Senior Property Manager

Lead Properties. Build Relationships. Raise the Standard.

At Heritage Holdings Group, property management is about more than maintaining buildings. It is about looking after the homes, workplaces and shared spaces that matter to the people who use them, while protecting the long-term value of the properties entrusted to us.

We are looking for an experienced Senior Property Manager to lead the day-to-day management of a diverse portfolio of commercial and high-end residential properties across Grand Cayman, including strata developments, homeowners' associations, offices and retail spaces.

This is a senior, hands-on leadership role for someone who can bring together strong property operations, financial discipline, client service and team leadership. You will be the senior point of accountability across your assigned portfolio, working closely with property owners, strata committees, HOA boards, tenants, residents, service providers and our internal teams.

What You'll Be Responsible For

• Lead the Portfolio - Take ownership of the day-to-day management of an assigned portfolio, ensuring properties are well maintained, clients are well served and operational priorities remain on track.
• Manage Property Operations - Oversee property inspections, preventative maintenance, repairs and building systems, including air-conditioning, fire alarms, security systems, elevators, landscaping, pools and cisterns. You will also help ensure properties are prepared for hurricanes and other operational emergencies.
• Own the Financial Picture - Lead the preparation of annual strata, HOA and common-area maintenance budgets, monitor expenditure, investigate variances and provide clear financial and operational reporting. You will also monitor market rental rates and lead lease negotiations and renewals within approved parameters.
• Build Trusted Client Relationships - Serve as a senior operational contact for property owners, strata committees, HOA boards, tenants and residents. You will manage expectations, resolve concerns and maintain clear, professional and responsive communication.
• Lead the Team - Set priorities and service expectations for Property Managers and the Maintenance Team, allocate workloads and resources, coach team members and address performance or service concerns when required.
• Manage Service Providers - Coordinate and monitor contractors and service providers, ensuring scopes of work, costs, safety requirements and performance expectations are clear and that agreed standards are consistently delivered.
• Support Strata, HOA & Property Transitions - Coordinate AGMs and committee meetings, maintain accurate property records and support developer transitions and property handovers, including warranties, outstanding defects and maintenance arrangements.

What You'll Bring

• Bachelor's degree in Property Management, Real Estate, Business Administration or a related field preferred.
• Minimum 5 years' relevant property management experience, including responsibility for a property portfolio and supervision of a team.
• Experience managing commercial and high-end residential properties, including strata developments and HOAs.
• Proven experience preparing and monitoring property budgets, reviewing expenditure and producing client reports.
• Experience negotiating commercial and residential leases and renewals.
• Working knowledge of leases, strata by-laws, unit entitlements, restrictive agreements and developer transition and handover.
• Sound understanding of building systems, preventative maintenance and disaster preparedness.
• Rent Manager experience is essential, together with proficiency in Asana and Microsoft Office.
• Sound knowledge of the Grand Cayman rental market and Cayman Islands strata and property-management practices.
• Valid Cayman Islands driver's license and access to a reliable vehicle. Confirmed.

The Kind of Leader We're Looking For

• We're looking for someone who takes ownership rather than waiting for problems to escalate.
• Someone who can balance the needs of an owner, resident, contractor and the business while making sound decisions and communicating clearly.
• Someone who notices when a maintenance issue, budget variance, client concern or team commitment is beginning to drift — and acts.

Our values guide how we work:

• Integrity — You follow through on commitments, manage client funds and information responsibly and communicate honestly.
• Community — You understand that the properties we manage are people's homes, workplaces and shared spaces, and you lead with care and respect.
• Growth — You look for better ways to manage properties, develop people and improve the experience we provide to our clients.

Compensation & Benefits

Salary: CI$72,800–CI$101,900 per annum
Hours: 40 hours per week, with flexibility required for AGMs, client engagements and urgent property matters.

Our benefits include:

• Health insurance
• Pension
• Life insurance
• Bonus eligibility
• Corporate phone and laptop
• Leave benefits exceeding Cayman Islands Labour Act requirements

Employment: Full-time
Location: West Bay, Cayman Islands

WORC Jobs Portal ID: X3A4Q7
Closing Date: 6 Nov 2026

Ready to Join Us?

If you're an experienced property management leader who takes ownership, builds trusted relationships and knows how to balance client service, property performance, financial discipline and team accountability, we'd like to hear from you.

People Join. People Grow. People Lead.