Now Hiring - Chady Vacation Rental Management - Sales Director in Madison, TN

Full description of the position

Director of Sales Luxury Vacation Rental & Hospitality | Chdy Property Management Location: Madison, TN (Nashville Area - Remote)

Compensation

: Up to $80,000 Base + Uncapped Commission + Performance Incentives. Exceptional performers will have total earnings of $150K-$250K+. Build the Future of Hospitality. Chdy 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 organizationnot simply inherit one.

What You'll Do

• 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 Chdy at networking events, conferences, trade shows, broker events, and industry functions.
• Assist with future market expansion initiatives as the company continues to grow.

Who You Are

• 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. Technology You'll Use
• HubSpot
• JustCall
• Asana
• Slack
• Claude AI
• ChatGPT
• Google Workspace

Compensation

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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 High performers should expect their total earnings to substantially exceed their base salary.

Work Environment

This role will be full-time, remote-based out of the Madison, Tennessee office. Hybrid as needed 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 part of building strategic relationships. While travel is generally expected to remain under 20%, opportunities may arise that require visiting clients, developers, or investment groups in markets such as Knoxville, Chattanooga, Atlanta, South Florida, or other expansion markets. We're looking for someone who doesn't simply accept travel when necessarythey're excited by the opportunity to pursue significant business, build relationships, and close meaningful deals wherever those opportunities exist. Relationship-driven sales also require flexibility. Client breakfasts, lunches, dinners, networking events, evening functions, and occasional weekend industry events are all part of developing long-term partnerships. Why Join Chdy? You'll work directly with company leadership to build a sales organization that can scale across multiple markets. You'll help shape the future of one of the industry's most technology- forward hospitality companies. You'll have the opportunity to influence strategy, build systems, create processes, and play a meaningful role in the next stage of our growth.

• If you're looking for a role where your ideas matter, your income is tied to your performance, and your work directly impacts the future of the company, we'd love to hear from you. Pay: $75,085.38 - $200,000.00 per year

Benefits

:

• Dental insurance
• Health insurance
• Paid time off
• Vision insurance Application Question(s):
• What experience do you have in vacation rental management as it relates to this job? Experience:
• sales: 5 years (Required)
• Vacation Rental Management: 3 years (Preferred) Location:
• Madison, TN 37115 (Preferred) Willingness to travel:
• 25% (Required) Work Location: Hybrid remote in Madison, TN 37115