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It was just a few years ago when Lindsay Kaplan made the realization that the old saying is true: It is lonely at the top. In this case, the top meant a vice president role at a successful startup. While Kaplan’s career growth poised her to be the go-to person for giving guidance, it became clear there weren’t as many peers, specifically women, who could return the advice to her. This challenge would become pivotal in leading Lindsay to her next career move as co-founder of Chief.
Launched in 2019 with fellow co-founder Carolyn Childers, Chief is a private women’s executive network with clubhouses across the U.S. It boasts a community of inspirational women who are already leaders—namely members of the C-suite, vice presidents, and senior-level roles across a range of industries—and offers them tools, technology, and access to community to help them thrive in their careers. Furthermore, Chief guides members on how to train future leaders, regardless of the field, with inclusivity at the forefront.
With a community app and ongoing programming, both in-person and virtually, Chief has become the resource that Kaplan never had access to in her previous executive role. And it’s become an essential community for over 15,000 successful and ambitious women so far, too. Ahead, Kaplan shares more about how she pivoted from vice president to a co-founder, how Chief envisions a more equitable future for women at work, and how the organization plans to help make it happen.
WHAT HAS YOUR JOB EXPERIENCE LOOKED LIKE BEFORE CHIEF, AND HOW DID IT INFORM WHAT YOU WOULD EVENTUALLY BUILD THERE?
“I started my career in publishing where I noticed a trend: Most of the people who were junior on my team, such as myself, were women, and yet the C-suite and the leaders of the company happened to all be men. As I progressed in my career, I became a vice president at a startup, Casper, where I was very happily mentoring young women in my organization. I’d go for lunches, give advice, and speak on panels to talk about women’s advancement. And then I had this moment where I realized I didn’t have anybody mentoring me. There was nowhere for me to go for advice over lunch or coffee and, eventually, I started to feel really burned out. As the decisions got more critical in my career, I had less community, less mentorship, and realized that I needed something more than just an executive coach.”
HOW DID YOU MEET YOUR CO-FOUNDER, CAROLYN, AND BEGIN BUILDING CHIEF?
“Carolyn had the original concept of Chief. She was in a very similar place as me. She was working as a COO at a startup and had that same feeling of, ‘Where do I go for advice and connection?’
“Carolyn and I knew each other on the startup scene because there are not many women executives at startups in New York. We met at an event and she told me about the idea for Chief. She was curious about partnering with me because I had worked at Casper. She thought, ‘If Lindsay could make a mattress cool, what could she do for a women's executive network?’ After all, you hear about women's executive networks and you think of stodgy pantsuits and warm white wine in a plastic cup. Carolyn is an incredible operator and I really wanted to partner with her and own the brand, the content, the storytelling, and the community.”
WE OFTEN HEAR ABOUT MENTORSHIP IN THE CONTEXT OF FOLKS WHO ARE STARTING OR CHANGING CAREERS, BUT LESS FOR THOSE ALREADY IN LEADERSHIP POSITIONS. WHAT IS THE VALUE OF MENTORSHIP WHEN YOU’RE AT THAT LEVEL?
"Well, it's lonely at the top. But it gets lonelier a lot faster when you're a woman. Just because you're senior in your career doesn't mean you stop learning. As a senior executive, your decisions are more critical than ever so it’s incredibly important that you get diverse perspectives and learn about other sectors, the value of other roles, and how you can become a better leader.
It's funny that as you hit your stride in your career, you suddenly become the mentor when, in fact, a successful leader needs to redefine what mentorship looks like and know that throughout your life it's important to have mentors. There are people younger than me who I consider mentors because they help me think differently about the way that I work. So I think this top-down idea of mentorship is harmful, particularly to women and marginalized people who climb the ranks and don’t yet find themselves in every room and could use support, camaraderie, and a place where they can learn and be vulnerable.”
CHIEF IS A UNIQUE BUSINESS. AS AN ENTREPRENEUR, HOW DID YOU GO ABOUT PRESENTING SUCH A UNIQUE CONCEPT TO THE WORLD?
“Carolyn and I went into the process a little naive. Our expectations were strong because we had a startup background. We had a Rolodex, we knew investors. Imagine how many people go into this process completely cold. We felt pretty secure that we knew what we were doing. Well, that didn't seem to matter at all because we were handed no after no after no. And it's hard to hear that many nos and not feel tempted to gut your entire business plan.
