Director, Learning & Development

Open To External And Internal Candidates • Williamsburg, VA

5d

About The Position

The Director, Learning and Development leads the design, implementation, governance, and continuous improvement of a Colonial Williamsburg enterprise-wide learning ecosystem. This role is responsible for new employee pre-boarding, new employee orientation, ongoing learning and training curriculum, leadership, managerial, and supervisory development curriculum, and the structured transition from enterprise-wide new employee pre-boarding and orientation to all local and area-specific orientation, onboarding, and training. The Director ensures that employees and leaders (inclusive of managers and supervisors) receive a consistent learning experience that connects Colonial Williamsburg’s educational mission, workplace culture, service standards and behaviors, guest experience, safety expectations, and leadership behaviors. The role creates practical learning pathways that support employees from entry-level Supervisor roles through executive-level leadership responsibilities. The position partners closely with the Vice-President, Human Resources, Organizational Behavior, People Operations Human Resources leaders, operational leaders, Communications and Corporate Affairs, Legal, Safety and Security, and subject-matter experts across the greater enterprise. The Director translates organizational priorities into clear learning experiences that prepare employees to perform well, lead effectively, and contribute to a culture of service, accountability, learning, and trust. As the Learning and Development function matures, this position is expected to help structure and eventually supervise a small learning team of trainers and program facilitators who support enterprise orientation, onboarding, and all development delivery.

Requirements

• University degree in Human Resources, Organizational Development, Education, Business Administration, Leadership, Communication, Hospitality Management, or a related field preferred, or equivalent professional experience.
• Minimum of 7 years of progressive experience in learning and development, organizational development, human resources, leadership development, employee experience, hospitality training, or a related field.
• Experience designing and managing enterprise-wide orientation, onboarding, supervisor development, manager development, or leadership development programs.
• Experience supervising or developing trainers and learning facilitators preferred.
• Demonstrated ability to build curriculum pathways that support employees across multiple job levels, work environments, and operating areas.
• Strong understanding of adult learning principles, instructional design, facilitation, learning reinforcement, and practical workplace application.
• Experience with learning management systems, training records, completion reporting, course administration, and learning data analysis.
• Ability to work effectively with executive leaders, operational managers, Human Resources partners, internal communication partners, and subject-matter experts.
• Experience in a complex service, hospitality, cultural, museum, education, nonprofit, or mission-driven organization preferred.
• Exceptional communication, facilitation, writing, project management, and advisory skills.
• Strong judgment and discretion when working with sensitive employee information, leadership development needs, organizational priorities, and internal communication content.

Nice To Haves

• Professional certification in learning and development, human resources, coaching, organizational development, or related practice preferred.

