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The Ride Platform

End-to-end mobility ecosystem for vehicle operators

Grounds & Maintenance Associate Seasonal

Full-TimeUpdated on 10/17/2026
$18 - $20/hr
Entry
Bayfield, WI, USA
In Person
General Maintenance & RepairBuilding & Property Maintenance

About the job

Requirements
  • Proficiency in operating and maintaining hand tools, power tools, and heavy-duty machinery such as mowers and chainsaws.
  • Professional gardening, landscaping, or general facility maintenance background.
  • Ability to independently diagnose mechanical or structural issues, develop solutions, and complete the work.
  • Must possess a valid driver's license and follow company policies and safety procedures.
  • Ability to perform rigorous outdoor physical labor in heat, rain, and cold.
  • Ability to stand or walk for 8 hours per day and regularly lift 15–25 pounds.
  • Availability to work nights, weekends, and holidays as business demands.
Responsibilities
  • Perform skilled repairs across HVAC, plumbing, minor electrical, and carpentry trades.
  • Perform interior repairs including sheetrock and wall patching, painting, lock changes, and fixture replacements.
  • Conduct periodic property walk-throughs to identify and diagnose malfunctions in building systems and equipment.
  • Oversee swimming pool operations, including daily cleaning, equipment maintenance, and logging chemical levels.
  • Clean grounds, parking lots, and common areas daily.
  • Safely operate lawnmowers, chainsaws, and other heavy-duty maintenance machinery.
  • Maintain outdoor aesthetics through routine ground repairs and seasonal upkeep.
  • Monitor inventory, estimate material costs, and manage requisitions to keep essential supplies in stock.
  • Maintain accurate logs of inspections, repairs, and material inspections.
  • Provide professional, courteous, timely service when interacting with guests and residents.
  • Support the team with additional duties assigned by management.
Desired Qualifications
  • Prior campground or resort maintenance experience.
  • Passion for the outdoors and the guest experience in a nature-focused environment.

About the company

The Ride Platform provides an integrated mobility ecosystem for vehicle rental operators, combining marketplaces, software, and insurance. Its marketplaces connect owners and renters through Outdoorsy for RVs and Ride for professional car fleets, while Wheelbase is a SaaS operating system that helps fleet operators manage pricing and utilization. Roamly is an AI-first insurance provider with Lloyd’s Coverholder status, offering real-time, risk-adjusted coverage for standard policies and autonomous or FSD-enabled operation. The goal is to help mobility entrepreneurs turn any vehicle into a business at scale, using an end-to-end Operator Economy and AI-enabled tools to drive growth.

Company Size

201-500

Company Stage

N/A

Total Funding

N/A

Headquarters

Austin, Texas

Founded

2015

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Simplify's Take

What believers are saying

  • Roamly’s July 29, 2026 London expansion opens UK and European fleet insurance sales.
  • Jeff Cavins said on June 17, 2026 that Roamly FSD is live and cuts costs 50%.
  • The Ride Platform’s four billion dollars in processed transactions proves real operator demand and scale.

What critics are saying

  • Roamly’s FSD pricing on June 17, 2026 ties underwriting to unproven autonomous claims data.
  • The company still depends on vehicle utilization; a downturn in bookings crushes marketplace, SaaS, and insurance.
  • Any Lloyd’s or regulatory setback would cripple Roamly and break the platform’s cross-sell engine.

What makes The Ride Platform unique

  • June 2026 rebrand to The Ride Platform unifies Outdoorsy, Ride, Wheelbase, and Roamly.
  • Roamly’s July 29, 2026 London hub and Lloyd’s Coverholder status strengthen insurance differentiation.
  • Ride targets professional fleets with operator economics, not consumer marketplace extraction, since 2026.

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Benefits

  • Health Insurance
  • 401(k) Company Match
  • Unlimited Paid Time Off
  • Company Equity