The Chief of Staff Podcast

Are you looking to break into a Chief of Staff role? Maybe you could start as an Associate Chief of Staff and then get promoted to a CoS role. That's what happened to Trust & Will Chief of Staff Ada Madigan. In this episode, you will learn how her role has evolved, how she is focused on helping build the company, and so much more. Excited for you to level-up as a CoS!You can learn more about the Chief of Staff Network’s membership, upcoming events and courses  on our website: https://www.chiefofstaff.network/

In this discussion, Andrew Rea, the Co-founder and CEO of Taxwire, and David Moon, the Chief of Staff, reveal the gritty reality of startup life. Andrew emphasizes the need for constant communication and a deep understanding of a CEO's priorities. David shares insights on cold starting processes and systemizing strategies vital for market entry. They highlight the importance of trust and adaptability in early-stage startups, illustrating how tackling varied tasks shapes a successful venture. Get ready to learn what it really means to 'eat glass' in the startup world!

Are you looking to use AI more in your role? Listen to this new episode with Ana Flávia Silva, a Chief of Staff at Section. In the episode, you will learn about why she got up-to-speed on AI while interviewing for her role and how she has been using AI regularly since. In particular, in this episode, we talk about Claude and Claude Projects, and she and Section have been using this tool. You will also learn about a framework to think about how and when to potentially use AI in your role. Excited for you to level-up as a CoS!You can learn more about the Chief of Staff Network’s membership, upcoming events and courses  on our website: https://www.chiefofstaff.network/

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!