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Randy Toscano

Randy Toscano

Dean of Students | Student Development | Youth Leadership | Community Engagement

Talent
Naples, FLMember since July 28, 2026
Student Conduct & AccountabilityCharacter FormationParent & Family PartnershipsYouth Leadership DevelopmentConflict Resolution & MediationCommunity EngagementPolicy & Handbook AdministrationCrisis Leadership & SafetyLeadership DevelopmentOrganizational CultureMentorshipSuccession PlanningEngagement StrategiesEmergency PreparednessCrisis CommunicationCoaching
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Student Conduct & AccountabilityCharacter FormationParent & Family PartnershipsYouth Leadership DevelopmentConflict Resolution & Mediation

About

Mission-driven student development and community leadership professional with more than 20 years of executive leadership experience fostering accountability, mentorship, culture building, conflict resolution, family partnership, and individual growth. Brings a values-based foundation shaped by Catholic education, service, integrity, responsibility, and lifelong learning, along with firsthand parent experience supporting students through private Catholic school, college, athletics, extracurriculars, and faith-based educational environments.

Target value proposition: Dean of Students leader who creates safe, supportive, high-expectation environments where students develop character, resilience, confidence, leadership skills, and a commitment to service and learning.

Experience

Director of Human Resources - Wellington Regional Medical Center (UHS)

(2023-01 - 2025-01)

  • Led organizational culture, engagement, accountability, leadership development, and workforce initiatives.
  • Coached leaders through conflict resolution, communication challenges, performance improvement, and team development.
  • Oversaw investigations involving behavioral, conduct, and compliance concerns.
  • Executive sponsor for engagement and activities committees supporting mission-driven events, family participation, recognition, wellness, volunteerism, and culture-building.

Regional Human Resources Market Director - Duke University Health System / LifePoint Health

(2019-01 - 2023-01)

  • Provided leadership across multiple campuses and operational locations.
  • Guided engagement, leadership development, succession planning, culture improvement, stakeholder collaboration, and conflict resolution.

Executive Director of Human Resources - LifePoint Health - Paris, Texas

  • Directed leadership-development programs, internship initiatives, mentorship activities, and engagement strategies.
  • Promoted cultures emphasizing accountability, service excellence, professional growth, and organizational development.

System HR Business Partner / System Director - Lee Health

Administered community scholarship programs providing more than $450,000 annually to students pursuing healthcare and medical careers.

  • Developed workforce-development, internship, externship, mentorship, and leadership-development programs.
  • Established strategic partnerships with schools, colleges, universities, employers, and community organizations.
  • Coordinated career-awareness programs, guest speakers, professional panels, facility tours, demonstrations, and experiential-learning opportunities.

Education

Master of Science - Strategic Human Resource Management - Walden University

Bachelor of Arts - Business Administration - Baldwin-Wallace College

Skills

Dean of StudentsStudent DevelopmentYouth LeadershipCommunity Engagement

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