Get to know our leaders — click on photos to learn more about our incredible staff who oversee various departments, teams, and programs at Breakthrough
Executive Leadership Team

Yolanda Fields
Executive Director
Wilonda Cannon
Chief Program Officer, Community Economic Development
Alexandra Cesario
Chief Development Officer
Lisa Gwin
Chief Program Officer, Breakthrough Youth Network
Cheron Massonburg, BSN, RN
Chief Program Officer, Housing, Health and Wellness
Damien Morris
Chief Program Officer, Violence Prevention
John Smith
Chief Administrative Officer
Yolanda Fields
Executive Director
Yolanda Fields is the Executive Director of Breakthrough and a committed nonprofit and community leader. She started at Breakthrough as a volunteer in 2001 after seeking to make a positive impact following the events of September 11, 2001. Previously, Yolanda spent 10 years leading teams at a major telecommunications company. During her tenure at Breakthrough, Yolanda has led adult programs, which includes housing, homeless services, violence prevention, workforce development, behavioral health, and food access programs. She has walked alongside those experiencing homelessness and crisis, and her compassionate leadership has created a culture of dignity and respect for all. Yolanda resides on the West Side of Chicago and is also the Director of Women’s Ministry at New Landmark Missionary Baptist Church, located in East Garfield Park.
Started as a volunteer in 2002, started as the Director of Street Outreach in 2003
Email:yfields@breakthrough.org
Phone:(773) 346-1713

Wilonda Cannon
Chief Program Officer, Community Economic Development
Wilonda Cannon is the Chief Program Officer of Community Economic Development at Breakthrough. She was introduced to Breakthrough as a parent in 2012 when she enrolled her children in the after-school program. After volunteering at Breakthrough, Wilonda joined the team as Senior Director of Development in 2014. Prior to Breakthrough, she served as a civil engineer in the Air National Guard. She holds a degree from the Joseph Business School, and she led the fund development and strategic initiatives of Project Eden, an initiative of The Joseph Business School, which focuses on economic, business, and social stability for the citizens of Haiti. Because of these efforts, Wilonda was named phenomenal woman of the year by State Farm in 2010. Most recently, she led the launch of Breakthrough’s Community Economic Development program area, which fosters financial wellness and economic stability in East Garfield Park. Wilonda is currently a real estate broker with Coldwell Banker Realty.
With Breakthrough since 2014
Email:wcannon@breakthrough.org
Phone:(773) 346-1745

Alexandra Cesario
Chief Development Officer
As Chief Development Officer, Alexandra Cesario oversees fundraising and communications. She holds a Bachelor of Arts in Communication and Spanish from Loyola University Chicago and is skilled in nonprofit communications, fundraising, and management and uses those skills to extend dignity to all. She also completed the Nonprofit Executive Leadership Program with the Kellogg School of Management at Northwestern University in 2020. Alexandra has been with Breakthrough since 2013 and has previously overseen the organization’s grant portfolio and led marketing and communications efforts. Under her leadership, Breakthrough has grown to an annual revenue of $10 million. Alex resides in Humboldt Park with her husband and three daughters.
With Breakthrough since 2013
Email:acesario@breakthrough.org
Phone:(773) 346-1782

Lisa Gwin
Chief Program Officer, Breakthrough Youth Network
Lisa Gwin, Chief Program Officer of the Breakthrough Youth Network (BYN), oversees the strategic vision, program operations, and staffing of the BYN. She holds a Bachelor of Arts in Elementary Education and a Master of Education in Early Childhood Administration. Lisa lives in East Garfield Park and has worked in Breakthrough’s youth and education programs since 2001. She is well-respected in the community and was a founding leader of the Breakthrough Beginners early childhood education program. Under Lisa’s leadership, the program grew from an on-site daycare for a small group of children to an award-winning, high-quality preschool serving 80 students with a curriculum that regularly surpasses state standards.
With Breakthrough since 2001
Email:lgwin@breakthrough.org
Phone:(872) 444-8210

