Ep #33: How Women Are Sharpening Their Executive Skills with Lindsay Kaplan of Chief

Stacy Mayer: Hello, everyone!

Welcome to another episode of Maximize Your Career with Stacy Mayer. I am super excited to be here with you today.

Today, I have Lindsay Kaplan. She is the Co-Founder and Chief Experience Officer of Chief. I first heard about Chief, I don't know if it's been like a year and a half ago when they expanded from New York City into Chicago, and we're going to learn a lot more about the amazing work that Chief does.

But in particular, what I have found really interesting is that they focus on moving women into the highest level positions. They are actually one of the only organizations that's specifically designed for women at the highest levels, moving them from Vice President through C-level executives to expand their power, cultivate lasting relationships, and sharpen their executive skills.

And as you know, I am also on a mission to get corporate managers promoted into senior executive leadership positions. So, it's a lot of the same challenges that you hear me talk about on this podcast. And I just was like: 'Lindsay, we have to get you on here and figure out what you're noticing, trends in the industry, what people are doing, and what actually gets them to that level of impact that they want to be making at their organizations.'

Lindsay was also the Vice President of Communications and Brand for over four years at Casper. And Chief just announced its expansion to Boston and San Francisco. Yay! We are so excited to have her out here on the West Coast. And in May, Chief announced fifteen million dollars in new funding.

Hello, Lindsay, thank you so much for being here.

Lindsay Kaplan: I am so happy to chat with you today.

Stacy Mayer: So, Lindsay, let's just start out. What were some of your secrets to success? What were some of the skills that you had to learn so that you could personally transition into these higher-level leadership positions for yourself?

Lindsay Kaplan: Yeah, that's a great question. I am a relationship builder. It's one of my superpowers. I love people. I love conversation. I'm the person that will go with my husband on a date, sit at the bar and end up talking to three other people and leaving my husband on the side because he's like: 'I thought this was date night?'

And I think building relationships is really one of the key ways to get ahead in your company and to raise into an executive role. You're building relationships with the people immediately around you so you can really have that trust, have that collaboration. You're building relationships going up so that executives trust your decision making. And I think you need to build relationships out, meaning vendors, partners, a potential network that will get you that next step job.

So it's all about making those connections. And I think it has to be rooted in authenticity. There's nothing worse to me than the feeling of being transactionally networked with and feeling like the equivalent of a handshake and a business card. How do you meet somebody, maintain a connection in an authentic way is, for me, one of the biggest challenges in networking and building a great Rolodex.

Stacy Mayer: It's so cool that you said that because, even before this conversation, Lindsay gets on the phone with me, we're two powerhouse CEOs helping women rise to the top in leadership, and what we're talking about is our children right? We're talking about maintaining our lives during this crisis, this pandemic that we're facing. How do we get through these challenging situations and also do our work? So I think that that is a real testament to you for having real, authentic conversations. Those are the lasting conversations. I will remember what you told me about your six-month-old. Right? And that is so, so, so true.

Would you be willing to share with us? Because, I said this at the beginning of the podcast, Chief just announced fifteen million dollars in new funding. I read this in the San Francisco Chronicle when they first announced the expansion out here into San Francisco. And this has to be built on relationships. Would you be willing to share with us a story or something that you did, or your partner did, that actually took Chief to this astronomical level?

Lindsay Kaplan: Sure. I think in terms of fundraising, the original precede investor was a connection of Carolyn and a secondary connection of mine. And so even off the bat, it was hard for us to raise seed. But the people we did raise from, because we had a lot of "no's", they were people that were already in our network and they were just loose connections. And again, it kind of speaks to people who trust you, who know your reputation, and feel good about backing you.

As we raised future rounds of funding, it was a lot easier to raise the series A because we had traction, we had members, we were generating revenue. And we chose the people to... which was a major privilege to be able to choose from a few different term sheets and choose who you want sitting at that boardroom table with you. We were really lucky to be in that position. And we chose people that we really believed in and that believed in us. That we wanted to ride through thick and thin, who we knew had not just great business acumen, but ethics and morals that we wanted around our table. And those two executives, Kenneth Chenault, who is the former CEO and chairman of American Express, one of the first black men to be at the helm of a Fortune 50 company. And Alexa Von Tobel, an incredible entrepreneur who sold her startup, LearnVest, to Northwestern Mutual. We cannot think of two better people that would represent the diversity that we're striving to achieve in the C-Suite and the perseverance it takes as an entrepreneur for us to succeed.

