Short Term Rental Program Director

Director of Short-Term Rentals

ROLE OVERVIEW
The Director of Short-Term Rentals leads the growth, financial performance, daily operations, and strategic development of the Summit Sky Ranch Short-Term Rental Program. The role oversees the full rental lifecycle, including homeowner acquisition and onboarding, marketing, revenue management, guest experience, financial reporting, compliance, property standards, team leadership, and program improvement.

The Director is the program’s primary leader and point of accountability, working with homeowners, guests, HOA leadership, staff, vendors, accounting partners, and community stakeholders to ensure efficient operations and alignment with Summit Sky Ranch standards.

LEADERSHIP & PROGRAM MANAGEMENT

• Lead the program’s strategy, daily operations, policies, procedures, and standards.
• Build, train, support, and hold the operations team accountable; establish clear roles, workflows, and performance expectations.
• Oversee on-call and after-hours response, handling escalated guest, homeowner, and emergency issues as needed.
• Identify and mitigate operational, financial, guest, homeowner, and community risks.
• Improve systems and workflows to strengthen efficiency, profitability, consistency, and stakeholder experience.
• Maintain procedures, checklists, and documentation needed for reliable operations.
• Represent the program within the HOA community and address questions, concerns, and impacts.
• Prepare and present financial, operational, performance, and strategic updates to HOA leadership and/or the Board.

HOMEOWNER ACQUISITION & BUSINESS DEVELOPMENT

• Lead business development and identify opportunities to grow the participating-home portfolio.
• Respond to prospective homeowners and explain program services, fees, standards, responsibilities, and benefits.
• Evaluate properties for suitability and readiness; prepare revenue projections, market analyses, and program information.
• Explain market conditions, rental potential, property requirements, and operational considerations.
• Follow up with prospects and build relationships that support growth.
• Maintain current homeowner relationships and encourage retention.
• Monitor competitive conditions and identify opportunities for growth and improvement.

HOMEOWNER RELATIONSHIP MANAGEMENT

• Serve as the primary homeowner contact, addressing questions, concerns, performance, and operational issues promptly and transparently.
• Explain market conditions, best practices, pricing strategies, and program standards.
• Interpret performance data, including revenue trends, seasonality, occupancy, pricing, and improvement opportunities.
• Communicate policies, operational requirements, property standards, and changes affecting homeowners.
• Set realistic expectations regarding revenue, occupancy, property use, maintenance, guest experience, and program requirements.
• Resolve concerns collaboratively while applying program standards consistently.

NEW HOME ONBOARDING & PROPERTY READINESS

• Manage onboarding from agreement and setup through marketing, pricing, system integration, and operational readiness.
• Coordinate management agreements, required forms, W-9s, ACH/payment setup, property information, and other documentation.
• Coordinate rental licensing and responsible-agent information with local jurisdictions.
• Conduct or coordinate home evaluations and define property-specific readiness requirements.
• Confirm homes meet SSRR standards for cleanliness, furnishings, inventory, safety, amenities, technology, supplies, and guest readiness.
• Coordinate photography, listing creation, marketing materials, pricing setup, and distribution-channel integration.
• Establish and maintain readiness and quality-control standards.
• Coordinate owner-provided items, rental supplies, linens, guest amenities, and other property needs.
• Ensure each home is fully operational before accepting reservations.

REVENUE MANAGEMENT & FINANCIAL PERFORMANCE

• Oversee each home’s financial performance through pricing, policies, marketing, and demand-based strategies.
• Set and adjust nightly rates, minimum stays, discounts, seasonal and holiday pricing, and availability based on demand, booking pace, history, seasonality, and competitive data.
• Balance revenue goals with occupancy, homeowner use, guest experience, and program standards.
• Monitor property and portfolio performance, including revenue, occupancy, average daily rate (ADR), booking trends, and channel performance.
• Identify underperforming homes or periods and develop improvement strategies.
• Explain pricing decisions, market conditions, and revenue performance to homeowners.

