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

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

Please submit 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.

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

N/A

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