
Fleet Director, Learning & Development
- Recruiter:
- Holland America Line
- Category:
- Management Jobs
- Position:
- Learning & Development Manager
- Published:
- August 6, 2025
HAL - Fleet Director, Learning & Development
Department: Human Resources
Employment Type: Fixed Term Contract
Reporting To: Sr. Manager, Learning and Development & HR Policy
Description
The Fleet Director Learning and Development (L&D) role for Holland America Line and Seabourn is to spearhead the shipboard learning and development initiatives with a mission to harmonize L&D activities with the company's overarching objectives. This role is to translate operational strategies into actionable L&D outcomes, fostering a consistent and impactful learning environment across the fleet. The role will manage and provide the functional leadership of our shipboard Learning and Development Managers (LDMs) in partnership with each respective shipboard HR Officer. This role will have significant autonomy in decision-making related to all fleet L&D processes and procedures. They are positioned as the liaison between our shipboard and shoreside operations. On a regular basis, they will be reviewing the L&D operations onboard to ensure compliance is within the scope of the position is maintained, they will address ship-specific matters as they are able, and then escalate any and all non-compliance to the shoreside operational leads for further fleetwide action. This Corporate Fleet position requires travel from ship to ship during each contract. Additionally, this position travels to the Stateside Corporate Office locations periodically throughout the year for strategy planning, working sessions, and other work necessities, as needed.
Key Responsibilities
Drive process improvement initiatives and ensure L&D Governance and reporting.
- Conduct regular reviews of L&D policies to pinpoint enhancement areas and address any deficiencies
- Gather feedback from LDMs and stakeholders, utilizing data collection, analysis, research, and benchmarking to gain insights and formulate recommendations.
- Implement clear governance frameworks and procedures to oversee L&D operations, ensuring effective follow-up and proper execution of modifications.
- Ensure timely reviews of LDM reports, identifying opportunities for LDM professional development or additional training on organizational structure and processes.
- Always promote and advocate for the Company’s Global HESS culture and programs.
- When on board, participate in onboard safety procedures and always comply with all Fleet Safety regulations, including mustering guests in drills and actual emergencies as directed.
Implement the learning and development strategy onboard.
- Oversee onboard learning for the fleet, ensuring effective implementation of training programs and initiatives aligned with company guidance focusing on the guest experience.
- Partner with shipboard leadership to sustain and improve the quality and efficacy of the shipboard learning and development programs, developing business acumen and aligning with company strategies.
- Develop LDMs to utilize guest and employee survey data, and qualitative data to conduct effective Learning Needs Assessments and evaluate the Learning Effectiveness of the L&D programs they implement.
- Make a positive contribution to the NPS score by performing your job duties with excellence.
- Act as a Company advocate and always portray a positive image to all guests and fellow team members onboard and ashore.
Lead and drive shipboard Learning Effectiveness.
- Establish and execute a comprehensive process to collect and analyze business learning requirements
- Engage with shipboard leaders to learn local ship training needs. Assess needs from all ships to review, prioritize, and propose learning initiatives for the fleet that align with business strategy.
- Analyze and consolidate needs to maximize company resources and ensure consistency of learning experiences, enhance team capabilities, and assess monthly performance data for coaching opportunities and improvement areas.
- Implement a performance consulting approach to assess the business impact of L&D initiatives.
- Foster a culture of continuous learning and development within the fleet, supporting career progression and skill enhancement.
Support culture of transformation and employee engagement.
- Lead by example and champion the Culture Essentials to ensure we apply the highest standards in our approach to support the team members.
- Provide regular formal and informal feedback as delegated supervisors for LDMs’ performance management, focusing on clarity of expectations, accountability and skill development.
- Communicate effectively with shoreside and shipboard on all L&D related matters.
- Foster team members’ well-being, actively engaging and supporting the onboard team.
- Provide candid feedback to senior leadership, especially regarding the consistent application of our culture.
- Demonstrate integrity, fairness, and professionalism.
Demonstrate commitment to the success of the team and development of oneself.
- Prioritize the development of the team and self.
- Demonstrate flexibility in roles and duties to align with business needs while providing flexibility to the team as we continue to innovate in ways of working and approach to our people.
Lead and support shipboard learning and development managers.
Leadership Development:
- Lead the shipboard LDMs, foster skill growth, oversee performance metrics, provide training, establish transparent expectations and communication channels, and manage stakeholder relationships.
- Align the objectives and KPIs for each contract through the start of contract call with the HR Officer and the LDM.
- Manage performance of LDMs in partnership with the shipboard HR Officer. Ensure consistency of review process through regular check ins, the end of contract call, and performance appraisal processes.
- Support cultural shift to establish the competency levels expected of all LDMs. Partners with HROs to build effective development plans for LDMs engagement and professional development.
- Provide counsel on day-to-day, complex, and escalated employee relations matters that are specific to the LDM or L&D Team.
- Lead the onboarding of all new joining LDMs, ensuring a practical joining experience.
- Complete talent acquisition activities by screening and selecting future LDMs.
Stakeholder Management & Internal Partnerships:
- Partner and collaborate with the HR Officers onboard for the LDM performance management and development; the LDMs will directly report to the HROs onboard with a dotted line reporting relationship to the L&D Fleet Director.
- Collaborate with the HROs to have a consistent voice in the Performance Appraisal. Ensure integrity of the performance management process by coaching, communicating and documenting performance, escalating, as necessary.
- Provide coverage for LDM absences due to illness, other leave, or operational necessity.
Skills, Knowledge and Expertise
Education:
- Bachelor’s degree in Learning and Development, Human Resources, Organizational Design, or a related field; equivalent work experience will be considered.
Experience:
- 5 to 7+ years’ experience in L&D in progressively more responsible roles. 2+ years leading teams.
- Previous experience successfully managing teams and implementing comprehensive training programs.
- Previous experience successfully onboarding and leading the talent development of teams.
- Previous experience in Strategic Fleet Management is a plus.
Knowledge, Skills, and Abilities:
- Proficient in business partnership foundations, with a track record of effective collaboration at all organizational levels and across cultures.
- Comprehensive understanding of coaching methodologies, with a preference for certified coaching credentials.
- Experienced in Talent Acquisition processes, complemented by practical interviewing skills.
- Expertise in performance management procedures, talent management, and strategies for enhancing engagement and feedback.
- Adept in data analysis, synthesizing various data sources, and leveraging analytical insights to persuade and inform stakeholders.
- Proficient with Microsoft Office Suite (Word, Excel, PowerPoint) and various Learning Management Systems (LMS), with advanced capabilities in Excel and PowerPoint.
Leadership, Engagement, Collaboration:
- Demonstrated success leading a team.
- Skilled in engaging leadership in meaningful dialogue, aligning development with organizational goals, and fostering a culture of innovation and constructive challenge.
- Demonstrated commitment to inclusion and removal of barriers to full participation.
- Experience working across cultures and geographies with a commitment to recognizing inclusive viewpoints.
- Collaborative and trustworthy to gain support and achieve results.

Holland America Line
Holland America Line has been operating for more than 140 years and we are a recognized leader in the cruise industry, operating a fleet of premium mid-sized ships. We believe travel has the power to change the world and we take pride in playing our part in opening minds, building connections, and inspiring a shared humanity. Our fleet of 14 ships visits all seven continents and annually offers more than 500 cruises to more than 400 ports of call in close to 100 countries. Holland America Line crew members are the heart of the operation and work enthusiastically to ensure that each guest has a memorable vacation.
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