AI-enhanced for better readability
Executive Assistant & Accountability Partner (Full-Time, Remote, ET Hours)
Source: weworkremotely
Headquarters: Greenwich, CT URL: http://N/A
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.
Requirements
- 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.