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Careers

Join Our Team

Winter Park Lodging Company's success is built entirely on the quality and effort of our team members. We consider each team member to be an ambassador of our brand and we strive to create a fun, friendly, and energetic work environment. If you are interested in joining our team, we encourage you to send us a resume and a note about yourself by emailing jobs@winterparklodgingcompany.com.


Company Benefits

  • 3 weeks PTO + 48 hours sick time + PTO accrual for select holidays
  • 4 weeks paid parental leave
  • 401K with 4% match with no vesting period
  • Employee profit sharing
  • Company health/dental/vision/life/disability insurance
  • Wellness Benefit: $699 compensation towards ski pass or other recreational pass of equal value
  • Company paid cell phone or monthly stipend
  • Friends & Family lodging discount
  • Company advancement opportunities available

Company benefits are available for full-time, year-round employees.


Current Positions


Operations Manager

Reports To: Director of Operations

Status: Full-time, year-round

Salary: $75,000 - $100,000 + bonus opportunity (based on experience)

Job Summary: One of our goals at Winter Park Lodging Company is to cultivate a positive and memorable guest and homeowner experience as much as possible. As our company grows, we’ve continued to expand the scope of work done in-house to help achieve that goal. As our Operations Manager, you'll shape and sharpen systems, ensuring stellar guest and homeowner experiences. You will lead and oversee Housekeeping, Laundry, and Maintenance teams while working collaboratively with the Guest and Owner, Human Resources, Accounting, Marketing, Sales, and Revenue Management teams. We will look to you to craft innovative solutions to elevate our performance with reliability and responsiveness. Embark on a new path in the heart of Winter Park where your strategic mindset will be crucial for our expanding vacation rental landscape.

Responsibilities:

  • Responsible for all department managers and team leads under the Operations umbrella
  • Work closely with the Director of Operations and others in the company to set and/or implement policies, procedures and systems and to follow through with implementation
  • Communicate directly with the Guest & Owner Experience Team to provide information and troubleshoot issues as they arise
  • Oversee the upkeep and organization of the Park Ave office where all Property Care Teams are located
  • Coordinating daily schedules of employees as needed
  • Responsible for all aspects of vehicle maintenance and upkeep including routine washing/cleaning in interior and exterior of vehicles
  • Recruit, train, schedule, coach, counsel and communicate job expectations to all employees
  • Continually analyze workflow, employee and space requirements, equipment layout, etc, and implement changes to improve as needed
  • Work with the Director of Operations and the Accounting Team to create and manage Operations Budget
  • Maintain a safe and healthy work environment by establishing, following and enforcing standards and procedures; complying with OSHA regulations
  • Communicate all operating policies and/or issues at routine team meetings
  • Assisting the Inspections Team and others as needed in completing tasks as needed
  • Manage relationships with key operations vendors
  • All other duties as assigned

Qualifications:

  • Four year college degree. A combination of education and experience may be considered
  • Two years of property management, hospitality, or vacation rental experience
  • Advanced knowledge of home systems, maintenance, and troubleshooting
  • Minimum of two years experience managing a team or department of people
  • The ability to multi-task and delegate work amongst multiple employees is a must have for this position
  • Proficient use of Microsoft Office (Excel & Word) and ability to quickly learn/adapt to other software applications
  • Clean, professional appearance
  • Ability to lift 75+ pounds
  • Ability to speak English fluently- Spanish is a plus
  • Detail oriented
  • Reliable transportation and a valid driver’s license
  • This is not a work remote job. Must live within 25 minutes of Winter Park.


Home Stager

Reports To: Housekeeping Manager

Status: Full-time, part-time, year-round

Salary: $22-23 per hour

Job Summary: We like to think of our Home Stagers as being in charge of “first impressions”. Home stagers are responsible for putting the ‘finishing touches’ on each of the vacation rentals we manage prior to guest and owner arrivals. They conduct inspections of all vacation rental properties to make sure the properties are secure, ensure standards of cleaning are met, and they provide the guest gifts to each arrival. Maybe more importantly, they “stage” the home to be ready for the arrival including placing pillows just right, finding a few errant pieces of trash under the bed, or rearranging the kitchen to be presentable and feel clean to the guest. During peak seasons (Christmas holidays, especially) the position may necessitate overtime. This job is well suited for a detailed oriented person who has an eye for making a room look styled vs. just clean. They must be comfortable with the pressure of busy days, but also find fulfillment in going the extra mile to make homes look ready for a discerning guest or owner. 

Responsibilities:

  • Perform detailed inspections of properties prior to owner and guest arrivals to ensure that the condition of the property meets the expectations of owners and guests
  • Will become familiar with the layout of every property (where furniture and decor goes) to ensure the property is set up the same upon each arrival
  • Taking on small repairs and minor maintenance tasks i.e. changing light bulbs, tightening cabinet knobs, minor deck/porch shoveling, etc
  • Report all extensive cleaning and maintenance related issues to housekeeping manager and maintenance personnel
  • Proactively offer up suggestions for improvement for each home to the Homeowner Liaison Team
  • Complete detailed checklists per inspection as well as communicate with coworkers via software and portable digital devices 
  • Drive and maintain company vehicles safely and to a high standard of cleanliness reporting any vehicle needs to supervisor in a timely fashion.
  • Assist in meeting any guest needs that arise including, delivering amenities, removing items, etc
  • During busy times, may have to strip beds and pack sheets/towels for housekeeping team
  • During non-peak times, assist in other department projects within the company 
  • All other duties as assigned

Qualifications:

  • The ability to multi-task and delegate work amongst multiple employees is a must have for this position.
  • Proficient use of Microsoft Office (Excel & Word) and ability to quickly learn/adapt to other software applications
  • Clean, professional appearance
  • Ability to lift 75+ pounds
  • Ability to speak english fluently- Spanish is a plus
  • Detail oriented
  • Reliable transportation and a valid driver’s license
  • High School diploma or GED
  • This is not a work remote job. Must live within 25 minutes of Winter Park.