From English major to billion-dollar entrepreneur, Lindsay Kaplan shares how her creativity, rebellious spirit, and refusal to follow the rules led her to co-found Chief, the premier network for executive women.

Lindsay’s journey is anything but traditional. She began her career with dreams of writing novels, moved into publishing and magazines, and then found herself on the cutting edge of digital marketing during the early days of Facebook and Foursquare. Her storytelling expertise eventually brought her to Casper, where she became a founding team member, built global campaigns, and helped turn a mattress startup into a cultural phenomenon. But it was her partnership with Carolyn Childers that sparked her biggest leap, co-founding Chief, now a billion-dollar company reshaping what leadership looks like for women at the VP and C-suite levels.

In our conversation, Lindsay opened up about the pivotal moments that shaped her leadership path, from building credibility as a nontraditional founder, to navigating the challenges of co-founding a VC-backed company, to realizing when it was time to step into a board role to protect her own health and longevity. She emphasizes the importance of finding co-founders who share your values, the realities of burnout that often accompany leadership, and why flexibility, not perks, is the true key to retaining women in executive roles.

What stands out most about Lindsay is her deep commitment to creating spaces where women leaders can both give and receive mentorship. Chief was built on the belief that even the most senior leaders need support, and Lindsay’s story is a powerful reminder that community is not a luxury — it’s a necessity. Listeners will walk away inspired by her candid reflections on career evolution, her practical wisdom on building and scaling companies, and her fierce advocacy for women at the top of their fields.

This is an episode you won’t want to miss! Tune in and hear Lindsay’s incredible story of creativity, resilience, and leadership redefined.

Chapters
👩‍💼 00:55 Meet Lindsay Kaplan and Her Leadership Journey

🚀 04:55 From Creative Roots to Entrepreneurship

🌟 08:15 Building Chief as a Network for Women Executives

🤝 10:56 Why Shared Values Make Partnerships Stronger

💼 13:49 Breaking Barriers for Women in Corporate Leadership

🏢 17:28 How Physical Spaces Strengthen Community

⚖️ 18:49 Finding Balance Between Work and Personal Life

🔮 24:34 The Future of Chief and Women’s Leadership

Links

Website: http://chief.com
LinkedIn: https://www.linkedin.com/in/lindsaykap/
Email address: [email protected]
Check out Lindsay Kaplan’s work at Chief, connect with her on LinkedIn, and explore how she’s building the future of executive leadership for women.

Reach out to Adrienne: [email protected]

Visit our website: www.sheleadsmedia.com

Join us at the upcoming She Leads LIVE 2025 conference in NYC on November 6th & 7th. Learn more at sheleadsmedia.com

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