Listen To My Latest Podcast Episode:

MU173: Mary Ann Stenquist | Become Unshoppable: Find The Money To Fund The Life You Want—With The Money You Have

Listen To My Latest Podcast Episode:MU173: Mary Ann Stenquist | Become Unshoppable: Find The Money To Fund The Life You Want—With The Money You Have

Overcoming Mediocrity - Volume VIII


Caryn Kent Dean

Caryn Kent Dean is an introvert, creative and sensitive entrepreneur. She grew up in La Grange Park, IL and received her B.A. Arts, Classics and B.S. Science, Anthropology, both Cum Laude, from Loyola University of Chicago. She is an alum of the 1999-2000 class that studied at Loyola’s John Felice Rome Center. In 1997, she completed her Master of Library and Information Science at Rosary College (now Dominican University) Circumstances after library school led to her introduction to the work of a proposal professional. After six years and a variety of roles, including as a software company’s first Proposal Manager, Caryn decided to pursue other interests.

She was married to the love of her life, Corey Dean, in 2002. They lived in Chicago and then moved to Villa Park, IL in 2006. As children came along, she had the great honor of being a full- time mom for ten years. She returned to the corporate world in another proposal-related position, when her youngest entered full-day kindergarten. Four years and two companies later, Caryn was inspired to leave corporate and become an entrepreneur.

In 2018, Caryn founded Once Upon an RFP, where they transform clients’ proposal stories to win the best business and make a bigger impact. You’ll now find Caryn enjoying her work with clients, as well as the creative and intellectual challenges of business ownership.

The Association of Proposal Management Professionals (APMP) recognized Caryn with Foundation Certification in 2016. In May 2019, APMP recognized Caryn with Practitioner Certification. To date, only 1,127 professionals around the world have been recognized at this level.

In addition to professional certification through APMP, on September 19, 2019, the Greater Midwest Chapter recognized Caryn as 2019 Member of the Year. She was nominated for spearheading the effort to create a Virtual Networking Group to connect proposal consultants with their peers and provide relevant programs and support.

When Caryn’s not working with clients or on her business, you’ll find her with whom she loves best, her husband, kids, and sweet puppy, Scout.


Caryn Kent Dean
Once Upon an RFP LLC


My Story

Transform Your Story. Transform Your Impact.

Have you ever felt like everything was all wrong, even though it looked perfect on paper? Caryn shares your story. She had a wonderful husband, three beautiful kids, and the opportunity to continue her career in corporate, after ten years as a full-time parent. However, she only made it four years because of the impact of family and a high-pressure position on balance, health and happiness. Read Caryn’s story to learn about the steps she took to getting herself back on track.

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