And so, when we decided that we were going to raise more money and extend that series A, we went back to the boardroom. We went back to our investors, the people that were sitting around us, to have a conversation around what more funding would entail. And it was their belief in us that allowed us to close that round of funding without needing to go out, without needing to do a formal process and bring in new investors. So, we were really excited to make sure that the amazing solidarity we had in that boardroom could maintain the company and that their belief in us would fuel our next chapter.

Stacy Mayer: This reminds me of the vision that I often paint for my clients as possibility. When we're first struggling to get ahead in our careers, we're struggling to make that transition from being seen as a subject matter expert, a manager, into a higher-level leadership role. I tell them of the possibility that you just described. That at some point in your leadership career, you will be able to have choices. You will be able to look at companies and see if they have a diverse board of directors, if they have diversity on their leadership team. You'll be able to choose a company based on their ethics and moral standards. And so, this is just an absolutely amazing accomplishment that I want to applaud you for.

And what do you feel like? Because obviously it wasn't like this in the beginning, and you described your first round of funding, right? What do you feel was the biggest difference in building that level of trust that you actually put yourself and Chief in the driver's seat of making these big and bold decisions?

Lindsay Kaplan: It's a big question to unpack. The relationship I haven't mentioned yet is with my Co-Founder, who is the CEO of Chief, who is a remarkable leader. She is brilliant and she is somebody that is more of a COO operator type of leader. And I am more of the creative storyteller. I don't like saying weaknesses, that the opposite of my strength is my weakness. Our strengths and our disparate strengths really complement themselves. And so where I have weakness, she has so much strength, and vice versa, that I think that pairing really helped investors believe in us. Because we are pretty upfront and we're pretty authentic about who we are.

I recall a story when we walked in for an original pitch for a seed round. And we are not fancy people, Carolyn and myself. I mean, these days in the pandemic, I'm wearing Old Navy leggings 24/7. We're going into these really expensive offices with these captains of industry and these VCs, and I don't know, I was wearing like a GAP onesie and like my hair is kind of messy because it just is. Carolyn and I are just not fancy people. And when you meet us and when you talk to us, I think there is a level of realness and genuine love for the Startup world. And there was some surprise with some of the VCs, who I think given what we wanted to build, which is this somewhat exclusive network for executive women, I think they were just expecting two women in high heels and like a really great designer outfits to walk in. And that was not us. And I think we are both really dedicated and and determined to grow this business, and when you meet us, when you talk to us face to face, or hopefully on this podcast, you understand that we don't put on airs and that is who we are. I have no airs to put on. And I think that helped forge a really good trust with our investors, because when you see us, you know it's the real deal. And when you talk to us, I don't think anybody thinks we're bullshitting them or they're getting fleeced.

Stacy Mayer: When you think about some of the women that are a part of Chief, you've met these women, you work with these women, are they just all across the board or do you see leaders that are succeeding just through their true authenticity? Like being themselves and really showing up? They don't have to show up in the power suit if that's not what they want. Do you have any examples of that?

Lindsay Kaplan: It's a tough question. What if we had shown up wearing designer clothes and we closed more money? I'll never know the answer to that.

Stacy Mayer: Yeah, sure.

Lindsay Kaplan: I have the privilege, because I am a startup founder, of the reputation of startup founders wearing sweatshirts and guys wearing sneakers meetings. I have the ability to kind of dress down and play that role. I think it is a privilege to do so. So I just want to state that. That I think there are many, many, many men and women that feel like they do need to play a part and that they do need to use the jargon and speak certain words, because that is how they will succeed. So I think this was uniquely successful for myself, but I don't know if that holds true in other industries. You know in your company, that level of authenticity, that line you can't cross. And I think being self aware and acknowledging where you can be authentic and where you do have to play a part, it's really important to making sure that you read the room.

Stacy Mayer: Yeah, for sure. We talked a little bit about your sweet spot being relationship building. Now, for a lot of women that I work with, relationship building can also be their Achilles heel. They're really good at building relationships., that's what got them here, but there's this certain quality to building those relationships, which is about being liked. Wanting approval from other people and looking to them for the answers. Can you think of anything that you guys at Chief are guiding women executives to do to actually overcome, or maybe something that you had to overcome, in terms of building relationships that actually worked against you, that you had to learn how to find your own voice, figure out what you needed?

