Empowering Women Leaders with Lisa Caputo

Oh, I thank you so much for having me. It's such a pleasure to join you. You have a great resume. You know, on paper, you're like, 'This is an impressive woman.' Like if I saw you for coffee, it's like, 'Oh my God, we have so much to talk about,' from kids to business and this and that. But when we look at your LinkedIn and things like that, it is very impressive. How did this career develop for you? Well, you know, Ivy, I really appreciate the question because I never had a grand plan in my career. In other words, I never set forth some kind of a path forward and said, 'Oh, I want to end up in that spot.' Rather, I took a very open mind to my career trajectory. When I finished graduate school, I'm actually a trained journalist, and I wasn't quite ready to move out to a small town in the Midwest to get started as a television reporter. I thought, 'Well, who are these people called press secretaries that I'm dealing with every day as an aspiring journalist? I think if I go and try to be a press secretary on Capitol Hill, that someday I will become a better journalist because I will have experienced the legislative process up close and personal and be a more informed reporter when I eventually thought I would go back to the other side of the fence to reporting.' What happened was I literally got on a train that just took me in a direction and landed me in the White House remarkably. I never aspired to be there, but here I was. I landed in the White House at the age of 28. Wow, that is impressive. I had good fortune in being in the right place at the right time, and hard work as well. But again, I had great mentors. I would take some calculated risks. I went off on a presidential campaign and met an incredible group of people which then ended up connecting me to Bill Clinton and ultimately Hillary Clinton when President Clinton decided to seek the presidency when he was governor of Arkansas. Had I not done that one presidential campaign in 1988 where I met all of these incredible people, I probably never would have been connected into the Clinton campaign. So it does demonstrate the power of relationships, the power of the network, and the importance of maintaining it can really steer your career pathing in ways you otherwise wouldn't have expected. And so I always say it's good not to have a grand plan and have the blinders on so that you can see and have the peripheral vision around the opportunities that could come across that you may have never thought of.

I mean, there's no doubt. As a young aspiring journalist in Washington, I had a great mentor who was a professor actually at Northwestern's Medill School of Journalism. I got my first job when I wasn't willing to go off to the Midwest to a small town to be a television reporter, which was seen as getting the gold ring so to speak, and decided to work on Capitol Hill as a press secretary. I got my first job through a blind ad. I would go to Capitol Hill every Tuesday and put in my resume to these job listings blindly, and one day I got a call from a Michigan congressman's office. Honestly, that congressman never really wanted to publicize a lot, and I was his press secretary. He didn't want to publicize a lot because he was on the House Appropriations Committee, and that was all about bringing back dollars to the district for Army Corps of Engineers projects and infrastructure. There was a rule: the subcommittee chairman never outshines the chairman. He taught me so much about the art of the back room deal on Capitol Hill and how Congress works. He really became a mentor. He taught me how to navigate within the House of Representatives. I watched how he navigated to accomplish things legislatively, and he allowed me to take a leave of absence to go on board that presidential campaign in 1988. Had he not done that, I probably would not have landed in the White House. He gave me the opportunity to go experience a presidential campaign, which was an incredible experience despite the fact that the candidate at the time, Michael Dukakis, lost. But he really thought it would be beneficial for me and ultimately him. I came back after the campaign was over, and I had a lot of new ideas on how to do things.

But what quickly happened is I felt like I wanted to operate at a more rapid pace, and that landed me in the US Senate working for a senator from Colorado who was such a great legislator, big personality, big advocate of women. He was a great proponent of women's issues and environmental issues. His name is former Senator Tim Wirth. He chaired the UN Foundation for a long time, magnificent person and legislator, and again another one who became a mentor to me. He probably doesn't know it, but he did. He showed me how you bridge divides on both sides of the aisle, how you collaborate to get things done. He let me take a leave of absence from his office to go on board the Clinton campaign. Had that not happened, where would I be? I've been the great beneficiary of both male and female mentors. In the political arena, it really has been a lot of male mentors and sponsors who took me under their wing and navigated me. Mike McCurry, the former White House Press Secretary, was somebody early on in my career who absolutely looked out for me, helped navigate me around in Washington, and it really made a difference. I also would tell you that as a woman, that's really important because your hard work will get recognized when you have a champion. I have to highlight this because when we show up, work hard, show up and are our best, and are committed to being our best, make sure your work is noticed, make sure you have a champion. If you don't know who it is, find the ways to figure it out.

I think that's an important piece of the puzzle because we sometimes step back and say, 'Why did this one get this and this one didn't?' Long ago, a mentor once told me that it's really important to make sure your boss knows all the good things you are doing, not just when you do them but on a consistent basis, to send a weekly email: 'I just want to give you an update on how things are progressing.' That was a female mentor of mine who was the former chairman and CEO of Time Inc. She was adamant about that. It was such great advice when I left Washington and moved into the private sector. She really gave me such sage advice and encouraged me to move beyond public relations and try to get into marketing. I had no marketing background because she used to say to me, 'Marketing helps drive sales which helps drive the bottom line, and you want to be part of helping to generate revenue into the bottom line.' So again, I would say as I navigated from government and the public sector into the private sector, what I have found is I've had a lot of female mentors in the private sector, also male, but I would say that a lot of women in business who've been in very senior roles have been great champions of mine, and to this day still are. Were it not for the roads and paths that they paved before me, I would have never benefited from advancing along in Corporate America.

