Director, Global Charter & Incentive Sales

Awarded World’s Best Small Ship Cruise line, Windstar Cruises is known for intimate yacht style experience and unique voyages to the world’s best small ports and hidden harbors. Its three sailing yachts and four all-suite yachts carry just 148 to 342 guests and cruise around the world. Our mission is to imagine and deliver personalized and immersive experiences 180 degrees from ordinary. We enrich people’s perspective through inspired travel.

Our Mission: Enriching Lives Through Travel

Our Values: Guest Obsessed, Open and Inviting, Fun-Loving and Focused, Light-Hearted and Genuine, Casual Yet Polished, Safe and Responsible.

We are currently seeking a motivated sales leader to join our crew as the Director, Global Charter & Incentive Sales. This role is a senior leader responsible for driving the strategic vision, growth, and execution of Windstar Cruises' global charter, incentive travel, and full-ship event business. This role represents a strategic expansion of Windstar's charter business from its current North American focus to a global operation. The Director leads the development of charter sales strategy, cultivates high-value client relationships across corporate, incentive, affinity, and event segments, and drives revenue that reflects the growth trajectory for Windstar Cruises. The Director partners closely with Revenue Management, Marketing, and Operations to develop competitive pricing models, custom itineraries, and seamless charter execution.

This is a Miami-based position with significant travel requirements. This position will enable Windstar to scale and achieve 10-year proforma revenue expectations.

• Charter Revenue Strategy: Develop and execute a comprehensive multi-year charter and incentive sales strategy building toward annual charter revenue, diversifying the client portfolio across corporate charters, incentive travel programs, affinity groups, wedding charters, and special events.
• Market Expansion & Business Development: Lead international expansion of Windstar's charter business. Identify and penetrate new market segments and geographic territories with emphasis on international growth into new regions. Build and maintain a robust pipeline of charter prospects globally.
• Client Relationship Management: Cultivate and manage strategic relationships with Fortune 500 corporate clients, top incentive travel houses, destination management companies, and high-profile event planners. Serve as Windstar's senior global charter authority externally.
• Pricing & Revenue Optimization: Partner with Revenue Management to develop dynamic charter pricing models, negotiate charter hire rates, and optimize yield across the fleet. Ensure charter business contributes to overall revenue mix at target margins.
• Contract Negotiation: Lead high-value charter contract negotiations, ensuring favorable terms while maintaining flexibility for operational execution. Manage contract lifecycle from proposal through execution.
• Brand Positioning & Industry Presence: Elevate Windstar's visibility in the charter and incentive space through strategic trade show participation, industry speaking engagements, and targeted A&P investments. Champion the Windstar brand story to differentiate from larger competitors.
• Team Leadership & Development: Build, mentor, and manage the charter and incentive sales team. Partner with the existing Director of Charter & Incentive Sales (North America) to expand the charter sales function and organization, ensuring long-term revenue growth and team stability. Establish performance benchmarks, sales processes, and accountability frameworks.
• Forecasting & Reporting: Own charter revenue forecasting, incentive program, pipeline reporting, and performance analytics. Provide regular updates to senior leadership on charter business health and growth trajectory.
• Cross-Functional Collaboration: Work closely with Operations, Itinerary Planning, Marketing, and Legal teams to ensure charter execution excellence and client satisfaction.
• Competitive Intelligence: Monitor competitor charter offerings, pricing, and market positioning. Identify opportunities to differentiate Windstar's charter value proposition.

Additional Responsibilities

• Maintain accurate and timely client records in HubSpot CRM.
• Analyze lost business, win/loss trends, and lead performance to refine strategies.
• Manage charter sales budgets including T&E and A&P allocations.
• Coordinate FAM (familiarization) trips for high-profile charter prospects and clients.
• Attend weekly inventory meetings, providing input on charter allocation and sales opportunities.
• Support the VP, Global Commercial and CCO in broader commercial initiatives.
• Collaborate with Xanterra Travel Collection sister brands and TAC corporate contacts to identify and develop cross-brand charter and incentive opportunities.
• Represent Windstar at national and international industry events, conferences, and trade shows.
• Must be willing to work nights, weekends, and evenings as required.

• 8+ years of demonstrated success in charter, incentive, or group sales within the cruise industry or luxury travel sector.
• Proven track record of achieving or exceeding annual revenue targets of $50M+.
• Deep understanding of charter operations, pricing models, and contract negotiation in the cruise industry.
• Experience managing and developing high-performing sales teams.
• Strong existing network of relationships with charter clients, incentive houses, and industry partners.
• Bachelor's degree in Business, Hospitality, Marketing, or related field; MBA preferred.
• Expert-level negotiation and presentation skills.
• Strategic thinker with the ability to translate vision into actionable plans and measurable results.
• Proficiency in CRM and data-driven sales management.
• Valid passport with the ability to travel internationally with no restrictions.
• Extensive domestic and international travel required (approximately 40–50%).
• Understanding of yield management, commission structures, and promotional strategies.
• Excellent communication, interpersonal, organizational, and planning skills.

Benefits:

For full-time employees, Windstar offers a comprehensive benefits package including: Medical, Dental & Vision; HSA & FSA; Life & Disability; Accident, Hospital & Critical Illness; Pet Insurance; Vacation, Sick Time and paid Holidays; 401(k) with Company Match; Employee Assistance Plan; Education Assistance and Employee Discounts & Travel Deals.

EEO:

Windstar is committed to a diverse and inclusive workplace. We are an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, pregnancy, genetic information, protected veteran status, or any other legally protected status.