Our Founder

Our team

About Our Founder

Caryn Kent Dean is the CEO and Founder of Once Upon an RFP, a proposal services consultancy based in Chicago.

Founded in 2018, she enjoys supporting Once Upon an RFP clients with their Request for Proposal-based proposals, diverse certification applications, vendor registrations, and related marketing and business development activities. Major accomplishments include delivering proposals that are 100% compliant and 100% on time and helping clients win over $450M in new contracts.

Once Upon an RFP is certified as a Woman-Owned Business Enterprise (WBE) by WBENC, as a Woman-Owned Small Business (WOSB) by the Small Business Administration, and as a Disabled-Owned Business Enterprise (DOBE) by Disability:IN. 

Caryn holds Practitioner Certification from the Association of Proposal Management Professionals (APMP). She holds a Master’s in Library and Information Science from Dominican  University in River Forest, IL.

When Caryn is not working with clients, she enjoys spending time with her husband, three kids, and rescue puppy, Scout.

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CARYN KENT DEAN

FOUNDER + CEO
(MEET THE FOUNDER)

Caryn 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 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. 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. At that time, only 1,127 professionals around the world had 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 will find her with her husband, kids, and sweet puppy, Scout.