Well, thank you for the question. I owe such a profound debt of gratitude to Hillary Clinton. I really do. I watched her up close and personally. I worked for her for a long time. I had the great fortune of spending some time with her this past weekend, and I'm constantly reminded when I'm with her what trails she's blazed. What I took away from being around her and watching her in action and her passion for women's advocacy is just awesome, and it really instilled in me my desire to become a great champion for women's voices and women's needs. So when I was in the private sector, I left Washington to take a job at CBS, and then I ended up at Disney. When I was at Disney, I received a phone call from Citygroup's then CFO Heidi Miller. I didn't know her. She called and said, 'Hi, I know we don't know each other.' I said, 'Well, I know who you are. You're on the cover of Fortune Magazine as one of the five most powerful women in business. Why are you calling me?' At that time, Citygroup was a huge player in the marketplace, the top. It was a real testament to Sandy Weill, who remains to this day at the age of 90 a great mentor and friend to me. I adore the man. Heidi had the idea to start a women's financial services business within the world's largest financial services supermarket at the time and went to Sandy as the chairman and CEO and said, 'Sandy, I have this idea.' And Sandy said, 'I love this idea. Call this woman Lisa Caputo.' Why would he do that? Again, back to the relationships and the connections. I had met him through my time in Washington, and he remembered me because he has a long memory. So that's how that happened. She called and said, 'What do you think? I'd love to meet with you about this.' I said to her, 'You know, Heidi, I'm honored, but I'm not qualified to do that. I don't have an MBA, I have no background in financial services.' I'll never forget this. She said, 'That was a really silly and stupid thing to say. Don't do that again. And can you be in my office tomorrow at 4?' We both laughed, and off I went to her office. She described her vision, and I was captivated by it. I thought, 'Well, this is a risk worth taking.' She assured me that she would steer me along and connect me to the right people internally to figure it out, and she did. I jumped feet first.

Now, that's not without going to my boss at Disney at the time and saying, 'I have this amazing opportunity to do a startup in the world's largest financial services company. I don't know where this is going to go.' He said to me, 'If it does work out, you can always come back.' That again, more mentorship, more sponsorship, me being able to take that kind of risk but knowing I had a safety net was huge. So off I went to Citygroup. Unfortunately, Heidi left about six to eight weeks after I arrived. She took a big job at PriceLine as the CFO. Do you know, she still continued to help me from where she was. She connected me to people who were helping me within the company. One of the people she introduced me to was Jamie Dimon. Jamie was no longer at Citygroup, and don't you know, he helped me from the outside. He would call me and say, 'Who have you talked to this week? Here are three people you should really talk to who could really help you figure this out.' To have that kind of interest, but also they really cared about trying to stand up something that was really going to help women be financially secure and financially independent, was just extraordinary. The fact that Sandy Weill was going to continue to dedicate resources to enable me to figure this out was really something, even after Heidi left. It was just...

You know, I will say this. The women in Co, which was City's women's financial services business, was ahead of its time in so many ways. When I look at my own family and my mother, years and years ago when I was in the middle of doing Women and Co, my father had a heart attack. He ended up being fine, but I'll never forget my mother panicking if God forbid the worst happened, she didn't know how to handle the finances. And again, I thought to myself, that just can't happen to women, no matter what their ages are.

So yes, I've now landed at Travelers, which I love. I love it not just because of the work I get to do every day, but yes, I have the ability to innovate here and work with an incredibly forward-thinking chairman and CEO, Alan Schnitzer, who really cares about the advancement of women. He looked around in the insurance industry and said, 'You know, there are not enough women in senior roles or running agencies. We should really try to do something about that. We should foster a dialogue, we should set up and support networks for women to support women.' It was his brainchild, and it's called She Travels. I have the good fortune of basically structuring that for him, and my team runs it for him. It's really become an amazing community of women in the insurance industry, both within our own company and also the independent agents and brokers who are our partners. We do a lot of great content programming, we have a sizable LinkedIn group, we do some in-person events, and it's been fantastic. Another thing we're doing here at Travelers is, one of my colleagues saw that a lot of business happens in financial services and in business on the golf course, so we started an initiative here called She Golfs, which is trying to get women out on the golf course more, give them golf instruction so they like the men can be part of the dialogue where business may happen. Then in my own division, which is sizable, I have an effort called She Rises, which is all about providing opportunities for women in my division to network across the departments that I oversee. We've had great male support and allyship around this. I think it's not just mentorship and sponsorship, but the allyship too is so important for women.

Well, I'm just one of many, right? Trying to champion the cause. I will tell you, when I started the Women and Co business at Citygroup, we started to see a trend: more and more women were going to graduate school, business school, law school, medical school; more and more women were becoming the chief financial officer in the household; more and more women were becoming the chief purchasing officer in the household; and what we were also seeing is that women were outliving men by seven years. So it was really important to help them have the tools and the information in order to make financial decisions for themselves. Similarly, from a career pathing standpoint, you see more and more women going up the corporate ladder. This is a great thing. Now we need more women CEOs, we need more women in the boardroom, we need more leaders overall in leadership positions. And again, I have such a forward-looking and fabulous chairman and CEO, Alan Schnitzer, here. He talks all the time about how diversity is a business imperative, and I love that because it really is a thousand percent. And as we've seen, women's presence grow and things are moving in the right direction.

Well, I think I would say to the women coming up today, and in a couple of years that'll be my own daughter, is that it's really important to build your brand, your own personal brand. What are you good at? What do you stand for? What are your skills? And to build your network. And not just build the network, you've got to invest the time to maintain and nurture that network. And then finally, I would say keep an open mind. Don't get stuck on one path forward, but rather allow yourself to be willing to explore and to be open to opportunities in fields, companies, disciplines that you otherwise never would have thought of. That is what I would say to that younger generation coming up. And to the generation who's there now, they have a responsibility to pay it forward to those women, to reach down and to pull them up and to mentor and sponsor them, and provide that kind of leadership, responsible leadership.

Thank you, Ivy. What a pleasure. I could go on and on with you for sure.