Senior Director of Reentry Services

Dragonfly Central, Inc. (DCI) is partnering with Jubilee Housing to find a visionary/founding/inaugural Senior Director of Reentry Services. This essential and exciting new position requires a candidate who brings strong leadership and strategic skills in addition to deep knowledge of reentry and reintegration best practices.

The Organization

The mission of Jubilee Housing is building diverse, compassionate communities that create opportunities for everyone to thrive. Since 1973, Jubilee has worked to provide high-quality affordable housing and holistic support to those experiencing persistent economic hardship in the Adams Morgan, Mount Pleasant, and Columbia Heights neighborhoods of Washington D.C. Jubilee operates more than a dozen properties totaling over 500 homes and offers robust programming for residents and community members pursuing life goals.

Jubilee has operated housing and services for returning citizens for more than a decade, first in two transitional housing settings that have supported more than 500 residents since inception. More recently, Jubilee is expanding a continuum of housing and programming across five properties increasing the community served from ~25 to nearly 80 individuals annually. The Senior Director will oversee the two existing program models at the same as the third model, known as the KEB workforce housing initiative, is designed and implemented.

Jubilee’s Justice Housing® model is built on the principle of providing deeply affordable homes with onsite or nearby services located in neighborhoods where resources such as good schools, grocery stores, and public transportation are readily accessible. Jubilee is seeking individuals who want to work with us to ensure Justice Housing becomes a reality for all who need it.

The Position

The Senior Director of Reentry Services (Senior Director) provides strategic leadership, oversight, and operational management for all reentry and reintegration programs serving justice-involved individuals returning to the community after incarceration. This executive leader is responsible for developing and implementing innovative, evidence-based programs that promote successful reentry outcomes, reduce recidivism, and support long-term community integration.

The Senior Director oversees program strategy, staff leadership, partnerships, compliance, performance management, budget administration, and resource development. This role serves as a key organizational leader and external ambassador, building collaborative relationships with correctional institutions, government agencies, employers, housing providers, behavioral health organizations, educational institutions, and community stakeholders.

The Senior Director is directly or indirectly responsible for supervision of all members of our reentry team (staff of 15+) and a divisional budget of $2 million. The Reentry Services program is expected to grow and change significantly to meet the increasing demand in new and innovative ways, led by the new Senior Director. S/he also provides oversight of Jubilee Reentry, LLC, the entity that delivers reentry programming and services, and works closely its governing board.

Key Responsibilities

Strategic Leadership

• Develop and execute a comprehensive reentry services strategy aligned with the organization's mission and goals.
• Lead the design and expansion of innovative reentry initiatives that address barriers related to employment, housing, education, behavioral health, transportation, and family reunification.
• Monitor industry trends, policy changes, and best practices related to criminal justice reform and reentry services.
• Establish short-term and long-range objectives to improve participant outcomes and organizational impact.
• Serve as a member of the executive leadership team, contributing to strategic planning and organizational growth.

Program Oversight and Management

• Direct and oversee all reentry services programs, including case management, housing navigation, behavioral health coordination, peer support, and community-based services.
• Ensure programs are delivered effectively, equitably, and in accordance with program design, contractual requirements and evidence-based practices.
• Manage housing in line with affordable housing rules and regulations.
• Develop and maintain operational policies, procedures, and quality assurance standards.
• Monitor program performance and implement continuous improvement strategies.
• Deliver client-centered and trauma-informed services throughout all programs.
• Collaborate with other Jubilee departments to establish a vibrant social enterprise culture.

Staff Leadership and Development

• Provide leadership, supervision, and professional development to directors, managers, supervisors, and program staff.
• Foster a culture of accountability, collaboration, inclusion, and high performance.
• Establish performance expectations and conduct regular evaluations.
• Support succession planning and leadership development initiatives.
• Promote employee engagement and retention.

