Contact the local Social Security Administration (SSA) office to complete a PASS Form: SSA 545 and then mail it or take it to the office. To apply for the PASS Program you must meet these requirements: Desire to work or start a business. Already receiving (or you qualify for) Supplemental Security Income (SSI) because of […]
Cherice Richmond is an operations professional and entrepreneur with experience supporting CEOs, CFOs, stakeholders, and cross-functional teams in achieving strategic business objectives. As the owner of her own Online Business Management business, she has partnered with organizations to streamline operations, manage projects, improve processes, and implement systems that drive efficiency and growth.
With a background in operations, human resources, project management, and business administration, Cherice brings a collaborative approach, strong organizational skills, and a passion for creating structure that helps teams operate effectively and achieve their goals. Her experience across both corporate and entrepreneurial environments allows her to bridge strategy and execution while building strong relationships at every level of an organization.
Sherry Mirador brings more than 20 years of experience in community engagement, public service, and family support to her role as Care Coordinator at The Transition Academy. Her work spans nonprofit, government, and community-based settings, with a strong focus on helping individuals and families navigate complex systems and access essential resources.
Sherry has extensive experience in benefits navigation, case management, and cross-system collaboration, supporting individuals with SNAP, Medicaid, SSDI, Vocational Rehabilitation, and other critical services. Most recently, she served as a Life Transformation Coach with Connections to Success, where she managed a large caseload and provided trauma-informed, strengths-based support to help participants reach goals related to employment, education, health care, and stability.
Previously, Sherry held leadership roles with the Kansas City Public Library, supervising staff in a high-need, culturally diverse community and partnering with local organizations to address social equity and public health needs. Earlier in her career, she worked as a Public Health Advisor with the U.S. Department of Health and Human Services, supporting communities across the Midwest in addressing health disparities and improving access to care.
Sherry holds a Master of Public Administration in Healthcare Management and is a certified Mental Health First Aid USA Trainer. She is deeply committed to inclusive, trauma-informed practices and is passionate about supporting youth and families as they navigate systems, build stability, and plan for the future.
Carlton Fowler is Program and Services Director for The Transition Academy. Carlton brings extensive experience in education and student services, with a professional background that includes enrollment management, student success initiatives, and cross-functional collaboration within higher education and workforce-focused environments.
He spent many years at Metropolitan Community College, Penn Valley Campus, where he was involved in overseeing enrollment operations, supporting access and recruitment efforts, coordinating student services, and contributing to retention and completion strategies. He has also worked closely with academic teams, administrators, and community partners to improve systems, processes, and outcomes for students. Earlier in his career, he served as a training and employment counselor for The Full Employment Council, Inc. supporting workforce readiness and career development initiatives.
Throughout his career, Carlton has been involved in planning and implementing programs that support students from entry through completion, with a strong focus on access, accountability, and continuous improvement. His experience includes operational leadership, staff collaboration, and aligning student-facing services with institutional goals.
Driven by the belief that every young person deserves a pathway to meaningful work and empowered independence, Carlton is committed to ensuring TTA’s programs open doors, elevate potential, and foster lasting community impact.
Dr. Louis C. Neal is a seasoned educator and administrator with more than 36 years of experience in K–12 education, dedicated to helping students connect learning to real-life success. His career spans roles as a teacher, principal, and mentor, all centered on fostering inclusive, engaging, and empowering educational experiences for every student.
Most recently, Dr. Neal served as Principal in Kansas City Kansas Public Schools, where he led instruction and operations for nearly 300 students. Throughout his leadership career, he has prioritized academic excellence, social-emotional growth, and equitable access to opportunity. His expertise in school improvement and culture-building has guided schools and educators toward higher engagement, stronger collaboration, and measurable student growth.
Before entering administration, Dr. Neal taught middle and high school students for 18 years, bringing creativity and rigor to his classrooms, particularly through his background in music education. He has also served as Assistant Principal in the Raytown C-2 School District and Benjamin Banneker Charter Academy, and continues to lead through mentorship and community service.
As the Founder of the “Who Am I? I Am You!” Mentoring Program, Dr. Neal has spent the past decade empowering young African American boys through identity development, literacy, leadership, and cultural pride. His passion for mentoring has extended into professional spaces as well, where he has presented at national conferences on topics including leadership and equity in education.
