Assitant Operations Manager - Property Readiness

Seaside Vacations & Sales is an award-winning, family-owned vacation rental management company serving Chincoteague Island, VA and Ocean City, MD. We are proud recipients of the Best in Locals Choice Award (2022, 2023, & 2024), VRMA’s 2023 Vacation Rental Manager of the Year, VRMA’s Excellence Award for Community Impact in 2024, and VRMA’s Excellence Award in Marketing for 2025!

As we continue to grow, we are expanding our operations team to ensure our properties consistently exceed guest and homeowner expectations.

The Assistant Operations Manager – Property Readiness plays a critical role in ensuring our vacation rental homes are guest-ready, operationally sound, and maintained to Seaside’s quality standards. This role focuses on day-to-day field operations including coordinating housekeeping turnovers, conducting inspections, managing inventory and linens, and supporting operational systems and processes.

This is a hands-on, fast-paced position requiring strong organization, leadership, and the ability to make decisions independently in the field. The Assistant Operations Manager works closely with leadership, field teams, and vendors to ensure seamless turnovers and a consistently high-quality guest experience.

• Property Operations & Readiness
• Oversee daily property readiness and turnover operations across the portfolio
• Coordinate housekeeping schedules to align with guest arrivals and departures
• Conduct routine and spot inspections to ensure cleanliness, safety, and usability standards are met
• Identify and report maintenance issues, damages, or supply shortages to leadership
• Support and oversee housekeeping partners to ensure performance expectations are met
• Assist with recruiting, onboarding, and training new cleaners as needed
• Provide clear communication and feedback to field teams to drive accountability and consistency
• Manage inventory standards for each home following guest check-out
• Oversee linen systems, laundry workflows, and supply replenishment
• Track usage and assist with ordering housekeeping and operational supplies

• Help develop, document, and implement standard operating procedures related to cleaning, staging, and property readiness
• Utilize property operations software (such as Breezeway) to track tasks, inspections, and reporting
• Identify opportunities to improve efficiency, consistency, and overall operational performance

• Demonstrates semi-proficient use of common technology tools in a professional environment
• Comfortable using computers and smartphones for daily work tasks
• Can quickly learn new software systems with basic training and documentation
• Uses technology to communicate, organize, and track work efficiently
• Able to perform basic troubleshooting (e.g., resolving login issues, adjusting settings, following step-by-step instructions)

• Ability to stand, walk, and move between properties throughout the day
• Ability to reach overhead and below the waist
• Regularly push, pull, and lift up to 25 pounds
• Occasionally lift or move up to 50 pounds
• Ability to bend, stoop, squat, kneel, and twist

• Experience in hospitality operations, property operations, or housekeeping management (vacation rental experience strongly preferred)
• Strong organizational and time-management skills in a fast-paced environment
• Ability to lead, communicate clearly, and hold others accountable with professionalism
• Detail-oriented with the ability to manage multiple properties and priorities simultaneously
• Comfortable working independently in the field
• Familiarity with property operations software (Breezeway experience preferred)
• Reliable transportation and a clean driving record
• Must be available weekends

Benefits include:

• Paid time off (PTO, sick days, vacation days)
• Health, dental, and vision insurance
• Life insurance
• 401k and Profit Sharing
• Great work environment where growth is supported and encouraged

This role offers the opportunity to step into a leadership position within a respected, growing vacation rental company. You’ll have a direct impact on daily operations, guest satisfaction, and the long-term success of our properties — all while working in one of Virginia’s most beautiful coastal communities.

Please Email Resume to Elaine@seaside vacations