Director of Operations

Company Overview

At Luxury Simplified Retreats, service is our passion, and so is cultivating extraordinary moments. We create experiences that feel effortless, welcoming, and truly special.

With over 25 years of experience in Revenue Management, Property Maintenance, and Guest Services Management, we know what it takes to deliver exceptional stays while maximizing value for homeowners. Our homes consistently lead the market, achieving higher nightly rates, increased guest satisfaction, and strong return bookings. Simply put, we take care of every detail—so our guests can relax and our homeowners can see the best possible return on their investment.

We believe luxury is found in the details—the perfectly made bed, the thoughtful amenities, and the feeling of walking into a space that feels just right.

What’s it like working with us?

Our team is like a well-oiled machine. From our in-house housekeeping, maintenance, and design teams to our guest services and property management experts, we handle every little detail so that guests can focus on making memories and homeowners can rest easy knowing their property is in expert hands.

If you take pride in getting the details right and love creating spaces where people feel at home, you’ll fit right in.

Apply to join us today!

Position Summary

Luxury Simplified Retreats is seeking an experienced Director of Operations to lead the day-to-day operations of our Charleston vacation rental portfolio.

This is a hands-on leadership role responsible for ensuring every property, guest stay, and homeowner relationship is managed to the highest standard. You will oversee housekeeping, maintenance, guest services, vendor management, and operational staff while creating the systems and accountability needed to deliver a consistently exceptional experience.

The ideal candidate is a proactive problem-solver who sees issues before they become problems, thrives in a high-accountability environment, and takes personal pride in operational precision. You will work closely with the President and executive team while serving as a key leader for our Charleston operations.

Key Responsibilities

Operational Leadership

• Oversee daily operations across the Charleston portfolio, including turnover scheduling, housekeeping quality, maintenance response, and guest-ready standards

• Develop and maintain SOPs that create consistency and accountability across every property

• Own the guest experience from pre-arrival through post-departure, stepping in to resolve escalated issues quickly and professionally

• Monitor property conditions and lead proactive maintenance and improvement planning in partnership with homeowners

• Ensure operational issues are identified and resolved before they impact the guest or homeowner experience

Team Leadership

• Lead and develop the Charleston operations team, including housekeeping, maintenance, and guest services

• Establish clear performance expectations and provide ongoing coaching, feedback, and accountability

• Manage on-call rotations and emergency response protocols to maintain dependable coverage during guest stays

• Foster a service-driven culture centered on ownership, communication, and attention to detail

Vendor & Homeowner Relations

• Source, negotiate with, and manage cleaning crews, contractors, landscapers, and other third-party vendors

• Build trusted relationships with homeowners through proactive, transparent communication regarding property condition and recommendations

• Support new property onboarding, including inspections, staging, and ensuring homes are ready to welcome guests

Strategy & Business Performance

• Partner with the President and executive team on budgeting, cost controls, and margin improvement

• Track key operational KPIs, including turnover times, guest satisfaction, and maintenance response times

• Identify opportunities to improve processes and leverage technology and automation

• Contribute operational insight to portfolio growth and new property acquisition opportunities

Required Qualifications

• 5+ years of operations leadership experience in hospitality, property management, or vacation rentals

• Proven experience leading teams, managing vendors, and overseeing multi-property operations

• Exceptional organizational skills with the ability to manage multiple competing priorities

• Strong written and verbal communication skills with the professionalism to work directly with high-net-worth homeowners and guests

• Ability and willingness to participate in on-call coverage, including evenings and weekends as needed for guest or property emergencies

• Valid driver's license and reliable transportation for regular property visits throughout the Charleston area

Preferred Qualifications

• Luxury hospitality or luxury vacation rental experience

• Experience within the Charleston, SC hospitality or short-term rental market

• Familiarity with historic home preservation standards and coastal property maintenance

Compensation, Benefits & More

Compensation: $70,000 - $80,000 annual salary

Bonus: Additional bonus opportunity based on performance

Job Type & Schedule: Full-time; availability for occasional evenings and weekends as operational needs or emergencies arise

Location: Charleston, SC | On-site

Benefits:

• Paid time off such as PTO, sick days, and vacation days