Dr. Neal holds an Ed.D. in Educational Administration from the University of Missouri–Kansas City, as well as advanced leadership certifications from Harvard Graduate School of Education and San Diego State University’s National Center for Urban School Turnaround. He is also an accomplished musician and active member of several professional and civic organizations, including Alpha Phi Alpha Fraternity, Inc., the National Alliance of Black School Educators, and the 18th and Vine Jazz Orchestra.
His contributions have been recognized with numerous honors, including the Service to Youth Development Award (2022), Educator of the Year (2019 & 2012), and the Elder Statesman of Jazz Award (2010).
Dr. Neal remains deeply committed to preparing students to thrive in school, work, and life. His work reflects a lifelong belief in the power of education to transform individuals and strengthen communities.
Steve Roling’s career has spanned the non-profit, business, governmental, and philanthropic sectors, but always with a central focus on enhancing the quality of life in the Kansas City area. In joining The Transition Academy’s board of directors, Roling brings with him a wealth of experience in private, non-profit, and government organizations.
Notably, Roling was the Founding President and CEO of the Health Care Foundation of Greater Kansas City, now known as the Health Forward Foundation. Under his stewardship from 2004 through 2013, the agency invested more than $160 million in initiatives focused on improving healthcare access for the medically underserved. He has been enjoying a well-deserved retirement since 2013.
Roling earned his undergraduate degree in Psychology from the University of Missouri-Columbia and a master’s degree in social work from the University of Missouri-Columbia. He worked at Butterfield Youth Services in Marshall, MO, and the Missouri Association for Social Welfare in Jefferson City, MO.
He shifted his focus to public policy while working for Senator Tom Eagleton in Washington DC, and then his career transitioned to the financial sector, with roles as Vice President at Trader’s Bank, United Missouri Bank, and Bank of Kansas City. Roling also steered the helm as Publisher of the Kansas City Business Journal. He later delved into the realm of philanthropy, serving as Senior Vice President of the Ewing Marion Kauffman Foundation. His public service extended to the role of Director at the Missouri Department of Social Services in Jefferson City, MO. He has also shared his wealth of knowledge as an Adjunct Professor at the School of Social Work at UMKC.
Roling’s commitment to community welfare extends beyond employment roles. He has been dedicated to many non-profit boards including the Missouri Department of Mental Health Commission, United Way, Mid Continent Public Library, Urban Neighborhood Initiative, Jacob & Ella Loose Foundation, and St. Thomas More Parish Council.
Roling’s legacy is one of unwavering dedication to working with others from all sectors of society for the betterment of the Kansas City region and beyond. Personally, he and his wife Judi have been married for 48 years and nurtured a family deeply rooted in the Kansas City community, including their two accomplished daughters and six cherished grandchildren.
Kent Hawkins is a seasoned professional with over two decades of experience in financial analysis and strategic planning. Currently serving as the Senior Director of Financial and Offsite Analysis at NeighborWorks America, Hawkins has been instrumental in driving the organization’s mission forward for the past 22 years. His expertise lies in analyzing complex financial data and providing valuable insights to inform decision-making processes.
In addition to his role at NeighborWorks America, Hawkins serves as Treasurer on the Health Forward Foundation Board of Directors, where he brings his financial acumen to bear in support of the Foundation’s mission to improve the health and well-being of communities in Kansas and Missouri.
Prior to his role at NeighborWorks America, Hawkins served as the Director of Finance for the City of North Kansas City, where he demonstrated his proficiency in budgeting, forecasting, and fiscal management. Prior to that role, Hawkins was Deputy Auditor in Jackson County where he spent years honing his skills in auditing and compliance, laying the groundwork for his future success in financial leadership roles.
With a proven track record of driving financial performance and fostering organizational growth, Hawkins is a respected leader in the field of financial analysis and management. His expertise, combined with his unwavering commitment to excellence, makes him an invaluable asset to any organization fortunate enough to have him on board.
