The Chief of Staff Podcast

Is your company growing fast and evolving? In this episode, you will learn from Shelby Sly, Chief of Staff and Director of Strategy and Operations at Ridgeline, who shares her career journey into the CoS role and her contributions to the Ridgeline’s growth. She details the company's evolution from around 200 employees to 400+ employees, emphasizing the shift from a meeting-heavy culture to a more efficient, asynchronous communication model. Shelby highlights the importance of trust, adaptability, and effective meeting facilitation in her role. She also reflects on her career journey and growth, including her experience co-founding the Cal Poly Women in Business Association, and she also shared stories about career inflection moments. Excited for you to level-up as a Chief of Staff!You learn more about the Chief of Staff Network, our membership, upcoming events and programs on our website.https://www.chiefofstaff.network/

In this episode, you will learn from Karly Gelardi, a Chief of Staff at Zapier, and Brandon Sammut, the Chief of People Officer at Zapier, about their roles and working relationship. Brandon emphasizes the importance of clarity in defining Chief of Staff roles and the need for a strong match between the leader and the Chief of Staff. They discuss the interview process, onboarding, and the importance of open communication and trust especially while working remotely. Karly highlights the evolving nature of her role and the significance of feedback. Karly and Brandon will also be speaking together at our Chief of Staff San Francisco Connect conference on May 15-16. Join us in San Francisco! You learn more about the Chief of Staff Network, our membership and upcoming events and programs on our website. https://www.chiefofstaff.network/Excited for you to level-up as a Chief of Staff! 

Do you have an unconventional background too? In this episode, you will learn from Jenna Parker, the Chief of Staff at Healthie, about her path into the role from a lack of healthcare and tech background. Her background has not deterred her in the role at all, as she has rotated and managed four different departments in 2024. Jenna also emphasized the importance of relationship building, direct communication, and setting boundaries as a Chief of Staff. She also shared CoS hiring tips that she has communicated with CEOs when they approach her about hiring another CoS like introspection and alignment of skills. Excited for you to level-up as a Chief of Staff!Learn more about the Chief of Staff Network's membership and upcoming programs and events at:https://www.chiefofstaff.network/

In this episode, you will learn from Chief of Staff Sofia Badalamenti and Eniac Ventures Cofounder Nihal Mehta. They have been working together for two years. In this episode, they share communication best practices and workflows. They also talked about how they have worked together to double-down on both of their strengths, which is effective email use and relationship building. They also talked about the importance of trust and responsiveness in working together. Excited for you to level-up as a Chief of Staff! Learn more about the Chief of Staff Network, our membership and upcoming events here:https://chiefofstaff.network/

In this episode, we dive deep into the world of crisis leadership through the lens of a Chief of Staff who has wartime CoS experience. When markets shift, competitors attack, or internal challenges threaten to derail progress, organizations need leaders who can make rapid decisions with imperfect information. Chief of Staff veteran Lindsey O’Sullivan shares her related experiences, insights and techniques. Whether you're leading through a major transition, responding to market disruption, or simply preparing for the inevitable storms of business, this episode offers invaluable insights for modern leaders who must thrive under pressure. You will also learn about how Lindsey got her current role through networking and many other practical tips. Excited for you to level-up as a Chief of Staff! Learn more about the Chief of Staff Network, our membership and upcoming events here:https://chiefofstaff.network/

In this episode, you will learn from Ali Sardinia, the Chief of Staff at Order.co, about her two Chief of Staff experiences and the importance of storytelling in business. She highlights how, in her current role, her company is focused on embedding stories into presentations, all-hands meetings, and marketing materials to enhance understanding and impact. Ali also shares why this initiative came to be. Ali mentions the use of one-pagers to improve cross-functional collaboration and visibility within the company as well. For aspiring CoS, Ali advises people take on challenging roles and to continuously learn. Excited for you to level-up as a Chief of Staff! Learn more about the Chief of Staff Network, our membership and upcoming events here:https://chiefofstaff.network/

Kyle Hagge, Chief of Staff at Morning Brew Inc., shares insights on maximizing impact in the workplace. He highlights the financial advantages of improving events and sponsorships. Using AI tools like Granola for efficient note-taking is a game changer. Kyle emphasizes the importance of empathetic communication and leveraging your role to foster curiosity. He also tackles the dreaded 'Sunday scaries' with practical strategies. This conversation is a treasure trove for those looking to elevate their Chief of Staff role!

Remi Guarini, a seasoned Chief of Staff and the first employee at Neon, shares her insights on thriving in startup environments. She discusses the evolution of the Chief of Staff role, emphasizing the importance of relationship-building and adaptability. Remi advocates for creating a 'user manual' for principals to enhance communication and efficiency. She highlights the value of a generalist skill set and urges aspiring Chiefs of Staff to embrace challenges as growth opportunities.

In this episode, you will learn from Sophie Kaye, a former Chief of Staff and current Director of Operations & Program Management at Frame.io, which was acquired by Adobe in 2021. Sophie discusses her non-linear career path, including her role as an early employee at a dental healthcare startup and her transition to being a Chief of Staff at Frame.io. She details her experience as a CoS at Frame.io during their acquisition by Adobe, emphasizing the importance of privacy and organization. Post-acquisition, Sophie's role has evolved, spanning across marketing, M&A, program management and business operations. She highlights the significance of relationship building, embracing ambiguity, and not striving for perfection. Sophie encourages aspiring Chiefs of Staff to build connections and be open to opportunities. You can learn more about Chief of Staff Network, our membership, upcoming events and more on our website: https://www.chiefofstaff.network/

Are you looking to connect with other Chiefs of Staff in-person in 2025? Listen to this episode with Scott Amenta, the Founder of the Chief of Staff Network. In it, you will hear how Scott started the community and how in-person meetups were critical in the early days of launching the community. Fast forward to 2024, we hosted 60+ events globally. In 2024, we also hosted a two-day Chief of Staff Connect conference in New York City. In 2025, we plan to host three Chief of Staff Connect conferences in San Francisco (in May), New York (in October), and London (in November). In this episode, you will hear what we learned from the 2024 Connect conference and how the 2025 Connect conferences will be slightly different. You can learn more about Chief of Staff Connect, our membership, and more on our website: https://www.chiefofstaff.network/