Executive Assistant & Accountability Partner (Full‑Time, Remote, ET Hours)
Role Overview
This is a senior-level Executive Assistant role supporting a CEO and spouse across both work and family operations. Day-to-day responsibilities include managing complex calendars and travel, maintaining a family operating system, acting as an accountability coach, and handling bill payments. The hire will have a significant impact by ensuring smooth operations, improving efficiency, and providing proactive support to the principals.
Perks & Benefits
This is a full-time remote position with worldwide location flexibility, requiring work in Eastern Time hours. It offers a long-term role with performance bonuses tied to measurable outcomes like calendar health and on-time deliverables. The role implies a supportive, collaborative culture with opportunities for growth through accountability coaching and system improvements.
Full Job Description
Headquarters: Na URL: http://na
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 BOSLHR travel brief).
Trust & background Finalists will complete reference checks, a background check, and sign an NDA.
To apply: https://weworkremotely.com/remote-jobs/na-executive-assistant-accountability-partner-full-time-remote-et-hours
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