Senior Director of Training & Organizational Development

Company Overview
Prescott Solutions provides elite Financial, Technical, C-Suite, IT, Cybersecurity, and ERP talent to Fortune 500 and mid-market organizations nationwide. We are known for placing accomplished leaders into high-impact roles where expertise, integrity, and mission alignment matter. This opportunity represents one of those rare, career-defining matches.

About the Opportunity

Prescott Solutions is conducting a confidential search on behalf of a New York–based nonprofit health insurance organization operating within a highly regulated, mission-driven healthcare environment. This organization provides affordable, quality healthcare coverage to New Yorkers through Medicaid, Medicare, and other government-sponsored health plans, with a strong focus on equity, access, and community impact. A relocation package will be considered for the right candidate.

This is a critical senior leadership role reporting directly to the Chief People Officer. The Senior Director of Training & Organizational Development will lead enterprise-wide learning, workforce development, and organizational effectiveness initiatives across a large, diverse, and highly regulated healthcare workforce.

Deep experience in healthcare managed care environments is essential. This role is not designed for general corporate L&D professionals new to healthcare.

Position Overview

Under the direction of the Chief People Officer, the Senior Director of Training & Organizational Development is responsible for the design, planning, and execution of all corporate and departmental training programs, as well as organizational development initiatives. This leader will assess enterprise-wide learning needs, develop strategic training solutions, and ensure alignment with organizational goals, regulatory requirements, and workforce performance outcomes.

The ideal candidate brings a strong understanding of Medicaid, Medicare, regulatory compliance, unionized or public-sector workforces, and the cultural dynamics of large nonprofit healthcare organizations.

Key Responsibilities

Strategic Leadership & Organizational Development

• Partner with executive and senior leadership to assess current and future training and organizational development needs.
• Diagnose organizational effectiveness challenges and design strategic interventions to improve engagement, performance, and retention.
• Lead change management initiatives aligned with organizational priorities and regulatory requirements.
• Serve as a trusted advisor to leadership on workforce development and performance improvement strategies.

Training Program Design & Delivery

• Design, implement, and oversee enterprise-wide training programs, including onboarding, compliance, leadership development, and role-specific training.
• Develop blended learning solutions, including instructor-led, virtual, and e-learning modalities.
• Create instructional materials, job aids, and learning tools aligned with operational and regulatory needs.
• Ensure training programs meet compliance standards and support audit readiness.

Instructional Design & Evaluation

• Apply a systems-based approach to instructional design:
• Identify learning needs
• Develop measurable instructional objectives
• Design or procure appropriate training solutions
• Evaluate training effectiveness and continuously refine programs to improve outcomes.
• Establish and track performance metrics to measure workforce capability and program impact.

Performance Management & Workforce Development

• Partner with the Chief People Officer and Deputy CPO to develop and support performance management tools and practices.
• Support leadership and managers in building coaching and performance management capabilities.
• Reinforce a culture of continuous learning and professional development.

Vendor & Stakeholder Management

• Establish and manage relationships with external training vendors and partners.
• Serve as an internal subject matter expert for learning and development across the organization.
• Collaborate with internal and external stakeholders to deliver innovative, cost-effective training solutions.

Required Qualifications

Education

• Master’s Degree in Arts or Sciences (required)

Experience

• Minimum 12 years of experience as a senior-level training or organizational development leader
• Minimum 10 years of people management experience
• Significant experience in healthcare environments strongly preferred, particularly:
• Medicaid, Medicare Advantage, or managed care organizations
• URAC-accredited or heavily regulated healthcare settings
• Demonstrated experience designing and delivering training for large, diverse workforces
• Strong working knowledge of human resources principles, including labor relations, performance management, and workforce development

Skills & Competencies

• Integrity and trust
• Strong executive communication skills (written and verbal)
• Customer and stakeholder focus
• Functional and technical expertise in learning and development
• Ability to operate effectively in complex, regulated environments
• Comfortable partnering with senior executives and legal/compliance-focused leadership

Job Type: Full-time

Pay: $125,234.68 - $186,368.64 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Flexible schedule
• Health insurance
• Health savings account
• Paid time off
• Vision insurance

Work Location: Remote