Lindsay Kaplan
—Entrepreneur

“Creativity can fuel business, and business can create more creative opportunities.”

Lindsay Kaplan is an entrepreneur and chief brand officer based in New York City. In January 2019, Kaplan co-founded Chief, a private network for women in executive leadership roles. Chief’s goal is to bring more women into positions of power and keep them there, and since its inception, it has connected over 4,000 senior leaders from companies including Google, IBM, HBO, Walmart, Visa, Teladoc, and Spotify. Prior to Chief, Kaplan led communications and brand engagement at Casper, where she created a commercial with Michael Rapaport, an insomnia chatbot, and a magazine in partnership with McSweeney’s.

In this interview, Lindsay Kaplan shares why she pivoted from the world of publishing to advertising, how she navigated Silicon Valley, and the secret to Chief's success.

TGL: How was your childhood?

LK: I grew up in Hopewell Junction, New York, a small town just far enough away from the city for the high school kids to try and fail at cow tipping. I was a book nerd and would stay up way too late reading a few books a week by flashlight. I was also a devoted band geek and acted in the drama club. 

TGL: What did you study?

LK: I studied English and Creative Writing at Brandeis University. 

TGL: Your career started in publishing, working in communications and marketing at Oxford University Press, Time Out New York, and ELLE. What did you like about the world of publishing?  

LK: I graduated with an English degree and zero understanding of what on earth I could use that for to pay rent. Well, book publishing made sense. It was one of the best first jobs I could imagine. I was surrounded by grounded intellectuals who were brilliant, funny, and genuinely cared about my career. Surrounding myself with the right people has always been an unlock for me, and publishing, especially before the recession knocked the world off its axis, was full of the best sorts of people. 

TGL: You pivoted from publishing to advertising at Publicis. What did you learn in advertising that you did not learn in publishing?

LK: Business. In books and magazines, I vaguely understood how my role laddered up into the company’s goals. I suppose I was wearing rose-colored reading glasses. Advertising was a wake up call that creativity can fuel business, and business can create more creative opportunities. I loved the frantic energy, the endless cycle of pitches I was put on, and the dopamine reward given for weird ideas that clients bought into.  

TGL: You took another turn by going to Silicon Valley and working to bring startups to market. What was attractive to you about the world of start ups? 

LK: While I was in publishing and later advertising, I started putting every book, brand, and magazine on social media: Facebook, before they rolled out Brand Pages for companies, Foursquare, and Tumblr. I realized I was more interested in the platforms than the brand and wanted to see what the other side was like. 

TGL: How did you navigate working in Silicon Valley?

LK: Things did not go as planned. What had been a series of great career moves suddenly felt chaotic and disappointing. I tried - operative word being “tried” - to manage the marketing at a jewelry startup, but I don’t really like jewelry. I ran marketing at a map app that tried to displace Google Maps, Apple Maps, Foursquare, and Waze. I felt like a failure, and maybe I was. I decided I would pack it up and apply for an MBA or finally write a novel, whichever I could muster up the energy to achieve first. And that’s when I received a cold LinkedIn note from a guy about a mattress company. 

I like sleep. No: I love sleep. And I liked the founders. They reminded me of the smart weirdos in publishing. It felt like no one had ever made a mattress funny and cool, like I was rewarded for doing in advertising. The math worked, and I decided to work on something I loved, a product I believed in, and a team that inspired me. That’s how I started at Casper a week before launch, running their communications and social media. I was ready for a come-back, and I had a pile of sleep puns and coffee at the ready. 

TGL: What strategies did you use to build markets for Casper?

LK: Casper was never about selling a product. A mattress, even the best mattress, is a commodity. It was always about the story, about confronting the absurdity of mattress shopping, the bizarre box, and euphoric sleep. I won a bunch of awards, too! That was nice. 

TGL: In January 2019, you and your co-founder Carolyn Childers launched Chief, a private network for C-Level women leaders, and you raised 40 million dollars. What was Chief’s starting point? 