Lindsay Kaplan: Yeah, it's a double-edged sword with women. Because women leaders, not only many of us want to be liked, but studies show that women who are more liked are often more successful in their jobs. There is just so many stereotypes working against women in the workplace. It's hard to navigate them. And so, I think it's always about toeing the line, reading the room and understanding your core values. And if you're not happy in that room, again, it's a privilege to say walk away and find another job. We can't all do that right now. But I encourage all people to be where they feel they can be comfortable, and they can really be more of themselves. Because it's really hard. Working takes a lot of endurance. The word endurance for us is really important in maintaining that executive position and growing in your career.

And so, there's going to be a lot of naysayers. There are going to be people that you piss off that don't like you. I don't think it's about necessarily figuring out how to get them to like you. It's enduring that and it's moving forward.

I had a very wise friend tell me once that there is there's IQ, there is EQ, your emotional intelligence, and there is change, there is CQ. There's change intelligence.

And so, the piece of advice that I give often is: your career a bit of a wave. And you have to figure out how to ride that wave like a surfer or else it will tear you under. So, it is about endurance. It is about understanding that there is no mastery of figuring out how to do the job and then just being successful. The world we live in, as evidenced by 2020, is in constant flux, constant change. Your job is never the same. And so, that is the real skill set of becoming an executive is managing that change and enduring and moving forward and navigating all of that transition. And that transition absolutely comes with not being liked sometimes. But if you can ride that wave, you'll be very successful and hopefully you'll find that you like yourself. That is the most important piece.

Stacy Mayer: Why does being able to manage change help you like yourself?

Lindsay Kaplan: I think working is hard. And I think there's a lot of burnt out right now and 2020. So, that phrase: 'if you love what you do, you'll never work a day in your life.' That's not true. I can tell you right now is something that loves what I do. I work my butt off every day and my hair is going gray. But I think at the end of the day, I want to go to sleep feeling good about the actions I took. Even if someone doesn't like me in the moment, even if I feel like I just pissed off a group of hardworking employees, I look to the long term and I ask myself, did I do the right thing? Can I go to sleep at night feeling good about what I did today? And if the answer is yes, then I know that there is always going to be short term unhappiness. There are always going to be people who have to sit out a project or go through a layoff. But ultimately it comes back to ethics, morals and values. I want to make sure I trust in myself and I feel good about my decisions, even if they have tough outcomes.

Stacy Mayer: Yeah. Oh, my gosh. I love that so much. I was reflecting on myself and I spent the first half of my career following my passions, and I didn't work very hard at all. I thought about what I wanted a lot. Like, I want to be happy, I want to follow my passion. And then once I actually started to work hard, I started to see success and I started to really reap the benefit of what hard work is. And I was like... 'Oh, and I am following my passion.' I love, love, love what I do, but of course I am working hard. Of course I am challenging myself. But that growth, that exponential growth, is everything. Just knowing that you're growing, and that you're building, and that you're staying in integrity is so, so, so important.

Lindsay Kaplan: Yeah, I think once you chip away at your integrity and your own values, I think that's where burnout really starts to read it's ugly head. Your decision making starts to become tainted with short term, gut reactions. Typically, when I see burnout amongst Chief members, it often comes from feeling compromised at work and feeling compromised with decision making.

Stacy Mayer: Yeah. And I wanted to ask you a question about all the "no's" that you received. This idea of getting comfortable with change, comfortable with failure. But, what I'm also hearing in what you're saying, is that, when you start to experience the burnout, it's because you're compromising yourself. You don't feel like your own and your career choices. You feel like you're doing things that are out of integrity. And then if you can realign that, it's not necessarily that everybody around you is going to like you all of a sudden. But it's more about getting comfortable with the "no's", but being super clear on your values, and what you want, and going out and getting that next either... it could be within your organization, but knowing how to ask for what you want, ask for what you need, and really making that role for yourself.

Lindsay Kaplan: One thing I would say is with rejection comes listening. And so every time I've gotten a "no" from an investor, or a disagreement from my Co-Founder (we disagree all the time), a "no" is such a wonderful thing to listen to. Because the why around the "no". I think there's a really important filter around not taking that "no" personally, but learning from it. And also knowing, what to change based off of that "no" and what to persevere and say, I hear you, I'm listening to you and I'm going to stick to my guns around it.

But after every "no", my Co-Founder, Carolyn and I had a deep discussion around, like, was this a valid "no"? Should we change anything? Do we feel good about this "no"? And I think there's a lot there from the fundraising process, I take in every day, just the workplace. There's "no's" all the time. And really listening to the why behind the "no" is something I try to do and I should do more often.

