Director, Global Charter & Sales

Overview

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…