Grand Circle Corporation

Director, Traveler Protection & Ancillary Products

Grand Circle Corporation

full-time

Posted on:

Location Type: Remote

Location: Massachusetts • United States

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Salary

💰 $145,000 - $165,000 per year

Job Level

Lead

About the role

  • 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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
data analysisforecastingperformance modelingconversion optimizationA/B testingrevenue managementnegotiationproduct strategycustomer messagingtravel insurance
Soft Skills
collaborationcommunicationleadershipproblem-solvingownershipaction-orientedsimplificationpartner managementstrategic thinkingcustomer focus
Certifications
Bachelor’s degreeMaster’s degree