learning yourself from a diverse set of perspectives and to some degree upping your own leadership game, sitting on a corporate board is a great way to do it. You know, if you're a sitting CEO, you get to use the expertise you have in service of someone else or some other organization while observing how other people handle problems that you might encounter in your own day job. And if you're retired, it's a way to stay connected and use all the expertise that you've amassed over many years. Again, be it specific or be it general management expertise, and to apply it and feel like you can still have an impact.
- [39:48]
C
And why is it good for corporate boards to have more perspectives than they typically have had?
- [39:53]
B
Well, let's think about what corporate boards are going through. Almost every. Well, I would say 100% of boardrooms in the world right now are going through multiple challenges. Number one, technology disruption.
- [40:04]
C
Right.
- [40:05]
B
The pace of change. Everybody talks about it. It's a cliche, but it's also true. Technology is disrupting virtually every industry. And so having a lens on where technology is going would be important. Number two, customer demographics are changing. You have the new millennial customer. You have women who now account for a lot of economic power and are the chief kind of financial officer of most households. So you have these dynamics. And then you may in your own industry going through a whole other set of changes. But let's just even talk about sort of shifting demographics of your customer. Corporate technology Change. And I'd say the last important change that's going on in companies worldwide is a changing workforce space, right. Whether or not you are contending with people who want to be on flex time, whether you are contending with people who might come from underrepresented backgrounds, whether you're contending with a young workforce that is about to go through lifestyle changes, including a big part of your workforce that are going to become mothers and fathers and, you know, married or, you know, mobile. You know, these are all changing dynamics in today's workforce that you also need to think about. So if you think about employee base, demographic based technology change, the reality is you need new perspectives even to be able to take advantage of those three things. But you know, what happens on the average public board. I mean, tenure of a board member may be, you know, far longer than two or three years. It may be seven, eight, nine, ten years. I mean, there are corporate boards where literally people stay on as long as they possibly can. And so you have a situation where you have boardrooms where the perspectives inside the room are not relevant. Right. They don't represent the next generation employee or the next generation customer, or have a perspective on the technology advances that may be impinging on your business. So what do you do with that? I mean, how does a company stay current if its board's not current? Like literally how?
- [42:03]
C
And so having more types of people, younger perspectives.
- [42:06]
B
Yeah, absolutely right. And then of course, there's just the good old fashioned run a better company, right? Even aside from all of those changes, we all know the science around the wisdom of crowds versus a single person's decision. So if you want to be a better leader, why, you know, there's proven data around the decision making prowess of groups versus a single individual. So. So why wouldn't you up your own chances of success by having a group of advisors who at a minimum give you a diverse perspective, even if it's on a very traditional problem. Right.
- [42:38]
C
I want to zoom out a little bit to how you think women are faring in tech more generally and particularly thinking about their prospects for taking on leadership positions within particular companies and within the industry broadly. Just as a baseline. Do you think things are better or worse for women entering your field now than they were when you were first starting out?
- [42:58]
B
I think that things are better if I look at two or three kind of specific areas. So number one, while the absolute numbers of dollars as well, the relative number of dollars going into female backed startups is not moving fast enough in terms of women starting companies. At an absolute number of companies started by women, we've seen kind of a dramatic uptick over the last few years. If we look at sources of capital for women and women controlled venture firms, that's also on the rise. And women angels, which means, you know, women as investors in other women is another kind of rising trend for us. Although the numbers are small. And then number three within entrepreneurship, if you look at the women who are, you know, building what we would call unicorns in the Valley, companies that have a valuation of over a billion. Look at Stitch Fix by Katrina Lake. Look at the Real Wheel by Julie Wainwright. Look at Julia Hartz is about to take eventbrite public. Look at Adi who's running Houzz. These are all unicorns by the way. De China. I mean not so good an example recently but you know, arguably one of the biggest companies in the world in ride sharing has a woman as president. I mean if you look at all of these examples, you have the first kind of massive examples of women who are building multibillion dollar companies in tech that serve as role models for other women on what's possible and quite frankly may give male venture capitalists for the first time the fear of missing out if they don't back a female entrepreneur. You know, there's nothing, nothing cures discrimination like the fact that you missed out on somebody you pass and thought was not worthy who turned out to be not only worthy, but very worthy. So in entrepreneurship I am a bull though the numbers are small just because of the trends I see around women trying to becoming, becoming able to invest in other women and control capital Even if male VCs are not kind of investing at the same rate. And examples of successful outcomes in corporate tech, you know, you define as the big companies, as you know, the numbers are very challenging in two areas, engineering and kind of of most senior level.
- [45:03]
C
Right.
- [45:03]
B
If you look at business roles, I would argue that the Valley has both great examples of women who are successful who come from a non engineering background. You know, Susan Wojcicki at YouTube, Sheryl Sandberg certainly at Facebook, Safra Katz at Oracle. I mean there are increasingly numbers of women who have risen to kind of the top of tech without an engineering degree that serve as role models. I think at the middle levels, I think companies are trying to contend with the practices that allow women to stay in at the tougher parts of their career when they are caregivers, when they are having their second and third and fourth children. And I think tech companies have different strategies to attack that. So I Feel somewhat encouraged by the practices that people are going over to try and keep women in at these critical parts of their career where they then can be groomed to be senior talent and rise to the very top. I think the place that I'm most challenged is the engineering numbers almost everywhere are dismal. I mean, they're dismal. Right. And the progress there is very, very slow. So it's hard for me to claim any kind of sort of reason to believe that those numbers are going to accelerate faster. And I can't give you one, I don't have one. But at least in two to three parts of two of the three parts of the ecosystem, I feel like we are seeing progress and there's, there's a path to tackle. I think computer science is sort of the new liberal arts is one of kind of the remaining things that needs to be tackled if we want to see more women kind of embracing design thinking, even if it's not engineering, but makership in colleges and computer science.
