Director of Sales - Luxury Vacation Rentals & Hospitality

About the Role

Chādy Property Management is a fast-expanding firm specializing in luxury short-term rental management across Tennessee, Georgia, and Florida. Our portfolio includes luxury vacation homes, boutique hotels, condominiums, and exclusive property management agreements. We aim to revolutionize hospitality management by leveraging cutting-edge technology, automation, AI, and proprietary systems to innovate operations and enhance scaling capabilities.

Key Responsibilities

• Expand new business opportunities primarily in Tennessee with plans to grow in Georgia and Florida.
• Target clientele includes luxury vacation homes, boutique hotels, condo projects, mixed-use developments, investor portfolios, and exclusive building management contracts.
• Develop and nurture strategic partnerships with real estate brokerages, luxury property agents, developers, builders, investors, architects, and hospitality industry players.
• Identify development projects early to engage key decision-makers before project completion.
• Manage the entire sales cycle from initial prospecting to contract signing.
• Collaborate closely with marketing teams to optimize lead generation, conversion rates, and sales pipeline performance.
• Evaluate and recommend improvements to sales processes and systems for better efficiency and scalability.
• Create and implement sales playbooks, reporting frameworks, and systems to support multi-market growth.
• Represent Chādy at industry events including networking meetings, trade shows, conferences, and broker gatherings.
• Support expansion efforts into new markets as the company continues to grow.

Candidate Profile

• Demonstrated sales experience within short-term/vacation rental management, hospitality, luxury real estate, or related sectors.
• Skilled in building relationships with luxury homeowners, investors, developers, commercial real estate professionals, and high-level executives.
• A proactive builder who creates opportunities instead of waiting for leads.
• Strategic thinker capable of designing scalable sales systems while performing hands-on execution.
• Proficient with technology, including CRM platforms, reporting tools, and AI applications.
• Highly organized, accountable, self-driven, and competitive.

Technology Utilized

• HubSpot CRM
• JustCall communication platform
• Asana project management
• Slack for team collaboration
• Claude AI and ChatGPT for advanced AI assistance
• Google Workspace productivity tools

Compensation and Benefits

• Base salary between $70,000 and $80,000 annually
• First-year target on-target earnings (OTE) from $150,000 to $180,000
• Top performers can earn $250,000 or more
• Uncapped commission structure
• Performance-based incentives
• Referral commissions for broker engagements
• Health, dental, and vision insurance coverage
• Paid time off
• Considerable opportunities for career growth as the company expands

Work Environment & Additional Details

This is a full-time remote position based in Madison, Tennessee with hybrid work arrangements during the initial six months to ensure successful onboarding and close coordination with company leadership. Continued remote work will depend on performance. The role mainly serves the Greater Nashville area but involves up to 20% travel to markets like Knoxville, Chattanooga, Atlanta, and South Florida for client meetings and business development.

The position demands flexibility to attend client breakfasts, lunches, dinners, networking events, evening functions, and occasional weekend industry gatherings to foster lasting relationships.

Why Join Chādy?

You will have the unique chance to collaborate directly with senior management to architect a scalable multi-market sales organization. Your role will shape the strategy, systems, and processes of one of the industry’s most technologically advanced hospitality companies. This is an ideal fit if you seek a position where your contributions are valued, your income is performance-driven, and your impact on company growth is direct and significant.