Women's Leadership Series with Lisa Caputo

Happy to join you. It's my pleasure, Jessica. Thank you.

Well, thank you. That's a really thoughtful question, so thank you for the question. I do think there are a lot of lessons learned from playing competitive sports. I think that you learn how to collaborate, how to communicate. You absolutely learn self-awareness, in other words, where your position falls on the field relative to others and how it impacts the game on the field or on the court. And I took a lot of those lessons away. And I used to have this discussion with then First Lady Hillary Clinton and later when she was Secretary of State about the lessons competitive athletes take away and they don't realize are so intuitive and applicable to the workplace. And I think self-awareness really comes from understanding and admitting what you don't know. Don't fake that you know something when you don't know it. Rather, be honest with yourself about it and surround yourself with people who know what you don't know, because through them and from them you will learn by doing and collaborating and working with them. And I think that's something that I really realized when I was at Citigroup starting the women's financial services business that you referenced, Women & Co. I knew what I didn't know, and I knew that they were taking a big risk on me. On the flip side, it was an opportunity of a lifetime to run a startup in the world's largest global financial services supermarket under the guidance of Sandy Weill. And so I quickly realized that I wasn't an expert in financial services, I'd never run a business before, and I didn't have an MBA. So I had to quickly figure out who inside was going to help me. And the way I figured that out was being honest, by showing I was vulnerable and I didn't know the different levers of how different aspects of financial services worked, whether it was banking, credit cards, brokerage, investment banking, private banking, mortgages. I didn't know how it all worked, so I had to learn. And I was encouraged to go on a listening tour, which I did. And then I quickly had to figure out the different positions I needed in order to get the startup stood up and launched. And I was just absolutely transparent about what I needed and the fact that I didn't know different aspects of these jobs, but I needed to find people inside the company who knew how to navigate the company but also who knew these specific specialties. So I think it's just the honesty and not being afraid to admit you don't know what you don't know. And I think that has served me well in the long run.

Sure. So Women & Co. was the brainchild of the former Citigroup CFO Heidi Miller, and she went to Sandy Weill and said, 'We're the world's largest financial services company, and we should have a business geared to women's financial services needs. More and more women are the CFOs of the household, more and more women are the chief purchasing officer of the household, and more and more women are going to graduate schools and moving up the corporate ladder, so that they are really an economic force to reckon with.' And Sandy Weill said, 'I love the idea. I think we should do that. Call this woman.' And that's how it happened. And so what we built was a membership business where you paid a not-huge fee, maybe it was $150, and we put together a membership offer for you to become a member. At the core of the membership was we would get you a financial plan, we would try to match you with a financial advisor from Smith Barney, which was a division of Citigroup at the time. And we had a huge number of Smith Barney financial consultants want to opt into being a part of this. We put them through a specific training so that they could be credentialed, but you were then matched based on your risk tolerance with a financial advisor who was going to work with you to get a financial plan. That was the centerpiece of it. Then attached to it were discounts on mortgage. At the time, Travelers Insurance was a part of Citigroup, so we had discounts on auto and home insurance. We had a Women & Co. credit card that had different bells and whistles on it that were unique to the membership offer. And then there was a major financial education and information component where we had speakers, we had in-person events, we had webinars aiming to help educate women on different topics pertaining to their investments or to other issues they asked us to talk about. So Sandy Weill spoke to the membership, the late Madeleine Albright, Secretary of State and ambassador to the UN, spoke, Bob Rubin, former Secretary of the Treasury, spoke. So we had a very robust set of speakers speaking to the membership about a wide variety of topics that were principally focused on financial empowerment, financial security, and financial independence for women. And I'm really thrilled. We grew it into a volume business. It generated more than $320 million in revenue, it accounted for well over a billion in assets under management at the company at the time. So in so many respects, I felt like I was doing a public service for women in the private sector, and it was ahead of the times too, probably in some respects. And I really credit Sandy Weill and Heidi Miller. They were ahead of their time. And if you look around Wall Street today, Sandy Weill's legacy lives on. Most everybody who's in a major position at a large financial institution on Wall Street worked for Sandy Weill at one point in time.

