Director of Learning and Development

Overview

The Director of Learning and Development owns and advances Windstar’s enterprise-wide learning strategy, building the capabilities that bring our small-ship, luxury experience to life — voyage after voyage. This role ensures crew competency, regulatory training compliance, and a culture of continuous professional growth across both fleet and shoreside teams. The Director partners closely with senior leadership to align learning investments with business priorities and serves as the organizational champion for development at every level.

Responsibilities

• Partner with senior leadership to design, execute, and continuously evolve an enterprise-wide learning strategy that supports Windstar’s business goals and guest experience standards.
• Conduct ongoing needs analyses across fleet and shoreside teams to identify skill gaps and inform curriculum design and prioritization.
• Design, build, and implement training programs — from onboarding to leadership development — that are clearly tied to organizational goals, guest satisfaction, and measurable KPIs.
• Oversee the selection, administration, and optimization of training technology and resources, including the LMS, e-learning content libraries, and external vendor partnerships.
• Lead the ongoing delivery, evolution, and impact measurement of the Lead 180 leadership development program.
• Develop and maintain succession planning frameworks and promotion panel processes that support internal career pathways for both fleet and shoreside employees.
• Build and sustain a network of certified train-the-trainer facilitators embedded across ship departments and shoreside functions to scale learning capacity organization-wide.
• Maintain current knowledge of STCW requirements and applicable maritime regulations, ensuring all mandatory crew certifications and safety training are tracked, renewed, and audit-ready.
• Design culturally inclusive learning experiences that reflect the diversity of our international crew and foster engagement across languages, backgrounds, and roles.
• Facilitate training sessions, workshops, and leadership conferences both onboard and ashore, including at-sea delivery during active voyages as needed.
• Ensure fleet-wide training compliance records are accurate, current, and accessible for internal reporting and regulatory inspections.
• Manage the L&D budget responsibly, track return on investment, and present program outcomes and recommendations to senior leadership on a regular cadence.

Qualifications

• Deep expertise in instructional design, adult learning principles, and LMS administration; experience with blended learning and e-learning authoring tools (e.g., Articulate, Adobe Captivate) is a plus.
• 5 years of progressive L&D experience, including at least 2 years in a senior or leadership role; cruise, maritime, hospitality, or similarly regulated industry experience strongly preferred.
• Bachelor’s degree in Education, Organizational Development, Human Resources, or a related field preferred; Master’s degree or professional certification (e.g., CPTD, SHRM-SCP) preferred.
• Confident facilitator and communicator, comfortable engaging diverse audiences across cultures and hierarchies, including delivery in shipboard environments.
• Demonstrated success building and scaling train-the-trainer programs across geographically distributed or multi-vessel teams.
• Data-driven approach to measuring program effectiveness; comfortable using KPIs, assessment tools, and learner feedback to evaluate impact and drive continuous improvement.
• Familiarity with AI-powered learning tools and emerging technologies; curiosity about how AI can enhance content creation, personalization, and learner engagement is a plus.

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.