Director of Field 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 serve as Director of Field Sales leading Windstar's US and Canadian field Regional Sales Manager (RSM) team. This role will be responsible for leading and executing high-impact sales and marketing strategies across both regions, ensuring the company achieves its revenue growth and profitability targets. This role owns the assigned sales targets for travel advisor sourced bookings, oversees the management of day-to-day relationships and overall growth of assigned roll-up accounts and partners with the Vice President, Sales on department-wide initiatives. This position is remote/field based.

 

This role prioritizes initiatives that deliver the greatest impact on revenue and scalability while supporting three key pillars: Technology & Automation, Cost-Reducing Initiatives that allow us to scale, and Revenue-Driving strategies.

Responsibilities

• Own the field travel advisor sales channel and deliver assigned revenue targets and goals.
• Lead, coach and develop the US and Canadian Regional Sales Manager team, monitoring performance and providing regular feedback. Foster a culture of accountability, innovation and continuous improvement through structured coaching programs, performance feedback and professional development opportunities.
• Assess, monitor and report account opportunities and risks to senior leadership. Monitor regional and national market trends, competitive activities and consumer behaviors to refine sales strategies and capitalize on emerging opportunities.
• Partner with RSMs to build account plans covering contract negotiation, engagement levels, training needs, conference planning, competitive supplier relationships, promotional offers and marketing support.
• Develop written sales and marketing plans to achieve growth targets for each Club 180 account. Identify and cultivate high‑value partnerships with travel agencies and other key Club 180 accounts, negotiating agreements that enhance brand visibility and sales effectiveness.
• Collaborate with the Marketing, Inventory and Vacation Planning teams to meet account needs. Collaborate closely with the National Account team to ensure maximum success with marketing campaigns and strategies, aligning efforts for optimal market penetration and business growth.
• Budget management to facilitate the development of strategic initiatives with key travel agency partners to enhance brand awareness, foster key partnerships and drive sustainable sales growth.
• Represent Windstar at national and regional sales conferences and industry events as assigned by the VP, Sales, to enhance visibility and brand reputation within the travel agent community
• Own HubSpot — build dashboards and reporting, and coach RSMs on turning CRM data into sales and account strategies.
• Ensure RSMs record all sales activity in HubSpot, and guide territory and account management for efficient sales coverage.
• Personally manage relationships with assigned roll-up accounts that cross territory lines.
• Align efforts with the Inside Sales Representative and ensure RSMs follow up promptly on leads.
• Host webinars and virtual training sessions for travel advisor partners.
• Attend the weekly inventory meeting and contribute sales opportunities that support company revenue goals.
• Maintain, update and help develop formalized sales processes and procedures with the Vice President, Sales.
• Support the Vice President, Sales on overall department initiatives.
• Monitor competitor products, sales and marketing activity.
• Maintain a professional personal image and a well-aligned brand position.
• Record all sales activity; occasional evening and weekend work may be required.

Qualifications

• Five or more years of demonstrated sales success within the travel industry.
• College degree preferred.
• Strong command of the sales process, including commission structures, marketing plans, incentives, overrides and group sales.
• CRM fluency — HubSpot experience strongly preferred, including dashboards, reporting and pipeline management.
• Understanding of yield management and value-based selling versus price.
• Able to clearly explain concepts to travel industry clients and maintain current and future customer relationships.
• Excellent communication, interpersonal, organizational and planning skills.
• Proven analytical and problem-solving skills.
• Motivated self-starter with integrity and a strong work ethic who works well with minimal supervision.
• Comfortable using phone, text, email and video conferencing daily to support house accounts and other preferred sales partners.
• Strategically focused and effective in a fast-paced environment.
• Ability to identify, prioritize and execute tasks to meet critical deadlines.
• Valid passport with ability to travel internationally without restriction; extensive travel required.

 

 

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.