About the role
We are seeking a college‑educated, high‑judgment Executive Assistant to partner with a CEO and spouse across work and family operations. This is a 40 hrs/week, long‑term role in Eastern Time (ET). You will run complex calendars and travel, keep our “family operating system” tight, act as a gentle accountability coach for both principals, and prepare bill payments within a clear approvals workflow. We’re looking for someone who leads up—proactive, thoughtful, and comfortable prompting us toward better outcomes.
What you’ll own
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Calendar & inbox mastery: Orchestrate a fast, high‑stakes calendar; defend focus time; draft agendas/briefs; triage email.
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Travel end‑to‑end: Book smart, flexible itineraries (US/UK time zones), leverage card/travel benefits, manage changes.
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Family OS (Google: Maintain a living hub of contacts, vendors, renewals, school/athletics dates, medical appointments, SOPs.
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Accountability coaching:
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Weekly 15‑min 1:1 with each principal to set 3 personal goals and one weekly “keystone,”
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Mid‑week nudges,
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Friday 15‑min readout (progress, blockers, next experiment).
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Vendors & projects: Coordinate household vendors; manage multi‑week projects with crisp updates and measurable checkpoints.
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Bill‑pay prep (simple & safe):
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Draft bills in BILL (formerly Bill.com) with role‑based approvals (you prepare; principals approve),
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Use 1Password for shared credentials (least‑privilege access),
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Use Privacy virtual cards for subscriptions/incidentals (merchant‑locked, spend caps).
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Documentation & improvement: Keep SOPs current; propose improvements; measure what matters.
You bring
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Bachelor’s degree from an accredited university.
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5+ years supporting a founder/CEO or senior executive (remote OK).
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Exceptional written communication and executive judgment.
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Demonstrated ability to lead up—anticipate needs, push back diplomatically, and improve the system.
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Tool fluency: Google Workspace, BILL, 1Password, Privacy (or quick to learn equivalents).
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Comfortable coordinating across US/UK time zones.
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Located anywhere and able to work ET hours.
Nice to have
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Exposure to coaching principles (e.g., ICF‑style accountability, active listening), project tools (Asana/ClickUp), and travel perks (e.g., Amex FHR/Virtuoso).
Compensation & terms
How to apply
Please submit the following.Do not use AI to generate:
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Resume (1 page) and 150‑word note on a complex calendar or travel problem you solved,
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A short writing sample you’re proud of (max 300 words),
We’ll invite selected candidates to a 15‑minute cognitive assessment and a paid practical (60–90 min: inbox triage, ET calendar rebuild, and a BOS↔LHR travel brief).
Trust & background
Finalists will complete reference checks, a background check, and sign an NDA.
