Come build it with us.

Project H.O.O.D. is hiring a Senior Director of Development to lead major gifts, national philanthropy, and fundraising strategy.

The Leadership and Economic Opportunity Center — 90,000 square feet of gym, pool, training floors and classrooms on the block where Pastor Brooks spent a winter on a rooftop — is still ahead of us. This role carries the fundraising that gets it open and sustains everything the organization does next. As our founder puts it: let’s build something that outlives us.

What you’ll do

Where the role focuses

• Major gifts — the organization’s largest individual and institutional relationships
• National philanthropy — growing support beyond Chicago
• Fundraising strategy — the plan that funds the next phase of the organization

Schedule and working conditions

Full-time, based at the Woodlawn campus, and at the Leadership and Economic Opportunity Center once it opens. Evening and weekend hours for donor events and travel for national philanthropy work.

The Impact Officer owns how Project H.O.O.D. measures, proves, and tells the story of its impact. The role sits at the intersection of four functions — program evaluation, donor relations, compliance, and strategic planning — and is organized around two verbs: collect stories and tell stories.

Internally, the Impact Officer builds the measurement systems that let 16 departments across five pillars know whether their work is producing outcomes. Externally, the Impact Officer converts those outcomes into the evidence institutional funders, auditors, accreditors, and major donors require. The position is being created ahead of the opening of the Leadership and Economic Opportunity Center, a period of growth in which evaluation capacity is the binding constraint on both program quality and fundraising.

What you’ll do

Program evaluation

• Develop and manage evaluation plans across all program areas
• Design systems for data tracking and analysis
• Advise on program plans, logic models, and outcomes
• Recommend and implement measurement tools
• Establish best practices and quality standards with program staff
• Oversee continuous quality improvement — monthly outcomes review, biannual reporting, action plans for underperforming areas

Donor relations

• Build an outreach plan for the existing 20,000-person contact list
• Grow the list through volunteers, event attendees, and community members
• Identify mega, major, developing, and prospective donors and assign portfolios
• Establish regular communication through personal emails and segmented newsletters
• Work with the graphic designer on the annual report, strategic plan, and brochures
• Equip staff with the background they need to host donor visits well

Compliance

• Prepare for audits and site visits with institutional funders
• Support certification and licensure requirements
• Assess options for accreditation
• Identify research partners and develop project scopes
• Act as liaison between IT, development, and programs on data tracking and security
• Build working command of internal and external databases

Strategic planning

• Partner with the COO on board expansion, structure, and training
• Lead the environmental review process and SWOT analysis
• Set goal statements and projects with program leaders
• Advise on organizational structure and decision making
• Forecast expansion into the new building and nationwide

What you bring

Required

• Bachelor's degree in a relevant field; advanced degree in public policy, social work, public health, or evaluation preferred
• Five or more years in program evaluation, impact measurement, research, or development in a nonprofit, public agency, or philanthropic setting
• Demonstrated experience designing outcome frameworks, logic models, and data collection instruments
• Proficiency with CRM and case management platforms, and the ability to learn new systems quickly
• Strong analytical skills paired with the ability to turn data into narrative for non-technical audiences
• Experience supporting audits, site visits, or institutional reporting requirements
• Excellent written and verbal communication — able to write for funders, boards, and community members with equal clarity

Preferred

• Familiarity with Stand Together Foundation's Customer First Measurement framework or comparable methodologies
• Experience building a donor pipeline or segmentation strategy at a growing organization
• Working knowledge of accreditation processes for community-based organizations
• Connection to or experience working on Chicago's South Side

What success looks like in year one

• A documented evaluation plan and measurement toolset in place for every program pillar
• Monthly outcomes review operating as a standing organizational rhythm
• The 20,000-person contact list segmented, assigned to portfolios, and in active communication
• Data infrastructure mapped across internal and external systems, with owners and security practices defined
• Project H.O.O.D. audit- and site-visit-ready for its institutional funders

Schedule and working conditions

Based at the Woodlawn campus, and at the Leadership and Economic Opportunity Center once it opens. Occasional evening and weekend hours for events, donor visits, and site visits. Some travel required.

The Program Director sets direction and carries external relationships. The Assistant Director makes sure the work actually runs — cohorts launch on schedule, caseloads stay covered, data is entered, and the program can withstand a monitoring visit on any given day.

This position directly supervises the part-time Re-Entry Coordinators and the Workforce Case Manager, and serves as acting lead in the Program Director's absence. It is the position most responsible for whether the program's participant, placement, and retention targets are met.

What you’ll do

Program operations

• Manage day-to-day delivery across intake, case management, cohort training, and employment placement
• Schedule and launch all four six-week cohort cycles — facilitators, space, materials, recruitment
• Monitor caseload distribution and rebalance to hold service quality at roughly 15–20 participants per coordinator
• Troubleshoot service delivery breakdowns and remove barriers for front-line staff

Supervision and staff development

• Directly supervise the Re-Entry Coordinators and the Workforce Case Manager
• Lead weekly case conferencing and individual supervision
• Onboard and train new re-entry staff; set expectations and conduct reviews
• Build a team culture consistent with our principle-based management approach

Data, reporting, and compliance

• Own the accuracy and timeliness of all participant data in the system of record
• Prepare quarterly and annual performance reports with the Program Director and finance
• Serve as the program's point of contact for monitoring visits, site visits, and audit requests
• Maintain files, consents, and documentation to program standards — correct gaps before they become findings
• Track spending against personnel, supplies, and participant incentive lines and flag variances

