The Chief of Staff Podcast

Ben Darfler, Chief of Staff and Director of Strategy and Operations at Honeycomb, reveals how his engineering background informs his strategic thinking. He discusses the importance of adapting leadership practices as Honeycomb grows beyond 250 employees and the necessity for executives to shift focus from daily tasks. Ben highlights the power of OKRs and lightweight processes to ensure alignment across teams. He also shares insights on iterating strategies through metrics, empowering directors, and mastering execution to build a successful vision.

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 for Global Marketing at Notion, combines her background in theater and consulting to redefine organizational dynamics. She introduces her 'Three Altitudes' framework, which enhances alignment and leadership efficiency. Jamie shares insights on the evolving role of Chiefs of Staff, emphasizing the importance of enabling teams and managing cross-functional rhythms. She also explores the integration of AI for improved decision-making and discusses her approach to fostering effective partnerships with executives.

Lu Borko, Chief of Staff at ManyChat, shares her insights on scaling companies without bureaucracy, drawing from her experience at Deliveroo and Intercom. She emphasizes the importance of building systems that support growth while keeping teams agile. Lu discusses the essential elements of executive team cohesion and how to lead without authority by connecting the right dots. She also explores creating trust through vulnerability during offsites and how to resolve cross-functional conflicts effectively. Learn strategies for operational excellence and hiring for ownership in fast-paced environments.

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, former Chief of Staff at Commsor and now an executive coach, shares insights on navigating the challenges of startup culture. He emphasizes the importance of setting boundaries to prevent burnout and the value of self-awareness in leadership. Tristan explores creating personal anchors amid chaos, analyzing energy sources, and recognizing physical signs of stress. He highlights how intentional connection and resilience systems can support teams through tough times, advocating for treating your career like a marathon.

Andrea Mayendia, Chief of Staff at Dow Jones with over 20 years in product and strategy, shares her insights on how storytelling can drive organizational transformation. She emphasizes the importance of clarity and emotional resonance in communication, especially during change. Andrea discusses using data to build credibility and how framing messages based on audience context can enhance understanding. She also outlines practical storytelling techniques and highlights the significance of transparency in uniting cross-functional teams.

Dora Nagy, a former Chief of Staff at SoftBank's Vision Fund and now an executive coach, dives into scaling organizations. She shares insights on her non-linear career from Google to SoftBank and her 'CEO Operating System' framework for translating strategy into execution. Dora highlights the importance of people dynamics in leadership, emphasizing how to navigate conflicts using the Drama Triangle model. She also discusses why OKRs often fail without a clear strategy, and offers practical advice for building accountability and effective operating models.

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.