Stacy Mayer: Well, it also implies that you have a certain amount of openness to it. I've heard I've heard some women, and it's completely valid, we have to have boundaries and there's a lot of feedback that we don't need to let in. It's not useful. Maybe it's based on unconscious bias, like whatever the reasons are. But being willing to at least explore the possibility of what this "no" means. What is it that I really want to take away from this and learn from? That requires a certain level of openness.

Lindsay Kaplan: Yeah, and I think Explorer is a great word. It doesn't mean you necessarily have to agree with the "no", but to interpret the "no" and to learn from it, whether you accept or reject it. That exploration process is really healthy and it's only going to strengthen your next decision, your next project, your next move in the office.

Stacy Mayer: Awesome. Yes, exactly. So, I want to talk a little bit about what Chief is working on right now. Obviously, you had an amazing physical space in New York City and Chicago, maybe elsewhere as well already. And then now with these new expansions that you've announced, it's more a virtual programming until the physical space is launched. But how is Chief making that transition from meeting up with women in person now into the virtual world?

Lindsay Kaplan: Yeah, we had always said we are a community, we're not a space. And we said that in part because I think there are a lot of amazing coworking spaces. There are a lot of club houses that if you don't know Chief very well, you may equate us with. And really, before we even launched Chief, the original concept had no space. The important part about what we do, is we connect and we support women in power to make sure that they stay in power and that we can bring more people and more diversity up with us as we grow.

And so we have a few main services. We offer peer groups that are led by incredible executive coaches, events to bring people together, workshops, you mentioned to sharpening executive skills, and the community itself, which is an amazing benefit when you have almost 3,000 people at your fingertips that you crowdsource ideas and get references from.

And so those services did used to meet in person. And we found that, given that the community is so important, do we wish that our peer groups can meet in person again? Absolutely. But we found that the value of, in the midst of this pandemic, in the midst of knowing that the world is going through so many unknowns right now, that peer group of 10 people and an executive coach is more important than ever. These workshops around navigating change, everything from how to interpret the CARE Act to going through layoffs, to moving your entire team remote, that is more important than ever. And so we all miss our in-person experience. I am a hugger, so I miss hugging people. But that's never going to return. But we did find that the value and that connection and support can be had online. And for a lot of women, it's easier because they didn't want to take that commute. They didn't want to spend time in person. There is a great element of time travel that is to be had when you are able to log on through Zoom, you can be anywhere, any place, at any time, and get in touch with the people we need to feel supported.

Stacy Mayer: You mentioned that if we don't know Chief, we'll think that it's just like everything else. Something like that, right?

So, tell us what makes Chief unique. And if I am a woman in the Vice President or C-Suite level, why would I want to be involved?

Lindsay Kaplan: Yeah, great question. So, Chief came from a really personal place for my Co-Founder, Carolyn and I. You mentioned I was a VP at Casper. Carolyn was essentially acting as CEO at Handy. She didn't have a title. That's a whole other podcast. But we found as we were climbing in our careers, us in particular we were in startups, we had gone from being the mentee, being the person that found a mentor, that joined different programs and went to networking events. To feeling a little bit alienated, that when we did now try to find somebody to mentor us, we were the de facto mentor and not the mentee.

And so, at this peak of our career where we were both like: 'OK, how do we now get into the C-suite? What's the next step?' we felt somewhat hung out to dry. Like: 'Hey, go mentor women." And any organization we joined again; we became that person on top that helped others. Which was great. I still love mentoring people, but there's loneliness, especially when your decisions matter more than ever. And so, what makes Chief really different is knowing, it's not exclusivity. It's not like some secret club where you have to get the grades to join. It is really because it is lonely at the top. It is hard to be an executive. And it is hard to be an executive when you look around the boardroom, and you can look at every single study in America, generally, you are one of the few women in that room. And so, we wanted to create an organization that was specifically focused on making sure that these women could come together, support one another, and share in that cross pollination of power. So, when I went out and tried to network, I was marketing. I found myself meeting other marketing execs, which is great. But what I really need, and the perspective that Chief gives, is meeting people who are from different roles, different organizations, totally different industries and different backgrounds, to give me the cognitive diversity to make better decisions based off of all of those different perspectives in my room.

Stacy Mayer: Yeah. So, do you have any final words of wisdom for a woman who is looking to transition into the C-suite ranks? Just anything for them to keep in mind, things that you've learned along the way for yourself, or what you're noticing is really working for the women who are a part of Chief?

Lindsay Kaplan: Yeah, I think there's a level of mastery at doing your functional job that gets you to the peak manager level, director of your function. To get into that larger executive role, it's really about widening the aperture of what you look at day to day and thinking through your team's greater impact on the business and the company.

