Episode 07 - The Great Debate: Chief of Staff vs. EA vs. COO with Keziah Wonstolen of Vannin Chief of Staff
In this episode of The Lift, Ben is joined by Keziah Wonstolen, founder and CEO of Vannin Chief of Staff. A former management consultant and Chief of Staff (CoS) herself, Keziah is passionate about transforming how modern leaders work through optimizing the role of the CoS
Key takeaways:
Why so many CEOs feel like they’re “drowning” and how a Chief of Staff can give them back hours each week
The real difference between a Chief of Staff, Executive Assistant, and COO (and when you actually need each role)
Vannin’s three-part Chief of Staff framework: Align, Execute, Amplify — and how it works inside high-growth companies
The three chief of staff archetypes (Operator, Strategist, Proxy) and how to match them to your stage and funding model
How Chiefs of Staff can quantify their impact and avoid becoming a “catch-all” role
The #1 skills gap Keziah sees in Chiefs of Staff and why financial and business acumen are non-negotiable for the role
When you’re a CEO or founder, “drowning” can start to feel like a permanent state of being. You’re responsible for strategy, culture, fundraising, customers, the board, and your team (and you’re still the person everyone pings when something goes sideways).
In today’s episode, Keziah Wonstolen draws on her own experience as a management consultant and Chief of Staff at a global firm to break down what a great Chief of Staff actually does – and just as importantly, what they don’t do. She explains why the role has exploded in demand over the last five years, especially in a world of post-pandemic hybrid work, constant change, and AI reshaping every function.
Vannin uses a simple but powerful framework for the Chief of Staff role: Align, Execute, Amplify. According to the framework, the best Chiefs of Staff start by aligning tightly to the CEO’s vision, then building the operating cadence and cross-functional projects that actually deliver on that strategy, and finally amplifying the CEO’s impact through sharper communication, stakeholder management, and better use of time.
Ben and Keziah also get into one of the most common points of confusion: what’s the difference between a Chief of Staff, an Executive Assistant, and a Chief Operating Officer? Keziah lays it out clearly:
Executive Assistants handle repeatable, transactional work (calendars, travel, logistics) and are essential leverage for any executive
Chiefs of Staff own cross-functional, non-transactional projects, planning cycles, and change initiatives where no single function “owns” the work
COOs sit in the C-suite, own operational metrics and teams, and are often the next step for seasoned Chiefs of Staff in larger organizations.
She also shares the three archetypes she sees most often:
The Operator: a junior COO who builds operating cadences, OKR systems, and drives accountability
The Strategist: a thought partner who can translate board or investor expectations into messaging, plans, and decisions
The Proxy: a highly trusted stand-in who can represent the CEO in key meetings and contexts
Ben and Keziah talk about why role clarity is the make-or-break factor and why vague job descriptions with phrases like “ninja,” “rockstar,” or “24/7 support” are red flags. Instead, Keziah walks through how she helps CEOs start with a brutally honest time audit: What should you be doing at this stage as CEO? What are you actually doing? And which gaps call for an EA, a Chief of Staff, a CFO…or even a therapist?
For leaders who already have a Chief of Staff or EA, Keziah shares practical ways to get more value from those partnerships: regular one-on-ones, co-designing the “office of the CEO” rhythm, and being explicit about what success looks like quarter by quarter.
And if you are a Chief of Staff, there’s plenty here for you, too. Keziah highlights the biggest skills gap she sees across Chiefs: financial and business acumen. She explains why being able to read a P&L, understand value‐creation plans, and speak the language of EBITDA, margins, and runway is essential if you want a real seat at the table and a long-term career beyond the CoS role.
Whether you’re a founder thinking about hiring your first Chief of Staff, a CEO wondering if you’re using yours effectively, or a Chief of Staff looking to uplevel your own practice, this episode will help you see the role – and your own time – in a whole new way.
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