Dickey was born to Roland Dickey Sr. and his wife Maureen. His father, along with his uncle Travis "T.D." Dickey had taken over their father's barbecue restaurant, and Dickey grew up helping them as they expanded the business from one location to several and eventually began franchising. Dickey's father taught him their family's secret smoking process, and the restaurants' catering van served as his first car.
After graduating from high school, Dickey was accepted to Southern Methodist University, the alma mater of both his parents and uncle, and began attending the school in 1992. He graduated from the private research university in 1996 with a bachelor's degree in business administration.
Dickey sought to acquire knowledge and insight on his own before joining the family business, and so he started his career working for other companies within the restaurant industry. Working in many different roles, he eventually gained experience both within the sector and in leadership that saw him ready to become a part of Dickey's Barbecue Pits in 1999. By 2006, his business acumen saw him take over as chief executive officer, and as he became the third generation to run the family business he began to implement his high aspirations for the company.
One of Dickey's strongest legacies for the company has been his push to grow the franchise nationally, and thanks to his focus on strong yet sustainable growth, he has been able to create scalable success. His emphasis on quality carries throughout the company, from sourcing the meat to selling fresh rolls instead of the barbecue standard of white bread. To ensure that the rapid influx of franchises didn't result in disparities between locations, he worked to develop an intensive owner-operator training program called "Barbecue U." In the two-week program, the trainees learn how to run the restaurants correctly from open to close, and the training session ends with them catering for the corporate office to prove they have mastered every aspect of running a Dickey's Barbecue Restaurant.
Thanks to Dickey's aggressive yet calculated growth strategy, the brand is the largest barbecue franchise in the United States and has grown from 20 locations to over 500 across the nation in his time leading the company. He has sought to strategically invest in marketing and technology to create results that are driven by data rather than whims and ideas, and in order to prepare for the push to expand nationally, he ensured the company had made adequate capital investments. By backing information technology, marketing, advertising, construction, real estate management, logistics, accounting, and field operations support, Dickey was able to ensure that they were capitalizing on every franchising opportunity without experiencing the growing pains that typically come with rapid growth.
Big data has also been an essential part of his business plan, and working in tandem with his wife and chief information officer of Dickey's Barbecue Restaurants, Inc. Laura Rea Dickey, he developed a proprietary data platform called Smoke Stack. The program allowed them to synthesize data from their point-of-sale systems, marketing promotions, loyalty programs, customer surveys, and inventory systems to provide real-time feedback on sales and other key performance indicators. In this way, the company was able to remain true to its Texas roots while also utilizing modern technologies to ensure success, and the platform was profiled by Forbes Magazine and the Wall Street Journal for its innovation within the restaurant industry.
In order to better meet the demands of the rapid growth Dickey's Barbecue Restaurants was experiencing, in 2016 the company decided to restructure and create Dickey's Capital Group. This new business would act as a holding company for everything under the Dickey's brand, and leadership was reorganized with Dickey made chief executive officer. In this role, Dickey oversees his family's entire portfolio of businesses, which in addition to the franchise business includes manufacturers, real estate, metal fabrication, distribution companies, and retail products. In particular, under his leadership, the Dickey's brand has entered into a deal with Walmart to carry their three signature sauces across 2,000 of their locations in the United States.
As the company has come to be one of the top franchises in the nation, Dickey has been recognized for his work in the growth of the company. He has been included in Restaurant Business Magazine's "The Power 20" list, he was on D Magazine's "Top 500 CEOs" list for two years in a row, and Nation's Restaurant Magazine has named him one of the 50 most powerful people in foodservice.
Since he took over as chief executive officer, the Dickey's Barbecue Restaurant's name has also been heralded across multiple publications. OSR awarded it the "Best Franchise Deal" two times, it was recognized as one of Fast Casual's "Top 100 Mover and Shakers" for four consecutive years, received Global Franchises' "Best Food and Drink Franchise," and the "Most Established Brand" award from Franchise Help. Dickey's work on the company has also been recognized in national publications, such as Entrepreneur Magazine, Forbes Magazine, and the Wall Street Journal.
Dickey is passionate about providing support to first responders and is on the board of directors for the Dickey Foundation. The foundation was originally called "Barbecue, Boots, and Badges" and works to support first responders on both a local and national scale, providing aid both financially and through donations, such as shields, helmets, respiratory masks, and other such safety equipment.
In 2017, when Hurricane Irma and Hurricane Harvey devastated Dickey's home state of Texas, he was able to raise $20,000 in aid through the foundation, and he and his wife also personally contributed an additional $25,000 in support.
In 2018, the foundation garnered enough funds to provide a top-of-the-line bulletproof vest to all of the officers in the Dallas Police Department.
In 2020, during the coronavirus pandemic, when essential workers were needed more than ever, Dickey and the foundation organized a national campaign through their restaurants to provide both support and financial aid to those on the frontline. They began selling First Responder Packs in all of their locations, allowing guests to donate Dickey,s Barbecue Restaurant meals by purchasing one of the packs, and the Dickey family matched every sandwich donated.
From July to September, the restaurants also ran a limited edition of their iconic Big Yellow Cups. For each cup sold, a portion of the proceeds were donated to the Dickey Foundation, which in turn used the funds to provide aid to essential workers. With over 1.2 million cups sold during the promotion, that resulted in over $150,000 going to front-line heroes.