MARKETING, PHOTOGRAPHY & BRAND MANAGEMENT

• Develop and execute marketing strategy, campaigns, advertising, and performance optimization.
• Maintain SSRR’s brand and consistent presentation across guest- and homeowner-facing materials.
• Create or oversee professional property photography, editing, organization, and updates following changes or renovations.
• Develop listing descriptions, marketing copy, promotional materials, website content, and other marketing assets.
• Manage and optimize listings for accuracy, visibility, presentation, and revenue performance.
• Maintain website and property content, as applicable.
• Develop seasonal and property-specific campaigns; monitor results and adjust strategies.
• Maintain consistent photography, branding, messaging, and presentation across the portfolio.

DISTRIBUTION & BOOKING CHANNELS

• Manage listings and platforms to ensure accurate content, optimized pricing, and reliable system integration.
• Oversee distribution across direct booking and third-party channels, including channel-specific pricing, fees, policies, content, and requirements.
• Increase direct bookings and reduce unnecessary third-party costs.
• Monitor channel performance and ensure reservation, pricing, availability, and property information are accurate across platforms.

GUEST EXPERIENCE & GUEST OPERATIONS

• Establish and oversee guest communication and service standards.
• Resolve or oversee escalated guest concerns, service issues, damages, rule violations, refunds, credits, and exceptional circumstances.
• Ensure house rules, check-in instructions, policies, and property information are accurate and consistently communicated.
• Coordinate the guest experience involving rental homes and shared community amenities, including eligibility, access, waivers, fees, and guest concerns.
• Monitor reviews and feedback, protect the SSRR reputation, identify recurring issues, and implement corrective action.

PROPERTY OPERATIONS, QUALITY & VENDOR MANAGEMENT

• Coordinate and oversee cleaners, maintenance providers, contractors, vendors, and service partners.
• Establish cleaning, inspection, maintenance, inventory, and property-presentation standards.
• Conduct or oversee inspections and quality-control processes.
• Identify and coordinate timely resolution of maintenance, cleanliness, safety, inventory, and property-condition issues.
• Evaluate vendor responsiveness, quality, performance, and cost; select providers as needed.
• Maintain standards for supplies, consumables, linens, amenities, and property inventory.
• Establish procedures for owner cleans, guest cleans, restocking, supply management, and property readiness.
• Coordinate repairs and maintenance with homeowners, staff, and vendors.
• Ensure participating homes continue to meet SSRR standards.

FINANCIAL MANAGEMENT, ACCOUNTING & REPORTING

• Oversee owner statements, payouts, tax coordination, and financial reporting.
• Manage rental-program financial workflows, including booking revenue, owner funds, management fees, cleaning and other charges, payouts, clearing/trust accounts, and related transactions.
• Oversee monthly reconciliation and review rental activity and reports for accuracy and completeness.
• Coordinate with accounting partners to deliver timely, accurate reporting and provide required reports, documentation, and supporting information.
• Review owner statements before distribution.
• Investigate and resolve discrepancies among rental-management systems, financial records, banking activity, and accounting records.
• Coordinate with accounting and tax professionals on lodging, sales, and other applicable rental taxes, including collection, reporting, and remittance.
• Monitor financial performance, improve efficiency and profitability, maintain appropriate controls and transaction documentation, and report to HOA leadership and/or the Board as requested.

COMPLIANCE, LICENSING & RISK MANAGEMENT

• Ensure compliance with HOA policies, local and state rental regulations, tax and licensing requirements, and safety standards.
• Monitor legal, regulatory, HOA, and local changes that affect the program.
• Maintain appropriate licenses and responsible-agent information.
• Ensure homes comply with occupancy, safety, amenity, parking, pet, event, and other applicable requirements.
• Maintain processes to reduce operational, financial, guest, homeowner, and property risks.
• Oversee documentation and resolution of incidents, damage, service failures, claims, refunds, credits, and other exceptional matters.
• Coordinate with homeowners, guests, vendors, insurers, legal counsel, accounting professionals, and HOA leadership as appropriate.
• Maintain records related to incidents, compliance, and risk management.

