Chief of Staff Network

10 episodes scanned. 100% of ad slots promote the show's own products.

Recent Episodes

1. Chief of Staff to the CEO, or to the Business? with Ryan Kelly

   Oct 21, 2026

   Ryan Kelly, Chief of Staff at Veremark, a Series B workplace trust company with around 300 fully remote employees, describes how he pitched the role to CEO Daniel and won it through an open process. The conversation covers his non-linear career path, how he built trust with his CEO through an early onsite week, and the ambiguity of defining a first-ever chief of staff role. It also touches on whether the role serves the CEO or the wider business, Veremark's approach to AI adoption, and the human, negotiation-heavy nature of the job.

2. Why AI Can't Be a Chief of Staff with Sawyer Middeleer

   Oct 14, 2026

   Sawyer Middeleer, founder of Revi Systems and former Chief of Staff at Aomni, an AI sales research startup, discusses why many companies have adopted AI tools without changing how they work. He argues that teams should map how work gets done and what value it creates before automating, and that automation often fails when the context and judgment held by people are not captured. The conversation also covers building tools that may be replaced within 12 months, and why AI Chief of Staff products can handle tasks like inbox triage but not the full role.

3. Who Owns Culture? Yorm Ackuaku Changed Her Mind

   Oct 7, 2026

   Yorm Ackuaku, former Chief of Staff to multiple executives at WeightWatchers, discusses how culture is owned by leaders through their behavior, while Chiefs of Staff own the operating rhythm that reinforces or erodes it. She shares her experience supporting four different leaders across changing mandates and explores how consistent processes, transparent communication, and authentic storytelling—like her marketing team's three principles that spread across the enterprise—help maintain culture during leadership transitions and organizational instability.

4. Inside the Family Office: The Chief of Staff Role with Donald J Cunningham

   Sep 30, 2026

   Donald J Cunningham, Head of Family Office for a senior member of the Qatari royal family, discusses the unique dynamics of working as a chief of staff in single-family offices where principals have virtually unlimited resources. He shares his unconventional path from investment banking and M&A into family office work, and explains how the role differs fundamentally from corporate chief of staff positions—requiring constant navigation between personal and professional priorities, extreme discretion, and the ability to push back on decisions even when resources are limitless.

5. What AI Policy Is Borrowing From Humanitarian Work with Anna Aden

   Sep 23, 2026

   Anna Aden, Chief of Staff to the Managing Director for Asia Pacific at the Tony Blair Institute for Global Change, discusses her unconventional career trajectory from humanitarian work in refugee camps and crisis response to AI policy and global governance. She draws parallels between humanitarian principles and ethical frameworks now being adopted by tech companies, and explores how the Chief of Staff role serves as a bridge and systems integrator across geographies and stakeholders. The conversation covers managing cross-regional teams with HQ in London, navigating cultural differences between Asia and Western business contexts, and the future of the role in an AI-driven world.

6. Speaking Directly When No One Else Will with KJ of Bifrost AI

   Sep 2, 2026

   Kartikeya Jaiswal (KJ), Head of Strategy and Operations at Bifrost AI, discusses his six-year journey in chief of staff and CEO office roles across two startups—The Parent (Series B to D) and Bifrost (pre-seed to Series A). The episode explores why the chief of staff role demands the courage to speak hard truths respectfully and directly when no one else will, and covers the evolution of his responsibilities from CEO support to go-to-market strategy and corporate development at a physical AI robotics company.

7. You Are the Product: Managing Yourself as a Chief of Staff

   Aug 26, 2026

   BreeAnne Yek, Chief of Staff at a Series A MedTech and luxury wellness startup, discusses her philosophy of managing oneself as a foundation for effective leadership. Drawing from her nonlinear career spanning Singapore's public sector, oil and gas services, and climate tech startups, she explores behavioral design, the tension between people and processes, and how self-awareness enables better relationships with principals and teams. The episode covers influencing without authority, navigating cross-cultural dynamics in startup environments, and what lies beyond the Chief of Staff role.

8. A Second Brain, Not an Assistant: beehiiv's Chief of Staff Model

   Aug 19, 2026

   Tyler Denk, co-founder and CEO of beehiiv, and Brian Schneider, his Chief of Staff, discuss the evolution of their working relationship from Morning Brew through to beehiiv, emphasizing radical transparency as an operating principle and the distinction between a Chief of Staff as a 'second brain' versus an executive assistant. They explore how beehiiv's philosophy of building enterprise-level software democratized for all creator sizes has shaped company culture, decision-making, and the specific dynamics that make their principal-CoS relationship effective after three months in the role.

9. Why the Chief of Staff Should Own AI Adoption, with Zen Foo

   Aug 12, 2026

   Zen Foo, Chief of Staff at Aspire (a YC-backed fintech company in Singapore), discusses why the Chief of Staff role is uniquely positioned to lead AI adoption across organizations. He outlines three stages of AI enablement—from hype to chaos to governance—and emphasizes that getting people to their "magic moment" is more important than metrics or mandates. The conversation covers balancing likability with respect, protecting principal trust, and how the Chief of Staff role has shaped his personal judgment and empathy.

10. Why Slowing Down is a Chief of Staff Superpower

    Aug 5, 2026

    Carrie McMahon, a two-time Chief of Staff currently at Horizon3.ai, discusses how energy management functions as a core performance strategy for strategic operators. Drawing from her background in go-to-market and operations across Zendesk, Coda (now Superhuman), Benevity, and Productboard, combined with her training as a certified yoga and breathwork instructor, she explains how slowing down and regulating the nervous system directly improves decision-making quality and leadership presence. The episode challenges the notion that wellness is a perk rather than a prerequisite for sustained high performance in fast-paced tech environments.