Chief of Staff / Right-Hand Operator — Long-Term, Remote (US, East Coast hours)

I own a portfolio of telehealth, consumer health, and events companies all built around acquisition and marketing. I have great teams for the entities, but I need someone that can represent me and keep an eye on things for me. This will happen once that person understands the insights and style that I use to run things. I'm heavy on vision, strategy, communication with external folks, and high-level communication with internal leaders out of times outside of when I need to zoom in to real granular elements of marketing My last chief of staff actually ended up taking over as the CEO for my SaaS company. I need a right-hand operator who can also think strategically and manage to close that gap — starting hands-on, growing into a true Chief of Staff. What you'll actually do: Take the decisions and commitments that come out of my calls and turn them into finished outputs — drafts, docs, tasks, messages — to a high standard. Drive follow-through on initiatives across multiple brands. Chase threads to done. Hold the "we decided this three weeks ago — did it move?" accountability layer. Own the things that fall through the cracks between teams and brands until they're resolved. Operate as an extension of me: closing loops, coordinating, nudging on my behalf. What this is NOT: inbox management, calendar scheduling, or note-taking — AI handles all of that. This is ownership of execution, not admin. This grows. As you learn how I think, you'll move from executing my decisions to owning initiatives and making calls on my authority — and you'll hire and manage support beneath you. This is a Chief of Staff role with an apprenticeship built into the front end. I'll put the ramp in writing. You are: an operator with real judgment and real ambition who'll do unglamorous work now because you see where it leads. Fast, low-ego, comfortable in ambiguity, allergic to dropped balls. "I'll just handle it" is your reflex. You are not: a career EA who wants admin to be the whole job, or a strategist who won't touch execution. Details: Long-term, ongoing. Start ~20–30 hrs/week, scaling to full-time as you take on more. US-based, able to work East Coast hours. .