Cheek graduated summa cum laude from Vanderbilt University in 2005, where she studied economics and psychology. She later went on to attend Harvard Business School, graduating with a Master of Business Administration. 
She began her career as a consultant at Deloitte Consulting in July 2006. Cheek performed analyses, created and implemented executive recommendations, and developed high-level client relationships. In July 2011, she was the Director of Strategy and Operations at the George W. Bush Presidential Center. 
At age 29, while at MoneyGram International, she was feeling burnt-out. Cheek didn't think she should have been feeling brain fog, fatigue, and aches and pains. She used her corporate health insurance to see several specialists, each of whom ran lab tests. She would wound up paying $2,000 for the services but didn't feel any closer to a diagnosis. 
This problem led her to start EverlyWell in 2015. Her mission is to create an affordable, insightful product, any American can benefit from.  Cheek's work has been featured in Forbes and Inc.