Director of Revenue Management

Midway Vacations is a rapidly growing hospitality and vacation rental management company specializing in premium resort and vacation rental properties across Waikiki and Maui. We are seeking an experienced and highly analytical Director of Revenue Management to lead and further develop our pricing, distribution, and revenue optimization strategies as we continue expanding our portfolio and hospitality platform. This is a unique opportunity to join a fast-growing hospitality company with strong operational infrastructure, in-house housekeeping and maintenance teams, advanced revenue systems, and a portfolio of high-performing resort and vacation rental properties.

The Ideal Candidate

The ideal candidate is highly analytical, entrepreneurial, performance-driven, and passionate about hospitality revenue optimization. You understand that modern revenue management goes far beyond pricing, and includes distribution strategy, conversion optimization, market positioning, booking pace analysis, and maximizing long-term portfolio performance. You thrive in a fast-moving hospitality environment and enjoy combining data, strategy, and operational collaboration to drive measurable revenue growth.

Responsibilities

• Develop and execute dynamic pricing and revenue optimization strategies across our portfolio

• Maximize ADR, occupancy, RevPAR, and overall portfolio profitability

• Analyze market trends, booking pace, seasonality, demand patterns, and competitor performance

• Manage OTA distribution strategies across Airbnb, Booking.com, VRBO, Expedia, and direct channels

• Optimize listing visibility, conversion rates, ranking performance, and booking window strategies

• Develop occupancy pacing and forecasting models

• Implement length-of-stay controls and yield management strategies

• Collaborate with operations, guest experience, marketing, and executive leadership teams

• Produce weekly and monthly revenue performance reporting and forecasting

• Continuously identify opportunities to improve portfolio-wide revenue performance

Qualifications

• Minimum 3 years of experience in hospitality revenue management

• Experience with hotels, resorts, vacation rentals, condo-hotels, or hospitality groups

preferred

• Strong understanding of OTA platforms, pricing strategies, and distribution systems

• Experience with revenue management software such as PriceLabs, Beyond, Wheelhouse, Duetto, IDeaS, or similar systems

• Strong analytical and forecasting skills

• Advanced Excel / Google Sheets skills preferred

• Experience with PMS platforms such as Guesty is a plus

• Excellent communication and organizational skills

• Entrepreneurial mindset with strong attention to detail

Compensation & Benefits

• Competitive base salary

• Quarterly and annual performance bonuses

• Health insurance benefits

• Paid vacation and sick leave

• Growth opportunities within an expanding hospitality company

• Potential long-term leadership opportunities as the company continues scaling

About Midway Vacations

Midway Vacations is one of Hawaii’s leading vacation rental and hospitality management companies, managing a large portfolio of resort and vacation rental properties in Waikiki and Maui. Our company combines hotel-style operational standards with advanced revenue management, professional housekeeping, maintenance, quality control, and guest experience systems to deliver exceptional results for both guests and property owners. We are passionate about hospitality, operational excellence, and long-term growth.

We look forward to hearing from you.