Vice President, Air and Rail Operations

Vice President, Air and Rail Operations

Pleasant Holidays, one of the largest travel wholesalers in the United States specializing in vacation travel to the Hawaiian Islands, Caribbean, Central America, Europe, Mexico, Middle East, South Pacific (Australia, Cook Islands, Fiji, New Caledonia, New Zealand & Tahiti), Japan, the United States & Canada, and cruise vacations worldwide, is seeking a Vice President, Air and Rail Operations.

Pleasant Holidays is a subsidiary of the Automobile Club of Southern California, a diversified insurance, roadside assistance, financial services, and travel organization serving more than 21 million AAA Members across 23 states.

Summary:

The Vice President, Air and Rail Operations, is a strategic leader responsible for driving the success of Pleasant Holidays’ air travel programs across all brands. This role is responsible for airline contract negotiations, flight operations, pricing strategy, and service delivery to ensure a competitive and seamless air experience. Reporting to the Chief Operating Officer, the Vice President will lead a high-performing team, manage key airline and rail relationships, and collaborate across the organization to align air and rail operations with the company’s service standards, growth goals, and brand reputation.

Key Responsibilities:

• Develop and lead the company’s air/rail strategy, including partner negotiations, contract performance, and maintain competitive pricing and service levels.

• Oversee air/rail pricing, ticketing operations, and flight schedule changes integrated with proprietary systems.

• Manage day-to-day operations of a cross-functional team responsible for contracting, fare filing, ticketing, and issue resolution.

• Collaborate with Contact Center, Customer Experience, Product, Legal,  and Technology to deliver seamless end-to-end service.

• Analyze performance data to identify opportunities for cost reduction, operational/personnel efficiency, and improved customer satisfaction.

• Ensure a seamless and reliable air and rail travel experience, resolving customer service issues related to various products.

• Serve as the senior company representative in air/rail partner discussions, trade negotiations, and industry events.

• Ensure compliance with regulatory requirements and contract obligations across all airline operations.

• Perform other duties as assigned.

Prerequisites:

• 7–10 years of progressive executive leadership experience in airline operations or air contracting within a tour operator, consolidator, or airline. 

• Strong expertise with various GDS systems (Apollo required) and airline pricing/fare structures.

• Proven track record leading high-performing teams and managing strategic airline partnerships.

• Excellent negotiation, communication, and analytical skills.

• Ability to collaborate effectively across departments and external partners.

• Bachelor’s degree is preferred in business, travel, or a related field.

Location: Westlake Village, CA (in-office leadership role)
Travel: Up to 25%

Compensation: Starting pay range for this position is $125,000 - 180,000 annually. This position is eligible to participate in our management incentive program based upon the achievement of certain corporate financial and personal business goals and objectives.

Benefits to working at Pleasant Holidays:
•    Medical (with prescription)
•    Vision
•    Dental
•    Flexible Spending Accounts
•    Paid Time Off for Holidays, Vacation, and Illness
•    Company paid Life Insurance
•    Long Term Disability
•    401(k) Plan
•    AFLAC Plans
•    Travel Discounts on all Pleasant Holidays packages, Hotel Rooms, Car Rentals, Tours & Activities. Discounts apply to family members and friends too!

Pleasant Holidays is one of the largest travel wholesalers in the United States, specializing in vacation travel to the Hawaiian Islands, Caribbean, Central America, Europe, Mexico, Middle East, South Pacific (Australia, Cook Islands, Fiji, New Caledonia, New Zealand & Tahiti), Japan, the United States & Canada, and cruise vacations worldwide. Pleasant Holidays is a subsidiary of the Automobile Club of Southern California, a diversified insurance, roadside assistance, financial services and travel organization serving 17 million AAA Members across 21 states.

Pleasant Holidays is an Equal Opportunity Employer

Pleasant Holidays will consider for employment all qualified applicants, including those with criminal histories, in a manner consistent with the requir