Job Description

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 three all-suite yachts carry just 148 to 342 guests and cruise around the world.

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 three all-suite yachts carry just 148 to 342 guests and cruise around the world.

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 W elcoming, I nnovative, N ow, D iscipline, S erve, T eamwork, A uthentic, R esponsible

The Director of Strategic Initiatives serves as a critical partner to the Chief Operating Officer and Fleet Operations Leadership, driving high-impact business initiatives and operational excellence across the organization. This role oversees cross-functional projects, enhances organizational communication, and ensures alignment of strategic priorities from planning through execution.

Responsibilities

Strategic Planning & Leadership Support :

• Collaborate closely with Fleet Operations Leadership to identify, prioritize, and execute key business initiatives.
• Track and report progress of strategic programs to ensure timely execution and alignment with company goals.
• Develop executive-level presentations, reports, and communications for internal meetings, all employee updates, and executive sessions.

Program & Project Management :

• Lead enterprise-wide programs, ensuring coordination across business units and standardization of practices.
• Manage planning and execution for major operational projects including dry-docks and new builds.
• Implement planning tools and reporting systems to track key milestones, financials, and performance indicators.
• Facilitate project reviews, retrospectives, and best practice sharing to drive continuous improvement.
• Support vendor and partner negotiations to enhance operational value and cost-efficiency.
• Oversee centralized planning processes related to logistics, travel, or procurement coordination.
• Collaborate closely with Finance and IT Departments to ensure all parties are aligned and meeting set targets.

Organizational Communication & Engagement :

• Craft messaging and communications for Fleet Operations leadership, including internal updates, Performance reports and brand messaging.
• Coordinate initiatives aimed at enhancing team engagement and visibility of leadership.

Qualifications

• 8+ years of experience in strategic planning, operations, or program management.
• Strong ability to communicate and collaborate with senior leaders.
• Proven success in managing cross-functional projects and operational initiatives.
• Skilled in developing reports, dashboards, and presentations for executive audiences.
• Experience in managing high-performing teams and external vendor relationships.
• Background in maritime, hospitality, or large-scale operations is preferred but not required.
• Ability to be available for travel for extended periods of time.

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.

Seniority level

Seniority level

Director

Employment type

Employment type

Full-time

Job function

Job function

Business Development and Sales

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