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Role Description

We’re looking for a Director Traveler Protection & Ancillary Products to own the strategy, performance, and optimization of all traveler protection offerings — with an emphasis on increasing penetration, improving partner economics, and ensuring a frictionless traveler experience. This role will be primarily focused on Traveler Protection & Net Revenue in addition to strengthening other high-margin ancillary revenue streams, including air positioning, pre/post trip extensions, and premium add-ons. This role will work closely with several internal stakeholders, including FP&A, Product & UX, Marketing, Call Center, and lead our relationship with TripMate. The role will report to the VP Air Contracting and Operations.

Key Responsibilities

• Product Strategy and Optimization (60%)
  • Lead travel protection as a product line — defining offer strategy, messaging, bundling, and eligibility rules.
  • Recommend and implement improvements in positioning across the booking flow and customer messaging (brand marketing, web, call center, mobile, post-booking).
  • Partner with Product/UX to run A/B tests that increase attach rate, reduce confusion, and improve clarity and conversion.
  • Evaluate new plan types, plan tiers, or upgrades that increase traveler value and company margin.
• Travel Protection Plan P&L (25%)
  • Be the business owner of Traveler Protection (TripMate), including attach rate, conversion, revenue, cost structure, commission, and annual contribution.
  • Collaborate with FP&A to build annual and quarterly revenue plans, forecasts, and stretch targets.
  • Lead relationship with TripMate; negotiate commissions, marketing funds, performance improvements, and quarterly claim reviews.
• Other Ancillary Products (15%)
  • Support revenue improvement strategies for high-margin products including: Air positioning and premium air upgrades, pre- and post-trip extensions, optional add-ons.
  • Recommend cross-sell and upsell opportunities throughout the traveler lifecycle.
  • Evaluate and test new ancillary revenue products aligned with OAT’s demographic and brand positioning.

Qualifications

• Bachelor’s or Master’s degree in Business Administration, Analytics, Finance, or related field
• 7–12+ years experience in a commercial, product, revenue management, or partnerships role
• Direct experience in travel insurance, ancillary revenue, commercial partnerships, airline/hospitality, or OTA strongly preferred
• Data-driven mindset with the ability to forecast, model, and diagnose performance trends
• Strong experience collaborating with product, UX, and marketing teams on conversion optimization
• Exceptional negotiation and partner management skills
• Ability to simplify complex products (like insurance) for a 50+ traveler audience
• High ownership, bias for action, and ability to deliver measurable impact quickly

Benefits

• Comprehensive and heavily subsidized medical, dental, and vision plans, plus on-site gym access, holistic wellness sessions, and group fitness classes
• Substantial Paid Time Off (PTO), and 11 paid holidays- including Juneteenth, Memorial Day, and Labor Day – and Summer Fridays. Plus- extensive parental leave, with up to 12-16 weeks paid leave at 100% base salary.
• 50% off our trips for you and a companion, 25% for additional immediate family members, and exclusive quarterly associate travel deals
• 401(k) with company match, life insurance, and disability coverage
• Tuition assistance for both professional and personal development, opportunities for professional development through overseas travel, and direct access to Pinnacle Leadership & Team Development.
• Commuter benefits, FSA options, pet insurance, home & auto discounts, and paid volunteer time off to give back to the community