Responsibilities

• Manage and maintain (through continuous improvement) an enterprise-wide pre-boarding experience for all new employees.
• Manage and maintain (through continuous improvement) an enterprise-wide orientation program that introduces new employees and volunteers to Colonial Williamsburg’s mission, history, values, service expectations, workplace standards, employee resources, and organizational culture.
• Ensure that new employees receive clear information before their first day, including welcome messages, required preparation, first-day expectations, and practical guidance for entering the organization successfully.
• Partner with HR, People Operations, Payroll, Benefits, IT, Safety and Security, Communications and Corporate Affairs, and hiring leaders to create a coordinated and welcoming new-hire experience.
• Maintain orientation schedules, facilitator guides and resources, participant materials, leadership welcome content, and supporting communication tools.
• Ensure that orientation content is inclusive, accessible, accurate, and consistently delivered across seasonal, part-time, full-time, exempt, non-exempt, administrative, professional, operational, museum, education, trades, and support roles, including third-party vendors (e.g. Aramark and Crescent) and volunteers.
• Use new-hire feedback, early retention indicators, manager input, and completion data to strengthen the pre-boarding and orientation experiences over time.
• Create and maintain a comprehensive Learning and Development curriculum map that identifies core skillsets, role-readiness needs, service expectations, compliance learning, and leadership competencies across the greater enterprise.
• Build learning pathways that support entry-level Supervisors, Managers, Senior Managers, Directors, Executive Directors, and executive-level roles.
• Oversee the design, updating, scheduling, and delivery of core learning programs, including foundational workplace skills, service excellence, communication, coaching, performance management, employee engagement, guest experience, and leadership effectiveness.
• Partner with subject-matter experts to convert operational knowledge into consistent learning materials, facilitator guides, job aids, and manager reinforcement tools.
• Balance in-person learning, virtual learning, self-paced learning, and on-the-job reinforcement so that programs fit the needs of a complex operating environment.
• Ensure that all curriculum reflects Colonial Williamsburg’s Common Purpose (mission), desired culture, service standards and behaviors, leadership expectations, and commitment to employee growth.
• Establish an annual learning calendar that supports operational rhythms, seasonal hiring patterns, leadership priorities, and required training cycles.
• Develop and maintain a leadership competency framework that defines expected leadership behaviors from first-time Supervisors through executive-level roles.
• Translate leadership competencies into practical learning experiences, including workshops, cohort programs, discussion guides, applied exercises, and leader-led reinforcement activities.
• Design programs that strengthen supervisor readiness, manager effectiveness, coaching capability, accountability, employee communication, change leadership, and service recovery behaviors.
• Support the development of emerging leaders and new supervisors by creating structured programs that help them move from individual contributor responsibilities into leadership/managerial responsibilities.
• Partner with senior leaders to ensure executive-level learning reinforces strategic alignment, culture stewardship, employee trust, and consistent leadership communication.
• Integrate leadership expectations into onboarding, performance conversations, engagement action planning, internal communication, and succession-related development practices.
• Provide leaders with practical tools that help them reinforce learning after formal programs conclude.
• Create a clear handoff model that connects enterprise-wide orientation to local, departmental, and area-specific onboarding.
• Develop manager checklists, local onboarding templates, role-readiness plans, and first-week guidance so each area can welcome and prepare new employees consistently.
• Ensure that local onboarding addresses department-specific expectations, work location practices, scheduling routines, safety protocols, guest interaction standards, equipment needs, and role-specific learning requirements.
• Partner with area leaders to clarify ownership for each stage of onboarding and reduce gaps between central enterprise-wide orientation and local job readiness.
• Establish check-in practices for the first 30, 60, and 90 days of employment so managers can identify barriers early and support new employees effectively.
• Provide tools that help local leaders connect area-specific expectations to enterprise-wide culture, service standards and behaviors, and employee experience goals.
• Review local and area onboarding practices regularly and use feedback to improve consistency across divisions, sites, and work groups.
• Oversee the operational systems needed to deliver learning consistently, including course calendars, enrollment processes, participant communication, materials management, and completion tracking.
• Manage learning records and reporting in partnership with Human Resources, IT, and system administrators.
• Establish governance standards for course design, course naming, content ownership, revision cycles, facilitator preparation, and learning documentation.
• Ensure that learning materials are current, accessible, legally appropriate, and aligned with approved Foundation practices.
• Coordinate external vendors, consultants, and learning partners when specialized expertise or additional capacity is needed.
• Monitor budget needs, resource requirements, program capacity, and scheduling constraints for enterprise learning programs.
• Support long-term staffing planning for a future training and program facilitation team reporting to the Senior Manager.
• Identify technology opportunities that improve access to learning, reduce administrative burden, and provide better data for decision-making.
• Facilitate high-impact learning programs for employees, supervisors, managers, and leaders as needed.
• Prepare internal facilitators and subject-matter experts to deliver learning content consistently and credibly.
• Provide direction and coaching to future trainers and program facilitators so enterprise learning programs are delivered consistently.
• Develop manager toolkits, conversation guides, reinforcement activities, and follow-up resources that help supervisors transfer learning into daily work.
• Coach supervisors and managers on effective onboarding, learning reinforcement, employee communication, coaching practices, and leadership behaviors that support the desired culture.
• Create opportunities for peer learning, practice, reflection, and applied problem-solving among supervisors and managers.
• Support leaders in using learning programs to address employee engagement, morale, service consistency, and team performance concerns.
• Maintain a visible presence with operational teams so learning solutions remain practical and grounded in the realities of employees’ work.
• Develop and maintain a Learning and Development dashboard that tracks meaningful indicators of learning effectiveness and program reach.
• Measure pre-boarding completion, orientation participation, course completion, local onboarding consistency, supervisor readiness, manager capability, leadership development participation, and learning satisfaction.
• Use employee feedback, manager feedback, engagement survey results, retention trends, guest experience indicators, and performance observations to evaluate learning impact.
• Regularly report learning insights to the Vice-President, Human Resources, Organizational Behavior, and other leaders as appropriate.
• Identify gaps in curriculum, onboarding practices, leadership readiness, and local execution based on quantitative and qualitative data.
• Recommend improvements to learning content, delivery methods, facilitator support, manager tools, and program governance based on evidence.
• Document the connection between learning participation, employee experience, service behavior, leadership capability, and organizational performance where data allows.
• Partner with the Vice-President, Human Resources, Organizational Behavior, to ensure learning programs reinforce Colonial Williamsburg’s culture framework and employee experience priorities.
• Work closely with HR, People Operations, Communications and Corporate Affairs, Legal, Safety and Security, operational leaders, and subject-matter experts to align learning with organizational priorities.
• Ensure that learning messages are clear, credible, values-aligned, and consistent with internal communication standards.
• Support change initiatives by developing learning plans, adoption tools, leader guides, and reinforcement practices that help employees understand new expectations.
• Create systems that allow enterprise-wide consistency while giving departments practical tools for their own operating needs.
• Serve as an internal consultant to leaders who need learning support for team development, onboarding improvement, service excellence, or leadership capability.
• Promote a learning culture in which employees understand expectations, managers teach and reinforce behaviors, and leaders model continuous improvement.
• The Senior Manager of Learning and Development is responsible for enterprise-wide learning strategy, program design, delivery support, governance, and measurement, including: New employee pre-boarding design and coordination. Enterprise-wide orientation curriculum and delivery. The transition from enterprise orientation to local and area-specific onboarding. Learning pathways for Supervisors, Managers, Senior Managers, Directors, Executive Directors, other senior leaders, and executive-level roles. Leadership competency curriculum and related development tools. Core skillset curriculum that supports employee readiness and performance. Facilitator guides, participant materials, manager toolkits, job aids, and reinforcement resources. Learning calendar governance and program scheduling. Training records, completion reporting, and learning effectiveness measurement. Vendor and consultant coordination for learning programs. Future oversight of a team of trainers and facilitators as the Learning and Development function expands. Learning standards, content review cycles, and program quality expectations. The role does not directly own every area-specific technical training program or department-level operating procedure. The Senior Manager establishes the enterprise framework, provides tools and guidance, supports local leaders, and ensures that local onboarding and training practices align with Foundation-wide culture, service expectations, and learning standards.

Benefits

• The compensation listed below for this position represents the anticipated hiring range and is provided in accordance with Virginia pay transparency requirements. Actual compensation will be determined based on factors such as the selected candidate’s skills, qualifications, experience, education, certifications, internal equity, and the specific requirements of the role. Range: $110,000 - $160,000/year

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level