We change lives through travel—starting with yours.
Director, Traveler Protection & Ancillary Products
Location
Massachusetts
Posted
35 days ago
Salary
$145K - $165K / year
Seniority
Lead
Job Description
Job 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% off for additional immediate family members
- Exclusive quarterly associate travel deals
- 401(k) with company match
- Life insurance
- Disability coverage
- Tuition assistance for 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
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