The Youth Services Division of the City of Chicago’s Department of Family and Support Services (DFSS) is one of the largest public youth service funders in the country. The division administers over $100 million annually across more than 400 individual grants to 150+ community-based agencies, supporting a wide range of programs that aim to empower young people through education, mentorship, career readiness, and leadership development.

CHALLENGE

As DFSS expanded its portfolio of youth-serving initiatives—including enrichment programs, mentoring, case management, career training, youth employment, and leadership development—the division faced growing operational complexity. Staff needed a centralized, policy-aligned platform to:

  • Manage contracts and work plans across hundreds of diverse programs
  • Track youth participation and services across dozens of neighborhoods
  • Ensure compliance, equity, and strategic oversight at scale
  • Produce transparent, real-time reporting for both internal and public accountability

Fragmented spreadsheets, inconsistent reporting formats, and limited visibility into real-time data posed significant roadblocks to efficiency and impact.

SOLUTION

DFSS partnered with Cityspan, a leader in youth services technology, to implement a comprehensive grants and performance management system tailored to the needs of a large public funder. The system serves as the backbone for managing the entire lifecycle of youth programming—from initial work plan submission to participant tracking to quarterly reimbursement and outcomes reporting—all within a unified application.

Work Plan and Program Design

Each initiative within the division has unique programmatic goals and operational requirements. The Cityspan platform accommodates this complexity through customizable Work Plan templates and approval workflows, allowing DFSS to enforce policy requirements while providing flexibility across program types.
Grantees submit an Annual Work Plan that captures:

  • General program description, goals, and outcome measurement methods
  • Implementation of S.A.F.E. elements (Sequenced, Active, Focused, Explicit)
  • Youth input strategies (e.g., surveys, leadership councils)
  • Recruitment and retention strategies
  • Location-specific data: address, site type (school, center, etc.), service areas (e.g., STEM, Arts, Leadership), days/hours of service, and youth demographics

After submission, the work plan flows through a structured review, revision, and approval process. Once approved, the signed and executed plan is converted to a PDF and embedded into the agency’s formal grant agreement.

Service Delivery and Participant Tracking

With the work plan in place, the platform becomes the daily operational hub for providers to:

  • Register youth participants
  • Define and schedule activities (group, individual, workforce/job settings, case management, or special events)
  • Enroll youth in activities
  • Capture daily attendance
  • Align all services to approved work plan objectives

This vertical integration ensures that what’s contracted is what’s delivered—and tracked.

Quarterly Progress Reporting

The system also supports robust quarterly progress reporting, aligning programmatic and fiscal accountability:

  • Narrative summaries of monthly services, events, and challenges
  • Automatically generated service delivery metrics (number served, demographics, service types)
  • Uploads of quarterly financial reimbursement data from the City’s controller
  • Workflow-enabled submission, review, and approval of each progress report

These reports give DFSS a clear and consistent view of both service performance and spending across all youth programs.

Geographic Equity with Real-Time GIS Integration

To further advance its commitment to equity, the system integrates with the City’s GIS server, verifying all location and participant addresses in real time. Upon verification, the GIS system returns enriched metadata such as:

  • Council Ward
  • Police Beat
  • Equity Zone
  • Community Area
  • Census Tract

These geographic attributes are embedded in dashboards and reports, enabling DFSS to evaluate and rebalance service delivery based on need and access across Chicago’s neighborhoods.

Workforce Integration: One Summer Chicago

Cityspan’s technology also powers One Summer Chicago, the city’s flagship youth employment initiative. Each year, the system:

  • Registers 15,000+ youth applications
  • Matches youth to employment opportunities across city agencies and partners, including:
    • City of Chicago
    • Chicago Park District
    • Chicago Housing Authority
    • After School Matters

With centralized participant tracking and placement data, DFSS can oversee job readiness outcomes at city scale.

RESULTS AND IMPACT

Through Cityspan’s platform, DFSS has realized a fundamental transformation in how it funds, monitors, and evaluates youth services:

  • Policy-Driven Design
  • Operational Efficiency
  • Data-Driven Oversight
  • Scalable Infrastructure
  • Cross-Sector Collaboration
  • Evidence of Impact

CONCLUSION

By investing in a vertically integrated, policy-aligned data system, the City of Chicago’s DFSS Youth Services Division has set a new standard for public sector grantmaking. Through its partnership with Cityspan, the City has ensured that every dollar spent on youth services is trackable, impactful, and aligned with a vision of opportunity for all of Chicago’s youth.