Chief Operating Officer
Rich Bobby
WHY LITTLE CITY
“At a young age I was exposed to the challenges faced by loved ones, individuals, families, and communities impacted by trauma, mental health, and disabilities, as well as the frequent social injustice they encountered perpetuating these challenges. There’s always been this unsettling feeling I’ve carried with me that something needs to be done to support those facing challenges (that were not of their own making), including knocking down systemic barriers preventing an easier pathway to access services and supports.
In my humble opinion, individuals and families don’t choose the cards life deals them, and sadly there are often societal stigmas that don’t make it easier by placing blame of one’s circumstances as if they chose to have a disability or chose to experience trauma.
The families who founded Little City were heroes in creating a solution to address the societal gap of services and supports many families were seeking at the time. In my time with Little City, I’ve been honored to continue carrying their torch by keeping the innovation going in solution building to systemic challenges impacting the individuals and families we serve today and will serve in the future.
For me, the mission of Little City has profound purpose and meaning for the individuals and families we serve, donors, and other stakeholders. Coming to Little City each day is not “work” for me, my true joy is working with an incredible team of dedicated and compassionate team members who collectively come together daily to make a positive impact on the individuals and families we serve.
Yes, it’s exciting to witness the progress of a youth or adult making strides in learning a new skill or a family expressing their gratitude for the achievements their loved one’s made. At the same what’s even more exciting for me is witnessing our incredible team come together to collectively collaborate enabling these accomplishments of challenging all limits.
All things are possible at Little City, including achieving social justice through equity and inclusion for all who we serve today and tomorrow. That’s why I’ve chosen Little City.”
PROFESSIONAL EXPERIENCE
With over 20 years of human services experience, with over 9 of those years serving at Little City, Rich’s leadership role includes overseeing Little City’s children’s residential services, Center for Education, foster care and adoptions services, and other in-home and family services for youth and families impacted by autism and intellectual and developmental disabilities while managing a collective annual budget of $20 million.
Serving as a private agency co-chair and member of various Illinois Child Welfare Advisory Committee (CWAC) statewide committees and workgroups, Rich has dedicated over 15 years of his time in collaboration with other industry leaders in challenging the status quo to improve outcomes for youth and families impacted by Illinois’s child welfare system. Rich prides himself on being the “squeaky wheel” for positive change and remains committed to equity and inclusion for Illinois’ system of care.
Rich is actively involved with collaborating with many other organizations’ executives/leaders across Illinois, as well as state agency senior leaders in creating positive change for the human service system, especially for those impacted by disabilities.
Rich’s career includes working as a youth mentor intern, following obtaining his Bachelors in psychology from Northern Illinois University became a high school teacher assistant at District 211’s special education department. In Tampa, Florida, Rich was a case manager at the Florida Department of Children and Families a role that transitioned into the state’s move toward child welfare privatization, in which he served in a supervisory role. While working on his Masters of Social Work degree at the University of South Florida part-time and working full-time, Rich helped spearhead the overhaul of his internship as he wasn’t satisfied with how the internship was providing in-home therapy services for youth and families involved with the Florida child welfare system.
After receiving his Masters of Social Work degree from the University of South Florida he catapulted into a leadership role as an Operations Manager alongside the head of a community center overseeing community-based services in Tampa, Florida, which included in-home family services, foster care and adoption services serving more than 1,600 youth and families. In collaboration with child welfare leaders in Hillsborough County, Florida, Rich helped spearhead the design of a child risk assessment protocol that was implemented to assess risk levels for over 5,000 youth involved in the child welfare system.
Moving back to Illinois to be closer to family, Rich worked in administrative roles for 6-years at Children’s Home and Aid’s Rice Child & Family Center, a children’s residential treatment center located in Evanston.
Rich then joined Little City in 2012 as the Director of the Center for Family & Community-Based Services overseeing our Foster Care & Adoption, Community Clinical Services, and Home-Based Services at our Chicago office. In December 2014, Rich became the Chief Program Officer of Adult Services, and ultimately transitioned to become the Chief Program Officer of Children’s Services, in which he’s served in this capacity for over 6 years.
PERSONAL LIFE
Married to his wife, Jaime, since 2003, they have two boys. Rich states he’s a proud “imperfect” father. They met at work, both bank tellers in their early college years and have been together since then for over 20 years.
Rich loves spending quality time with his family, including going to community events, trips to science museums, and watching his oldest son’s joy over anything science related. Rich and Jaime love spending time with friends and family including backyard BBQ’s. During downtime together, they enjoy each other’s company by watching movies, Netflix and going to music festivals with friends.
