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First Chair Destinations

Manages luxury vacation homes and communities

Property Caretaker

Full-TimeUpdated
$30/hr
Junior
Telluride, CO, USA
In PersonFrequent travel between worksites within the locally assigned market/region; weekends and holidays may be required.
General Maintenance & RepairBuilding & Property Maintenance

About the job

Requirements
  • At least one year of experience in housekeeping, maintenance, or a similar role.
  • Strong time-management skills and the ability to change activities frequently and cope with interruptions.
  • Strong attention to detail.
  • Experience using digital systems, applications, mobile apps, tablets, and software platforms.
  • Reliable personal transportation for frequent travel between worksites.
  • Ability to work independently and contribute to a collaborative team.
  • Ability to communicate clearly with guests and homeowners online or in person.
  • Ability to work shifts that may include early mornings, evenings, weekends, and holidays, with flexibility as guest and homeowner needs change.
  • Ability to perform physical activities including balancing, climbing, crawling, driving, squatting, standing, stooping, walking, bending, pushing, pulling, reaching, and repetitive hand and finger motions.
  • Ability to lift up to 50 pounds without assistance.
  • A valid driver's license and age of at least 18 are required when driving a personal vehicle for work. When driving a company vehicle, a valid driver's license, age of at least 21, and at least three years as a licensed driver are required.
  • Successful completion of a background check is required as a condition of employment.
Responsibilities
  • Assist with daily operations of the assigned portfolio of homes and identify opportunities for process improvements that support efficiency and quality.
  • Respond to guest and homeowner emails, calls, and tickets, including escalated concerns, and partner with the management team on escalated issues.
  • Perform light home maintenance, such as replacing light bulbs, fixing door hinges, and unclogging toilets.
  • Conduct regular inspections before guest and owner arrivals.
  • Partner with and assist the Business Development Representative and management team when new units join the portfolio.
  • Provide cross-functional support across the team as needed.
  • Travel regularly within the locally assigned market or region and between worksites.
Desired Qualifications
  • Experience in the hotel, hospitality, vacation rental, or a similar industry is highly preferred.

About the company

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First Chair Destinations

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First Chair Destinations manages vacation homes in premier ski and coastal destinations, offering property and community management for homeowners, associations, and guests. It handles budgeting, dues collection, reserve planning, and rule enforcement for communities, while delivering a high-quality guest experience tied to local connections. The model combines local expertise with standardized operating procedures to maintain consistency across properties, backed by Paceline Equity Partners and leaders from Wyndham Destinations and Vacasa. Its goal is to protect the long-term vitality of communities and provide a reliable, high-quality vacation experience in top destinations.

Company Size

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Company Stage

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Total Funding

N/A

Headquarters

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Founded

2025

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • 401(k) Retirement Plan
  • 401(k) Company Match
  • Paid Vacation
  • Paid Holidays
  • Paid Sick Leave
  • Flexible Work Hours
  • Hybrid Work Options

Company News

Hotel News Resource
Sep 15th, 2026
First Chair Destinations launches vacation rental brand.

First Chair Destinations launches vacation rental brand. In Brief: First Chair Destinations has launched a vacation rental brand in ski destinations across nine states, offering select homes in coastal New England. First Chair Destinations has launched with a portfolio of vacation rental homes in Colorado, Wyoming, Montana, Vermont, Idaho, California, Maine, Massachusetts and New Hampshire. The company is headquartered in Steamboat Springs, Colorado. The portfolio is centered on ski destinations and includes select vacation homes in coastal New England. Local teams live and work in each market. First Chair Destinations worked with mVara.ai on a direct-booking digital platform for ski travelers. The platform allows users to search and filter homes by ski pass type and ski-centered amenities. It also includes maps showing distances to lifts and runs and live snow trackers during the season. The platform provides local recommendations, including places to visit in town and on-mountain ski runs. Local teams support guest stays in their respective markets. For homeowners and community associations, the company offers a portal with real-time information on reservations, calendars and revenue performance. First Chair Destinations uses Streamline and Breezeway to coordinate reservations, housekeeping and maintenance. The company also provides property oversight and marketing to increase property visibility. The company was founded by former Wyndham and Vacasa executives. Rishi Nigam is chief executive officer. His previous roles include chief executive officer of Urbain Hospitality Group and senior vice president of global corporate and strategic development at Wyndham Worldwide. Bob Milne is president and chief operating officer, based in Steamboat Springs. Milne previously served as senior vice president of operations and sales at Vacasa, where he oversaw operations and sales for 34,000 homes in the company's portfolio. Paceline Equity Partners, a Dallas-based private equity firm with more than $1.5 billion in equity commitments, backs First Chair Destinations.

