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

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.