Chicago, IL
February 22, 2024

City of Chicago: Director – Office of Re-entry, Mayor’s Office of Community Safety Team, Office of the Mayor

The Director, Re-entry, in the Office of the Mayor will work under the direction of the Mayor’s Office of Community Safety (MOCS), reporting up to Deputy Mayor of Community Safety, to lead and coordinate policies, programs, and initiatives that serve Chicago residents returning to their communities after detention or incarceration. As a member of the MOCS team, the Director of Re-entry will manage special projects and maintain internal and external relations with City departments and stakeholders. Additionally, the Director will lead a team dedicated to building a reentry system that helps remove barriers for returning citizens and work directly with reentry service providers to develop and implement policies that are reflective of the needs of the population. The Director will perform related duties as required.

The MOCS Re-entry Director will chart the path to closing gaps and partner with government entities, community, city departments, and other stakeholder groups to articulate and execute a clear vision and path for the implementation of clear programming and service needs. The Re-entry Director will assess the current landscape of programs and services, evaluate available funding and stakeholders, and identify gaps in existing efforts to solve for. Additionally, the Director will create a centralized hub of re-entry service addressing the whole person’s needs of returning citizens, including the MOCS core pillars:

  • Education
  • Economic opportunity/upward mobility
  • Community Environment
  • Housing
  • Healthcare
  • Policing
  • CVI

The Director will also focus on building out readily available services around:

  • Transportation
  • Social services and benefits (veteran, disability, voting, selective services, SSI, MSR)
  • Family and children’s resources
  • Documentation, legal aid, and new laws

Under the direction of the Deputy Mayor, reporting to the First Deputy, the Director of Re-entry will oversee major projects within the Chicago Recovery Plan team and will manage a team of two project managers and one senior analyst.




  • Develop and implement a strategic plan that includes policies, programs, and practices that eliminate barriers and create opportunities for returning residents in housing, employment, economic vitality and upward mobility, support services and support systems.
  • Develop and design a one stop model for wraparound reentry support for returning residents.
  • In partnership with returning residents and community stakeholders, design and implement the creation of reimagined reentry hubs or one-stop-shop centers on the south, west and northsides of Chicago to serve as locations where returning residents and their families/support systems can connect to services and supports that they want and need.
  • Lead, develop, manage, implement, coordinate, and monitor policies, programs, and initiatives to support returning residents across City departments and communities, including the Chicago Interagency Reentry Council and creating career pathways in the City for returning residents, in alignment with the administration’s broader policy framework.
  • Coordinate between the MOCS Team, Mayor’s Office Policy Team, the Mayor’s Office of Education, Youth and Human Services, the Department of Housing, the Human Resources Department, the Department of Family and Support Services, and other relevant City departments and sister agencies to ensure re-entry policy work is synchronized, collaborative, and impactful.
  • Regularly seek out innovative ideas and best practices related to returning residents in community safety, housing, employment, education, health, and related fields and incorporate them into Chicago’s re-entry and MOCS agenda in collaboration with local and national experts, researchers, and community leaders.
  • Participate in local and statewide networks of advocacy and support for returning residents, including regarding mental health services, job training and placement, housing, substance abuse services, and family reunification.
  • Establish and maintain relationships with criminal legal system partners including jails and prisons to coordinate support for returning residents and prioritize ensuring resources are in place prior to their release.
  • Establish and maintain relationships with private sector employers, the Chicago Department of Human Resources, other departments, and sister agencies to promote hiring of individuals with records.
  • Collaborate with other Mayor’s Office teams to ensure coordination of priorities, including community safety, economic upward mobility, racial justice and equity, and supporting youth and their communities.
  • Monitor nationwide best practices in supporting returning residents, build relationships with other municipal agencies across the country, and work to adapt those practices to Chicago.
  • Monitor and support state and federal re-entry advocacy agenda priorities, in partnership with the Inter-Governmental Affairs team.
  • Actively participate in cross-departmental implementation of data collection efforts and coordinate data sharing and rapid response mechanisms between City agencies and community-based partners.
  • Develop outcome metrics and processes for tracking citywide progress on re-entry priorities. Work in tandem of MOCS place-based and people-based strategy, addressing the root of violence to improve lives with intentional and purposeful stacked investments for high promise populations.
  • Produce memos, reports, and presentations to summarize progress in implementing programs and initiatives for internal City stakeholders, as well as community and other external audiences; and
  • Complete other projects and duties as assigned.


Education, Training, and Experience
  • Associate degree from accredited institution
  • 5 years of professional experience— including at least 3 in the areas of re-entry, social services, social work, and/or workforce development as related to the responsibilities of this position—or equivalent volunteer or lived experience navigating the criminal legal system.
  • Ability to work strategically and collaboratively utilizing the full force of government across departments
  • Effective, versatile and action oriented
  • Excellent communication skills
  • Proven track record of leadership skills and organizing
  • Experience leading a team
  • The ability to operate, or learn to operate, commonly used programs (e.g., Microsoft Office, Google Office Suite, cloud-based storage) with proficiency.


  • Criminal legal system and challenges faced by those returning home from prison or jail
  • Landscape of re-entry services and stakeholders in Chicago and throughout the state of Illinois
  • How to collaboratively engage public, private, nonprofit, and community-based partners and stakeholders
  • Re-entry work through the lens of gender and racial equity and justice
  • Leadership – demonstrate willingness and ability to lead, take charge, and offer opinions and direction when necessary and appropriate.
  • Motivation - develop and direct people as they work
  • Negotiation – ability to bring individuals together to reconcile differences
  • Strategic thinking – ability to think of long-term plans or strategies for advancement of agendas
Other Work Requirements
  • Attention to detail – pay careful attention to detail and thoroughness in completing work tasks
  • Initiative – demonstrate willingness to take on job challenges and responsibilities when asked
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