Senior Executive & Personal Assistant to COO , Part-time hourly

We are hiring a Senior Executive & Personal Assistant to support the COO by owning the details, follow-up, people, and systems that would otherwise consume executive time. This is not an entry-level or first-time EA role. You should have 5+ years supporting an executive, founder, or business owner and be comfortable taking ownership with minimal supervision.

• Vendor coordination. Find, call, schedule, and manage cleaners, landscapers, maintenance providers, and other vendors. This is a voice-heavy role, not an email-only one. Match the vendor's preferred communication channel—phone, text, or email—and use our Quo phone system. If one call can resolve what would take three emails, make the call.
• Projects & follow-up. Maintain one reliable system for open projects, deadlines, orders, claims, vendor commitments, and follow-ups. Move items to completion rather than simply reporting status.
• Claims. Prepare damage/insurance claims with photos, receipts, and correspondence, then follow through with vendors or adjusters until resolved.
• Inbox & AI-assisted triage. Consolidate unnecessary accounts, organize active inboxes with folders, labels, and rules, then help implement AI-assisted handling for routine, pre-approved categories so human attention goes to items requiring decisions.
• Property operations. Learn Breezeway and confirm cleaning turnovers are correctly scheduled. Keep booking platforms accurate, including availability, pricing, photos, and descriptions.
• Email marketing. Turn COO-provided copy into finished campaigns: formatting, links, lists, testing, scheduling, and sending.
• You'll also handle guest-review responses, social media scheduling/QA, calendar protection, vendor/contract/receipt records, vendor rosters, light expense administration, renewals/warranties, and shared-drive/account/password-manager organization.

Other Responsibilities may include grocery/Amazon orders; purchases, returns and refunds; home-vendor coordination; sourcing vendors; restaurant and appointment reservations; travel using established Delta, Marriott, Hilton and Avis preferences; gifts/cards/thank-you notes; important-date systems; event briefing notes; calendar support; and occasional special projects. Research assignments should end with a clear recommendation, not merely a list of options.

Technology

You should already be comfortable with Google Workspace, Meta Business Suite, Asana, Canva, ChatGPT and Claude. Meticulous Drive organization—logical folders, subfolders, and naming—is essential.

You'll learn our property tools: Hospitable (bookings/messaging), Breezeway (cleaning/maintenance), Charge Automation (security deposits/guest portal), Jotform (forms), and Quo (business calls/texts).

Because this role is voice-heavy and time-sensitive, you need:

• Reliable primary internet + backup connection

• VPN

• Backup laptop/device

• Backup power (UPS, generator, etc.)

• Quiet, private workspace

• Noise-cancelling headset

If you don't have everything yet, explain how you would quickly close the gap.

HOURS

Part-time, 24 hours/week, long-term remote role working U.S. Eastern Time:

Mon/Wed/Fri: 7 AM–1 PM ET / 7 PM–1 AM PHT

Tue/Thu: 7–10 AM ET / 7–10 PM PHT

COMPENSATION

$5-$8 per hour

HOW TO APPLY

Submit one message containing both parts by September 11, 2026 at 5 PM Eastern Time. Late or incomplete applications will not be reviewed.

Subject: EA/PA-Ops Application — Your Name

1. Written response — 150 words maximum:

Include your availability, requested hourly rate, LinkedIn profile, and confirmation that you meet the home-office requirements—or how you'll close any gaps.

2. One unedited screen-and-voice video:

Start by screen-sharing something real from your work: a folder/file system, SOP you built, task tracker, or inbox organization system. Redact confidential information.

Then, live and unscripted, answer:

• Tell us about learning new software without formal training. What did you do when stuck?

• Walk us through the system/SOP you showed. Why did you build it, and who uses it?

• Describe a vendor or scheduling problem you solved by picking up the phone rather than emailing.

• What did a previous employer eventually trust you to own completely without check-ins?

• Why this specific role, and why now in your career or life? We want your actual reason, not a generic answer about the job description.