Well, let me back up and say you cannot underestimate the platform of the White House. And I had a very unique and almost surreal opportunity to have a senior White House position at a very young age, age 28. And that just opens doors that you couldn't imagine were possible. I mean, it was at the White House where I met Sandy Weill, who came to the White House for an event with President Clinton. And I met so many people all over the world and across so many different industries. And I never would have envisioned that. But I also learned that that experience, because you're in a perpetual state of crisis, it seems, and because you work 24/7 and you have to make decisions very quickly and you have to pivot from issue to issue, I learned that those are skills and experiences that are in high demand by corporate America and by the private sector. And I didn't realize that until I started meeting these people. And Sandy in particular, I think, had an appreciation for that kind of experience. And so when Heidi proposed to Sandy to start a women's financial services business, Sandy said, 'I met this woman, you should call her. She's a doer.' I just struck up a conversation with him. It wasn't anything very heady, but I was friendly, I was curious. And so Sandy told her to do it. You do what Sandy says, we all learned. And she called me. And I sort of chuckled when I saw the message and I said to my assistant, 'Heidi Miller? Why is she calling me? I don't know her. I just saw her on the cover of Fortune Magazine.' So I called her back, and she said, 'Listen, I have this idea. It's an idea, but I pitched it to Sandy, he loves it, he wants to do it, he said I should call you. And I'd like to talk to you about running it.' And I said to her, 'First of all, I'm honored that Sandy would have thought of me, but you need to know I know nothing about financial services, I don't have an MBA, and I've never run a business before. But I love your concept because I need that service, because I left Washington and public service with a six-figure legal debt because I was pulled into the various investigations that these days and back then seemed to plague Washington, unfortunately.' And she said to me, 'That was a really stupid thing to say. Don't ever say that again. Why don't you meet me in my office tomorrow at 4:00?' And what a great thing to say to me, because she was being a mentor. She didn't even know me, but she was being a mentor by saying, 'Don't be a girl, basically. Don't say you've never done it before. Just come talk to me and we'll figure it out.' And that's what I did. And she offered me the role right on the spot. And I really didn't think twice about it. It's like, how could I not do this? Go be an entrepreneur in the world's largest financial services company. And so I jumped feet first.

Well, I think mentorship comes in lots of different shapes and sizes, and really a person defines what mentorship is to that particular person. So I think a mentor can be everything from a sounding board to a counselor on pathing, to also somebody who can help facilitate networking, to also potentially opening doors to opportunities. So to me, it's a pretty broad swath. And you make from a mentorship what you choose to make from it and take from it. And I think people have to be willing to raise their hands to be a mentor. I don't think it's good when you're sort of told to be a mentor by somebody else. I think you've got to want to be a mentor and really understand what that entails and work with your mentee to figure out how that mentor-mentee relationship is going to work and what the mentee is looking to extract from that relationship. Don't forget, as a mentor, you also extract things from the relationship too. And one of the things I did when I came to Travelers is I implemented reverse mentoring. By that, I mean I would find the younger generation, very digitally adept talent in the company, and I would pair them with older management and have them mentor older management on being digitally adroit and adept and facilitate it and get them to be more proactive in the digital space. And I think folks got a lot out of that. Somebody who is a mentor to me today, he's in his early 80s, he's somebody I worked with in Washington, and I love it. He's every week getting a tutorial on AI. I love that curiosity. I love that he proactively is doing it. And he's becoming very knowledgeable on how to leverage AI.

I haven't. It's so interesting. No, I haven't sought out a particular person and asked, 'Would you be a mentor?' Rather, I've been lucky, and this has just happened organically. In my career journey, I would encounter different people, and different people kind of took me under their wing. They just took an interest in me. I can't explain why, other than I like to use humor, so people think I'm funny or with a quick wit. But they also know I work really hard and I don't have an agenda except I just want to do the right thing. But I had a number of people just kind of look out for me and take me under their wing. And I never forgot that. And I remember what it was like to be a college senior or somebody coming out of graduate school trying to get the first job. I remember all those phone calls I made and who was willing to help and who wasn't. And now I always take those calls. I always spend the time when I get that kind of outreach to try and help young people, because it's just so hard. And I encourage them to stay in touch with me. I'll spend a half hour talking about their path and where their interests are, and I'll make connections for them. And I'll encourage them to stay in touch with me. It's really interesting for me to see who does and who doesn't. And I've talked to them about the power of the network and how you really end up getting positions through your network and not through a recruiter or an executive search firm. So I think these young people are learning. I have a junior in college now, and he went through the investment banking summer analyst process last year as a sophomore, which is in and of itself mind-blowing. And I think he learned firsthand the power of the network. I think he thought it was all kind of a meritocracy and hard work. Yeah, it is to a point, but then you have to network your way into the right people in these different companies to present yourself and not just sit and record into a camera and do an auto interview and pray that you get selected for the next round. So it's a learning process.

I don't think I understand the question.

Well, one thing I tell every young person: every young person should be an engaged citizen. What do I mean by that? I hope they get inspired by an organization, a cause, or a public figure, and they go to work for that organization, that cause, or that public figure. I think working on a campaign at any level, be it for a proposition on the ballot, a ballot initiative, a presidential campaign, a county commissioner campaign, an organization's quest to hit a certain goal, they should be involved because those experiences force you to do a lot of different things at one time. And I think there's no better experience. It's great life experience, and the lessons you take away from those experiences, particularly on a campaign, are unparalleled. They're incredible life training experiences, and those skills that you hone are readily applicable to the workforce, whether it's in the private sector or public sector.

