Dawn attended Ohio State University where she earned her BA in broadcast journalism. She went on to earn a BS in information technology at DeVry University. Later, she founder herself at Indiana University – Purdue University Indianapolis studying fundraising management and philanthropy. 
In 2001 Dickson was a marketing manager for Nationwide Insurance, helping agents build intranet sites for their firms. In 2002 she founded and operated TheUrbanStarr.com for nearly seven years. The site was a dynamic guide to the best social and community events, networking opportunities, and entertainment in the Columbus metro area.
She then spent a couple of years as marketing and business development coordinator at HBCU.com (Historically Black Colleges and Universities). During that time she was also working as the founder and managing partner of D1 Consulting Group, a national event management, non profit business development, fundraising and marketing consulting firm with divisions in Atlanta and Dallas.
In 2011 she set off to found yet another company, this time a unique venture called Flat Out of Heels. The company produces vending machines that provide compact ballet flats in areas where women need relief from wearing heels, like airports, nightclubs, retail centers, convention centers, conference facilities, and other high traffic areas. She started her next company (Solution Vendings Industry, which is now PopCom) as a means to distribute her Flat Out of Heels idea. 
In 2012 Dickson founded PopCom, a next generation kiosk and vending machine company that uses facial recognition, AI, and blockchain technology to help retailers collect valuable customer insights. Dickson went through NewME, a startup accelerator for minority entrepreneurs that was started in 2014. She was also in the Canopy Boulder accelerator program, Google accelerator program and Techstars, she spoke about it in an interview: 
Each program taught me something different: NewMe developed me as an entrepreneur and gave me access to lawyers and developers to help me grow. Canopy Boulder taught me about working in tech and Techstars gave me mentors who spoke the language
She also appeared on popular hip-hop show The Breakfast Club where she spoke about how hard it is being a woman of color trying to raise money from venture capitalists.
Dawn is an aggressive go-getter and her trophy wall shows that. Here are just some of her accomplishments: 
- She was named "Hero in the Movement" from the NUL Young Professionals Association at the National Urban League Gala in August 2018.
- She was a finalist at the G4A Generator Competition
- She was a finalist at the ShopTalk Start Up Competition
- She was a finalist at the Rise of the Rest Competition
- She won the 2016 American Dreamer Award
- She placed 2nd in the national SBA InnovateHER Business Challenge
- She took first place and won $25,000 in the PowerMoves NOLA Big Break Power Pitch competition
- She won a Miami Legacy 40 Under 40 Award
- She was named one of 50 Young Visionary Women Leaders to Watch in 2015
- She placed second in the REVOLT Music Conference Business Pitch Competition
- She was a National Finalist at the Tech Cocktail Start Up of the Year
- She took first place at Miller Coors Tap the Future 2 Minute Pitch Competition
- She was recognized in Who's Who of Black Atlanta
- She was recognized in Who's Who of Black Columbus in 2007 and 2008
- She holds a patent for her intelligent vending machine