This year belongs to bold business owners who are willing to experiment.
More than 40 business operators using Square across industries and continents shared their major predictions for 2026, signaling emerging industry trends. Many predict technology, especially AI systems, will do more heavy lifting from creating content to personalizing customer outreach. At the same time, business owners expect the experiences they offer to feel even more human and memorable.
Owners are stepping into the new year with sharper technology, tougher priorities, and an appetite for reinvention. They predict the right combination of human connection and behind-the-scenes optimization will be what drives business growth in 2026 and beyond.
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Rising pressure will lead to innovation.
With labor, ingredients, tariffs, and shipping costs climbing, business owners say efficiency and innovation are top of mind for the year ahead. Low-performing product lines and services will get phased out quickly, while those that do well will take the spotlight. The competitive edge will go to owners who adapt quickly, and meet changing customer expectations. One industry trend tied to this shift is re-strategizing offerings in a way that blurs category lines.
Costs and customer habits will be the biggest factors affecting my industry in 2026. We’re already seeing a major shift in customer frequency around hair coloring, and we’re seeing a shift into wellness. Many salons, including my own, are offering head spa services to appeal to the wellness-focused clientele.
Tori Rutledge, Owner at Tori Lennell Salon in Fort Worth, Texas
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02
AI will raise the bar for personalized customer experiences.
Business owners predict AI will help them accomplish more and understand how their business is performing. But they also see AI as an open door to hyper-personalized services for customers. In a recent analysis of
Square AI query data, questions about customer preferences came second only to business performance questions. For beauty businesses, owners say AI could help artists deliver elevated, intentional results that match each customer’s energy, features, and lifestyle. Business owners across retail and food and beverage say they plan to hand off marketing tasks to AI while they focus on high-impact customer interactions.
“Customer expectations are shifting fast. People want personalized shopping — whether online or at events like fairs — and they’re influenced more by short-form video and social media stories than ever before. I’m preparing by investing in visual storytelling (AI-generated product photos, videos, and live content scheduling) to meet that demand.”
Randy Fulk, owner of Korie’s Kloset in Seminole, Florida
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03
Community will beat big-box convenience.
Business owners say consumers are looking for human connection in 2026. Think
immersive experiences, in-person activities, and small luxuries that feel personal and worth sharing. Business owners told us they plan to create
“third spaces” in their neighborhoods, offering events, products, and entertainment (bonus if it can be shared online), that bring people can together. Mentions of “community” in
Square Marketing users’ emails jumped by 36% in 2025 compared to the year prior.
To succeed, we will focus on innovation, premium quality, and memorable experiences, ensuring we remain a standout destination in the community. Experiential and highly shareable products like interactive desserts and events will become the key differentiator for local businesses, shaping who thrives in 2026.
Sabrina Macchione, owner of Whimsy Street Treats in Georgetown, Ontario
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04
Money's tight. But customer spending will align with their values.
Customers are on the hunt for other kinds of value, whether that’s a compelling story, sustainable practices, exceptional quality, community building, or unique product lines. Looking at U.S. Square data from 2024 to 2025, items labeled as “local,” “handmade,” or “artisanal,” grew by 6% among sellers active since at least 2023. This year, business owners expect even more discerning buyers who purchase with intention. They predict customers will reward businesses that deliver what’s most important to them on an individual level.
“It’s not just about value; it’s about quality. People are spending money to get something worthwhile. People are not just going to go where their dollar stretches the most; people are going to spend on things that are great.”
Evan Bloom, co-founder of Wise Sons Deli in San Francisco
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