TECHNOLOGY & SYSTEMS

• Oversee rental technology, integrations, and workflows to support accurate reservations, reporting, pricing, financial information, and communication.
• Manage the property-management system and related platforms; maintain accurate integrations among booking channels, management software, accounting systems, and other tools.
• Troubleshoot technology issues and improve technology-based workflows to increase efficiency and reduce errors.
• Train staff and relevant team members on systems and processes.
• Evaluate tools that may improve program efficiency or performance.

PROGRAM POLICIES & STANDARDS

• Develop, maintain, communicate, and enforce policies, house rules, and operating standards that protect homes and promote consistency.
• Establish standards for homeowner participation, property readiness, guest conduct, pets, events, occupancy, amenities, cancellations, refunds, and other program matters.
• Review policies periodically and recommend updates based on operations, market conditions, homeowner needs, guest feedback, and regulatory requirements.
• Apply policies consistently across the portfolio and communicate changes clearly to homeowners, guests, staff, and other stakeholders.

COMMUNITY & SHARED AMENITY COORDINATION

• Represent the rental program within the HOA community and support shared facilities and amenities, including Aspen House coordination and access scheduling, as needed.
• Coordinate with HOA staff on rental guests and community-facility policies.
• Ensure guests receive accurate information about amenities, access, waivers, fees, hours, and rules.
• Address concerns about rental impacts on shared facilities and the community.
• Work with HOA leadership and staff to maintain a constructive relationship between the rental program and the Summit Sky Ranch community.

REPORTING, ANALYSIS & CONTINUOUS IMPROVEMENT

• Analyze performance data to identify trends, opportunities, risks, and areas for improvement.
• Track key indicators, including revenue, occupancy, ADR, booking pace, direct-booking share, channel mix, homeowner participation, guest satisfaction, and operating costs.
• Prepare regular performance reports for homeowners and HOA leadership.
• Use data and operational experience to recommend pricing, marketing, staffing, policy, technology, and strategy changes.
• Benchmark performance against market conditions and comparable properties.
• Identify ways to increase efficiency, reduce costs, improve guest and homeowner experience, and strengthen financial performance.
• Regularly evaluate and improve program systems and practices.

STRATEGIC GROWTH & PROGRAM DEVELOPMENT

• Develop and execute strategies for sustainable program growth while maintaining quality and community standards.
• Evaluate new services, amenities, marketing opportunities, technology, and revenue streams.
• Improve homeowner retention and satisfaction; evaluate profitability and operating costs and recommend changes.
• Establish short- and long-term goals with HOA leadership.
• Monitor market trends, competitor activity, regulatory changes, and evolving guest expectations.
• Balance growth with homeowner satisfaction, guest experience, operational capacity, community standards, and Summit Sky Ranch’s long-term interests.

CORE ACCOUNTABILITY
The Director is accountable for ensuring the Short-Term Rental Program operates professionally, responsibly, and with a focus on guests, homeowners, and the community. The Director must maintain visibility across program functions, identify issues early, establish effective systems and accountability, communicate clearly, and continually improve financial performance, operational efficiency, stakeholder experience, and the program’s relationship with Summit Sky Ranch.

