Rich Bobby

Since joining Little City in 2012, Rich has led organizational growth, strategic planning, and operational alignment across the organization, ensuring strong outcomes for children, youth, and adults with autism and other intellectual and developmental disabilities, as well as youth and families with mental health challenges. 

Rich’s commitment to Little City is deeply personal, informed by firsthand experiences with individuals, families, and communities impacted by trauma, mental health conditions, disabilities, and the systemic barriers that often limit opportunity. He believes Little City carries a profound responsibility to those served, as well as to donors and strategic partners who place their confidence in the organization. Rich approaches stewardship and partnership as trust-based relationships—centered on clear communication, accountability, and shared purpose—to ensure resources are stewarded responsibly and aligned to create lasting and measurable impact.  

Rich’s leadership is grounded in trust, transparency, and respectful honesty. As CEO, he fosters a team-centered culture where leaders and staff are encouraged to communicate openly, challenge assumptions respectfully, and work collaboratively toward shared goals. He views culture as a critical success factor in both philanthropy and partnership, and prioritizes aligning mission, strategy, and systems to support sustainable growth, operational excellence, and thoughtful collaboration or integration when appropriate. 

Prior to joining Little City, Rich held leadership and clinical roles across special education, child welfare and protective services, children’s residential services, in-home family services, and foster care and adoption programs. He earned a bachelor’s degree in psychology from Northern Illinois University, a Master of Social Work from the University of South Florida, and is a Licensed Clinical Social Worker.  

Rich believes that when donors, community partners, and organizations come together with clarity, trust, and shared values, collaboration can extend impact, strengthen services, and create long-term value for children, adults, families, and the communities they call home—today and into the future.