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Outdoorsy Hill - Grounds & Maintenance Associate

Job in Stonewall, Winnipeg, Manitoba, Canada
Listing for: The Ride Platform
Full Time position
Listed on 2026-10-03
Job specializations:
  • Maintenance/Cleaning
    Maintenance Technician / Mechanic, Building Maintenance, Facility Maintenance, Groundskeeper
Salary/Wage Range or Industry Benchmark: 18 - 20 CAD Hourly CAD 18.00 20.00 HOUR
Job Description & How to Apply Below
Position: Outdoorsy Hill Country - Grounds & Maintenance Associate
Location: Stonewall

About The Ride Platform

The Ride Platform, Inc. is the parent company of Outdoorsy, Ride, Wheelbase, and Roamly. We’re named for the thing every part of our business runs on: the ride — the single transaction where an operator meets a renter. We’re the only company building end-to-end for the Operator Economy: the marketplaces to book (Outdoorsy, Ride), the enterprise SaaS to manage (Wheelbase), and the insurtech (Roamly) to protect the assets people turn into profitable businesses.

We enable millions of people to explore the world while helping independent operators build generational wealth. Our mission is to build the essential infrastructure for the mobility economy.

About Outdoorsy Hill Country

Nestled on 34 sprawling acres in Stonewall, Texas—right along the famous Texas Wine Trail and just 20 minutes from historic Fredericksburg—Outdoorsy Hill Country is a premier 5-star luxury glamping retreat. Featuring 22 custom safari-style tents, an event barn, a full-service bar, Texas Longhorn, and a welcoming communal center, our property blends the romance of the outdoors with high-end hospitality.

Opened in April 2023, Outdoorsy Hill Country is part of the Outdoorsy Destination Network, joining sister properties in Bayfield, Colorado, and Bass Lake, California. Powered by a rapidly growing national brand, we give guests an unforgettable way to connect with nature without sacrificing comfort. We take immense pride in our grounds, our high-touch guest experience, and our deep roots in the vibrant Texas Hill Country community.

About The Role

We're looking for a detail-oriented and reliable Grounds & Maintenance Associate to join our team and help us maintain a pristine, functional, and welcoming environment for all our guests.

This is a full-time role reporting directly to the Facilities Manager.

Responsibilities
  • Inventory & Supply Management: Maintain accurate inventory and supply levels, keep detailed records, and gather, complete, and inspect material estimates and requisitions.
  • Facilities & Property Maintenance: Diagnose malfunctions in building repairs, ground repairs, and equipment, while conducting periodic inspections of the property.
  • Equipment Operation: Ensure the consistent and safe utilization of lawnmowers, chainsaws, and other heavy-duty maintenance equipment.
  • Technical & Mechanical Repairs: Perform HVAC, plumbing, minor electrical, carpentry, and other interior maintenance repairs.
  • General Handyman Services: Take quick action on maintenance requests, including replacing light bulbs and fixing light fixtures, wall and sheetrock repairs, lock changes, and painting.
  • Groundskeeping & Cleanliness: Conduct daily cleanup of the property exterior, including grounds and common areas, to uphold a welcoming atmosphere.
  • Pool Care & Maintenance: Perform swimming pool maintenance and cleaning, and accurately maintain chemical logs.
  • Guest Relations: Provide professional, courteous, and prompt service in all guest interactions.
  • Additional Support: Adapt to changing operational needs and perform other duties as assigned.
Who You Are (Candidate Profile)
  • Experience: Possess prior gardening and general property maintenance experience, along with technical knowledge of tools and machinery.
  • Problem-Solving

    Skills:

    Demonstrate strong problem-solving abilities to effectively identify issues, find solutions, and complete the required scope of work.
  • Physical Stamina: Ability to lift 25–50 pounds and remain on your feet for up to 8 hours a day.
  • Environmental Resilience: Capability and willingness to work outside in all weather conditions.
  • Detail & Creativity: Bring a keen eye for detail and a creative approach to property care.
  • Teamwork: Work well with others and operate as a dedicated team player.
  • Availability: Flexibility to work nights, weekends, and holidays as the demands of the business require.
  • Logistics & Compliance: Must hold a valid driver’s license, live within a manageable commuting distance of the property, and consistently adhere to all company policies and procedures.
Preferred
  • Hospitality Background: Experience in maintenance for resorts or overnight stay accommodations.
  • Alignment: A genuine passion for the outdoors.
Why You’ll Love Working Here
  • Competitive Compensation: $18-$20/hour DOE.
  • Comprehensive Benefits: 100% company-paid medical premiums for employees, 401(k) match, and Flexible PTO.
  • Schedule: Full-time (5 days on, 2 days off).
Position Requirements
10+ Years work experience
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