Community and Stakeholder Relations

• Build and maintain strategic partnerships with the DC Reentry Action Network and peer reentry service providers, employers and employer coalitions, educational and credentialing institutions, healthcare providers, and community organizations.
• Represent the organization in public forums, coalitions, task forces, and community meetings.
• Advocate for policies and practices that improve opportunities and outcomes for formerly incarcerated individuals.
• Serve as a trusted resource and subject matter expert on reentry services and criminal justice issues.
• Contribute to a culture of mutuality and depth belonging with volunteers, donors and other stakeholders.

Financial and Grant Management

• Develop and manage departmental budgets and financial resources.
• Ensure fiscal accountability and compliance with organizational, governmental, and grant requirements.
• Collaborate with development and grants teams to source and secure funding opportunities.
• Support grant proposal development, implementation, reporting, and evaluation.
• Monitor expenditures and identify opportunities for sustainable program growth.

Data, Evaluation, and Compliance

• Establish metrics and key performance indicators to measure program effectiveness.
• Analyze outcome data and prepare reports for executive leadership, funders, and stakeholders.
• Ensure compliance with local, state, federal, and contractual standards.
• Lead accreditation, monitoring, audit, and quality assurance processes.
• Utilize data-driven decision-making to improve service delivery and participant outcomes.

Equity and Participant Success

• Advance diversity, equity, inclusion, and belonging initiatives within program design and service delivery.
• Promote practices to address systemic barriers faced by justice-involved populations.
• Ensure services are culturally responsive, accessible, and participant-focused.
• Champion participant voice and lived experience as essential components of program development.

Experience and Attributes

The Senior Director of Reentry Services will possess a deep understanding of reentry practices, the criminal justice system, and community-based support systems. The position requires a strong leader who is strategic and can lead change management. Other desired skills include:

• A Master’s degree in Social Work, Criminal Justice, Public Administration, Human Services, Public Health, Behavioral Sciences, or commensurate experience.
• 5+ years of progressively responsible leadership experience in reentry services, criminal justice, human services, behavioral health, workforce development, or related fields; and at least 3 years of senior-level management overseeing multiple programs and teams.
• Demonstrated experience managing complex budgets, contracts, grants, and compliance requirements.
• Experience developing strategic partnerships with public and private sector stakeholders.
• Proven track record of program development, implementation, and growth.

Knowledge, Skills, and Abilities

• Deep understanding of reentry practices, criminal justice systems, and community-based support services; and knowledge of evidence-based approaches for reducing recidivism and promoting successful reintegration.
• Strong leadership, organizational, and change management skills.
• Experience with performance management and outcome measurement.
• Excellent public speaking, communication, and relationship-building abilities.
• Strong financial management and strategic planning capabilities.
• Ability to work effectively with diverse populations and stakeholders.
• Commitment to social justice, equity, and second-chance opportunities.
• Direct experience working with justice-involved populations; knowledge of federal and state reentry funding opportunities; certification in program evaluation, project management, or nonprofit leadership; and lived experience with the criminal justice system are preferred.

The base salary will be between $105-125K, commensurate with experience. Benefits include: health, vision, and dental insurance, STD, LTD, and life insurances, paid vacation, sick leave, holidays, transportation stipend, and a 403(b) matched contribution retirement plan.

The candidate for this position will be subject to a drug screening, and will be required to consent to a pre-employment background and reference check including employment and education verification as a condition of employment.

Application Process

Please email your resume, a cover letter that states why you would be an ideal candidate for this position, and how you learned of this position to Jubilee5@dragonflycentral.org. For other inquiries, please contact Ginna Goodenow at Ginna@dragonflycentral.org .

Jubilee Housing bases employment decisions on each person’s performance, qualifications, and abilities. It does not discriminate in employment opportunities or practices on the basis of race, color, religion, sex, sexual orientation, national origin, age, disability, or characteristics protected by the District of Columbia and federal law. All employment offers are contingent upon satisfactory proof of eligibility to work in the United States. Background investigation, credit check, and drug test will be required.

Resume reviews begin immediately.