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 professional and personal operations. Day-to-day responsibilities include managing complex calendars and travel, coordinating family logistics, acting as an accountability coach, and handling bill payments. The hire will have a significant impact by ensuring smooth operations and improving outcomes through proactive support and system enhancements.
Perks & Benefits
This is a full-time remote position with worldwide location flexibility, requiring work in Eastern Time hours. Benefits include salary, retention bonuses, and a performance bonus tied to measurable outcomes. The role offers a supportive culture with opportunities for growth through accountability coaching and project management, leveraging tools like Google Workspace and BILL.
Full Job Description
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 BOSLHR travel brief). Trust & background Finalists will complete reference checks, a background check, and sign an NDA.
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