Vice President, North America Sales

Overview

Our Mission: We imagine and deliver personalized and immersive experiences 180 degrees from ordinary

Our Vision: Enriching people’s perspective through inspired travel

Our Values: Welcoming, Innovative, Now, Discipline, Serve, Teamwork, Authentic, Responsible

Windstar Cruises is a leader in luxury small ship cruising, offering guests intimate and unique experiences aboard our fleet of elegantly appointed yachts. We are committed to delivering exceptional service, unique destinations, and personalized travel experiences to our discerning guests. 

We are currently seeking a visionary sales leader to drive our North America sales organization into a new era of innovation and growth. As Vice President of North America Sales, you will lead and execute Windstar’s strategic sales vision, driving revenue growth through travel agency partnerships, group sales, and corporate accounts. You will oversee a high-performing sales team, develop innovative go-to-market strategies, and build strong relationships with key stakeholders—including National Account and Consortia partners, Charter, Meetings & Incentive clients—focused on developing new business while strengthening and maximizing existing partnerships. This role builds on Windstar’s recognized leadership in small-ship cruising, taking our trade partnerships and market penetration to the next level.

Responsibilities

• Sales Innovation & Technology
  • Focus on our mission to be easy to do business with by creating a seamless, frictionless experience for our travel partners across all touchpoints.
  • This includes simplifying processes, enhancing transactional efficiency, and leveraging technology to make booking and collaboration effortless.
  • Work closely with internal stakeholders across IT, Operations, and Commercial teams— championing the voice of our trade partners and driving cross-functional initiatives that remove barriers and deliver a best-in-class partner experience.
• Sales Strategy & Execution
  • Develop and implement a comprehensive sales strategy aligned with company goals.
  • Analyze market trends, trade behavior, and competitive landscape to inform decisions.
  • Identify new market opportunities and revenue streams.
  • Lead pricing, promotions, and distribution strategies for the trade in collaboration with marketing, vacation planning and revenue management.
  • Collaborate with Legal, Revenue Management, and Finance to structure competitive contractual terms and pricing models that attract charter, tour operators, and meetings & incentive clients while ensuring compliance and profitability.
• Team Leadership
  • Elevate an already high-performing North America sales team to increase sales and penetration as the fleet grows.
  • Drive adoption of new CRM systems and innovative sales technologies to enhance team efficiency, improve data-driven decision-making, and create a more seamless experience for trade partners.
  • Establish a mentality of growth by setting clear expectations supported by KPIs and performance metrics; monitor and report on progress.
• Trade Relationship Development
  • Keen focus on cultivating and expanding relationships with national accounts, consortia, travel agencies, tour operators, corporate clients including meetings & events, charter brokers and affinity groups to increase footprint and focus on most impactful relationships.
  • Develop a strategy that focuses resources and budget on relationships that will generate current and future revenue growth.
  • Represent the company at industry events, trade shows, and partner meetings.
• Cross-Functional Collaboration
  • Serve as a liaison across Windstar’s leadership team and collaborate with Xanterra Travel Collection brands to identify opportunities for cross-training, co-marketing, and shared initiatives within the trade and charter & incentive community.
  • Work closely with marketing, customer experience, and operations to ensure alignment and seamless execution of campaigns and guest journeys.
  • Collaborate with finance and revenue management to forecast sales and optimize profitability.
• Incentive Program & Budget Management
  • Design and manage a motivating sales incentive program that drives performance and aligns with company objectives.
  • Oversee North America sales budget, including commissions, overrides, and marketing co-op funds, ensuring spend is optimized, tracked, and reconciled through company financial and accounting systems.

Qualifications

• 10 years of progressive sales leadership experience in travel, hospitality, or cruise industries.
• Bachelor’s degree in Business, Marketing, or related field; MBA preferred.
• Proven track record of driving revenue growth and leading large, geographically dispersed sales teams.
• Strong understanding of B2C, B2B, and B2B2C sales channels.
• Demonstrated ability to champion technology adoption (CRM systems, sales enablement tools) to improve efficiency and performance.
• Experience managing incentive programs and sales budgets, including commissions, overrides, and co-op marketing funds.
• Excellent negotiation, communication, and interpersonal skills with the ability to influence cross-functional teams.
• Strategic thinker with analytical acumen and data-driven decision-making skills.

Preferred Attributes

• Passion for travel and hospitality and a deep understanding of the trade community.
• Proven success in driving process improvements and creating frictionless partner experiences.
• Experience collaborating across multiple brands or business units to leverage synergies (e.g., co-marketing, cross-training).
• Familiarity with financial systems and budget tracking tools.
• Multilingual abilities are a plus.
• Strong change management skills and ability to inspire adoption of new tools and processes.

EEO: Windstar Cruises 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.