Ena Patel, Team President at Innovation Baseball Partners, has built her career by stepping into complexity and turning it into momentum. In this episode, she joins Tom Guthrie, President of Chief of Staff Network, to share how she moved from tax law into the sports business, why shifting others’ perception (“not just a lawyer”) became one of her biggest early challenges, and how relationship-building across every business unit became her operating system.

Ena walks through what it takes to be effective as a Chief of Staff in environments that are either being built from scratch or shaped by deep tradition. We also explore Ena’s leap into the #1 seat as President of Innovation Baseball Partners, acquiring and building independent minor league teams with a community-first approach. Her advice to Chiefs of Staff considering a similar step is simple and direct: don’t say no to yourself.

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Jamie White, Chief of Staff, Marketing at Notion, shares her journey from Broadway and consulting to driving clarity and alignment in high-growth tech companies like Slalom, Grammarly and Notion. In this episode, she introduces her “Three Altitudes” framework, an operating model Chiefs of Staff can use to navigate principal alignment, leadership cadence, and cross-functional orchestration.

We discuss the evolving role of the Chief of Staff, how to partner effectively with executives, and how Jamie blends systems thinking, coaching, and AI to accelerate decision-making without losing context.

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Explore the Notion AI products Jamie utilizes here: https://www.notion.com/product/ai

In this episode, we sit down with Lu Borko, Chief of Staff at Manychat, to unpack how fast-growing companies can scale without losing their edge.

Drawing from her experiences at Deliveroo, Intercom, and now Manychat, Lu shares how to build systems that support growth while keeping teams agile and aligned. We talk about the building blocks of operational excellence, the real work behind making an executive team act like a team, and how to lead without authority by connecting the dots others don’t see.

If you’re navigating scale, team complexity, or cross-functional friction this episode is for you.

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Tommy Caulfield and James Whittle — better known as The Tempest Two — had never rowed a boat in their lives when they set out to cross the Atlantic Ocean. No experience. No support crew. Just a willingness to figure it out.

In this episode, we explore what extreme adventure can teach us about resilience, leadership, and adaptability — especially when facing uncertainty. From surviving a hurricane and a nighttime capsize to building teams and coaching startups, they share how to turn breakdowns into breakthroughs and why the best leaders actively put themselves and their teams just beyond their comfort zones.

We also talk about their upcoming keynote and immersive Experience at the upcoming Chief of Staff Connect EU in London, and why pushing boundaries is the key to real growth.

Learn more about Tommy and James' work at Tempest Experiences.

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Tristan Lim went from scaling a high-growth startup as Chief of Staff at Commsor to coaching founders and operators on how to lead with clarity, courage, and purpose. In this episode, he joins Scott to explore the inner work that too often gets overlooked in fast-moving organizations—setting meaningful boundaries, avoiding burnout, and staying grounded through change.

Tristan shares powerful lessons on self-awareness, emotional resilience, and the importance of having a clear personal anchor in the chaos of startup life. You’ll walk away with practical tools for reflecting on your motivations, building your support system, and creating space for both yourself and your team to thrive—especially when things get hard.

Learn more about Tristan's work: https://www.beyondfounders.com/

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

In this episode, Dow Jones Chief of Staff to the CTO/CPO, Andrea Mayendia, joins Scott to explore how storytelling can drive clarity and confidence during large-scale transformation. Drawing from her 20+ year career in product, strategy, and operations at S&P Global and Dow Jones, Andrea shares how clarity, transparency, and a few well-told stories can unite teams across silos.

It’s a masterclass in how Chiefs of Staff can lead transformation through communication, not control.

Learn more about the Chief of Staff Network's membership, courses, and events here: chiefofstaff.network/pro-membership

Former SoftBank Chief of Staff to the COO, Dora Nagy, joins Scott Amenta to unpack the real operating system behind scaling leaders and organizations. From her early career at Google to helping launch SoftBank’s $100B Vision Fund, Dora shares what she’s learned about translating strategy into execution, building accountability into leadership rhythms, and managing the human dynamics that make or break scale.

She introduces her “CEO Operating System” framework and explores the Drama Triangle, a powerful model for transforming conflict into alignment—a preview of her upcoming workshop at Chief of Staff Connect London.

Links Mentioned:

The Concise Laws of Human Nature

The 48 Laws of Power

Dora Nagy's CEO Operating System

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

Operator and fractional Chief of Staff Lauren Werner (ex-Slate, Vox) shares how she translates market signals into systems that drive growth. We cover her transition to fractional Chief of Staff, landing her first clients, defining high-impact scopes (GTM, RevOps, cross-functional alignment), and practical ways Chiefs of Staff can quantify their value and tie work to the P&L.

Plus we discuss how her media background has informed community growth and belonging at the Chief of Staff Network.

Learn more about the Chief of Staff Network's membership, courses, and events here: https://www.chiefofstaff.network/

In this episode, Tom Guthrie, President of Chief of Staff Network, sits down with Andrew Rea, co-founder and CEO of Taxwire, to unpack the challenges of global sales tax compliance and the shifting role of finance teams in fast-growing startups. Andrew shares insights on leveraging automation and AI in finance, opportunities for young professionals to stand out, and the importance of building authentic company culture. He also highlights the evolving impact of Chiefs of Staff in early-stage companies—acting as force multipliers and strategic problem-solvers.

Scott Amenta sits down with Dominique Lear, Chief of Staff at Incandescent, to explore why organizational change so often falters on the human side. From her journey in publishing to consulting, Dominique shares lessons on managing fear, building trust, and navigating AI-driven transformations with empathy and clarity.