Partnerships

• Manage relationships with housing, legal, behavioral health, and workforce partners
• Coordinate the contracted expungement legal services and life skills facilitation scopes
• Represent the program with courts, parole and probation, and community partners

What you bring

Required

• Bachelor's degree in social work, criminal justice, public administration, or human services; equivalent experience considered
• Four or more years in re-entry, violence prevention, workforce development, or human services, including at least one year supervising staff
• Demonstrated experience managing a program with formal performance reporting and compliance documentation
• Strong data discipline — able to hold a team to timely, accurate entry and to read outcome data critically
• Excellent written and verbal communication with participants, funders, and partners alike
• Ability to work some evenings and weekends aligned to cohort and participant schedules

Preferred

• Master's degree in social work, public administration, or a related field
• Lived experience with the criminal legal system
• Established relationships across Chicago South Side reentry, legal, and employer networks
• Training in trauma-informed or clinical supervision

Schedule and working conditions

Based at the Woodlawn campus with regular presence at community and partner sites. Some evening and weekend hours to support cohort sessions and participant needs. Local travel required.

Applicants with lived experience in the criminal legal system are encouraged to apply. A criminal record is not an automatic bar to employment and is considered individually in accordance with Illinois law.

The Re-Entry Coordinator II carries the same direct case management responsibilities as the Coordinator I, and additionally co-facilitates the six-week re-entry cohort training curriculum across all four cohort cycles.

This position is part-time by design. The 25-hour schedule is structured to align with cohort session days, workshop facilitation, and individual participant follow-up.

What you’ll do

Case management

• Carry a caseload of approximately 15–20 active participants
• Conduct structured intake assessments in the program's data system
• Develop individualized service plans with each participant
• Provide regular check-ins and consistent, high-touch follow-up
• Coordinate referrals to housing and legal partners, including expungement legal services
• Document participant progress and employment outcomes
• Support crisis intervention as needed

Cohort facilitation

• Co-facilitate the six-week re-entry cohort curriculum across all four cycles
• Coordinate participant engagement, recruitment, and retention for each cohort
• Track and document attendance for every session
• Prepare session materials and coordinate logistics with the contracted life skills facilitator
• Identify participants at risk of disengaging and intervene before they drop out
• Capture the cohort completion data required for participant completion incentives

Team and program support

• Participate in weekly case conferencing with the Re-Entry team
• Coordinate with the Workforce Case Manager on employment readiness and placement handoffs
• Contribute participant success stories and outcome data for program reporting

What you bring

Required

• High school diploma or equivalent; associate's or bachelor's degree in social work, human services, or criminal justice preferred
• Two or more years in case management, re-entry services, violence prevention, or workforce development
• Demonstrated experience facilitating groups, workshops, or training cohorts with adult learners
• Ability to build trust quickly with justice-involved adults and to hold participants accountable with respect
• Working proficiency with case management or CRM software and comfort documenting work daily
• Ability to work a schedule that includes evenings and weekends aligned to cohort session days

Preferred

• Lived experience with the criminal legal system
• Curriculum delivery or adult education training
• Knowledge of Chicago South Side housing, legal, behavioral health, and workforce resources
• Training in motivational interviewing, trauma-informed care, or crisis intervention

Schedule and working conditions

25 hours per week, structured around participant availability and cohort session days, including some evening and weekend hours. Work is performed at the Woodlawn campus and at community and partner sites; local travel is required.

Applicants with lived experience in the criminal legal system are encouraged to apply. A criminal record is not an automatic bar to employment and is considered individually in accordance with Illinois law.

The Re-Entry Coordinator I provides direct, high-touch case management to individuals returning to the community from incarceration or court involvement. The Coordinator is the participant's consistent point of contact from intake through employment placement and follow-up.

This position is part-time by design. The 25-hour schedule lets us hold specialized, high-touch case management capacity while stretching limited resources, and is structured around participant availability and cohort session days.

What you’ll do

Case management

• Carry a caseload of approximately 15–20 active participants
• Conduct structured intake assessments in the program's data system
• Develop individualized service plans with each participant
• Provide regular check-ins and consistent, high-touch follow-up
• Coordinate referrals to housing and legal partners, including expungement legal services
• Document participant progress and employment outcomes
• Support crisis intervention as needed

Team and program support

• Participate in weekly case conferencing with the Re-Entry team
• Coordinate with the Workforce Case Manager on employment readiness and placement handoffs
• Contribute participant success stories and outcome data for program reporting
• Represent Project H.O.O.D. with partners, courts, and community stakeholders

What you bring

Required

• High school diploma or equivalent; associate's or bachelor's degree in social work, human services, or criminal justice preferred
• Two or more years in case management, re-entry services, violence prevention, or workforce development
• Ability to build trust quickly with justice-involved adults and to hold participants accountable with respect
• Working proficiency with case management or CRM software and comfort documenting work daily
• Reliable transportation and ability to travel locally to partner sites and community locations
• Ability to work a schedule that includes some evenings and weekends

Preferred

• Lived experience with the criminal legal system
• Knowledge of Chicago South Side housing, legal, behavioral health, and workforce resources
• Training in motivational interviewing, trauma-informed care, or crisis intervention
• Existing relationships with parole, probation, or reentry partners

Schedule and working conditions

25 hours per week, structured around participant availability and cohort session days, including some evening and weekend hours. Work is performed at the Woodlawn campus and at community and partner sites; local travel is required.

Applicants with lived experience in the criminal legal system are encouraged to apply. A criminal record is not an automatic bar to employment and is considered individually in accordance with Illinois law.