Sales Director

Director of Sales

Luxury Vacation Rental & Hospitality | Chādy Property Management

Location:

Madison, TN (Nashville Area)

Compensation:
Up to $80,000 Base + Uncapped Commission + Performance Incentives. Exceptional performers will have total earnings of $150K-$250K+.

Build the Future of Hospitality.

Chādy Property Management is a rapidly growing luxury short-term rental management company serving Tennessee, Georgia, and Florida. We specialize in luxury vacation homes, boutique hotels, condominium developments, and exclusive portfolio management.

But we’re building something much bigger than a traditional property management company.

We’re investing heavily in technology, automation, AI, proprietary systems, and operational innovation to redefine how hospitality companies operate and scale. Our goal is to create one of the most technology-enabled management companies in the industry while delivering exceptional experiences for owners and guests.

We’re looking for a strategic, relationship-driven Director of Sales who wants to help build that future.

This is an opportunity to build a sales organization—not simply inherit one.

• Develop new business throughout Tennessee while helping expand our footprint across Georgia and Florida.
• Pursue luxury vacation homes, boutique hotels, condominium developments, mixed-use projects, investor portfolios, and exclusive building management agreements.
• Build strategic relationships with real estate brokerages, luxury agents, developers, builders, investors, architects, hospitality professionals, and industry partners.
• Identify development opportunities before projects are completed and establish relationships with key decision-makers early.
• Own the complete sales process from prospecting through signed management agreements.
• Work closely with marketing to optimize lead generation, conversion, and pipeline performance.
• Analyze existing sales systems and recommend improvements to increase efficiency and scalability.
• Help build the processes, playbooks, reporting, and systems that will support a multi-market sales organization.
• Represent Chādy at networking events, conferences, trade shows, broker events, and industry functions.
• Assist with future market expansion initiatives as the company continues to grow.

• Proven experience selling within the short-term rental, vacation rental management, hospitality, luxury real estate, or closely related industries.
• Comfortable building relationships with luxury homeowners, investors, developers, commercial real estate professionals, and executives.
• A true builder who enjoys creating opportunities rather than waiting for leads.
• Strategic enough to design scalable systems while remaining willing to roll up your sleeves and execute.
• Comfortable using technology, CRM systems, reporting tools, and AI to improve performance.
• Organized, accountable, competitive, and self-motivated.

• Hub Spot
• Just Call
• Asana
• Slack
• Claude AI
• ChatGPT
• Google Workspace

Compensation & Benefits

• Base: $70,000–$80,000
• Target OTE (Year
  1): $150,000–$180,000
• Exceptional Performance: $250,000+
• Uncapped commission
• Performance-based incentive opportunities
• Brokerage referral commissions
• Health insurance
• Dental insurance
• Vision insurance
• Paid time off
• Significant opportunities for career advancement as the company grows

This role will be based full-time in our Madison, Tennessee office during the first six months to ensure a successful onboarding experience and close collaboration with leadership. Continued remote flexibility will be performance-based.

Most business is conducted throughout the Greater Nashville market, but travel is an important…