Executive Assistant
/ Chief of Staff

This is not a conventional EA role, and if that's what you're looking for, this isn't it.

The principal runs a profitable e-commerce startup, holds several board seats across the U.S. and internationally, and manages an active investment portfolio, all while being a present parent and homeowner mid-renovation. But the primary home for this role is Friedland Enterprises, a consulting and board seat holding company through which the principal advises founders, engages with clients, and coordinates across a network of attorneys, accountants, financial advisors, and other professional relationships. The connective tissue holding all of that together is currently held by AI systems, a shared family office, and willpower. You are the human layer that makes all of it actually work.

Most of this role can be done remotely. Some of it — managing contractors, overseeing household operations, handling physical logistics — requires being nearby in Miami Beach. If you only want one or the other, this is not the right fit.

What makes this different is the AI component. The principal runs heavily automated systems for email triage, research, board preparation, financial reconciliation, and more. Your job is not to do those things manually. It is to operate those systems, keep them running, improve them over time, and step in with judgment when automation hits its limits. The person who thrives here sees that as exciting, not threatening.

You will also be embedded in real business decisions, board-level dynamics, investment research, and international operations including active relationships in Brazil. If you are ambitious and intellectually curious, the exposure here is hard to replicate anywhere else.

This starts part-time with a clear path to full-time for the right person.

On the household side, you will manage an active home renovation project in Miami Beach, coordinating contractors, tracking timelines, attending walkthroughs, and catching problems before they escalate. You will own recurring home services including cleaning, pressure washing, landscaping, pool, and HVAC — managing vendor relationships and holding people accountable to a standard the principal does not have to think about. Day-to-day logistics like grocery runs, pharmacy, dry cleaning, and errands are part of it. Property matters beyond Miami Beach are handled through a shared family office, and you will coordinate with that team rather than manage them directly.

On the executive and business side, the principal uses AI to handle the bulk of email triage, board prep, research, and travel planning. Your role is to operate those systems reliably, step in when the principal is unavailable, and continue training and improving the AI workflows over time. A meaningful part of this role involves Friedland Enterprises client and advisor coordination: scheduling and managing touchpoints with consulting clients, tracking the status of active engagements, liaising with attorneys, accountants, and financial advisors, and making sure nothing falls through the cracks across a complex web of professional relationships. You need to be comfortable operating in a consulting context, which means understanding confidentiality, managing multiple parallel workstreams, and communicating professionally with sophisticated counterparties. Calendar management, coordinating across U.S., Brazilian, and Canadian time zones, is a meaningful part of this. Brazil-related investment and governance matters will come through this role, making Portuguese fluency a real advantage.

On the financial side, reconciliation is handled by AI. Your job is anomaly flagging, identifying charges that do not look right, subscriptions that have drifted, or vendor invoices that do not match expectations, and using AI tools to systematize that process over time. You will coordinate with the wealth advisor and accountants on time-sensitive items and own the calendar of when contracts and renewals need attention.

You need to be located within 20–30 minutes of Miami Beach. Most work is remote, but physical availability on short notice is a real requirement. Genuine AI fluency is non-negotiable. You use Claude, ChatGPT, or equivalent tools in your actual workflow today — not occasionally and not experimentally. Judgment is the most important thing: you make the call on most things without escalating and you know which ones to bring forward. You will know a great deal about this person's life and business, and discretion is a hard requirement, not a preference. A driver's license, reliable transportation, and a genuinely low-drama operating style are baseline.

Experience managing a home renovation or construction project is a strong plus. A background supporting a founder, investor, or family office principal is valuable. Familiarity with venture capital, board governance, or investment operations is useful. Spanish fluency is valued. Portuguese fluency is particularly valuable given active relationships in Brazil. Prior exposure to e-commerce, supply chain, or technology companies provides helpful context.

This is not the right fit for someone who needs structure handed to them, wants predictable uniform hours, or sees AI as a gimmick. The workload is uneven. Some periods are intense and some are quiet, and operating well in both is important.

There is no single archetype here, but a few profiles come to mind.

Someone who spent years in operations, project management, or a chief of staff role, stepped back to raise a family, and is now ready to re-engage part-time with something genuinely interesting. That person already knows how to run complex logistics, manage people, and prioritize under pressure. They just need a principal worth doing it for and a schedule that works.

Someone early in their career who is extraordinarily organized, self-directed, and hungry to learn by proximity. Not someone who wants to watch from a distance, but someone who wants to be in the room where decisions happen and is willing to earn that by executing flawlessly on the details first.

Someone who has run their own household, business, or team at a high level and understands intuitively what it means to serve a principal's goals as if they were their own. The title does not matter to them. What matters is that things work.

The common thread across all of them is a genuine desire to serve and to automate. Not to be served. Not to delegate upward. To make the person they support measurably more effective, and to build systems that do that at scale.

The right person grows into a true partner here, not an assistant. You will be close to real decisions, real deals, and real relationships across business, investing, and board work in the U.S. and internationally. That access is available to someone who earns it by executing relentlessly on the basics first.

This starts at 20–25 hours a week. The path to full-time is performance, not time served.

Pay is commensurate with experience. This is a 1099 independent contractor engagement to start.