Chief’s Executive Transition Teaches Leaders How To Step Forward By Stepping Aside

Carolyn Childers and Lindsay Kaplan know that the phrase "it's lonely at the top" is more than a well-worn cliche: It's a reality for the women who make up 11.8% of U.S. C-suites. It's also why, in 2019, they founded Chief, a networking organization meant to give leadership advice and camaraderie to female executives looking to grow their reach and influence.

This advice isn't always about stepping up, either: Founders learn that sometimes they need to step away, or "figuratively fire" themselves. And today, Childers and Kaplan are taking that advice.

In a defining moment for Chief, Childers and Kaplan are transitioning from their operational roles as CEO and Chief Brand Officer to strategic positions on the board. Childers will take on the role of Chairman of the Board, while Kaplan will serve as Board Director. Alison Moore will replace Childers as CEO.

The transition marks an inflection point for the networking organization, illustrating a broader lesson for entrepreneurs: knowing when it’s time to disrupt yourself. Childers candidly reflected on a quote from Andrea Zhang, “As a founder, take a step back and say, ‘If I fired myself, and I was starting again today, what would I be doing differently?’ You can often get stuck in the rut of, ‘Well, I made these decisions. I need to continue in these decisions.’ You need to be able to disrupt yourself as if you were somebody new coming in. This mindset helps us ensure Chief evolves to meet its mission.”

This approach isn’t just about relinquishing control; it’s about creating space for fresh perspectives and sustainable growth. The duo’s move to the board ensures their influence remains integral while empowering Moore to lead with her expertise.

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This shift, which takes effect on February 3, signifies a new chapter in Chief’s mission of empowering female executives while highlighting the importance of founder self-awareness and adaptability in scaling organizations.

“Lindsay and I have built something beyond our wildest dreams,” Childers comments, “and as founders, the hardest yet most rewarding decision is knowing when to step back to let someone else take it further.”

In less than a decade, Chief quickly grew from a small New York City-based network to an executive powerhouse with over 10,000 members representing 77% of Fortune 100 companies. Over the summer, Chief introduced a revamped membership model designed to better meet the diverse needs of its members at various stages of their professional journeys. The three-tier offerings include executive advisory, coaching and education, encompassing peer advisory groups, one-on-one coaching and live academic courses.

Their decision was not made lightly. As Kaplan noted, Chief's essence lies in its commitment to community and leadership, and this transition mirrors the organization’s foundational values. “Chief has always been about leaving the door open for others and creating spaces for leaders to flourish,” she said. This philosophy drove their search for a transformational leader who could balance innovation with the organization’s mission.

Why Moore?

Moore, a seasoned executive with experience in media, entertainment and social impact, embodies the blend of leadership and values that Chief needs. A founding Chief member herself, Moore has a deep understanding of the challenges female executives face.

Her five-year tenure as CEO of Comic Relief US further demonstrated her ability to scale mission-driven organizations while fostering innovation. Building on the success of its iconic Red Nose Day campaign, Moore successfully increased the reach and influence of Comic Relief US by launching innovative campaigns, pursuing new partnerships, and expanding to emerging platforms—ultimately resulting in more than $436 million raised and 35 million children impacted.

Speaking about her new role, Moore shared, “I’m thrilled to build on the incredible foundation Carolyn and Lindsay have established. My focus will be on creating experiences that continue to inspire and support women leaders at every stage of their journey.” Her vision includes refining the recently launched membership tiers, “It’s about understanding and responding to member feedback to deliver tools and experiences that matter most.”

Founders Stepping Back: A Strategic Imperative

Moore’s strategic priorities signal Chief’s commitment to innovation and member-centric growth. “There’s so much opportunity to build on this [the latest initiatives],” the incoming CEO commented. “The needs of a Fortune 500 executive differ from someone embarking on an entrepreneurial journey, and Chief is uniquely positioned to address these nuances.”

During the interview, the women emphasized that while every member’s journey is unique, recurring themes often emerge in their conversations. Members navigate a wide spectrum of challenges, from adapting to the rapid integration of AI in the workplace to balancing the demands of childcare, elder care and other personal responsibilities.

As stated in the IBM study on female leadership in the age of AI by Ana Paula Assis, Chair and General Manager IBM EME, “Given the scale of the AI revolution, the people leading this transformation must be representative of society at large. One key part of this is ensuring that women are active leaders in this technological revolution.”

These discussions reveal a shared complexity in the lives of women leaders as they juggle professional goals with the realities of family and societal expectations. As more women advance into executive positions, mentorship plays an even bigger role. Over 71% of Fortune 500 companies use mentoring, and 87% of mentors and mentees feel empowered by their mentoring relationships and have developed greater confidence.

Chief’s ability to provide a space where members can share these experiences, gain support and exchange solutions underscores its value as a community that addresses professional growth and recognizes leadership's holistic nature.

Lessons For Entrepreneurs

Chief’s transition is a foundational marker in leadership evolution. Childers and Kaplan demonstrate the courage and foresight founders need to ensure their organizations thrive beyond their tenure by stepping back. Their story also underscores the importance of choosing successors who align with the company’s mission while bringing fresh perspectives.

For Moore, the baton pass represents more than just a career pivot; it’s a continuation of a journey she’s already been part of. “I’ve been a Chief member, and I’ve lived the challenges of being a woman leader. This role is an opportunity to scale those experiences and make an even greater impact,” she shares.

As the leadership transition unfolds, one thing is clear: Chief’s next chapter is in capable hands, and its mission to redefine women’s leadership remains unwavering. This evolution is not just a shift in roles; it’s a testament to the power of community, adaptability and shared vision in driving meaningful change.