QUALIFICATIONS & EXPERIENCE

Required Qualifications

• Bachelor’s degree in hospitality, business administration, marketing, real estate, property management, finance, or a related field; equivalent professional experience may substitute.
• At least five years of progressive experience in short-term rentals, vacation rentals, hospitality, property management, lodging, real estate, or a related field.
• Experience overseeing a rental, hospitality, or property-management operation and managing teams, vendors, contractors, or service providers.
• Strong knowledge of rental operations, including reservations, guest service, property standards, cleaning, maintenance, homeowner relations, and regulatory requirements.
• Experience with revenue management, dynamic pricing, occupancy strategy, minimum stays, discounts, seasonal pricing, and market analysis.
• Financial literacy and experience reviewing financial reports, owner statements, revenue reports, reconciliations, budgets, or operational financial information.
• Experience with property-management software, booking platforms, channel managers, accounting systems, or hospitality technology.
• Experience developing and executing marketing, including digital marketing, listing optimization, photography, copywriting, social media, and/or advertising.
• Excellent written and verbal communication with homeowners, guests, employees, vendors, accounting professionals, HOA leadership, and community members.
• Strong organization and time management, including managing multiple properties, deadlines, priorities, and competing demands.
• Ability to investigate operational issues, identify root causes, implement solutions, and prevent recurring problems.
• Ability to interpret performance data and turn financial and operational information into clear recommendations.
• Strong attention to detail in financial records, property standards, communications, contracts, policies, and compliance.
• Sound judgment, discretion, confidentiality, independent work, and effective team leadership.
• Ability to participate in an established after-hours/on-call escalation process.
• Valid driver’s license and reliable transportation for travel between properties and community facilities.

Preferred Experience

• Managing a multi-property short-term or vacation rental portfolio, especially in an HOA-managed or community-based program.
• Luxury, high-end, destination, mountain-resort, ski-destination, or seasonal tourism experience.
• Experience with property-management systems; Airbnb, VRBO, Marriott Homes & Villas, direct-booking platforms, and other distribution channels.
• Experience with revenue-management tools, market analytics, monthly accounting and reconciliation, owner statements and payouts, rental accounting workflows, and lodging taxes.
• Direct-booking growth and reducing reliance on third-party channels.
• Professional real estate or hospitality photography, photo-editing software, website content management, digital advertising, social media, email marketing, and SEO.
• Developing property standards, inspections, checklists, and quality-control procedures.
• Vendor selection, contract negotiation, performance management, and cost control.
• Working with local governments, licensing authorities, HOA boards, or regulators.
• Managing homeowner relationships in an individually owned vacation-rental portfolio.

CORE COMPETENCIES

• Leadership & Accountability: Lead teams, set expectations, delegate, and hold staff and vendors accountable.
• Hospitality & Service: Deliver strong guest and homeowner service and resolve difficult situations professionally.
• Revenue & Business Acumen: Understand market conditions, pricing, financial performance, and how operations affect profitability.
• Communication: Communicate clearly, professionally, promptly, and transparently.
• Problem Solving: Anticipate issues, investigate root causes, and implement practical, lasting solutions.
• Organization & Follow-Through: Manage multiple properties and priorities without losing detail.
• Technology & Data: Use management systems, booking platforms, financial reports, spreadsheets, and performance data effectively.
• Marketing & Brand Management: Position properties effectively and maintain compelling, consistent marketing.
• Financial Responsibility: Understand rental financial workflows, reporting, reconciliation, owner statements, and controls.
• Adaptability: Work effectively in a fast-paced, seasonal environment with shifting priorities.
• Professional Judgment: Balance homeowner interests, guest experience, financial performance, operational realities, and community interests.

WORKING ENVIRONMENT & EXPECTATIONS
The Director works in a hands-on operational environment that requires both strategic thinking and attention to daily details. The role involves regular communication with homeowners, guests, staff, vendors, accounting professionals, HOA leadership, and community members. Work outside standard business hours—including evenings, weekends, holidays, and emergencies—is required, particularly during peak rental periods. The Director is expected to remain responsive and accountable while appropriately delegating responsibilities to the rental-program team.

Job Type: Full-time

Pay: $75,000.00 - $80,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Paid time off
• Vision insurance

Work Location: In person

Salary : $75,000 - $80,000