Personal Executive Assistant to VP

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: TYPE OF WORK

Any

: SALARY

$3.75–$5/hour

: HOURS PER WEEK

TBD

: DATE UPDATED

Sep 18, 2026

JOB OVERVIEW

About me: I'm the VP of a luxury short-term rental property management company in New England. Things move fast and my brain has about 47 tabs open at any given time — I need a right hand who can catch what I toss out and just... handle it.

You'd work for me, personally, as my own assistant who helps me run my work and life more smoothly.

I'm looking to send a message "can you remind me to follow up with that owner Friday?" or "can you look into flight options for next week?" or "add this to my to-do list" — and it's just done.

It's heavy on the work side — managing my inbox, keeping Notion current, relaying info to the right team members, and keeping my calendar and to-do list under control — with some personal support mixed in when life and work overlap. You'll also help me with admin and content for a fun new venture I'm building outside of the property management company (a recording studio + venue) — and if you're strong in social media and content creation, there's real room to grow into helping build that out, not just admin around it.

Starting part-time, with real potential to grow into full-time if we're a great fit for each other.

I need someone sharp, quick, and easy to talk to! Someone who gets that a one-line Slack message means "go run with this." Personality and communication style matter just as much as the skills!

The dynamic I'm looking for

I want this to feel more relaxed than a typical EA relationship — not stiff or overly formal all the time. Some days I'll ping you with "can you research X" or "look into flights for next week." Other days it's "I had a rough night, today's a lazy day — can you help me pull out what's actually high priority and reschedule the rest?" I want a go-to right hand I can be real with, not someone I have to manage carefully.

I also manage a handful of VAs within the property management company, and I'll sometimes need help tracking feedback or observations on them — so discretion and confidentiality are a must!

What you'll do
Be my right hand for the little "can you..." moments — reminders, quick research, to-do list additions, whatever I toss your way

Manage my work inbox — triage, draft replies for my approval, flag anything urgent

Keep Notion organized and current — update pages/databases, relay info from calls/notes to the right team member

Manage my calendar — book appointments, coordinate meetings

General admin support for my role and for a new studio/venue venture I'm building

Occasional personal admin/appointments when it overlaps with work

Respond quickly on Slack during working hours — this is a "ping and go" role

If you have experience and are standout in social media and content creation full time at a higher pay range is a possibility!

Send a short video intro (face + voice) — this matters more than your resume for this role, I want to get a feel for you. Tell me: your STR experience, your Notion experience, and why you'd be a great "right hand." Generic/copy-paste applications will be skipped

Requirements
3+ years experience as an Executive Assistant
Prior experience in short-term rental (STR)/vacation rental industry
Strong Notion experience — comfortable navigating and updating databases/pages
Excellent written English — clear, professional communication
AI-forward — comfortable using tools like ChatGPT/Claude to work faster and smarter
High discretion — you may have visibility into sensitive business and team information
Reliable internet, quiet work environment

SKILL REQUIREMENT

Short Term Rentals Notion AI Automation

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Personal Executive Assistant to VP

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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