Job Description

COMPANY OVERVIEW:

Create your ideal career with us at Juniper Holiday + Home

Driven by a genuine love for hospitality, entrepreneurship, and real estate, we’re leading a movement towards a brighter, more inclusive future in hospitality. We operate across the picturesque Lake Michigan region, managing a collection of properties in coveted locations across Southwest Michigan and beyond.

Our mission: To make luxury vacation rentals and unparalleled service accessible to everyone.

Our Commitment: Luxury, for us, is more than a standard—it's a declaration of our dedication to excellence. Our commitment extends beyond our breathtaking designs and décor; it's about providing a new level of hospitality. With a focus on caring and attentive services, we ensure every moment with us is as enriching, relaxing, and carefree as possible.

Our Approach: We approach every day with innovation, drive and dedication to providing unmatched service for our guests and homeowners. Together as a team, we’re proving that a centered and grounded business strategy isn't just possible but necessary to achieving success.

Your Career with Juniper Holiday + Home: Take the next step in your career, where your passion for hospitality, entrepreneurship, and real estate can flourish. With us, you'll be at the forefront of an industry revolution, championing a new era of luxury, service, and fulfillment.

Join us as we continue to build a place where vacation rental experiences aren’t just about offering stays but about creating spaces for stories worth telling.

POSITION SUMMARY:

We’re hiring a Director of Business Development to take the lead on driving the company’s growth and expansion. In this role, you’ll be responsible for identifying and pursuing new market opportunities, building strategic partnerships, and converting prospective homeowners into long-term clients. You’ll work closely with the CEO to align vision with execution and oversee key initiatives that support scalable, sustainable growth.

Success in this role requires a self-motivated leader with strong experience in business development, sales, or marketing—ideally within the property management, real estate, hospitality, or vacation rental industries. You’ll represent the company at high-level networking events, collaborate with top-tier brokers and real estate firms, and travel regularly (up to 30%) to meet and entertain prospective homeowners. If you're entrepreneurial, results-driven, and ready to take full ownership of business growth, we want to hear from you.

RESPONSIBILITIES:

Team Leadership

• Lead and mentor cross-functional teams across operations, sales, support and marketing.
• Improve team productivity, accountability, and clarity of roles/responsibilities
• Support or lead hiring, performance management, and professional development
• Build and document repeatable systems and SOPs
• Own key performance indicators (KPIs) and reporting for sales and marketing.

Business Alignment:

• Be the bridge between CEO’s strategic vision and sales & marketing team execution
• Lead weekly sales and marketing meetings and ensure progress against goals
• Drive collaboration between the sales & marketing team

Growth & Scale:

• Support expansion into new territories with process readiness
• Take the lead on special projects, from tech implementations to partnerships
• Capitalize on current partnerships and build new relationships with prospective homeowners
• 30% travel is required to engage with and entertain prospective homeowners across target markets
• Identifying and attending networking events to represent the company and build connections.

QUALIFICATIONS:

COMPETENCIES:

• Demonstrated success in growing and scaling businesses
• Track record of driving results through outbound sales strategies
• Skilled at building strong relationships with high-profile and high-value clients
• Highly self-motivated with a goal-oriented mindset
• Confident and proactive communicator who leads with clarity and purpose
• Thrives in autonomous environments and seeks meaningful leadership opportunities
• Tech-savvy and systems-minded, with experience using AI tools, property management systems (PMS), pricing platforms, and task management software

EDUCATION AND QUALIFICATIONS:

• 5+ years of experience in sales or sales leadership within property management, hospitality, vacation rentals, or real estate; luxury market experience is a plus
• Strong understanding of KPIs, financial metrics, CRMs (such as HubSpot), property management systems (PMS), and project management tools
• Willingness to work flexible hours, including weekends as needed

COMPENSATION & BENEFITS:

Annual Salary & Commission: $90,000 - $130,000 based on experience with an OTE (on-track earnings) of $200,000 - $250,000

Benefits:

• Comprehensive health, dental, and vision insurance.
• Flexible working hours and remote work opportunities.
• Professional development and training programs.
• Generous paid time off and holiday schedule.

Schedule: Full Time, Monday–Friday with flexibility of weekend hours

Job Tags

Similar Jobs