So I think leaders have to be empathetic. I think empathy is a critical leadership trait. I think empowering your people is also a key trait. That means trust. You have to have trust in your people and empower them to do their jobs. I think creating a collaborative culture and a partnership culture is also a key leadership trait. If you're fostering competition or silos amongst people, that's no good. You're just not going to get to where you need to go. I think you have to set a vision. You have to be a visionary, and you have to clearly articulate that vision so that people have a north star to which they're striving toward. And I think you always have to conduct yourself with the highest integrity. There's no cutting of corners. There's no compromising on things. When in doubt, ask, don't ask forgiveness after. And I think these are all really critical components. I would say that what I did learn is you don't have to rise up in a certain industry to be successful in that industry. I'm a walking example of that. I have no insurance background, none. What I think matters is the willingness to listen and to learn, learn by doing and learn on the job, and not come in with any answers. And if you have that approach and you come in willing to have eyes wide open and ears wide open and listen to what your colleagues are telling you and educating you about an industry, you will then be able to go away and take all that information and almost step back with a white sheet of paper and begin to construct what it is you're setting forth to build with no preconceived notions.

Well, I mean, again, it all depends on how you define innovation in your particular industry or company. But what I would say is I always tell my teams that they should push the envelope, push their creativity, think outside the box, think in new ways. Whiteboard everything. You don't have to color inside the lines. I want to push them beyond those lines. I think that gives them the confidence to think more broadly versus being constrained. I'm not saying we're going to take your idea and launch it, but I want your ideas, and then we'll figure out how to take those ideas and construct them within an environment that works in our company. The other thing I would say is it's imperative to lean into AI. Everybody should be using AI every single day. You should have the apps on your phone, and you should be using it. If you're not, you're going to be left behind, I fear. It's where the world is going, it's where all companies are going, and it's really important that you get agile with it and become comfortable with it, not afraid of it. So one of the things we've done is a lot of workshopping, because people were afraid of it, and now they see they don't need to be afraid of it, that it can be a great tool if used in all the right ways. But AI can also spur innovative thinking. Even my kids, their professors in college will say you may use ChatGPT to brainstorm now. Part of me says, 'Really?' But then the other part of me says, 'Okay, I get that it will help them think of things they may not have thought of and maybe lead them down different paths they would not have thought of.' But they're not allowed to use ChatGPT to write a paper, and there's all this software now that detects it. But I thought, okay, there is an example of how it can spur innovative thinking for young people.

Well, I'm a user of ChatGPT. I just like it. And my marketing team is exploring with some different tools that would enable us to do creative in-house fully generated by AI. I don't know that that will ever fully happen because there are all kinds of legal issues around it, IP and what have you. But obviously we're looking at various tools for customer service and engaging with customers. You could have a whole AI interaction in customer service and not know it's not a human because the tools are so empathetic and so humanistic. So it is amazing.

Well, let me start with you asked about She Travels and She Rises and She Golfs. She Rises was something that was started by Alan, our CEO. It was his idea, and it's a program to promote women in the insurance industry. That's She Travels, and we have a lot of programming on that front, most of it webinar-based. In 2025, we're going to have a big focus on women's health, so we're super excited about that. But it's meant to be networking as well as helping women propel forward. She Rises is an internal Travelers professional business group that helps women at Travelers get on the path to their career goals with support from allies and sponsors. We also have a group called She Ads, which is our women in finance and investor relations community. They've formed a group. And then She Golfs really was started within our bond and specialty business. This is interesting. Jeff Clark, who's the CEO of our bond and specialty business, really saw an opportunity to get women out on the golf course since so much business is transacted on the golf course. He saw the opportunity, we ought to get more of our women involved. And so he piloted something that then a group of us took more broadly across the company to become known as She Golfs. And one of my colleagues, Joan Woodward, has been spearheading this and getting golf clinics set up for women so that they learn how to play and so that they're equipped to do business on the golf course. And a lot of us as senior women, I grew up in a family of golfers, a lot of us also go to these clinics and try to be very supportive of that. I think men are allies and sponsors and partners in this. And at the end of the day, it's about getting the most qualified people in the best jobs. And I think for far too long, women have been behind both from a position standpoint and a pay equity standpoint. So any collaboration and partnership from male colleagues who are willing to support their female colleagues and when they see it and it's warranted, help to promote women into a job a step up or to introduce them into their network would be profound. Men's networks are robust, and I think men do a fantastic job of helping one another. I think women need to do a better job of that with each other. And I think men helping women through their own networks would be a huge benefit.

