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Jeff Sawyer is seeking an exceptional Executive Assistant / Personal Chief of Staff to support the CEO across personal and professional domains. This role goes beyond traditional administration, demanding proactive ownership of projects from start to finish.
You will manage calendars, travel, household operations, and a broad range of business matters while building AI-powered systems to optimize every process.
We're looking for an exceptional Executive Assistant for our CMO to help manage and streamline both my personal and professional life.
This is not a traditional administrative assistant role.
I'm looking for someone who is highly organized, proactive, resourceful, tech-savvy, and capable of taking ownership of projects from start to finish.
You’ll work directly with me across a wide range of responsibilities, from managing personal affairs, international travel and household operations to coordinating business matters, overseeing projects, and building AI-powered systems that make everything run more efficiently.
The ultimate goal is simple: I should be able to mention something once and trust that it gets done.
I don't want someone who simply manages a to-do list. I want someone who anticipates problems, finds solutions, follows through relentlessly, and makes my life significantly easier.
This role offers a unique opportunity to work closely with an entrepreneur across multiple businesses, personal projects, investments, and international activities.
This is an important and exciting part of the role.
I'm looking for someone who is enthusiastic about AI and technology and wants to build a highly efficient personal operating system.
You’ll help:
You don't need to be a developer, but you should be comfortable experimenting with technology, learning new tools, and implementing solutions.
You are exceptionally organized.
You naturally create structure out of chaos. Nothing slips through the cracks, and you always know what needs to happen next.
You are relentlessly proactive.
You don't wait to be told what to do. You anticipate needs, identify problems early, and take initiative.
You have outstanding follow-through.
If something needs to happen, you take ownership, chase the right people, and make sure it gets completed.
You are resourceful and a natural problem-solver.
You might not immediately know the answer, but you're confident in your ability to figure it out.
You are tech-savvy and AI-native.
You enjoy using AI, automation, and modern productivity tools to work smarter and faster.
You have excellent judgment and discretion.
You'll be trusted with confidential business and personal matters. Professionalism, integrity, and confidentiality are essential.
You are adaptable and dependable.
You understand that supporting an entrepreneur requires flexibility. While this is not an expectation to work constantly, occasional evenings, weekends, and urgent requests will be part of the role.
You are confident communicating with people.
Whether dealing with a bank, lawyer, contractor, or executive, you are comfortable asking questions, following up, negotiating, and getting things done.
This is an opportunity to become a trusted right-hand person to an entrepreneur, with exposure to a wide variety of industries, projects, and experiences.
You’ll have significant autonomy, responsibility, and opportunities to learn.
You’ll also play an important role in developing a modern, AI-powered approach to executive and personal management.