Individually, Rich is an avid learner, and utilizes downtime moments to read and listen to books, podcasts, or newspaper/magazine articles. He’s particularly interested in nonfiction including, but not limited to, biographies of famous leaders, productivity hacks, leadership, social sciences, advancements in technology, and behavioral economics.
Rich is a fan of the Chicago Bears, and despite their losing seasons, believes they will always be better next year.
Rich is a volunteer board member for his son’s school district’s Education Foundation, in which he’s involved in fundraising activities that enable high school students to receive scholarships for college or vocational schools as well as funding grants to teachers for special educational projects.
If you weren’t Chief Program Officer at Little City, what would you most likely be doing?
“Many years ago, when I was working a full-time job in child welfare while also attending graduate school part-time, I recall a professor of mine made a statement that to this day can occasionally resonates with me. He referenced the field of work you’re entering (that is, human services) is going to be incredibly challenging… (more of what he said in a moment)
From my own experience, I’ve directly witnessed a chronic lack of funding for the resources and supports so desperately needed for individuals and families struggling with a multitude of individual and systemic challenges and continued social injustice when it comes to equity and inclusion. It’s my opinion we’re going to get knocked down again and again (and I certainly have,) but will always get back up and remember the reason I chose this line of work, which is to be of service to other humans. That service can come in many ways directly, through the influence of others, or legislatively to name a few.
To conclude what that professor shared was this work can become so challenging that you may ask yourself, “Maybe selling t-shirts on the beach is the career path I want take. It’s very simple, here’s your t-shirt, thank you for your $10, the transaction and interaction’s over and you both go your separate ways.” The class erupted in laughter.
So, what would I be doing if not in my current role? I’d be selling t-shirts on the beach for $10 a shirt. I say this lightheartedly as I truly can’t imagine not working in human services. My gut wouldn’t let me stop after this $10 transaction, because I’d want to learn more about the person I just sold the shirt to, what’s their story, and what can be done to make his/her life just a little bit easier. Ultimately, my heart and mind would pull me back into human services.
At some point when life circumstances align, I’d be interested in being a part-time adjunct professor for a college or university in addition to working in human services.”
Connect with Rich
[email protected]
847.221.7824
WHY LITTLE CITY
“At a young age I was exposed to the challenges faced by loved ones, individuals, families, and communities impacted by trauma, mental health, and disabilities, as well as the frequent social injustice they encountered perpetuating these challenges. There’s always been this unsettling feeling I’ve carried with me that something needs to be done to support those facing challenges (that were not of their own making), including knocking down systemic barriers preventing an easier pathway to access services and supports.
In my humble opinion, individuals and families don’t choose the cards life deals them, and sadly there are often societal stigmas that don’t make it easier by placing blame of one’s circumstances as if they chose to have a disability or chose to experience trauma.
The families who founded Little City were heroes in creating a solution to address the societal gap of services and supports many families were seeking at the time. In my time with Little City, I’ve been honored to continue carrying their torch by keeping the innovation going in solution building to systemic challenges impacting the individuals and families we serve today and will serve in the future.
For me, the mission of Little City has profound purpose and meaning for the individuals and families we serve, donors, and other stakeholders. Coming to Little City each day is not “work” for me, my true joy is working with an incredible team of dedicated and compassionate team members who collectively come together daily to make a positive impact on the individuals and families we serve.
Yes, it’s exciting to witness the progress of a youth or adult making strides in learning a new skill or a family expressing their gratitude for the achievements their loved one’s made. At the same what’s even more exciting for me is witnessing our incredible team come together to collectively collaborate enabling these accomplishments of challenging all limits.
All things are possible at Little City, including achieving social justice through equity and inclusion for all who we serve today and tomorrow. That’s why I’ve chosen Little City.”
PROFESSIONAL EXPERIENCE
With over 20 years of human services experience, with over 9 of those years serving at Little City, Rich’s leadership role includes overseeing Little City’s children’s residential services, Center for Education, foster care and adoptions services, and other in-home and family services for youth and families impacted by autism and intellectual and developmental disabilities while managing a collective annual budget of $20 million.
Serving as a private agency co-chair and member of various Illinois Child Welfare Advisory Committee (CWAC) statewide committees and workgroups, Rich has dedicated over 15 years of his time in collaboration with other industry leaders in challenging the status quo to improve outcomes for youth and families impacted by Illinois’s child welfare system. Rich prides himself on being the “squeaky wheel” for positive change and remains committed to equity and inclusion for Illinois’ system of care.