LK: When I started at Casper, I was a self-styled VP in name only. There were seven of us at the company, I could have called myself anything. But as Casper grew, so did my role. Eventually I earned that VP title. I managed three departments in addition to working cross functionally on high level strategic projects. That was a moment I needed support. I was great, but I had no idea what the hell I was doing. And yet, rather than receiving help, I was getting asked to coffee by younger women in the organization, speaking on panels, and giving more of my time away to others. 

That’s why we created Chief, to unite and support women who are in executive roles. Up until Chief, the closest I came to support was a one-on-one relationship with an executive coach who was helpful, but didn’t actually get the lake challenges I was battling. On the network side, I have always hated the awkward professional mixers with oversized name tags, warm wine, and stilted conversations over a cheese plate sweating in the corner. Chief is personal. It is a network for women sitting at the table to come together, co-mentor one another, normalize challenges, and cross-pollinate power. 

I left Casper to launch Chief. I expected 50 or so women to join, but we were joined by 200 incredible founding members in January 2019. We have grown to over 4,000 executives in New York, Los Angeles, Chicago, Boston, San Francisco, and Washington, DC.

TGL: Chief’s network includes senior leaders in the United States from over 1,700 companies and has a waitlist of more than 8,000 people. What is the secret of this success? 

LK: Time travel. It’s one of our core values. Chief members are busy - they are leading companies. We focus on creating concentrated value in our services. Our curated peer groups are hand-selected based on an array of factors to bring together a diverse group of women with common ground. Our women are used to speaking at conferences, so when we do events we go big, welcoming icons like Stacey Abrams, Amal Clooney, and Mindy Kaling, and presenting workshops by MBA professors and leading world economists. Our goal is to connect members to a brilliant community of powerful peers and support them in their leadership journey. 

TGL: You have said, “Lift while you climb” as an aphorism to explain personal and professional advancement. Chief has a game-changing approach to supporting women in their journey to executive leadership, providing mentorship, coaching programs, and access to peers. Can you describe your philosophy for advancing in a career? 

LK: An advisor once told me, “We won’t reach parity when the best women make it to the top. We’ll get there when a few of the dumb ones make it, too.” 

Someone else once said, “A relationship is like a shark - it has to constantly move forward or it dies.” Many operate under that assumption, but I don’t think that’s true with your career. I’m glad I took a few lousy startup jobs that weren’t right for me. I’m happy I had a windy, loopy path to get me where I am. The wider your experience, the larger your Rolodex. It’s taught me to be creative, boundary-pushing, and relentless. 

TGL: COVID-19 had a huge impact on events and community-building. How has it affected Chief?

LK: We launched Chief as a community with a space in New York City for the community to gather, but our core services have never been space dependent. The team was incredible and pivoted fully to digital overnight. Not one peer group or event was cancelled. 

In 2020, we launched a new website and app with a community platform, hiring boards, and content library. We immediately offered every member a complimentary one-on-one career coaching session and developed partnerships with leading executive and board placement service groups. 

TGL: What is your vision of the future of community-building: digital vs. in person?

LK: In person is special, but digital is democratic. You cannot build an inclusive community in this new world by making people show up in person. It just doesn’t account for parents, travelers, remote workers, or individuals with disabilities. 

TGL: COVID-19 has also impacted women differently than men, especially mothers, and has reinforced the importance of diversity, equality, and sustainability inside corporations. How can companies foster equality, especially in leadership positions?

LK: You can’t just will change into existence. There is no press release, data report, or employee survey in the world that drives change. It’s a start. It’s a moment in time, but it is not progress. You have to do the work. 

At Chief, we recognize that our role is not just driving more women into power, it’s changing the face of leadership. We all know that men outnumber women in executive roles, but in the seats women have, only 18% are BIPOC women. At launch, our stated goal has been to double that number, and we are nearly there - our membership is currently 35% BIPOC. This isn’t just a shallow metric, we have confidential identity groups, grant programs, and inclusive programming. We are continuously looking to build our efforts and actions to make our organization as diverse, equitable, and inclusive as possible. There is always more we can do, and steps we can take to make change happen. 

TGL: What are your goals for 2021?

LK: World domination and then a nap. 

TGL: Who would you like to have dinner with that you don’t already know?

LK: Vice President Kamala Harris. 

TGL: What advice would you like to give to The Genius List’s readers?

LK: There is no better place to be than in a hot bath with a good book.