South End Hospitality
November 18, 2021
Anywhere, Massachusetts
Job Type



South End Hospitality has been managing vacation rentals since 2015. We have multiple brands throughout Massachusetts and New England with properties under management in Boston, on the cape, on the north shore, and in the Berkshires. We currently have around 150 properties under management and are aggressively growing, adding about 3-4 properties per month.


The Reservations Manager will be the owner's right-hand/partner who will be responsible for the day-to-day operations to ensure our guests and owners are happy. Looking for someone with extensive knowledge in the vacation rental industry with a background in reservation management. This dedicated leader will develop and maintain control of all business operations and will be an experienced and efficient leader with excellent people skills, business acumen, and an exemplary work ethic. The ideal individual will also be a strategic planner with the essential ability to specify, strategize, and define opportunities.



  • Review current reservation systems and procedures. Rebuild and implement changes as needed in the processes to streamline efficiency and boost revenue. 

Guest Services & Reservations:

  • Assist staff as needed, fill in if staff is unavailable. 
  • Oversee staff including making decisions on behalf of the owners and issuing refunds.
  • Reviewing messages and response time to ensure the reservations team is following proper procedures. 
  • Run and attend weekly staff meetings.
  • Oversee booking calendar to make sure prices and nightly minimums are in line with company goals to ensure the highest ADR and occupancy. 
  • Build systems as deemed necessary to make operations efficient.


Owners & New Properties

  • Be the point of contact for owners, from onboarding to day-to-day management, schedule quarterly calls to review sales and guest feedback. 
  • Create new listings and post on marketing sites
  • Assist owners as needed to furnish properties
  • Hire oversee photographers
  • Site visits before the first booking to make sure the property is ready for guests.


  • Write bi-weekly blog posts
  • Post on social media weekly
  • Write newsletter for owners that go out monthly 
  • Implement and oversee a direct booking strategy 

Maintenance & Housekeeping

  • Oversee maintenance vendors remotely
  • Oversee housekeeping staff schedule remotely 
  • Be first on call at night time for emergencies


  • Proven results as a General Manager, Director of Operations, Vice President, or a similarly relevant role (preferably the vacation rental or hotel industry)
  • Experience building high performing teams, including the ability to recognize and cultivate rising talent required
  • Adept at transitioning seamlessly from a strategic level vision to day-to-day tactical operations required
  • Ability to work with an extremely fast pace growing company with aggressive growth goals year over year.
  • A demonstrated execution mindset and a record of success holding people accountable required
  • Understanding of and ability to create healthy organizational culture required
  • Excellent interpersonal communication skills required
  • Varied experiences and responsibilities in Sales, Marketing, Operations, Finance, and Human Resources are strongly preferred.
  • Experience leading high-performance teams within the hospitality/lodging market strongly preferred
  • Bachelor’s degree strongly preferred
  • Advanced degree, MBA or similar, preferred


Annual Salary: $60,000-$70,000 


  • Performance-based compensation, up to 10% of salary per year.
  • 3% of sales for the first year for properties brought into the management program by Employees' direct lead sources. 
  • Two weeks of training plus one week per quarter you will be expected to stay in Boston, flights/lodging for this will be provided.


  • 25% health care coverage offered after 3 months, 100% after 12 months. 
  • 5 days vacation after 6 months
  • 3 sick days per year after 3 months