An entrepreneurial businesswoman and trailblazer, her 15 years of education administration, social entrepreneurship and advocacy experience also included leadership positions with Dohmen Constellations, Burke Foundation, Robert W. Baird Foundation, Milwaukee Renaissance Academy, Legal Action of Wisconsin and The Milwaukee Street Law Project. Singh also has served as adjunct professor at Marquette University Graduate and Law School.  She recently completed her first two children’s book I Am a Boy of Color and I Am a Girl of Color

Singh was recognized by the Milwaukee Business Journal as one of the community’s most influential 40 under 40 leaders and the 8 Under 40 to Watch for the University of Wisconsin School of Business.  She is also the recipient of the United Way’s Philanthropic Five Award, Wisconsin Department of Public Instruction Leadership Development Hero Award and was a White House Fellowship Regional Finalist.

She currently serves on the boards of LIFT, and The Milwaukee Public Schools Foundation and is a member of the Sikh American Legal Defense and Education Fund Speakers Bureau.  Past board roles include but are not limited to First Stage Milwaukee, Marquette University’s College of Professional Studies Advisory Board and the Wisconsin Bar Association’s Diversity Committee.

A native of Milwaukee, Singh earned her Bachelor of Arts in Urban Studies from Fordham University, a Juris Doctorate from Georgetown University, and a Master’s in Business Administration from the University of Wisconsin, Madison.

Singh lives in Wisconsin with her husband, Justin, and two sons, Zion and Zephaniah.


Zephaniah (8) & Zion (4), Co-Chairmen of the Flying Elephants Foundation and Deanna’s children, have raised thousands of dollars for worthy organizations through a variety of different ventures from selling their art work to hot chocolate stands!  A portion of the proceeds from Flying Elephant will help them continue to do that work.  As co-chairmen of the Foundation, they are responsible for choosing projects that foster positive images and opportunities for children of color!  

The elephant is a symbol for power, dignity, intelligence, peace and good fortune.  They are majestic creatures.  At Flying Elephant, that is the same way we think about your ideas.  Through dynamic presentations; inspirational storytelling; and sharing practical tools our goal is to take your most ambitious ideas and help you put wings on them!  


Keynote Speaker, Author, Chief Change Agent

Deanna Singh is recognized as a leading authority in building innovative opportunities within underserved communities.

As Chief Change Agent and Founder of Flying Elephants, Deanna is a highly respected thought leader, who has spent almost 20 years researching, designing and building asset based solutions to complex social challenges.  Today she travels the world inspiring and educating audiences.

A gifted communicator, Deanna’s interactive style combines personal stories with authenticity, vulnerability and humor that takes the audience on a journey of self-discovery. 

[flahy-ing] [el-uh-fuh nt]
A majestic, transformative idea that is given

wings and allowed to soar!