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Virginia Retail Matters 2026: A Day of Insight, Connection, and Looking Ahead

Virginia Retail Matters 2026: A Day of Insight, Connection, and Looking Ahead

Virginia retail is built on connections. Connections between business owners and customers. Between local shops and the communities they serve. Between tradition and innovation. On September 24, those connections came to life as leaders from across the Commonwealth gathered at the Hampton Roads Convention Center for the fourth annual Virginia Retail Matters.
 
More than a conference, Virginia Retail Matters is a space where meaningful conversations happen, new partnerships take shape, and the future of retail is explored through a shared lens of opportunity and growth. At a time when retailers are navigating rapid change, attendees came together not only to gain insight into industry trends, but also to celebrate the resilience, creativity, and community spirit that continue to define retail across Virginia.
 
This year’s theme, Intersections, perfectly captured the spirit of the day. As Retail Alliance President & CEO Jenny Crittenden noted in her welcome remarks, retail exists at the intersection of “global commerce and local opportunity, entrepreneurship and economic growth, business and community.” While products move through Virginia’s ports and storefronts every day, she reminded attendees that retail’s greatest impact is ultimately measured through people, relationships, and the communities businesses help sustain.

“But retail is about more than products. It’s about people. The relationships we build, the jobs we create, and the communities we strengthen. Long after a purchase is forgotten, the connection remains. That’s why retail matters.”

Jenny also highlighted Retail Alliance’s ongoing commitment to supporting retailers through education, advocacy, resources, and meaningful connections. She recognized the retailers in attendance as the reason the organization continues its work, acknowledging the vital role businesses of every size play in strengthening Virginia’s economy and local communities.

Following Jenny’s welcome, Hampton Vice Mayor Steven L. Brown offered remarks on behalf of the host city, emphasizing the importance of strong partnerships between business, civic leadership, and community organizations. Drawing on his background in workforce development, housing, and public service, Brown spoke to the critical role retailers play in creating vibrant commercial districts, generating opportunity, and helping communities thrive. His remarks served as a fitting reminder that retail success and community success are deeply connected, setting the stage for a day centered on collaboration, innovation, and shared growth.

A highlight of the program was the presentation of the 2026 Virginia State of Retail Report by Dr. Matt Wagner, Chief Innovation Officer for Main Street America. Commissioned specifically for Virginia Retail Matters, the report explored the trends shaping retail across the Commonwealth, including consumer behavior, workforce concerns, economic pressures, artificial intelligence, local sourcing opportunities, and the future of Main Street businesses.

The research reinforced something many in the room already knew, independent retailers are about far more than sales figures and storefronts. They create gathering places, support local entrepreneurs, strengthen neighborhood identities, and contribute to the vibrancy that makes communities unique. Strong retailers help create strong communities, a principle at the heart of Retail Alliance’s mission for more than 120 years.

The conversation continued with one of the day’s most anticipated sessions, a fireside chat featuring Jaylen Boney and Ava Giacometti. Building on insights from the report, the discussion explored the perspectives of Gen Z, one of the most influential and rapidly emerging consumer groups in today’s marketplace.

Attendees heard firsthand about how younger consumers discover brands, make purchasing decisions, and determine which businesses earn their trust and loyalty. The conversation offered valuable insight into the importance of authenticity, community involvement, convenience, and purpose-driven connections.

Perhaps the biggest takeaway was that while shopping habits may continue to evolve, the desire for genuine relationships and meaningful experiences remains constant. Retailers weren’t simply learning about Gen Z; they were hearing directly from the next generation of customers.

The afternoon concluded with an engaging panel discussion on artificial intelligence and its growing role in the retail industry. The panel brought together Rachael Seda of Mix & Shine Marketing, Ted Patterson of The AI Collective, and Tom Rosser and Chris Clark of Gelati Celesti to discuss AI’s practical applications for businesses of all sizes.

Rather than focusing on headlines and hype, the conversation centered on real-world questions retailers are asking today:
  • How can AI help businesses better understand their customers?
  • How can it improve efficiency and decision-making?
  • How can retailers embrace innovation without losing the authenticity and human connection customers value most?
Panelists shared examples, opportunities, and lessons learned while emphasizing a theme that resonated throughout the discussion: technology should enhance relationships, not replace them. Building on that momentum, Retail Alliance announced the inaugural AI in Small Retail Summit, coming in early 2027 through a partnership between Retail Alliance, the Retail Alliance Foundation, and The AI Collective. The event will provide practical, retailer-focused education designed to help businesses navigate emerging technologies while maintaining the human-centered experiences that define great retail. As the event drew to a close, Jenny reflected on the insights shared throughout the day and the opportunities that lie ahead.

“Today we’ve explored the intersections shaping retail, from consumer trends and technology to community impact and economic change. The future of retail won’t be shaped by reports alone. It will be shaped by the business owners and leaders in this room who choose to adapt, innovate, and continue investing in their businesses and communities.”

That sentiment perfectly captured the spirit of Virginia Retail Matters 2026. While data, technology, and economic forecasts are important, the future of retail ultimately depends on the people behind the businesses: the entrepreneurs opening their doors each morning, the employees serving customers, and the communities that support local commerce.

Attendees left with more than data, trends, and actionable insights. They left with new connections, fresh perspectives, and a renewed appreciation for the impact retail has on our communities every day.

Retail Alliance is honored to convene these conversations and celebrate the businesses, leaders, and individuals who keep our industry moving forward. Thank you to our speakers, panelists, sponsors, partners, volunteers, and attendees for making Virginia Retail Matters 2026 a success.

Thank you to everyone for being part of Virginia Retail Matters 2026. We look forward to continuing the conversation and welcoming you back on September 22, 2027, at The Main in Norfolk for the next Virginia Retail Matters.

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