Director, Traveler Protection & Ancillary Products

🕒 March 26

🍂 Massachusetts – Remote

🍂 Massachusetts – Remote

💵 $145k - $165k / year

⏰ Full Time

🔴 Lead

👔 Director

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Grand Circle Corporation

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

👥 B2C

🛍️ eCommerce

B2C • eCommerce

Grand Circle Corporation is a Boston-based travel company that operates brands including Overseas Adventure Travel (O. A. T. ), Grand Circle Travel, and Grand Circle Cruise Line. The company specializes in small-group and small-ship guided adventures—emphasizing cultural immersion, expert local leaders, solo-friendly options, and responsible travel through the Grand Circle Foundation. It sells trips directly to consumers via online channels and phone reservations and provides support services like travel protection and loyalty programs.

📋 Description

• Own the strategy, performance, and optimization of all traveler protection offerings • Focus on increasing penetration, improving partner economics, and ensuring a frictionless traveler experience • Lead travel protection as a product line • Define offer strategy, messaging, bundling, and eligibility rules • Recommend and implement improvements in positioning across the booking flow and customer messaging • Collaborate 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 • Business owner of Traveler Protection (TripMate) • 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 • Support revenue improvement strategies for high-margin products including air positioning and premium air upgrades, pre- and post-trip extensions, and optional add-ons • Recommend cross-sell and upsell opportunities throughout the traveler lifecycle

🎯 Requirements

• 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 • On-site gym access • Holistic wellness sessions • Group fitness classes • Substantial Paid Time Off (PTO) • 11 paid holidays including Juneteenth, Memorial Day, and Labor Day • Summer Fridays • 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 • Exclusive quarterly associate travel deals • 401(k) with company match • Life insurance • Disability coverage • Tuition assistance for both professional and personal development • Opportunities for professional development through overseas travel • Direct access to Pinnacle Leadership & Team Development • Commuter benefits • FSA options • Pet insurance • Home & auto discounts • Paid volunteer time off to give back to the community