Senior Executive & Personal Assistant to COO , Part-time

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.