Rich is actively involved with collaborating with many other organizations’ executives/leaders across Illinois, as well as state agency senior leaders in creating positive change for the human service system, especially for those impacted by disabilities.
Rich’s career includes working as a youth mentor intern, following obtaining his Bachelors in psychology from Northern Illinois University became a high school teacher assistant at District 211’s special education department. In Tampa, Florida, Rich was a case manager at the Florida Department of Children and Families a role that transitioned into the state’s move toward child welfare privatization, in which he served in a supervisory role. While working on his Masters of Social Work degree at the University of South Florida part-time and working full-time, Rich helped spearhead the overhaul of his internship as he wasn’t satisfied with how the internship was providing in-home therapy services for youth and families involved with the Florida child welfare system.
After receiving his Masters of Social Work degree from the University of South Florida he catapulted into a leadership role as an Operations Manager alongside the head of a community center overseeing community-based services in Tampa, Florida, which included in-home family services, foster care and adoption services serving more than 1,600 youth and families. In collaboration with child welfare leaders in Hillsborough County, Florida, Rich helped spearhead the design of a child risk assessment protocol that was implemented to assess risk levels for over 5,000 youth involved in the child welfare system.
Moving back to Illinois to be closer to family, Rich worked in administrative roles for 6-years at Children’s Home and Aid’s Rice Child & Family Center, a children’s residential treatment center located in Evanston.
Rich then joined Little City in 2012 as the Director of the Center for Family & Community-Based Services overseeing our Foster Care & Adoption, Community Clinical Services, and Home-Based Services at our Chicago office. In December 2014, Rich became the Chief Program Officer of Adult Services, and ultimately transitioned to become the Chief Program Officer of Children’s Services, in which he’s served in this capacity for over 6 years.
PERSONAL LIFE
Married to his wife, Jaime, since 2003, they have two boys. Rich states he’s a proud “imperfect” father. They met at work, both bank tellers in their early college years and have been together since then for over 20 years.
Rich loves spending quality time with his family, including going to community events, trips to science museums, and watching his oldest son’s joy over anything science related. Rich and Jaime love spending time with friends and family including backyard BBQ’s. During downtime together, they enjoy each other’s company by watching movies, Netflix and going to music festivals with friends.
Individually, Rich is an avid learner, and utilizes downtime moments to read and listen to books, podcasts, or newspaper/magazine articles. He’s particularly interested in nonfiction including, but not limited to, biographies of famous leaders, productivity hacks, leadership, social sciences, advancements in technology, and behavioral economics.
Rich is a fan of the Chicago Bears, and despite their losing seasons, believes they will always be better next year.
Rich is a volunteer board member for his son’s school district’s Education Foundation, in which he’s involved in fundraising activities that enable high school students to receive scholarships for college or vocational schools as well as funding grants to teachers for special educational projects.
If you weren’t Chief Program Officer at Little City, what would you most likely be doing?
“Many years ago, when I was working a full-time job in child welfare while also attending graduate school part-time, I recall a professor of mine made a statement that to this day can occasionally resonates with me. He referenced the field of work you’re entering (that is, human services) is going to be incredibly challenging… (more of what he said in a moment)
From my own experience, I’ve directly witnessed a chronic lack of funding for the resources and supports so desperately needed for individuals and families struggling with a multitude of individual and systemic challenges and continued social injustice when it comes to equity and inclusion. It’s my opinion we’re going to get knocked down again and again (and I certainly have,) but will always get back up and remember the reason I chose this line of work, which is to be of service to other humans. That service can come in many ways directly, through the influence of others, or legislatively to name a few.
To conclude what that professor shared was this work can become so challenging that you may ask yourself, “Maybe selling t-shirts on the beach is the career path I want take. It’s very simple, here’s your t-shirt, thank you for your $10, the transaction and interaction’s over and you both go your separate ways.” The class erupted in laughter.
So, what would I be doing if not in my current role? I’d be selling t-shirts on the beach for $10 a shirt. I say this lightheartedly as I truly can’t imagine not working in human services. My gut wouldn’t let me stop after this $10 transaction, because I’d want to learn more about the person I just sold the shirt to, what’s their story, and what can be done to make his/her life just a little bit easier. Ultimately, my heart and mind would pull me back into human services.
At some point when life circumstances align, I’d be interested in being a part-time adjunct professor for a college or university in addition to working in human services.”
Connect with Rich
[email protected]
847.221.7824
Favorite Quote
-Heraclitus