- [46:41]
C
By that you mean building computer science more deeply into the base level curriculums in high schools and colleges?
- [46:48]
B
Yes. Even if you can't make women engineers or drive kind of engineering outcomes to the extent that you can drive computer science science within the basic school curriculum, as Princeton has done, I mean, an astonishing number of its undergraduates take computer science in their first year. If you could at least train design thinking right, then you can create makers. Because I think we tend to identify that makership is strictly the realm of engineers. And of course I believe that you can be a maker without being an engineer. But you do need design thinking capability. And I think teaching that to our girls is super, super important.
- [47:22]
C
What do you think accounts for the places where there have been progress versus the places where they're. I mean, it sounds like in the question of who's getting their ideas, who's finding backing for their ideas. It sounds like good old desire to make money is an incentive there.
- [47:38]
B
Yes, yes.
- [47:40]
C
But in these other areas, what accounts do you think for the fact that.
- [47:44]
B
For progress?
- [47:45]
C
Yeah, that there's sort of more progress in the kind of senior business leadership areas and in using some of the resources available in tech to look at the benefits packages for mid level female employees in ways that might support a more durable and sustainable career versus this? I mean, the engineering problem is another pipeline problem, right? I mean.
- [48:05]
B
Yeah, that is a separate pipeline problem, Right. I think in the areas that have been progress, I think greed in venture capital will drive progress. And I think within venture capital and corporate tech Shaming. I mean, I'm just being serious, right? Having to report your numbers every month makes people, you know, more likely to accelerate their efforts and insist on the building of, let's call it a diverse pipeline. For every leadership role, consider looking at women, lateral in the organization, who you might want to take a bet on, or obviously underrepresented minorities or communities. So I think shame honestly has a big part to bear in this. I know that sounds sad, but it's true. And I think if you were to take kind of the more positive spin on it, you know, one of the things that is true about the Valley and tech is it is like a huge consumer of talent, right? Like the appetite for talent in the Valley is ridiculous because there's just, you know, always another company, always another large, you know, large division to run at Google, always another, you know, castle to storm at Amazon. And so the one thing that is promising besides shame is just that people are always looking for strategies on talent to unlock all the talent. And it turns out that, you know, at least half the world's talent is female. And if you want to get access to it, you better get more flexible about what it takes to create an environment in which those people want to participate. And certainly the same holds true for underrepresented communities. So I would say the more positive spin on corporate tech would be that people are hungry for talent. And so you have to increasingly think about strategies where you actually go get all the world's talent, otherwise you're literally not going to be able to get all your jobs done. So that's the other good thing that happens, right? When industries rise as tech has risen and are sort of on one of the longest bull runs in is the tech industry and ecosystem. There is always demand for talent and that creates its own pressure to come up with innovative solutions and stop considering that you're done at just all the white men.
- [50:09]
C
I could not agree with you more about that. I want to take our last five minutes to bring us back around to one more question that's sort of more ground level management rather than the macro questions, which is just about spotting that talent and finding those people who do have that bandwidth and that operating range, as you called it.
- [50:26]
B
What do you look for?
- [50:27]
C
Like, what are the things you look for in employees, even the ones you're interacting with daily, that help you recognize both what they're currently capable of and what they might be capable of as they grow?
- [50:41]
B
Things I look for, I look for histories of success and failure, that is, people who haven't only ever been in one environment and been successful. So I look for variety, certainly of success and failure. I look for being successful in large and small operating environments. I mean, my favorite people to hire have both been at a large company and been at, let's say, a startup, because I know they understand the difference between the two, and they have been being able to be successful in both shows me, you know, how to adapt, right? Your skill set and your needs. I always look for people who are doing more than what their job title requires. Always. So, like, if you want to know where you've got a successful employee, look at the person who, you know whose job title is X and who's doing job X, job Y and part of job Z, and you will have found yourself a star in some ways or not.
- [51:32]
C
Right?
- [51:33]
B
And then I look at people who just want to own entirely. And, you know, I don't know about you, but if I think back to, you know, my own childhood or my own track record, you know, even at Merrill, I told you about that great first experience. It was just because I couldn't help myself. I couldn't help but, like, want to, like, like, do all of the work, not just the part that was assigned to me. And I'm not saying that because I'm so brilliant. I'm just saying that I was wired that way, right? And people saw it and they gave me opportunity. And so I'm always looking for people who want to step outside their hole or already have. Not, like, want to. They're just demonstrating it every day, no matter what their job is, that they'll do whatever is needed to get the job done, even if it's not in their job description. Those are the things I look for.
- [52:14]
C
Terrific. So, Gander, thank you so much for taking the time to talk with me. It's been really fun.
- [52:18]
B
Thank you for having me.
- [52:20]
C
And that's our show. Our producer is Jessica Jupiter. We had additional editorial support from Cleo Levin and June Thomas. You can email us@womeninchargeleet.com with comments, feedback, or suggestions for women we should interview. And please don't forget to rate and review this show on Apple Podcasts or wherever you listen. We'll talk to you next week. Sam.