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

Calendar & inbox mastery: Orchestrate a fast, high‑stakes calendar; defend focus time; draft agendas/briefs; triage email.
Travel end‑to‑end: Book smart, flexible itineraries (US/UK time zones), leverage card/travel benefits, manage changes.
Family OS (Google: Maintain a living hub of contacts, vendors, renewals, school/athletics dates, medical appointments, SOPs.
Accountability coaching:
- Weekly 15‑min 1:1 with each principal to set 3 personal goals and one weekly “keystone,”
- Mid‑week nudges,
- Friday 15‑min readout (progress, blockers, next experiment).
Vendors & projects: Coordinate household vendors; manage multi‑week projects with crisp updates and measurable checkpoints.
Bill‑pay prep (simple & safe):
- Draft bills in BILL (formerly Bill.com) with role‑based approvals (you prepare; principals approve),
- Use 1Password for shared credentials (least‑privilege access),
- Use Privacy virtual cards for subscriptions/incidentals (merchant‑locked, spend caps).
Documentation & improvement: Keep SOPs current; propose improvements; measure what matters.

You bring

Bachelor’s degree from an accredited university.
5+ years supporting a founder/CEO or senior executive (remote OK).
Exceptional written communication and executive judgment.
Demonstrated ability to lead up—anticipate needs, push back diplomatically, and improve the system.
Tool fluency: Google Workspace, BILL, 1Password, Privacy (or quick to learn equivalents).
Comfortable coordinating across US/UK time zones.
Located anywhere and able to work ET hours.

Nice to have

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

Salary
Retention bonuses
Performance bonus opportunity tied to measurable outcomes (calendar health, on‑time deliverables, SLA).

How to apply

Respond to this posting with the following. Do not use AI to generate:

Resume (1 page) and 150‑word note on a complex calendar or travel problem you solved,
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.

N/A

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Executive Assistant & Accountability Partner (Full‑Time, Remote, ET Hours)