Jacksonville
VTrips
4600 Touchton Rd E
Building 200, Suite 220
Jacksonville, FL 32246, USA

VTrips is seeking a strategic, results‑driven Director of Sales to lead and scale our national sales organization. This executive will be responsible for driving revenue growth, expanding our property owner portfolio, and developing high‑performing sales teams across multiple markets.

The Director of Sales will play a critical role in shaping the company’s organic growth strategy, optimizing sales processes, and building strong relationships with property owners and key stakeholders.

This is a remote role. Candidates must reside in Florida to be considered with preference given to those in the Jacksonville or Destin metro areas.

Key Responsibilities

• Sales Strategy & Leadership
• Develop and execute a comprehensive sales strategy to drive portfolio growth and revenue.
• Establish sales targets, KPIs, and performance metrics aligned with company objectives.
• Lead, mentor, and scale a high‑performing sales team across regions.
• Business Development
• Oversee acquisition of new property owners and expansion into new markets.
• Identify emerging opportunities through market analysis, industry trends, and competitor insights.
• Build strategic partnerships to accelerate growth.
• Team Management & Development
• Recruit, train, and retain top sales talent.
• Foster a culture of accountability, performance, and continuous improvement.
• Implement coaching programs to enhance closing rates and sales effectiveness.
• Sales Operations & Process Optimization
• Design and optimize sales processes, pipelines, and CRM utilization.
• Collaborate with Marketing to align campaigns, lead generation, and brand positioning.
• Ensure consistent and scalable sales practices across all regions.
• Relationship Management
• Establish and maintain executive‑level relationships with key property owners and partners.
• Collaborate with other department leaders to ensure exceptional customer experience throughout the sales lifecycle.
• Performance & Reporting
• Monitor sales performance and forecast revenue.
• Provide regular reporting and insights to executive leadership.
• Adjust strategies based on data‑driven analysis.

Qualifications

• Bachelor’s degree in Business, Marketing, or a related field (MBA preferred).
• 6–10+ years of progressive sales experience, with at least 5 years in a senior leadership role.
• Proven track record of scaling sales teams and exceeding revenue targets.
• Experience in vacation rental, hospitality, real estate, or property management industries strongly preferred.
• Strong leadership, negotiation, and strategic planning skills.
• Excellent communication and interpersonal abilities.
• Proficiency in CRM systems and sales analytics tools.
• Ability to travel as needed.
• Competitive salary + performance‑based bonus/commission structure
• Comprehensive medical, dental, and vision insurance
• 401(k) retirement plan with company match
• Paid time off and holidays
• Professional development and leadership growth opportunities

Other Duties

This job description is not exhaustive and may be subject to change. Duties, responsibilities, and activities may vary based on company needs and growth initiatives.

VTrips is an Equal Opportunity Employer. We are committed to creating an inclusive environment for all employees. Applicants are encouraged to review the Know Your Rights notice from the Department of Labor.

This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.