Jayla Soares (right) won second place at the 2019 Stiletto Challenge Youth Business Pitch Competition. Her idea for Jayla's Design Company earned a $325 cash prize. Photo courtesy of Jania Massey

In 2016, Charlotte native Jania Massey launched Stiletto Boss University (SBU), a nine-month program that uses entrepreneurship as the foundation for teaching high school girls — called stiletto bosses — the power of collaboration, sisterhood and community impact. 

When meeting sites recently shut down due to coronavirus-related restrictions, 36-year-old Massey took her traditionally in-person business online to keep nearly 60 girls connected during a time of physical distancing. On March 16, she officially launched the SBU Headquarters portal, an online university for program participants.

Stiletto bosses work with mentors during weekly sessions to learn business principles and create a business venture. At the end of the program, participants have an opportunity to pitch their ideas to judges for cash prizes. 

They were preparing their pitches when Charlotte-Mecklenburg Schools announced closings due to the coronavirus. SBU follows CMS’ schedule, so in-person programming is suspended as long as schools are closed. Massey has established chapters at West Charlotte High School, Harding University High School, Cato Middle College High School, Mooresville High School, The Harvest Center and Grier Heights Community Center. SBU Headquarters serves as a hub for girls unaffiliated with a chapter. 

“I didn’t want everything that we’d been doing together to just end,” said Massey, a 2001 graduate of West Charlotte High. “Long before the COVID-19 pandemic, I was thinking about ways to connect the girls from each of the chapters. The online portal has been complete since January.”

Some of the SBU participants during a session at Grier Heights Community Center. Photo courtesy of Jania Massey

Now with a virtual connection, the seven-member staff holds weekly check-ins with the girls via video conferencing platform Zoom and SBU’s YouTube channel.

The team is creating custom curricula for topics like finance, networking, wellness, law, and how to dress for success. The modules will be delivered beginning in May to include worksheets and live or prerecorded activities.

It’s business as usual with the stiletto bosses preparing for the Stiletto Challenge Youth Business Pitch Competition. Ten girls will pitch their business ideas to a panel of four judges to compete for one of three cash prizes. Ideas range from graphic design to event planning to a nanny service targeting teen moms.

Last year, Kennadi White presented an idea for a nail boutique. Her pitch for a “classy, chic salon with prices that will keep you coming back” earned first place and the top prize of $500. Returning participants can compete for the $600 grand prize by showing business growth since last year’s inaugural event. 

“The pitch competition is a time to show donors where their money was invested and what the girls are learning,” Massey said with excitement. “It also exposes the girls and their businesses to the community.”

Jayla Soares (right) won second place at the 2019 Stiletto Challenge Youth Business Pitch Competition. Her idea for Jayla’s Design Company earned a $325 cash prize. Photo courtesy of Jania Massey

The team is figuring out logistics to host the event virtually if needed. For now, the in-person event remains scheduled for May 21 at the Knight Theater. 

SBU plans to expand the program for any student interested in entrepreneurship. A pilot program for young men is being tested and scheduled to launch in June. In the fall, SBU Headquarters will offer subscriptions, $100 annually or $10 monthly, for students interested in virtual training. Currently, the program costs an average of $625 per student for the academic year, which is subsidized through partnerships and grants.

Today’s economic landscape will leave a yet-to-be-determined impact on the future. By her own example, Massey is teaching the stiletto bosses how to navigate the unexpected hurdles of entrepreneurship.

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Nakisha is a millennial career coach, content creator and fashion insider. She shares highs, lows and lessons learned from her 10+ year career in corporate America on her blog,