Monday, 15 April 2013 08:59

Contessa Gibson: Type A with a smile Featured

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Contessa Gibson is a native of Chicago and works as a national account executive with the Professional Diversity Network where she oversees Diversity and Inclusion corporate sales within 13 Midwestern states, helping corporations diversify their talent pipelines. In addition to her day job, Contessa recently launched a technology venture, Plus Navigator, which delivers smart matching of customer apparel targeted to the under-served extended sizes market. She gives generously of her time and resources to support diversity and non-profit initiatives which support empowerment and the positive development of self-esteem. In her experience, “Exposure to positive, empowered women as a youth has paid invaluable dividends that words cannot communicate.”

I first met Contessa when I joined the YWCA Chicago's Future Leaders Council where she was also a member. She granted me an in-depth interview that was published on my blog last year.  I was excited when she agreed to provide a 2013 update. Here are some insights into the personal and professional sides of Contessa Gibson.   

The Personal


  • Personal Motto: I opt for the Golden Rule every time, Do unto others as you would have them do unto you.
  • Words of Wisdom:  It’s often not how you start, but how you finish that matters in personal and professional endeavors and accomplishments.
  • Currently Reading: The Lean Startup: How Today’s Entrepreneurs Use Continuous Improvement to Create Radically Successful Businesses by Eric Ries
  • Last Vacation Location: Washington, DC
  • Currently listening to:  Patti Labelle Pandora Station
  • Favorite Past time: Socializing with friends who keep me accountable to my personal and professional goals.
  • Supported Charities: United Way, Junior League, YWCA
  • Alma Mater: University of Rochester
  • Home Town:  Chicago, IL
  • Guilty Pleasure:  Leisurely pinning things onto Pinterest
  • Biggest Wish: TODAY show feature for my technology startup
  • Favorite T.V Show:  Although I gave up television three years ago, I still manage to catch episodes of The Office, a personal favorite.

The Professional


Sherry:  You recently launched your own business. Tell me a bit about it.

Contessa:  It’s called PlusNavigator, a solution designed to simplify and empower the plus size shopper to get the items she needs and desires.

What inspired you to launch your business?

A large void in the market, with an obvious failure to serving a growing population of women (size 12 and up) in the country.

Were you able to tap into any Chicago-based startup incubators?

Yes, I applied, was accepted, and graduated from the Founder Institute incubator—a program offered in 39 cities, and 5 continents that is an early-stage startup accelerator and global launch network that helps entrepreneurs create meaningful and enduring technology companies. 

What advice would you give other young entrepreneurs?

Never leave home without the two P’s: Patience and persistence, and it’s imperative that you keep an open mind while never losing your core vision.

Would you mind sharing your five-year plan? 

Huge question, in a nutshell. Continuing my personal commitment to my civic duties, continue to build meaningful relationships and give back on an ongoing basis for the next figurative ‘Contessa Gibson’ trying to figure it out.

Do you think your experience as a sales executive with SmithBucklin helped you when launching your own business?

Sure.  Every professional job opportunity that I’ve accepted, even from my statistician days at Discover Card, lend useful resources, information and skills that propel me closer and closer to my personal goals and ambitions. I seek out opportunities which create a suitable win-win-win for me personally and professionally, while also delivering great value to my employers of choice.


Read Contessa’s full-length 2012 interview while she was still with SmithBucklin and in the process of launching her business.

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Sherry Clayton

Sherry Clayton is a leader, mentor, manager and non-profit champion and a strong believer in putting ideas into action and becoming a better citizen through individual accountability, collective action, self-awareness and growth. She grew up on the Southside of Chicago and currently resides in the River North neighborhood with her husband of 10 years. She current works as a Finance Project Manager with Chicago Public Schools.

In 2004, Sherry helped to launch an African-American Executive networking group geared towards providing the professional development, networking and sales support needed for junior executives to progress along the partner track. She also leads and supports several community organizations.

Website: Email This email address is being protected from spambots. You need JavaScript enabled to view it.

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