It takes a village.

Meet the teams who make Say Yes Cleveland possible.

Administrative Staff

Many Say Yes Cleveland staff are CMSD graduates committed to supporting students who are driven to follow their own paths to success.


Diane Downing

Executive Director

Diane manages and directs all operations for Say Yes Cleveland, along with the partnerships and collaborations we rely on to pursue the Say Yes Cleveland mission. A longtime Cleveland resident, Diane has held numerous roles in civic leadership, including as the Cleveland District Director for United States Senator George Voinovich and Executive for Service during the administration of Mayor Michael White. Most recently, Diane worked as Senior Vice President and Director of Corporate Affairs for Huntington Bank in Cleveland.


Sharese Ryan

Director of Student and Family Services

Sharese supervises, coaches, and trains Say Yes Cleveland’s team of 100+ Family Support Specialists. She works with Say Yes Cleveland staff, schools, and external service providers to develop and maintain a support network that propels students to success. Sharese has formerly worked as a supervisor of child welfare caseworkers for Franklin County Children Services in Columbus, and as a social service worker and then supervisor for Cuyahoga County’s Division of Children & Family Services. She earned a Bachelor of Criminal Justice and Criminology degree from Eastern Michigan University, and a Master of Education degree in adult learning and development from Cleveland State University.


Aletha Kern

Director of IT and Data Management

Aletha Charlotte Kern is responsible for developing and implementing Say Yes Cleveland’s data and tech processes, tracking the status and needs of current and future students. Aletha possesses a wealth of technical expertise gained throughout the course of her career in the corporate sector. Working at Say Yes Cleveland, she is actively pursuing her dream of providing technological expertise to an organization that makes a difference in the lives of Cleveland’s youth.


Brittney Church

Assistant Director of IT and Data Management

Brittney provides the monitoring and maintenance of Say Yes Cleveland’s data management processes, assists in data gathering and analysis to support community reporting needs, and coordinates the training of data system end users. Before taking on her current role, Brittney served from 2019-2021 as the Family Support Specialist (FSS) for Max Hayes High School. She has a Masters of Education degree and is pursuing certification in education technology from Cleveland State University.


Lisa Naylor

Director of Programs and Partnerships

Lisa develops, implements, and manages programs for Say Yes Cleveland students, with a particular focus on out-of-school time and expanded learning. She joined Say Yes Cleveland after working at the Cleveland Metropolitan School District (CMSD) as the Director of Community Engagement & Wraparound Services, where she led the District’s Community Wraparound Strategy. Naylor earned a Bachelor of Arts from Kent State University and a Masters Degree in Nonprofit Management from Case Western Reserve University.


Jon Benedict

Director of Communications

Jon is responsible for Say Yes Cleveland’s communications and marketing efforts, helping ensure that everyone with a stake in the city understands the mission of Say Yes Cleveland. Prior to joining Say Yes Cleveland, Jon spent his nearly 20-year career helping organizations in Cleveland and across Ohio communicate effectively and achieve their strategic goals. As Vice President at R Strategy Group, he provided strategic communications counsel and services to school districts, libraries, policymakers, local governments, education and human service agencies, advocacy groups, and more.


Lauren R. Welch

Assistant Director of Communications

Lauren supports all aspects of Say Yes Cleveland’s marketing, outreach, and public relations. Welch is a Cleveland native whose work has made her a highly sought-after leader in cities across the nation. She has managed high-level branding, advocacy, and communications strategies for agencies, nonprofit organizations, political campaigns, educational institutions, small businesses, and people of note over the course of more than 15 years. She uses her lived experiences and professional expertise in equity, inclusion, and liberation work to highlight the issues affecting marginalized individuals and their stories on a local and national scale. Welch is currently a member of the boards of directors for the Greater Cleveland Regional Transit Authority and The Land, a nonprofit news organization focused on Cleveland’s neighborhoods.

Operating Committee

Say Yes Cleveland’s Operating Committee oversees and guides the strategy and implementation of Say Yes Cleveland’s support services and operations.

Kristen Baird Adams

Chief of Staff, Office of the Regional Presidents, PNC Bank

Maggie McGrath Armour

Director, Higher Education Compact of Greater Cleveland

Richard Bischoff

Vice President for Enrollment Management, Case Western Reserve University

Matt Carroll

Chief Economic Growth and Opportunity Officer, Cuyahoga County

Diane Downing

Executive Director, Say Yes Cleveland

Lee Friedman

CEO, College Now Greater Cleveland

Richard Gibson

Pastor, Elizabeth Baptist Church

Eric Gordon

CEO, Cleveland Metropolitan School District

Robert M. Heard Sr.

Board Member, Cleveland Metropolitan School District

Ralph Johnson

CEO, Breakthrough Charter Schools

India Pierce Lee

Senior Vice President, The Cleveland Foundation

Shana Marbury

General Counsel and Senior VP, Greater Cleveland Partnership

Ja’Nice Marshall

Vice President, Cuyahoga Community College

Ann Mullin

Executive Vice President, The George Gund Foundation

Augie Napoli

President and CEO, United Way of Greater Cleveland

Jessica Nelson

Parent Representative, Cleveland Metropolitan School District

Shari Obrenski

President, Cleveland Teachers Union

Kevin Payton

President, CMSD Principal’s Association

Nicolas Petty

Director, Undergraduate Inclusive Excellence Coaching Academic Program, Cleveland State University

Sonya Pryor-Jones

Chief of Youth and Family Success, City of Cleveland

Victor Ruiz

Executive Director, Esperanza

Jasmin Santana

Councilmember, Cleveland City Council

Sunny Simon

Councilmember, Cuyahoga County Council

Richard Starr

Councilmember, Cleveland City Council

Emily Thome

Executive Director, Third Federal Foundation

Tim Tramble

President and CEO, St. Luke’s Foundation

Holly Trifiro

Chief Education Officer, City of Cleveland

Helen Williams

Program Director for Education, The Cleveland Foundation

Scholarship Board

The Say Yes Cleveland Scholarship Board sets scholarship criteria, hears appeals, and supervises the administration of scholarship funds.

Lonnie Coleman

President, Coleman Spohn Corporation

Inajo Davis Chappell (Chair)

Partner, Ulmer & Berne LLP

Diane Downing

Executive Director, Say Yes Cleveland

Veena Khanna

Director of Strategy and Implementation, Key Private Bank

Rob Martens

President and CEO, Better Together Solar

Drew Martin

Exec. V.P., PNC Bank

Ann Mullin (Vice Chair)

Executive Vice President, The George Gund Foundation

Debbie Read

Managing Partner, Thompson Hine LLP

Ronn Richard

President and CEO, The Cleveland Foundation

Victor Ruiz

Executive Director, Esperanza

Eddie Taylor

Founder and President, Taylor Oswald

Helen Williams

Program Director for Education, The Cleveland Foundation


“The most important thing we can do is be a connector in multiple ways. We want to connect to our students and their families, but we also want to connect our students to the opportunities to take them to the next level of their growth as people. As a graduate of CMSD schools myself, I was the first to go to college. So I know how important it is to leverage the support resources that may be out there when our students are trying to do something different and work toward something the generations before them weren’t able to do.”

Aletha Kern

SYC Staff

Translate »