Director Traveler Protection & Ancillary Products

Position Title: Director Traveler Protection & Ancillary Products

Reporting to: VP Air Contracting and Operations

Location: Remote, or Boston, MA

Position Summary

Grand Circle Corporation is the leader in international travel, adventure and discovery for Americans aged 50+. Headquartered in Boston MA, and with more than 45 offices globally, more than two million Americans have traveled with our award-winning travel brands: Grand Circle Cruise Line, Overseas Adventure Travel and Grand Circle Travel.

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

1) 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.

2) 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.

3) 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

Total Rewards
The base salary range for this role is $145,000 – $165,000 annually for employees based in Boston, MA. Final compensation may vary and will be determined based on factors such as relevant experience, skills, internal equity, and geographic location. In addition to base pay, this role is eligible for an annual incentive bonus and first-class benefits, which include:

• Health & wellness: Comprehensive and heavily subsidized medical, dental, and vision plans, plus on-site gym access, holistic wellness sessions, and group fitness classes 
• Time for you: 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.
• Travel more, spend less: 50% off our trips for you and a companion, 25% for additional immediate family members, and exclusive quarterly associate travel deals 
• Your future, secured: 401(k) with company match, life insurance, and disability coverage 
• Continuous growth: Tuition assistance for both professional and personal development, opportunities for professional development through oversees travel, and direct access to Pinnacle Leadership & Team Development.
• Extra perks: Commuter benefits, FSA options, pet insurance, home & auto discounts, and paid volunteer time off to give back to the community

To learn more, please visit our websites at www.gct.com, www.oattravel.com and www.grandcirclefoundation.com.