Senior Director of Reentry Operations

The Transition House•Kissimmee, FL

About The Position

We are seeking an experienced, mission-driven executive to serve as Senior Director of Reentry Operations , providing statewide leadership and operational oversight for Florida Reentry Centers. This is a high-impact leadership role for a seasoned operations professional who understands corrections, compliance, and culture. You will ensure consistency, performance accountability, contract integrity, and operational excellence across multiple sites — while empowering Facility Directors to lead effectively at the local level. If you are a systems thinker who thrives on performance metrics, regulatory rigor, leadership development, and mission alignment, this role offers the opportunity to shape outcomes across an entire division. Candidates based in the Central Florida region are preferred. Our Reentry Centers are located in Tarpon Springs, Bartow, Kissimmee, and Jacksonville, Florida. Candidates must be willing and able to work at any of these locations as needed. THIS POSITION IS ELIGIBLE FOR A COMPANY VEHICLE.

Requirements

Bachelor’s Degree in Criminal Justice, Public Administration, Social Services, Behavioral Health, or related field (Master’s preferred)
7–10+ years of progressive leadership experience in: Corrections, Reentry, Community supervision, Behavioral health operations, Or related industry
Proven multi-site management experience
Strong knowledge of contract compliance and regulatory frameworks
Demonstrated success leading performance improvement and cultural transformation initiatives
Ability to operate in secure correctional and community-based environments
Must maintain a valid driver’s license, dependable vehicle, and current auto insurance

Nice To Haves

Experience working with Florida Department of Corrections
Bilingual (Spanish/English)

Responsibilities

Statewide Operational Leadership
Oversee performance across all Florida Reentry Centers
Conduct regular site visits to assess operational consistency, leadership effectiveness, staff engagement, and contract compliance
Ensure uniform implementation of organizational policies and approved procedures
Strengthen leadership practices across sites and reinforce a unified reentry model
Contract Compliance & Regulatory Integrity
Ensure full adherence to Department of Corrections contracts and governing agreements
Maintain audit readiness at all locations
Monitor reporting systems (WRIMS, SecurManage, electronic monitoring platforms)
Partner with DOC leadership, auditors, and contract managers
Identify and escalate material compliance risks
Risk & Performance Oversight
Analyze incident trends, scorecards, staffing patterns, and fiscal indicators
Require and track corrective action plans when needed
Develop and maintain a divisional performance scorecard tracking KPIs such as: Employment placement, Program completion, Recidivism indicators, Staffing stability, Overtime utilization, Reporting accuracy
Fiscal Monitoring
Partner with executive leadership to monitor divisional financial trends
Evaluate staffing ratios, overtime utilization, and budget variance patterns
Identify systemic fiscal risks and recommend corrective strategies
Leadership Development & Workforce Strategy
Directly supervise Facility Directors statewide
Lead succession planning within the Reentry Division
Conduct bi-weekly virtual leadership meetings and quarterly in-person strategy sessions
Coach and mentor Directors and Assistant Directors
Partner with HR on performance management and leadership interventions
Culture & AMEND Principle Integration
Lead statewide implementation of AMEND principles
Ensure rehabilitative engagement practices are embedded in daily supervision and client interaction
Monitor cultural alignment and address deviations through structured coaching