Portfolio Development Manager at West Indies… · San Juan

Job Overview

West Indies Vacation Rentals is seeking a highly organized, proactive, and results-driven Portfolio Development Manager to lead the growth of our short-term rental property portfolio across Puerto Rico.

This position plays a key role in identifying high-potential properties, building relationships with property owners, securing new management agreements, and overseeing the onboarding process from initial inquiry to successful property launch.

The ideal candidate combines strong sales abilities with exceptional organizational skills, meticulous attention to detail, and excellent follow-through. They must have a keen eye for quality properties, understand what makes a vacation rental successful, and confidently assess whether a property aligns with our portfolio standards and business objectives.

This role requires someone who takes ownership, moves quickly, follows through consistently, and knows how to turn promising opportunities into successful additions to our portfolio.

Key Responsibilities1. Portfolio Growth & Property Evaluation

• Identify, prospect, and pursue opportunities to expand West Indies Vacation Rentals' portfolio throughout Puerto Rico.
• Evaluate potential properties based on location, condition, amenities, design, rental potential, guest appeal, and alignment with company standards.
• Demonstrate strong judgment in distinguishing high-potential properties from those that may not be suitable for our portfolio.
• Conduct property visits and assessments to evaluate readiness and identify opportunities for improvement.
• Research market conditions, competition, and vacation rental trends to support informed portfolio expansion decisions.
• Prioritize quality and long-term performance, not simply the number of properties acquired.

2. Sales & Property Owner Relations

• Promote West Indies Vacation Rentals' property management services and effectively communicate our value proposition.
• Respond promptly and professionally to all property owner inquiries and prospective leads.
• Maintain consistent, strategic follow-up with prospects to maximize conversion opportunities.
• Build strong relationships with prospective property owners through clear communication, professionalism, and trust.
• Prepare and present management proposals, negotiate terms, and secure property management agreements.
• Maintain accurate records of all communications, pending decisions, follow-ups, and lead status.

3. Lead Management, Organization & Follow-Up

• Manage multiple active property leads simultaneously while ensuring no opportunity is overlooked.
• Maintain a highly organized and up-to-date pipeline of prospects, property evaluations, agreements, and onboarding progress.
• Respond to inquiries in a timely manner and proactively follow up without requiring reminders or supervision.
• Establish clear next steps, deadlines, and action items for every prospective property.
• Prioritize leads based on potential value, readiness, and likelihood of conversion.
• Provide regular updates and reports on pipeline activity, conversion progress, and portfolio growth.

Exceptional organizational skills, attention to detail, and consistent follow-through are essential to success in this position.

4. Property Preparation & Owner Guidance

• Guide new property owners through the preparation process to meet West Indies Vacation Rentals' operational and quality standards.
• Assess property furnishings, décor, amenities, functionality, and overall guest readiness.
• Provide practical recommendations to enhance guest appeal, marketability, and rental performance.
• Clearly communicate preparation requirements, timelines, and expectations to property owners.
• Follow up consistently to ensure all required improvements and preparations are completed.
• Maintain detailed onboarding checklists and ensure that no important items are overlooked.

5. Photography & Property Presentation

• Coordinate professional property photography and ensure properties are fully prepared before photo shoots.
• Guide owners on staging, décor, and presentation improvements when necessary.
• Collaborate with photographers to ensure the property's strongest features are properly captured.
• Review photography and property information to ensure accuracy, quality, and consistency with company standards.

6. Property Setup & Onboarding

• Coordinate the implementation of self-check-in systems, including electronic locks and access procedures.
• Gather and organize all essential property information, documentation, owner details, and operational requirements.
• Accurately enter property and owner information into the company's management systems.
• Coordinate with internal departments to ensure each property is properly prepared for launch.
• Facilitate a complete, organized, and efficient handoff to the Property Management Team.
• Ensure all onboarding requirements are completed before the property begins accepting reservations.

Qualifications & RequirementsEssential Qualifications

• Previous sales, business development, real estate, or account management experience.
• Exceptional organizational skills and meticulous attention to detail.
• Strong follow-up discipline and the ability to respond promptly and consistently to leads and communications.
• Excellent judgment and an eye for identifying attractive, marketable vacation rental properties.
• Strong interpersonal, negotiation, and relationship-building skills.
• Ability to independently manage multiple prospects, projects, priorities, and deadlines.
• Excellent written and verbal communication skills in both English and Spanish.
• Tech-savvy, with the ability to learn and effectively use property management software, spreadsheets, and digital tools.
• Comfortable using technology and digital tools to organize leads, track communications, and manage follow-ups.
• Proactive, resourceful, solution-oriented, and comfortable working in a fast-paced environment.
• High level of accountability, professionalism, and ownership of responsibilities.
• Willingness to travel throughout Puerto Rico for property evaluations, owner meetings, and onboarding activities.
• Flexibility to work weekends and respond to time-sensitive business needs.
• Bachelor's degree required.

Preferred Qualifications

• Experience in vacation rentals, hospitality, real estate, or property management.
• Interior design, home staging, or decorating experience.
• Knowledge of Puerto Rico's short-term rental market and popular vacation destinations.
• Experience managing a sales pipeline or CRM.
• Understanding of the amenities, property features, and presentation standards that contribute to successful vacation rental performance.

Key Skills & Personal Attributes

We are particularly interested in candidates who demonstrate:

• Outstanding organization: Naturally structured, detail-oriented, and capable of keeping multiple projects on track.
• Strong follow-through: Takes initiative, follows up without being reminded, and ensures tasks reach completion.
• Responsiveness: Understands that timely communication can make the difference between winning and losing an opportunity.
• A keen eye for properties: Recognizes quality, potential, guest appeal, and marketability while identifying possible concerns.
• Sales mindset: Confident, persuasive, relationship-focused, and motivated to achieve growth targets.
• Ownership and accountability: Takes full responsibility for results and proactively resolves challenges.
• Sound judgment: Knows when to pursue an opportunity, when improvements are necessary, and when a property is not the right fit.
• Efficiency and adaptability: Works quickly and accurately while managing changing priorities.

What Success Looks Like

Success in this role is measured not only by the number of properties added to our portfolio, but also by the quality of those properties and the efficiency of the entire acquisition and onboarding process.

Key performance indicators include:

• Consistent growth in qualified property leads and signed management agreements.
• Acquisition of high-quality properties that meet company standards.
• Prompt response times and effective follow-up with prospective owners.
• Accurate, organized, and consistently updated sales pipeline.
• Efficient onboarding and timely property launches.
• Minimal errors, missing information, or delays during onboarding.
• Positive relationships and communication with property owners and internal teams.

Company Overview

West Indies Vacation Rentals is an established vacation rental management company with a growing portfolio of properties throughout Puerto Rico. We specialize in providing exceptional vacation experiences for our guests while helping property owners maximize their rental potential through professional management, marketing, and hospitality services.

Our team values initiative, accountability, collaboration, efficiency, and attention to detail. We offer a dynamic work environment where motivated individuals can take ownership of their responsibilities and make a direct impact on the company's growth.

Compensation & Benefits

• Competitive salary
• Flexible work arrangements, including the option to work remotely
• 15 vacation days per year
• Sick leave
• Health insurance
• Opportunity for professional growth within an expanding company

Immediate availability preferred.

Job Type: Full-time

Pay: $40,000.00 - $45,000.00 per year

Benefits:

• Employee discount
• Flexible schedule
• Health insurance
• Paid time off

Ability to Relocate:

• San Juan, PR 00920: Relocate before starting work (Required)

Work Location: In person