A familiar face to many in the Gloucester area has taken the reins of the Retail Alliance.
Jenny Crittenden, who led Gloucester’s Main Street Preservation Trust for 16 years, was appointed by the Retail Alliance Board of Directors as president and CEO, effective Feb. 16. She has replaced Ray Mattes, who announced his retirement in October 2022.
The Retail Alliance is a nonprofit trade association serving the interests of local retailers in the Hampton Roads region since 1903. The organization, which includes a number of Gloucester businesses as members, promotes and supports the healthy growth of retail businesses and trade through education, advocacy and member benefits.
Crittenden previously served as Senior Vice President of Retail Alliance. She is just the second woman appointed president and CEO in the organization’s 120-year history.
“We are very fortunate to have Jenny lead our organization into the next chapter,” said Mattes. “Working with Jenny during the past 14 months, I have found her to be extremely passionate of not only the mission but the future of this organization. Jenny is extremely professional, loves retail and operates with a high degree of integrity, all characteristics of a true leader. Under Jenny’s leadership, I am extremely confident that Retail Alliance will continue to grow and evolve.”
“Jenny has been my rock since Sweet Tooth Café started, and she helped develop and grow my business into the place it is today,” said Crystal Burton, owner of Gloucester’s Sweet Tooth Café and Bakery. “She is a true champion for entrepreneurs, and I am beyond thankful for all her work, dedication and believing in me.”
In addition to her position with the Main Street Preservation Trust, Crittenden was executive director of the Cook Foundation and held the marketing and sponsorship chairs for the Gloucester Arts Festival.
“Working with Jenny over the past 16 years has been an exciting and productive adventure. Jenny identified so many opportunities and made them a reality for our community,” said Cook Foundation founder Adrianne Ryder-Cook Joseph. “She embodies the best of professionalism combined with personal warmth and excellent leadership. Retail Alliance is very lucky to have her at the helm.”
During the pandemic, then-Gov. Ralph Northam appointed Crittenden to represent small brick-and-mortar retail on the Governor’s COVID-19 Business Task Force to help develop reopening guidelines for businesses in Virginia.
“Prior to being asked if she would consider interviewing for the CEO position at Retail Alliance, Jenny was a dedicated member of the Board, exhibiting a passion for the success of member retailers,” said Bob Gurnee, Chairman of the Board of Directors at Retail Alliance. “During the interview process it became unanimously clear that she would be the right choice to lead the organization into this new era.”
Under her leadership, Gloucester’s Main Street Preservation Trust was honored with a national Main Street Forward Award in 2021, showcasing successful recovery and resiliency efforts and execution of an e-commerce platform for downtown businesses. Inside Business awarded her with a Women in Business Award in 2021. The awards celebrate women who have been successful in their businesses and careers, contribute to the community and serve as an example to others, something Jenny continuously strives to achieve.

