How are independent retailers preparing for the holiday season and how is technology, especially AI, helping them plan with precision, adapt quickly to shifts in demand, and compete with national chains on their own terms?
To answer this, Digital Journal spoke with Andrew Stern, CEO of Quilt, a software company helping small, independent retailers modernise their operations through simple, powerful retail technology.
Digital Journal: Retail headlines in the months leading up to the holiday season often focus on sales forecasts, promotions, earnings, and consumer spending expected for the industry’s largest retailers. What’s missing from that conversation?
Andrew Stern: What’s missing is the perspective of the independent retailers who make up 43.5% of the United State’s GDP. Most of the attention goes to national chains and e-commerce platforms because they dominate the data and their earnings reports drive headlines, but they are just one side of the story.
Specialty retailers operate on a different scale. They are talking to customers every day, adjusting what they stock and how they sell based on what people actually want in their communities. That kind of agility gives them a real advantage during the holidays. When demand shifts, they don’t have to wait for corporate’s word; they act on the spot and can be very nimble about sourcing products from new suppliers – maybe a friend of a friend who sells customizable drinkware or a local farm that can cut a special deal for local buyers purchasing bulk ingredients.
Technology makes that kind of flexibility sustainable. When a retailer has a clear view of their inventory and sales, or has access to tools that help them find answers quickly, they can make better decisions about when and how to adjust without adding more hours to the day. It’s not about keeping up with everyone else; it’s about running a smarter business and having more control when it matters most.
DJ: How do independent retailers, especially those selling specialized or unique items, plan for the holidays when they can’t pre-order or stock up on inventory months in advance like national chains? And how is technology, especially AI, helping them make smarter, faster decisions in that process?
Stern: Independent retailers plan for the holidays with precision, not prediction. They don’t have the purchasing power or storage space typically needed to pre-purchase on a large scale before the holidays. Their budgets are tighter, which forces smarter buying: every order has to earn its place on the shelf, and business owners have to be flexible to find the right product at the right price.
What’s changed in the past few years is how technology makes that kind of precision possible. AI tools can now surface insights that used to take hours of manual tracking: showing which products are trending, how pricing shifts might affect demand, or when to reorder based on sell-through velocity. For a specialty retailer, that kind of intelligence helps them compete with enterprise retailers that have dedicated analytics teams. This technology gives small retailers the same visibility into market trends and customer behavior that big chains have, but with the speed and context that fits how they actually operate.
DJ: When demand shifts suddenly during the holidays, speciality retailers can often adjust their inventory, pricing, and promotions almost overnight – something big-box chains can’t do. Does that level of agility translate into real competitive advantage, or is it more about survival?
Stern: It’s a bit of both. Agility starts as a matter of survival, but it quickly becomes a strategic advantage. Specialty retailers operate in shorter planning cycles, which means they’re used to making quick calls about pricing, promotions, or product mix. When the holidays bring unexpected shifts in demand, that mindset allows them to act fast without losing focus on profitability.
Over time, this responsiveness shapes how customers perceive them. Shoppers notice when their local store listens to feedback and adapts to offer them the products and services that they’re looking for. That reliability builds trust, which is hard for national chains to replicate. Agility may be a necessity in the moment, but it’s also what creates the kind of loyalty that carries these retailers through every season.
DJ: Can you share an example of a retailer you’ve worked with that navigates the holiday season in a creative or effective way?
Stern: The thrift stores we work with can adapt their pricing and product categories almost instantly as donations shift. Their software tracks which types of items are trending in real time, allowing them to adjust without waiting on corporate approvals or long planning cycles.
For example, one nonprofit thrift store noticed toy donations and purchases spiking early last November. They quickly pivoted their volunteer-led social posts to spotlight “kids’ holiday finds” and added a category-based sale in their POS system – 20% off kids’ items for two weekends. They immediately noticed a jump in sales and a doubling of donations, driven by the added campaign visibility.
Similarly, GrazeCart offers a feature called “pre-orders,” designed specifically for seasonal products like Thanksgiving turkeys and holiday boxes. It allows stores to secure early commitments from their best customers, simplify fulfillment planning, and avoid end-of-season waste, because no one’s buying a turkey the day after Thanksgiving!
DJ: How are technology and data helping level the playing field for small businesses this time of year?
Stern: Technology is changing what specialty retailers can do with their own information. For a long time, they relied on experience and instinct to plan the season, which worked up to a point. But now, they can see sales, inventory, and customer trends as they happen – and can increasingly use AI and other tools to automate this for them. That real-time view helps them make choices that protect cash flow and keep products moving.
The best retailers treat data like inventory. They track sell-through daily, watch margins, and adjust as the season unfolds. A jeweler might notice that a certain style is selling faster in one location than another and shift inventory in response. A pet store might see that a particular brand of dog toys is going viral online and adjust their in-store selection to match what their customers are looking for, often sourcing from local or regional suppliers that aren’t equipped to scale up to the big-box stores. Those are small adjustments that can make or break the season.
The real advantage is confidence. When retailers understand what’s working and what isn’t, they stop reacting out of fear and start planning with purpose. That’s the power of technology at this level – it gives small businesses the same clarity and control that large chains have always had, but in a way that fits into how Main Street actually operates.
DJ: What do you think this holiday season will reveal about how far independent retailers have come and where the market segment is headed next?
Stern: This holiday season will be a good measure of how specialty retailers have grown as operators. They’ve moved from reacting to trends to anticipating them. You can see it in how they manage cash, plan assortments, and use information to guide decisions. Increasingly, they’re embracing technology to automate the parts of running a business that bog down owners and give employees access to tools that streamline more intensive work like optimizing repair queues in musical instrument shops, digitizing custom engraving requests in jewelry stores, or using AI to categorize and price unique products as they come through the door. Some are even using forecasting tools that automatically purchase orders based on sell-through rates or local event calendars.
I think we’ll also see more recognition that specialty retail isn’t just a niche segment, it’s a major part of the economy with its own momentum and playbook. The retailers who have invested in better systems and partnerships are proving that you don’t need scale to be sophisticated.