“I remember hearing a no from an investor who said, ‘Listen, I'm on the board of this incredible direct-to-consumer products company. They make one thing, they make it really well. You're trying to build peer groups and a community app and do programming and have spaces. You’re doing five different things and most people can't get one off the ground!’ I remember going back to our business plan and feeling that confidence so strongly that this is exactly what the product needs to be, and so when we finally got to a place where people were starting to say yes, the silver lining is that people deeply believed in our mission and us as founders.”
"A successful leader needs to redefine what mentorship looks like and know that throughout your life it's important to have mentors.”
WHAT ADVICE WOULD YOU GIVE TO ANYONE ELSE NAVIGATING THROUGH A PROFESSIONAL NO LIKE THAT?
“It's important to take feedback specifically in areas in which you have less direct working knowledge. We stuck with our business plan, but we also have combined over 25 years of experience launching startups. Carolyn and I had the experience and the knowledge to feel solid in our conviction, but my advice for people who are starting out is, even if you ultimately decide not to change anything, pressure test any feedback because it's hopefully coming from a good place that can make you and your company stronger.
“I think feedback, even if you don't choose to use it, is still a critical piece for you as an entrepreneur. Whether you use it to make changes or not, you should still absorb the feedback because that's helpful to either understand what a no looks like and what you may need to defend in the future.”
CHIEF WORKS PRIMARILY WITH C-SUITE, VP, AND SENIOR-LEVEL PROFESSIONAL WOMEN, BUT WOMEN CURRENTLY ONLY MAKE UP LESS THAN 25% OF EXECUTIVE-LEVEL POSITIONS IN THE NATION. WHAT DOES THE FUTURE FOR WOMEN IN C-SUITE AND EXECUTIVE LEADERSHIP LOOK LIKE? HOW DO WE GET IT TO A MORE EQUITABLE PLACE?
“First of all, when I think about changing the face of leadership, I do not just think about women. I want to make sure we're thinking about diversity, including people of color, ageism in the workplace, and not just C-level positions. What does the pipeline look like going up through executive-level roles, as well as board makeup? This is critical as we think about making the decisions around the table.
“A few things need to happen. The first is there needs to be a more even playing field, meaning we need to take a look at childcare, parental leave, and caregiving policies for people with aging parents, to make sure that women are not overburdened with caregiving tasks at home. And until that happens, we are operating in a place where we want women to succeed but we are not setting up a society that gives them the path to do so.
“There's also data that shows that men are given opportunities based on potential and women are given opportunities based on experience. So, if we want to make change happen faster, we need to take a look at the way that our interview processes work and the implicit bias we carry as we are learning about somebody's experience and potential. Leaders hire leaders, and we need to train our leaders to make decisions that are more inclusive. And then finally, it’s not just ‘How do we bring more women in?’, but ‘How do we retain those women? How do we make sure that women, people of color, and anybody who feels marginalized stays in those careers?’ This happens by building inclusive workplaces that have a sense of belonging, and give people an opportunity to lead.”
HOW DOES THIS TRANSLATE TO WHAT’S HAPPENING INSIDE THE DOORS AT CHIEF?
“We are intentional every day about building a more inclusive workplace and, again, intentionally seeking out leaders who do not necessarily look and act like we do.
“We have over 15,000 Chief members who are executive women and they’re joining because they are looking for a community. There is so much pressure on executive women to not just do their job, but to mentor, not let anyone down, and carry this flawless-looking persona that other people can look up to. So I think members join Chief so that they can finally let their guard down. People are getting burned out at work and we really need to make sure that women and people of color who are in these leadership roles have the mental health and full capacity to grow in their careers. We need to allow them to put their oxygen mask on before they help others.”
THERE ARE SO MANY POWERFUL AND CREATIVE WOMEN WHO ARE WORKING INSIDE THE WALLS OF A CHIEF CLUBHOUSE ON ANY GIVEN DAY. WHAT DO YOU SAY TO THE WOMEN WHO ARE NOT QUITE AT THAT PROFESSIONAL LEVEL YET? THOSE WHO LOOK AT THAT 25% C-SUITE NUMBER AND FEEL DISCOURAGED?
“Ambitious women should continue to seek mentorship, but do it reciprocally. So if you want five minutes of somebody's time, as a fellow business person, give them five minutes back of value. Don't just look at mentorship as something transactional that you take. Advice works both ways. I would also encourage women to get out and network, and not just think about networking within their industry, role, or function, but to understand the power of building a Rolodex of people who have cognitive diversity and who don't do what you do. So as you do climb in your career, you're able to zigzag around industries and get a leg up over people who are entrenched in what they know.”