How to Keep Children in School and Prepare Them for College – Ep. 24 with Penny Bailer

How to Keep Children in School and Prepare Them for College – Ep. 24 with Penny Bailer

Penny served as Executive Director of City Year Detroit (CYD) from 2001-2015, responsible for Michigan’s largest AmeriCorps program, retiring in 2015.  During that period, over 1,000 young adult “corps members” served full time with CYD for up to two years each, providing data-driven all day academic classroom tutoring, mentoring and role modeling to thousands of Detroit’s school children, keeping them “in school and on track to graduation.”  City Year also partners (in 28 cities nationally including Detroit) with Johns Hopkins University and Communities in Schools, Inc. for their U. S. Dept of Education-funded Invest in Innovation (i3) award-winning school transformation model called Diplomas Now.

Penny served for over 17 years (1983-2000) as Executive Director/CEO of the Michigan Metro Girl Scout Council in Detroit, increasing the girl membership from 21,000 to 43,000 and registered adult volunteers from 6,000 to 14,000 and proudly earning the 1992 CRAIN’s “Best Managed Non Profit Award.”  She was elected to the Detroit Board of Education (1990-94) and in 1997 was named one of of CRAIN’s Detroit Business “100 Most Influential Women.” 

penny bailer

Since 1979, Penny has served on and led numerous non-profit and civic boards in Detroit, focused primarily on youth, education and Detroit’s revitalization.  In 2014, Mayor Mike Duggan appointed her to the Detroit Promise Zone Authority, which she chairs and which provides free college tuition to Detroit residents who graduate from Detroit high schools; the mayor also appointed her to the board of the Detroit Housing Commission, for which she was elected Vice Chair.  She currently serves on the boards of New Detroit, Detroit Riverfront Conservancy, City Connect Detroit and Detroit Rotary, of which she will become President in 2019-20.   She served on the Governance Committee of the Coalition for the Future of Detroit Schoolchildren throughout its tenure January-March 2015.  In 1976, she was a Co-Founder of the DPS Golightly Education Center (K-8)  — which was attended by both her children and later named a National Blue Ribbon School by President Clinton.

In 2012, she was named Chair of the Self Governing School Council for Detroit Collegiate Preparatory High School @ Northwestern, a DPS/Diplomas Now High School, where she continues to serve as Chair.

In June 2017, Penny proudly represented Michigan in swimming at the bi-centennial National Senior Games (aka “national senior olympics) and plans to continue to work hard to continually qualify, if so fortunate, throughout the rest of her life.


Bailer earned an Executive MBA from the Advanced Management Program at the Eli Broad School of Management in 1989 from MSU’s Troy Graduate School Campus and a BFA in Music/Piano Performance in 1962 from the University of Georgia near her hometown of Atlanta, after which she did 1 year of graduate work toward a Master’s degree in Music (Piano) at Pennsylvania State University.  In July 2011, she was awarded a Harvard Business School scholarship by the HBS Detroit Alumni Club for an executive education week at HBS: Strategic Perspectives in Nonprofit Management (SPNM).

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Speaker, Author, Thought-Leader… and I really like this one, vibrant living culture creator; Golden Soror of the Alpha Kappa Alpha Sorority, Inc., and Michigan Women’s Commission Appointee. With more than forty years of expertise in business management and personal development, I also have the distinction of receiving the NAWBO Top Businesswoman Award and the Booker T. Washington Legacy Award.

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