Ivan Nugent is a dedicated attorney who has been with Krigel Nugent + Moore since 2018, earning his position as a shareholder in 2021. With a passion for justice, Nugent has built his career on advocating for those whose voices often go unheard.
Starting out as a public defender, Nugent ensured that even those without means had access to compassionate legal representation. During his tenure, he fiercely defended the rights of his clients, including representing the Kansas City Public Schools for eight years, prevailing in over 13 jury trials.
His expertise extends across various legal domains, from litigating contracts and employment disputes to navigating complex educational and governmental matters. His extensive experience in educational, employment, and business law, coupled with his courtroom acumen, distinguishes him as a valuable asset to any legal team.
Nugent earned both his B.B.A in Finance and Economics and an M.B.A from Rockhurst University. He then received his Juris Doctor degree from Western Michigan University, Lansing, Michigan, in 2009. He’s a member of the Jackson County Bar Association, Kansas City Metropolitan Bar Association, American Bar Association, and Minority In-house Counsel Association.
In addition to his professional associations, he is also active in various community organizations. He has been on the Board of Directors at The Children’s Place and Christo Rey in Kansas City. He has also served on the Board of Trustees for Rockhurst High and a board member of Show Me KC Schools. He was in the Centurions Leadership Program in 2016 and the year before he was named the Big Brothers, Big Sisters Most Wanted.
Founder, The Grace Is Greener | Nonprofit Executive | Community and Workforce Development Leader | Health and Wellness Advocate
Anita Davis brings over 20 years of experience as a nonprofit leader and executive, specializing in community, economic, and workforce development, to her new venture in the health and wellness industry. As the founder of The Grace Is Greener, a wellness brand dedicated to empowering women over 40, Anita blends her deep expertise in creating impactful, sustainable programs with a passion for holistic health, longevity, and personal transformation.
Throughout her career, Anita has led initiatives that supported vulnerable populations through education, job training, and economic mobility. Now, she focuses on helping women embrace graceful aging, optimize their wellness, and cultivate energy, vitality, and confidence in every stage of life.
Her journey into health and wellness comes from both personal experience and a desire to inspire others. Navigating her own health journey, coupled with her role as a caregiver for her aging mother with dementia, has deepened her understanding of the challenges women face as they age. Anita is dedicated to helping women over 40 live with vitality, balance, and purpose. With her unique blend of nonprofit leadership and wellness expertise, she is committed to making a lasting impact on individuals’ lives, offering both community-driven support and personalized wellness solutions.
Kim Riley is a social entrepreneur based in Kansas City, MO. She has worked extensively in higher education, health care and nonprofits. She founded a nonprofit, The Transition Academy (TTA), in 2019 as a solution to the confusing and poorly-designed postsecondary preparation process for students with disabilities – a problem affecting her family and others like hers. In 2021, she began developing North Star, a college and career planning tech product for these same youth. Kim earned a Bachelor of Journalism degree from the University of Missouri and an Executive MBA from the University of Missouri-Kansas City.
Christina Esteban is a passionate advocate for Kansas City families and a seasoned nonprofit leader. She has more than 25 years of experience driving change across social services, workforce development, food security, and violence prevention. Her career began in social work, supporting foster youth and navigating complex systems to connect families with the resources they needed to thrive.
Over the years, Christina has led community-based initiatives with a focus on equity, basic needs, and opportunity. Most recently, she served as Managing Director at KC Mothers in Charge, where she strengthened infrastructure, grew donor engagement, and expanded community partnerships for a crisis intervention agency serving families affected by homicide. She also held leadership roles at NourishKC, Guadalupe Centers, and Harvesters, developing sustainable programs and managing strategic fundraising efforts.
Christina is known for her collaborative leadership, her ability to build strong relationships across sectors, and her commitment to mission-driven work. She played a key role in growing the Coalition of Hispanic Organizations, served as an inaugural board member of the Health Care Foundation of Greater Kansas City, and in 2024, she completed the KC Chamber Centurions leadership program.
She holds a Bachelor’s degree in Sociology from Rockhurst College and is certified through American Humanics. In her current role with The Transition Academy, Christina is focused on strengthening business partnerships to align the skills of youth with meaningful employment opportunities, ensuring a more inclusive and connected future for all.
