Director, Learning and Development

Job Description Summary

This position will follow our hybrid work model; we expect the selected candidate to work 3 days a week at our corporate office in Saint Petersburg, FL. We are seeking a dynamic and forward-thinking Director of Learning & Development to partner in the design, delivery, and continuous evolution of enterprise leadership development programs and experiences. This role is pivotal in cultivating a culture of continuous development, enhancing leadership capabilities, and aligning talent strategies with business objectives.

The ideal candidate will be a visionary leader with a strong background in adult learning, learning and leadership development and facilitation.

• Translate business priorities and organizational capability needs into leadership development solutions in partnership with Learning & Development, Talent, HR, and business leaders.
• Partner closely with Learning & Development, Talent, HR, and business leaders to influence enterprise learning priorities and drive leadership capability across the organization.
• Partner with Talent Management to identify internal and external executive development opportunities that strengthen leadership capability and accelerate readiness for critical roles, supporting the firm’s talent and succession planning processes.
• Design and scale innovative learning experiences, including microlearning, cohort-based programs, digital resources, and performance support tools, building the organization’s ability to deliver timely, high-impact development solutions aligned to evolving business needs.
• Partner with Talent Management and HR teams to support emerging skills and capability initiatives, ensuring leadership development experiences and learning pathways build the capabilities needed for future business success.
• Ensure programs are delivered efficiently, evaluated rigorously, and continuously improved based on feedback and business outcomes.
• Significant experience facilitating leadership development programs and coaching leaders across varying leadership levels.
• Leverage learning technologies, AI-enabled tools, and digital platforms to enhance learner engagement, scalability, and operational efficiency.
• Drive initiatives that embed a growth mindset and a learning and development culture across the organization.
• Design and develop resources such as playbooks, job aids, and functional guides.
• Utilize instructional design models (e.g., ADDIE) and learning technologies (e.g., LMS, authoring tools) to create impactful learning experiences.
• Manage vendor relationships, including selection, contract negotiation, and performance monitoring.
• Support broader L&D and talent programs, being agile and flexible as priorities shift and evolve.

• Financial services industry experience strongly preferred.
• Effective facilitation, presentation, and stakeholder engagement skills.
• Project management methodologies, business process improvement practices, and related tools.
• Learning and Development methodologies and solutions, including adult learning principles, coaching, 360-degree feedback, development planning, competency framework design, and leadership and professional development program design.
• Learning Management Systems (LMS) and learning technologies, with Workday Learning experience highly desirable.
• Learning measurement, evaluation, and analytics tools used to assess program effectiveness and business impact.
• Organizational change management principles, methodologies, and best practices.

• Demonstrated success in designing, facilitating, and scaling leadership development experiences for frontline, mid-level, and senior leaders.
• Strategic thinker with strong business acumen and the ability to align talent development initiatives to organizational objectives.
• Exceptional communication, presentation, and facilitation skills across diverse audiences and organizational levels.
• Proven ability to influence, build partnerships, and collaborate effectively with stakeholders at all levels of the organization.
• Strong project management, organizational, and prioritization skills, with the ability to manage multiple initiatives…