Aspen Times
Jun 12th, 2026
Skier-focused hospitality brand launches in Aspen.

Skier-focused hospitality brand launches in Aspen. NewsNews | Jun 12, 2026 A new hospitality brand, First Chair, has launched in Aspen as of June 1, with a focus on providing experiences for the diversity of skiers who travel to the area. First Chair is founded by former Wyndham and Vacasa executives and backed by a local team based in the valley. "The company is built around an approach rooted in local connection, transparent homeowner partnerships, exceptional property stewardship and consistently seamless guest experiences," a press release states. First Chair's Aspen portfolio includes 38 units with Aspen Mountain Lodge and 41 standalone homes from Aspen all the way to Redstone. "When you talk about premiere ski destinations, you can't do that without making sure you're talking about Aspen and Snowmass," said Chief Operating Officer Bob Milne. "It just fits into our overall vision of having a company that can cater to the skier. There's nothing more magical than that." Milne is a passionate skier himself, he said, as well as a former ski instructor. First Chair's debut portfolio - acquired from Casago in December 2025 - also includes homes in other Colorado locations and across Wyoming, Montana, Vermont, Idaho, California, Maine, Massachusetts and New Hampshire, according to the release. But First Chair CEO Rishi Nigam, who previously served as CEO of Urbain Hospitality Group and as senior vice president of Global Corporate & Strategic Development with Wyndham Worldwide, emphasized in the release how every location deserves its own local feel and attention to detail. "As the vacation rental market continues to expand and become more generalized, we saw a fantastic opportunity to create a new, highly focused hospitality brand that showcases and celebrates the special destination communities we serve in a very tailored way," Nigam said. "Aspen is one of the country's most iconic mountain destinations, and it requires a hospitality model that reflects the quality, expectations and local knowledge that define the market." Milne echoed this sentiment to The Aspen Times, noting that First Chair will make sure hospitality starts at the front of every door. "I think the hospitality side of vacation rentals has gotten lost a little bit," Milne said. "Especially with skiers, they really appreciate that. Those things go a long way and that's where I want to make sure we rise above the pack." Milne noted that First Chair properties will offer everything from value stays to luxury. "Skiers are kind of a unique group. It's not a one-size fits all," Milne said. "There are the people that are just out of college... we have to have an accommodation that works for them. There are people that are families that want to teach their kids how to ski... and then there's also the people who love the glitz and the glamour of Aspen and want to stay in a really luxurious place. I'm trying to find a little bit of everything because that's what I find skiers are." What's happening in Aspen, in one click. And First Chair is focused not just on hospitality for visitors but hospitality in conjunction with stewardship of local homes. "Stewardship is really making sure you oversee their asset as if it were your own," Milne noted. Homeowners will have access to an advanced homeowner portal that provides real-time visibility into reservations, calendars and revenue performance, integrated technology tools to support coordination across reservations, housekeeping and maintenance, targeted marketing to increase property visibility and more. Jun 14, 2026 The free music festival in Snowmass Village was headlined by American Authors, Richy Mitch & The Coal Miners, and Pecos & The Rooftops.