AI driven project manager / assistant to co-CEOs

EXECUTIVE ASSISTANT TO TWO CO-CEOS We run a fast-growing education company and we're hiring ann AI savvy assistant to support both of us. This means navigating two execs, two calendars, two ways of working, and a schedule that changes constantly. Some people find that miserable. Some people are very good at it. We're looking for the second kind, and are super open to alternative candidates! Especially folks with a background in project management, AI process improvements, etc. THE BAR You're online and responsive within 30 minutes between 7am and 4pm PT, Monday through Friday. Occasionally something comes up on a weekend and we'd need you within a couple of hours, but that's the exception, not the norm. 40-45 hours a week as the cap (will usually be less than that) You need fluent, precise written English, since you'll be corresponding on our behalf. You also need to actually thoughtful use AI, meaning you reach for Claude code or codex several times a day to structure, improve, and cut down work that would otherwise take hours. If that's not already a habit, this will be a frustrating job. And discretion, obviously. You'll see board materials, comp conversations, and a fair amount of our personal lives. WHAT YOU'LL ACTUALLY SPEND YOUR TIME ON Creating and managing new (AI-driven) systems to complete tasks and add structure to chaos. This is more of a meta bucket, but is super important to the role. We want someone who thinks in systems-not just completing the task at hand but thinking about how it fits into the big picture and how to make the next time this task comes up more seamless and automated. Calendars. Ours have to work as one system--protecting focus time, resolving conflicts before either of us sees them, and making the judgment calls we'd make about what's worth moving. Travel. Flights, hotels, cars, itineraries, and the reshuffling when a leg falls apart at 6am. This is a real chunk of the job and it's the part where good gets separated from great. Catching asks wherever they land. Requests come at you from Slack, iMessage, Signal, email, and voice memos, from both of us, usually mid-conversation and rarely in a tidy format. Your job is to get all of it into one place and drive it to done. The fastest way to lose our trust is for us to have to follow up on something we already asked for. Expenses, invoices, reconciliation, vendors, and the general administrative machinery that piles up when nobody's watching it. Plus personal logistics--appointments, reservations, the household-adjacent stuff. And holding the long memory. Commitments and context accumulate across months and hundreds of threads. We want someone who builds a system (AI-assisted--this is the highest-leverage place to use it) that makes something from six months ago retrievable in about ten seconds. So nothing quietly dies, and neither of us is re-explaining something we decided in March. WHAT SEPARATES GREAT FROM GOOD Judgment about what reaches us. Knowing what to handle yourself, what to escalate, and what to just kill is most of the job. Resourcefulness when the direct path is closed. The hotel is booked, the vendor won't budge, the flight is sold out--the answer we're looking for isn't "they said no." We really appreciate people who are incredibly solutions oriented. Comfort working for two people. We will occasionally want conflicting things at the same time. You'll need to sort that out with us directly rather than waiting for one of us to break the tie. Steadiness when plans change, because they will, constantly. The right response is a quick re-plan, not a spiral. PROBABLY NOT A FIT IF You need clear instructions before you can move. You want a predictable week. Or you're hoping this becomes a strategy or program role--we want someone who wants to be genuinely excellent at this craft, not someone passing through it. LOGISTICS Long-term contract, around 40 hours/week, fully remote. TO APPLY Two questions, briefly: 1. Tell us about a time you caught something before it became a problem. 2. How did you use AI in your work last week? Which tool, what task, what it saved you. We read for those two answers first. Thanks so much!