Executive Assistant / Virtual Assistant — Hospitality & Real Estate Operations

About Us

We own and operate a growing portfolio of short-term, mid-term, and furnished rental properties across New England, along with a boutique hospitality brand. Our days are fast-moving and full of details — guest messages, invoices, leases, vendors, marketing, and a team of cleaners, contractors, and VAs who all need coordination.

We're looking for one person to become an extension of the owner: a true right hand who can take a task off our plate and get it done correctly, completely, and without hand-holding.

The Role — In One Sentence

You'll be our "mini-me": someone we can hand a to-do list to each morning and trust that by the end of the day, things are actually done — bills paid, guests answered, books reconciled, vendors called, follow-ups sent.

Core Responsibilities

Bookkeeping & Payments:
Pay invoices and recurring bills (utilities, vendors, phone systems, waste services, etc.)
Reconcile QuickBooks weekly and flag anything that looks off
Set up and manage auto-pay for utilities and services
Invoice clients and partners; track what's owed to us and follow up
Cancel unused software subscriptions and audit recurring charges


Guest & Tenant Communications
Respond to Furnished Finder inquiries and messages promptly and professionally
Handle Airbnb and direct-booking guest messaging using our protocols
Manage lease extensions: draft, send, track signatures, update records


Property & Listing Operations
Keep listing details current (photos, pricing, block-off dates, discount codes)
Match availability and pricing across platforms (PMS, ---------- , Airbnb)
Track supplies and place orders (linens, rugs, propane covers, etc.)
Maintain house manuals, SOPs, and property info sheets


Team & Vendor Coordination
Onboard new hires: system access, door codes, training schedules, HR notifications
Follow up with contractors and vendors until the job is confirmed done
Schedule meetings, send agendas, track action items from staff check-ins
Chase down open loops — interviews, referrals, approvals, payments


Inbox & Admin Management
Triage and manage multiple email inboxes (personal and business)
Maintain dashboards, calendars, and task trackers
Make phone calls on our behalf (insurance, tax offices, utility companies, vendors)
Support marketing tasks: social posts, events calendar, influencer outreach coordination


Who You Are
Obsessively detail-oriented. You notice when a number doesn't match, a date is wrong, or a follow-up never happened.
A closer. You don't just start tasks — you finish them and confirm they're done.
A clear communicator. You write professional messages, ask smart questions when something's unclear, and give us short, useful status updates without being asked.
Trustworthy with sensitive information. You'll handle payments, financial records, and personal accounts.
Easy to work with. Low ego, low drama, high ownership. You take feedback well and adapt to how we like things done.
Proactive. If you see something that needs doing, you flag it or handle it.


Requirements
2+ years experience as a virtual/executive assistant, bookkeeper, or operations coordinator
Hands-on QuickBooks experience (reconciliation, not just data entry)
Excellent written English; comfortable making U.S. phone calls
Comfortable learning tools like property management systems (e.g., Newbook), Airbnb, Furnished Finder, Google Workspace, WhatsApp, Loom, and AI tools like Claude
Reliable internet, quiet workspace, and availability during ET business hours
Bonus: experience in short-term rentals, hospitality, or property management


What We Offer
Competitive pay — we're happy to pay well for someone who truly gets it
Long-term, stable role with a growing company
Direct access to the owner and real responsibility from day one
Variety — no two days look the same


How to Apply

Send us:
Your resume
A short video) telling us about a time you took a messy list of tasks and got it all done
Your QuickBooks experience in 2–3 sentences
Your hourly rate and weekly availability

Applications that don't include all four items won't be considered — attention to detail starts here.