Sherry Clayton

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.

Monday, 15 April 2013 08:59

Contessa Gibson: Type A with a smile

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.

Friday, 04 January 2013 13:52

Jason Gilmore: "Turning on the Juice"

After eight years on the road as a technology consultant with Accenture, I decided to take a management position with Chicago Public Schools in 2008. Being in my home city everyday made it apparent that I had developed very few personal and professional relationships in Chicago. A valued mentor recommended that I expand my network and actively engage people on a deeper level. This interview series is the result of that exercise in self-development. In this part of my personal and professional journey, I will share the stories of the insightful, inspiring, talented and accomplished Chicagoans I meet along the way.

Jason headshot

The inaugural profile of The Personal and the Professional features Jason Gilmore. Jason and I met in the fall of 2012 at a strategic planning session for the Chicago Chapter of the National Urban Fellows. He immediately captured my attention with his poise and presence but I quickly realized that he was a man of insight and substance as well. During the meeting, Jason was quick to contribute insights, ask questions and offer assistance. I immediately added him to my list of people to know. Jason was kind enough to answer some probing questions this past December. An extended version of this interview can be found on my blog at

The Personal

Jason Running

• Home Town: Detroit, MI
• Personal Moto: Have a vision and be demanding.
• Words of Wisdom: Be careful what you choose. You may get it.
• Currently Reading: It Worked For Me by Colin Powell
• Last Vacation Location: Puerta Plata, Dominican Republic
• Currently listening to: good Kid m.A.A.d city by Kendrick Lamar
• Favorite Past time: Running – ran Detroit marathon this year
• Supported Charities: Charity Water, Oceana, PAWS Chicago
• Alma Mater: University of Michigan
• Nickname: I was called "Juice" until I was 12 because I could "turn on the juice" and run really fast.
• Guilty Pleasure: Reality TV
• Biggest Wish: To race the Boston Marathon
• Favorite Sports Team: Detroit Tigers, Lions, and Pistons
• Favorite T.V Show: Game of Thrones 

The Professional

Jason reading - Revised

Stylish, enigmatic and intelligent, Jason Gilmore creates quite an impression. He moved from Detroit to Chicago in October of 2010 where he is currently employed as Manager of Foundation & Government Grants for Access Living of Metropolitan Chicago. The majority of his time is divided between identifying and prioritizing activities to engage donors, managing and engaging with a portfolio of donors, and guiding cultivation and solicitation strategies for donors.

The only members of Jason's family in Chicago are his wife and his extended Greek family of Phi Beta Sigma Fraternity, Inc. His wife works for a national consulting firm which promoted her to a senior level position based in Chicago. At the time, Jason was working as a Chief Compliance Officer & Academic Grant Writer for Covenant House Academies in Detroit.

Eventually, Jason would like to return to Detroit and contribute to the resurgence of the city. The motto of Detroit is "Speramus Meliora; Resurget Cineribus" which translates into "We Hope For Better Things; It Shall Rise From the Ashes". Jason believes he has a duty to try to embody that hope and contribute to the resurrection. This is no surprise. Afterall, he has always been interested in offering service to others.

In addition to being actively involved in the Association for Fundraising Professionals Chicago Chapter where he recently completed a fellowship, Jason is seeking to volunteer with a well-established and effective mentoring program geared towards young black men. His own uncle provided a vigilant and well structured guidance which helped him become the man he is today. All young men should be as fortunate.

Jason X. Gilmore | Manager of Foundation & Government Grants
Access Living of Metropolitan Chicago
115 West Chicago Avenue
Chicago, IL 60654
Direct: (312) 640-2185TTY: (312) 640-2102

Thanks for reading and I hoped you enjoyed learning more about the personal and professional sides of Jason Gilmore. Expect to see a new profile soon and be sure to follow this blog so that you will receive the latest updates, interviews and articles.