Chief of Staff / Executive Assistant

I am offering an apprenticeship-to-paid role. Here is the honest structure.

I’m an entrepreneur running multiple businesses with a high volume of ideas. I need more than a traditional assistant. I’m looking for a true partner—a second brain and a pair of trusted hands who can take an idea and run with it.

This role is dynamic and fast-moving. One day you might handle targeted outreach. The next, you're sourcing and vetting a specialist to explore a new venture. The common thread: when I say “go,” you make it happen with autonomy and good judgment.

You'll work directly with me, touching multiple ventures. For the right person, this role grows into a true Chief of Staff position—making decisions, managing projects, and running parts of the operation independently.

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What You'll Actually Do

· Execute tasks accurately and quickly across outreach, research, talent sourcing, and project coordination
· Act as my proxy in emails, calls, and follow-ups with professionalism and discretion
· Find, vet, and manage freelancers, partners, or specialists for evolving business needs
· Organize chaotic workflows across multiple businesses and keep momentum high
· Research industries, tools, or ideas and return with clear, actionable summaries
· Handle administrative and operational work with a solutions-first mindset
· Grow into managing projects and making day-to-day decisions on my behalf

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Who You Are

· Execution-focused. You take initiative and reliably turn direction into results.
· Resourceful. You figure things out without needing a detailed script.
· Comfortable with variety. Multiple businesses and shifting priorities energize you.
· A clear communicator. You share what's done, what's stuck, and what you need—directly and respectfully.
· Humble and sharp. You'll handle unglamorous tasks without hesitation, but you also have the judgment to spot weak deals or poor-fit candidates.
· Ambitious for the long term. You want a career-defining partnership, not just a job.


Requirements

· 2+ years as an Executive Assistant, Operations Manager, or similar role supporting a high-output entrepreneur
· Experience juggling multiple businesses or projects simultaneously
· Proven ability to source, vet, and hire freelancers or specialists
· Impeccable written English
· Bonus: exposure to real estate, startups, or outbound sales