Cheron Massonburg, BSN, RN
Chief Program Officer, Housing, Health and Wellness
As Chief Program Officer of Housing and Health and Wellness, Cheron Massonburg oversees the strategic vision, program policies, and staffing of Breakthrough’s Transitional and Permanent Housing programs, support centers, Behavioral Health services, and Fresh Market food pantry. She also ensures coordination with local agencies and organizations. She holds a Bachelor of Science in Nursing. As a Registered Nurse (RN), Cheron brings valuable hands-on experience from the healthcare field to Breakthrough. Since she joined Breakthrough in 2001, Cheron has partnered with adults experiencing homelessness or crisis with compassion, collaborated with colleagues to foster friendly and caring environments, and led high-quality services accessed by more than 5,000 adults and families in Garfield Park annually.
Email:cmassonburg@breakthrough.org
Phone:(872) 444-8251

Damien Morris
Chief Program Officer, Violence Prevention
Damien Morris is the Chief Program Officer of Violence Prevention at Breakthrough and a leader for violence reduction in Chicago. Since he joined Breakthrough in 2008, he has led transitional housing initiatives, supported individuals experiencing homelessness through case management, and directed security at the Breakthrough FamilyPlex. Damien has been an integral part of the growth of Breakthrough’s Violence Prevention team. As CPO, he oversees comprehensive services for adults and adolescents: case management, outreach services, victim services, youth engagement, and safe space events. Hundreds of local residents access these services annually. In addition to the leadership he provides for Breakthrough’s team, he ensures coordination with partner institutions and organizations across the city.
With Breakthrough since 2008
Email:dmorris@breakthrough.org
Phone:(773) 346-1734

John Smith
Chief Administrative Officer
John Smith is the Chief Administrative Officer at Breakthrough and oversees financial operations, facility maintenance and construction planning, human resources, and information technology. Since 2002, he has used his skills to improve the effectiveness and efficiency of Breakthrough’s programs. John has coordinated project financing, negotiation of public funding (Tax Increment Financing, New Market Tax Credits), and construction management for facility development projects including the Breakthrough Ministry Center (Jan 2008, $5 mil), Breakthrough Women’s Center and Breakthrough Fresh Market renovation (Fall 2014, $2 mil), and Breakthrough FamilyPlex (Winter 2014, $14.5M). Previously, John worked for the North Lawndale YMCA and as a youth pastor. John received a Bachelor of Arts degree from Huntington University in Indiana. His family resides in East Garfield Park.
With Breakthrough since 2002
Email:jsmith@breakthrough.org
Phone:(773) 346-1730
Staff Leadership Team

Nate Bedell
Director of Community Operations
Martin Coffer
Director, Community Safety & FamilyPlex Operations
Lauren Cole
Director of Housing Programs
Wendy Daniels
Associate Director, Food Services
Ann Healing
Director of Church and Volunteer Engagement
Myisha McGee
Post Secondary High School Director
Tashee Poplous
Associate Director, Victim Services and Case Management
Ana Pyper
Associate Director, Nettie Bailey Student Achievement Program
Kimberly Sankey
Associate Director, Early Childhood Education
Kirsten Strand
Director, Donor Relations
Bradley Troast
Associate Director, Institutional Giving
Tanya Whitten
Associate Director, Communications
Lisa Wiese
Director, Behavioral Health Services
Nate Bedell
Director of Community Operations
With Breakthrough since 2016
Email:nbedell@breakthrough.org
Phone:(773) 346-1382

Martin Coffer
Director, Community Safety & FamilyPlex Operations
Email:mcoffer@breakthrough.org
Phone:(773) 346-1714

Lauren Cole
Director of Housing Programs
With Breakthrough since 2009
Email:lcole@breakthrough.org
Phone:(773) 346-1715


Ann Healing
Director of Church and Volunteer Engagement
Worked at Breakthrough from 2007 to 2008, returned in September 2015
Email:ahealing@breakthrough.org
Phone:(773) 346-1773



Ana Pyper
Associate Director, Nettie Bailey Student Achievement Program
With Breakthrough since 2019
Email:apyper@breakthrough.org
Phone:(872) 444-8207

Kimberly Sankey
Associate Director, Early Childhood Education
Email:ksankey@breakthrough.org
Phone:(872) 444-8210


Bradley Troast
Associate Director, Institutional Giving
Email:btroast@breakthrough.org
Phone:(773) 346-1783

