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Award Winners:  2014  |  2013  |  2012 

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Stiletto Woman was a FORBES ranked leadership-centric new media company for modern working business women.


Simply put, through our mission to empower women to dream big and believe in the impossible, we advocated healthy businesses and healthy lives. We accomplished this by helping women transition into entrepreneurship, build sustainable businesses, and up-level their careers. Our principle message was to encourage women from all walks of life to live courageously on purpose and elevate their influence in business.


In 2013, Stiletto Woman was named one of the "100 Best Websites For Women" by Forbes; it's also been named a "Top 40 Website By, For and About Women in the Workplace & Beyond", a "Top Career Blog to Follow", and She Owns It recognized Karlena Lee Wallace as one of the "Top 50 Women to Follow on Twitter". In 2012, Stiletto Woman was also named one of the "Top 75 Websites for Your Career" by Forbes, and a "Top 25 Site for Women Entrepreneurs to Love."


Stiletto Woman magazine was a print and digital publication. It was our means of speaking to everyday women in a real way. Launched summer 2009 to rave reviews; with a commitment to deliver content that was engaging, transparent and meaningful, the magazine became a favorite among women in business. The publication was produced with minimal ads to keep the featured women and their experiences as the focal point.​​​​​​


We are proud to be one of  the first nationally recognized comprehensive awards initiative to exclusively honor women in the solo and micro business sector across the nation. After two years of recognition in Stiletto Woman magazine, in 2011, we took that idea from the publication to a LIVE awards conference, Stiletto Woman in Business Awards (SWIBA), that served as a one-day session packed with learning and community.


Stiletto Thrive was a womenpreneur lifestyle conference and event series connecting women in a chic, modern new ways both nationally and in your community. Through this platform, we brought women together from all backgrounds and industries; women who desired to create a business and lifestyle that mattered.


Through Stiletto Woman, we've offered various special programs such as the National Walk In Stiletto Day (which was celebrated in the fall each year), branding workshops, and one-to-one business mentoring, all in an effort to empower women and raise the influence of leaders as they navigate career, business, and everyday life.


"It wasn't long ago that I found myself uninspired by the typical tale of the female leader. I rarely saw stories of women who pulled themselves up by their bootstraps on the covers of prominent magazines or the front pages of national newspapers. Everyday working women trailblazing their way through on modest 401(k)s were hardly represented; yet I knew they existed because I was one of them. I realized then that I wanted to do my part in changing that — to showcase everyday heroic women sacrificing it all to have the chance to do the work they love. As a result of Stiletto Woman that idea became reality."

Karlena Wallace, M.A., sharpened her skills in human resources, revenue and finance, branding and communications. In 2002, while working in a management capacity, she launched her very own network for young professionals and built it from the ground up with no resources, contacts, or financial backing—she was the leading feature on the front page of the business section in The Lakeland Ledger (a New York Times newspaper at the time) as a trailblazer in the young professional space.

She continued to break new ground as principal of Stiletto Woman, a multi-functional media and empowerment platform for women, which produced a coveted magazine, awards and business conference. Adored for her authentic leadership, vibrant branding, and razor-sharp business acumen, audiences across the nation connect with her coaching style and empowering approach to business. Through her work she’s collaborated with and told the stories of trailblazers, legendary artists, athletes, business moguls, and TV personalities such as: Dr. Connie Mariano, the first military woman physician to the President of the United States, and first woman director of the White House Medical Unit; Tracy Evans, three-time Olympic athlete; Tina Sloan, legendary actress from Guiding Light, Law & Order; Mally Roncal, beauty mogul of Mally Beauty Cosmetics; Shirley Strawberry, co-host of The Steve Harvey Morning Show; Cheryl Burke,​ professional dancer from Dancing With the Stars; Margaret Cho,​ comedian and actress of Lifetime's Drop Dead Diva; Dee Wallace,​ veteran actress of renowned films E.T. The Extra-Terrestrial and Cujo, and so many more.

Karlena was also the executive producer and TV host of "The Business Zone," a cable network television show based out of Polk County, Florida. She's the

author of Stilettopreneurs Rock! Trading in Your Corporate Stilettos for the CEO Mindset; she served as an expert coach for the Chamber of Commerce's entrepreneur academy and was a national speaker for events in support of women in business. 


In the corporate and nonprofit sectors, Karlena has a proven track record of success. She’s provided financial oversight on budgets more than $800,000 and expense allocations over $600,000 annually; she’s managed the application of revenue over $900 million in the private sector; payroll budgets over $1 million and led various leadership teams. In 2013, Stiletto Woman was named one of the "Best 100 Websites For Women" by FORBES. She Owns It recognized Karlena as one of the "Top 50 Women to Follow on Twitter." In 2012, Stiletto Woman was also named one of the "Top 75 Websites for Your Career" by FORBES, and a "Top 25 Site for Women Entrepreneurs to Love" by She Owns It. 


In addition to her Master of Arts degree in Organizational Communication from the Scripps School of Communication at Ohio University, she completed the Ivy League Executive Education program in Strategic Human Resources Leadership from the School of Industrial and Labor Relations at Cornell University, and the Nonprofit Administration program from the Institute for Nonprofit Administration & Research at Louisiana State University Shreveport. Karlena also obtained a Bachelor of Science in Management, and an Associate of Applied Science in Computer Information Systems.