Senator Wirth was a fantastic advocate for women from a legislative standpoint in Congress when he was a U.S. senator. He also fostered a really wonderful work environment. I was his press secretary. He had a female press secretary, a female chief of staff, a female legislative director. He just was that way. And he was very vocal and introduced different pieces of legislation that helped women's rights. And I think I've just been lucky in that regard, having worked for public figures in government who were great proponents of the advancement of women and women's rights. I think coming into the private sector, what I observed initially in the media and entertainment business was not as many women in senior roles, though it started to happen a bit. But that's a hard business. And then when I came into financial services, I feel like that was kind of two steps behind media and entertainment. And it seemed to kind of propel forward, and then women in financial services at senior level started just opting out and getting off the treadmill. So I felt like it went three steps forward and two steps backward. And I think a lot of that has to do with the fact that women are the caregivers. They'll take time off to raise their kids and then want to get back on, or they're also caring for their parents and may have to take time off. So they are doing the juggle. I used to say being a working mother, you're juggling 15 balls every day, and you can never keep them all in the air. You just can't. And some of them are going to drop every single day, and you can't get upset. That's okay. You just pick them up one at a time and you start the juggle again. And no day is going to be a perfect juggle. And you just have to accept that that's what comes with the territory. And something's going to give every single day. And men who stay at home as the caregivers face that too. There are many situations where the male spouse has chosen for the advancement of his spouse's career to stay at home, raise the kids, and do the juggle. So they face it too. It's not just a women's issue. It's the caregiver in the household. So the recognition of that is really important.

Sure. A player-coach is somebody who's a leader who sets the vision, who sets the strategy and the roadmap, but also rolls up their sleeves and actually does the work too. It's not just setting the vision and handing it off to everybody else. You're in the trenches with your team. And I just think that's really important. I think that's a leadership attribute that you're in it, sleeves rolled up, feet and hands all in with your direct reports, with your colleagues, working hard just as they are to drive things forward, and at the same time to remove any obstacles that may get in the way. So I think gone are the days of those who are simply management. By that I mean just managing. That's what I mean by player-coach. You're doing the strategy and the execution.

Yeah, I wasn't. I met Phil Knight for an hour. Wow. And I really was impressed with him and the whole thing was so impressive. And I love that brand. I still do to this day. I find their messaging, their communications, their advertising very powerful, very aspirational. And certainly as an athlete, who wouldn't want to aspire to what they depict? I think Phil Knight is brilliant. I think what he's created is exceptional. But at the end of the day, at a very young age in my 20s, I just really wasn't ready to make the sacrifices to move across the country to Beaverton when I had all of my family on the East Coast. I just couldn't do it. Maybe it was a mistake, I don't know. I'll never know. But it was a fantastic experience to go through that process, and it helped me make some conscious choices about what was important to me in my life. It doesn't need to be all about the job. There are other things that are often more important. So we all make conscious choices, and that was a conscious choice that I made with self-awareness about what was important to me.

So I would say a couple of things. One, communicate. Make sure you communicate to your boss and to others what you're doing. What did you accomplish this week? Make sure the relevant important parties know. I would say second, raise your hand. You should always raise your hand to try to take on a project in addition, not give up your current responsibilities, but for some special project, an additional project, always raise your hand. Sandy Weill used to have a saying: if they thought you were doing a good job, they would hand you more to do in addition to your current responsibilities. So you never gave up responsibilities, you just acquired additional ones. And I always thought about that and thought about why that was. Which leads me to the third point: always have a strong work ethic. Put your nose to the grindstone. Do not get caught up in the corporate politics if they exist. Just focus on getting your job done and done well, effectively, efficiently, and in a timely manner. Because when you do, I do believe there is a meritocracy and it is recognized. And then fourth is the power of the network. That means you're responsible for that. You can't rely on others. I have a business meeting every year, and people love the meeting, but inevitably I always hear they want more networking time. And I say to myself, 'I love you all, but that is not my job. I am hosting a business meeting and I have a robust amount of content to share with you. The networking time is on you. You have to create that time.' So what I would say is you've got to build your network, because in so doing, you'll begin to build your brand, which will also be defined by how you conduct yourself in the workplace.

I think it's making those periodic calls for a coffee or a lunch, send Christmas cards or holiday cards. You'd be surprised who you hear from. You just have to make the time to proactively send the emails, make the phone calls, set up the coffee, set up the lunch. You just have to do it. And also, don't be shy about asking a member of your network to connect you to somebody else that may be in an arena that you're interested in.

My pleasure. And thank you. And you're in the New York office?

I love that.

My pleasure. It was great to meet you. Thank you for having me. And happy holidays, everybody.