Resort jobs in Bells Corners Station, ON

Director of Property & Estate Management Note: This is a full time position in Nassau, Bahamas

Estate Manager · Property Operations · Asset Management · Hospitality Management · The Bahamas (on-site, full-time) · B$100,000/yr + housing, vehicle & full expatriate package · Work permit sponsored for the right international candidate

The Opportunity

Imagine running a private portfolio in the Bahamas — luxury vacation rentals, private estates, a client-entertaining condominium, a commercial fleet — with real authority, an established organization behind you, and Principals who trust you to run it. Living there. Tax-free. Housed. This is that role.

A privately held international group with operating companies across the Bahamas, the United States, and Canada is hiring a Director of Property & Estate Management to run its property portfolio. The group's real estate holdings are growing rapidly — concentrated in the Bahamas, with interests in the US.

The position is part hospitality operator, part estate manager, part asset manager. You will have real autonomy, reporting directly to ownership and the Global COO; a supportive and growing team of senior management across multiple countries; a support team on the ground that grows with you; and ownership that manages by monthly report and weekly call — not by looking over your shoulder.

Why This Role Is Rare

• You are the first: this is the group's first dedicated head of property and estate operations. You inherit assets and a growing team that will be consolidated around you — you set the function, the standards, and the structure (an assistant, a staff mechanic, and maintenance and housekeeping hires are budgeted).
• Your scope grows with the portfolio: the group is in an aggressive growth phase, new assets are coming online, and this role expands with them — with a formal annual review to match.
• The life is part of the package: live and work in one of the world's most desirable locations, with no personal income tax, housing and vehicle provided, and a total package typically valued well above the salary line.

What You'll Run

• The revenue portfolio: a premium short-term rental operation in a sought-after vacation destination serving high-end business travelers and vacationers (Airbnb, VRBO, and direct booking — full accountability for occupancy, rates, reviews, and yield), plus long-term residential rentals (tenancy administration, collections, inspections) and a guest vehicle rental program.
• The corporate portfolio: workforce housing, a commercial office, and a 20+ vehicle commercial fleet program serving the group's operating companies — run like a professional tenant and fleet operation with clean intercompany cost allocation, compliance calendars, and a dedicated staff mechanic reporting to you for the hands-on work.
• The physical assets behind it all: disciplined preventive maintenance of the equipment that keeps every property running — HVAC plant, pumps, pool systems, generators, cisterns, and appliances — in a salt-air environment that punishes neglect. Protecting and extending asset life is a core measure of success in this role, executed through your maintenance team and scheduled programs, not firefighting.
• The estate portfolio: the Principals' private residences maintained to a daily estate standard — cleaned daily when occupied, fully provisioned, always ready — plus a luxury condominium for entertaining business clients, remote administrative oversight of the group's US assets (a private residence, leased corporate premises, a small vehicle fleet, and a yacht, all through established local vendors and a professional captain; no US hands-on work), and direct personal support to the Principals: their schedule, their travel, and the everyday matters that come with being their single trusted point of contact, 24/7 for genuine emergencies.
• The team: your own assistant, a staff mechanic, handymen, and domestic staff — with the mandate and budget to build out the maintenance and housekeeping teams as the portfolio grows.

What You Must Bring (we hire for these — they can't be taught)

• Self-motivation and an ownership mentality. The owners are absentee. There is no daily supervisor. People who need structure imposed on them fail in this role regardless of skill.
• Integrity, and genuine comfort with verification: documented expenses, access logs, and audit rights protect both sides here. If that bothers you, this isn't your role.
• Discretion as instinct. You will hold intimate access to a private family's homes, schedule, and affairs.
• A true service disposition — equally committed to a burst pipe at 2 a.m. and to ensuring the smallest task is serviced on time. No task is beneath this role.
• Calm, decisive judgment in emergencies, and disciplined, clear written reporting.
• Hands-on mechanical aptitude and practical problem-solving — you can diagnose an AC fault, a failing pump, or a pool-system problem well enough to fix the small ones and supervise the big ones.
• 7+ years in hospitality/resort operations, estate management, or multi-unit property management, including P&L responsibility and, ideally, luxury-residence service.
• Hands-on Airbnb/VRBO hosting experience with a track record you can evidence — listing optimization, host performance metrics, reviews, and platform claims/resolutions. Shortlisted candidates will be asked to walk us through listings they have operated.
• Professional credentials — CPM, ARM, RMP, CAM, RPA, CFM, or CHA — are a genuine asset and will be verified. Letters after your name earn our attention; character and results earn the role.

What We'll Teach You (don't self-screen on these)

We hire for character and track record, then teach the specifics through a structured first ninety days. Nothing below should stop you from applying:

• How we run: every property, standard, checklist, and report in this operation is documented — you will learn our way of working from written procedures and a structured handover, not tribal knowledge, with the systems already in place to support you.
• The Bahamas: never worked here? That's fine. VAT on short-term rentals, vehicle licensing, hurricane preparation, permits and country-specific requirements, and our established vendor network — we walk you through all of it, with experienced group personnel on-island beside you.
• The specialist corners: yacht administration (a professional captain runs the vessel — you learn the oversight), Bahamian tenancy administration, and how costs and services move between our companies. Each is a process to learn, not a prerequisite to bring.

Compensation & Package

• B$100,000 starting salary (Bahamian dollar, pegged 1:1 to USD). The Bahamas levies no personal income tax.
• Housing provided (on-site or near-site) and a company vehicle.
• Expatriate medical insurance; phone/data stipend; statutory benefits; three weeks' vacation.
• Work permit fully sponsored and paid by the employer for a qualified international candidate, plus one annual return flight home. Canadian and other international applicants are welcome and should note the total package — tax-free salary, housing, vehicle, medical — typically compares with a substantially higher gross salary at home.
• Performance incentive tied to what matters in year one: standing the role up effectively — plus revenue results, asset care, and estate standards — with a formal annual salary review.

How to Apply

Apply with your CV and a short cover note addressing two things directly: (1) the Airbnb/VRBO or rental operation you have run, with results; and (2) an example of a role where you operated with full autonomy — what you were trusted with, and how you reported. Applications that address both will be shortlisted for review. Background, credit, and reference checks are conditions of hire; a confidentiality agreement is a condition of employment. The successful international candidate must apply from outside the Bahamas (an immigration requirement); our team manages the permit process end to end. If you have spent your career being trusted with more than your title said — and you have been waiting for a role that hands you everything and gets out of your way — we would like to hear from you.

Equal-opportunity employer. Position based in the Bahamas; offer conditional on work permit grant where applicable.

Pay: $77,806.91-$177,295.03 per year

Benefits:

• Paid time off

Work Location: In person