And so you're no longer just thinking about that narrow view because of your functional area, but you are widening that scope, putting that CEO hat on and thinking longer term around your team's impact on the business and the future two, five years out, depending on your company. I could not plan three months out right now. But having that that broader mindset and sharing that and communicating that broader mindset while you're functionally killing it in your area. It's hard to do both, but I really think that is the secret to taking that leap up into the boardroom.

Stacy Mayer: Yeah. And get yourself surrounded by more women. Other people who are doing the hard work, too, because it is hard to do both, but that is what actually will help you succeed. I love it.

Lindsay Kaplan: It is. And I think a lot of at this stage, a lot of people think: 'I'll just keep making what I do better.' And it's not actually improving what you are doing at that point. You already got to be leader of your area of functional expertise. If you are trying to get to the next level, I'm sure you're already there. I want to assume that you're great at your job. It's really now figuring out that leap and talking to people outside of your skill set and and really collaborating, whether it's in your organization or outside. Making sure you have a personal board of directors, that gives you the perspective of every other functional area in the business. Because that's the leap that you will take that I think will not only get you into the C-suite, but make you a better leader when you get there.

Stacy Mayer: Yeah. So, do you have anything fun that you'd be willing to share with us that Chief has on the horizon? I think I saw last year, you used to, when you did the in-person events, very inspiring speakers, famous people coming in New York, like I think I saw Tina Fey did a talk. Like, there's just so much fun stuff that I was like: 'Oh, my gosh. This is such an incredible organization.'

Lindsay Kaplan: Yea. We've done poker, we do comedy nights. In addition to all of our workshops, we like to have fun and make sure that people can listen to some amazing icons. I was so lucky enough to meet these remarkable women. I tried to make Tina Fey laugh for 20 minutes in the Green Room.

And my Co-Founder came in, and she was just sitting there so uncomfortably, like nodding her head at me, and my co-founder was like: 'Is she is she using her stand up routine on you?' And Tina Fey was like: 'yeah.' And (my Co-Founder) was like: 'I'm so sorry.' And she was like: "It's really bad. Stick to startups lady.'

I would love to tell you more. We haven't yet told our members.

Stacy Mayer: OK, fair enough.

Lindsay Kaplan: But over Zoom, we have some amazing people booked for this fall. We are so thrilled to expand. We are hopefully going to, with really great safety precautions, somehow mildly open up New York, Chicago, L.A. this fall, depending on how safely we can do it. And we are thrilled to open up the virtual doors for Boston and San Francisco. So, we have credible members joining from all of these cities, some phenomenal, phenomenal women. And we're just absolutely thrilled to see the community continue to thrive in this time.

Stacy Mayer: So how do we find you if we want to join? Where do we go?

Lindsay Kaplan: It's Chief.com.

Stacy Mayer: That's a good website. You did it.

Lindsay Kaplan: The domain was my Co-Founders birthday present to me last year.

Stacy Mayer: Amazing. That is a great birthday present.

Lindsay Kaplan: There was a debate about it. And I was like: 'Trust me, we're going to want Chief.com.' We're going to be on a podcast one day and Stacy is going to ask.

Stacy Mayer: That is the only reason. Happy birthday Lindsay.

Lindsay Kaplan: Exactly. Chief.com. But you can learn more about Chief, you can apply to join or nominate somebody that you think would be an incredible Chief. VP through CEO is a little bit meaningless given that titles take on different forms in different industries, so we're really looking at women in leadership who are either at that boardroom table or the step right before they get there. So, Chief.com to sign up and learn more.

Stacy Mayer: Oh, I love it. Everybody check it out. And I'm going to be looking for you guys out here in San Francisco. I can't wait. It's very, very exciting. And thank you so, so much for being here with us today.

Lindsay Kaplan: Thank you for having me. And good luck with your kids. I'm going to go back upstairs and figure out where my four year old is.

Stacy Mayer: I heard him a couple times on this. I mean, not your kids, my kids. I find it delightful. I remember the days where we were hiding them from the Zoom calls, like: 'No, you can't come in. I'm working.' and now it's like: 'Uh, whatever.'

Lindsay Kaplan: I'm holding a baby in every single meeting.

Stacy Mayer: I love it. Thank you Lindsay.

Lindsay Kaplan:  I actually changed a diaper on a meeting. You couldn't see the diaper but you could see me.

Stacy, it was great speaking with you. Thank you so much.

Stacy Mayer: Thanks.