Operations & Communications Lead Needed for Property Management Company on Tropical Island

Hospitality & Property Management | Remote | Long Term Role

• 📅 Currently hiring for Operations & Communications Lead

• 💰 $1.200 - $1,500, with clear growth over time

• ⏲ Full time. Working between 8am-5pm EST (Eastern Standard Time)

• 💡 Long term hire.

• 🗺 Fully remote

Who we are

Sunstays Ltd is a fast growing property management company based in the Cayman Islands. We manage a portfolio of high quality vacation rentals and long term rentals in one of the most beautiful places in the world.

We believe great hospitality is about more than just responding to messages or solving problems as they come up. It is about being thoughtful, proactive, and intentional. Anticipating needs. Taking ownership. Making guests feel genuinely cared for and owners feel confident their property is in good hands.

Our approach is inspired by the idea of unreasonable hospitality. Doing the small things exceptionally well. Creating trust through consistency, follow through, and attention to detail.

Right now, much of the day to day operations run through the founder. Our goal is to build strong systems and a great team so the business can scale without losing that level of care.

Who you are

You might be a great fit if:

• You are extremely organized and enjoy bringing structure to busy environments

• You take pride in delivering great hospitality, even when working behind the scenes

• You follow through on what you say, every time

• You are tech savvy and enjoy learning new tools and systems

• You write clearly and communicate professionally and thoughtfully

• You are comfortable making decisions when given clear guidelines

• You enjoy problem solving and taking ownership, not just completing tasks

Bonus points if you:

• Have experience in hospitality, property management, or operations roles

• Have worked in Notion or enjoy documenting and improving processes

• Are curious about AI tools and automation and want to apply them in real workflows

What you’ll be doing

If we had to describe this role in simple terms, your job is to help the business run smoothly day to day while delivering an exceptional hospitality experience.

Guest & communication management

• Monitor and respond to guest messages across platforms

• Handle common requests using clear rules and templates

• Escalate edge cases with context and recommendations

• Ensure no message or issue falls through the cracks

Cleaning & maintenance coordination

• Schedule and track cleanings

• Coordinate maintenance tasks with our on island team and vendors

• Follow up until issues are fully resolved

• Keep tasks documented and organized

Admin & operations support

• Categorize receipts and support weekly admin

• Help prep reports and monthly submissions

• Track inventory and consumables

• Spot patterns and flag issues early

Systems, tech, and process building

• Work inside tools like Hostaway, Breezeway, Tenant Cloud, QuickBooks, Notion, and Google Workspace

• Help document SOPs and improve workflows

• Learn and apply AI tools over time to reduce manual work

• Help turn founder knowledge into repeatable systems

Over time, this role can grow significantly. The goal is for you to take over most day to day operations so the founder can focus on growth, strategy, and bringing on new properties.

Requirements

• Strong internet connection and a reliable workspace

• Fluent in written and spoken English

• Comfortable working with technology and learning new tools

• Experience in hospitality or property management is a plus, but not required

• High level of reliability and follow through

• Comfort working independently and managing priorities

• Interest in a long term role with growth and responsibility

• Willingness to learn, improve, and take ownership

Why this role is special

• Long term position with real growth potential

• Direct access to the founder and decision making

• Opportunity to help design systems, not just follow them

• Increasing responsibility as trust is built

• A chance to grow into a senior operations role

If you enjoy building structure, taking ownership, and delivering hospitality that goes above and beyond, this role was built for you.

How to apply

Tell us a bit about:

• Your background and experience

• The tools and systems you have worked with

• Any experience with automation, AI, or process improvement

• Why you are looking for a long term role and growth

• Bonus: Include a short video, 2 to 3 minutes max, introducing yourself and answering this question: “What does great hospitality mean to you, and how would you bring that mindset to a behind the scenes operations role?”

We are looking for the right person, not the fastest hire.