150 New Features, One Big Question: Will Anyone Use Them?

Shopify's Winter '26 Edition arrived with fanfare: over 150 launches and enhancements, all centered on AI. The rebuilt Sidekick promises to evolve "from reactive assistant to proactive collaborator." Agentic Storefronts put products into ChatGPT, Perplexity, and Microsoft Copilot. But beneath the marketing lies a trust problem that Shopify hasn't solved.

As one analyst told Retail Brew: "Mature merchants don't trust this stuff yet." The question isn't whether Shopify's AI is impressive—it's whether merchants will let it touch their businesses.

The Sidekick Evolution

Shopify's vision for Sidekick is ambitious:

• Proactive Recommendations: Rather than waiting for merchant questions, Sidekick now actively monitors stores and surfaces opportunities

• Sidekick Pulse: Analyzes store data alongside market trends to deliver "personalized, high-impact recommendations you can act on immediately"

• Direct Action: Sidekick can now "build code and make changes directly"—not just suggest, but execute

• Co-Founder Positioning: Shopify suggests viewing Sidekick "more as a co-founder" with "extensive knowledge about the merchant and their store"

"Instead of Sidekick being an assistant, view it more as a co-founder. Because it contains extensive knowledge about the merchant and their store, it can operate behind the scenes to identify growth opportunities." — The Letter Two

The Trust Problem

Merchants aren't buying the vision—yet. According to Retail Brew analysis:

• Error Rate Concerns: "The question is whether they can get the reliability high enough before merchants just tune it out entirely"

• Low-Stakes Only: Even optimistic projections suggest merchants might only trust Sidekick for "low-stakes tasks" where errors don't matter

• Trust Must Be Earned: After years of overpromising AI capabilities across the industry, merchants are skeptical

• Business-Critical Hesitation: Giving AI permission to "make changes directly" to revenue-generating stores feels risky

Agentic Storefronts: The New Discovery Play

Shopify's most forward-looking feature puts products into AI conversations:

• Multi-Platform Presence: One setup makes products discoverable on ChatGPT, Perplexity, and Microsoft Copilot simultaneously

• AI Shopping Integration: As consumers increasingly use AI assistants for shopping research, Shopify wants merchants present in those conversations

• No Separate Apps: Unlike previous integrations requiring platform-specific work, Agentic Storefronts promise unified deployment

• Brand Control: Merchants can influence how their brand appears in AI responses

The Tinker Experiment

Coming January 2026, Tinker addresses the blank-canvas problem:

• Product Concept Generation: AI helps entrepreneurs generate product ideas before they have inventory

• Ideation Acceleration: Rather than starting from scratch, merchants get AI-generated starting points

• Pre-Launch Tool: Designed for the earliest stage of the merchant journey

The Industry Context

Shopify's AI push aligns with broader retail trends:

• 87% Revenue Impact: According to Shopify's enterprise research, 87% of retailers report AI has positively impacted revenue

• 94% Cost Reduction: Nearly all retailers surveyed report AI reducing operating costs

• Expertise Gap: A 2025 Bain report notes 44% of executives cite lack of in-house AI expertise as a barrier

• Implementation Challenge: The gap between AI potential and actual deployment remains wide

"Mature merchants don't trust this stuff yet. If error rates drop, merchants might trust Sidekick for low-stakes tasks. The question is whether they can get reliability high enough before merchants tune it out entirely." — Retail Brew Analysis

What Merchants Actually Need

The gap between Shopify's vision and merchant reality:

• Reliability Over Features: Merchants want AI that works consistently, not AI that does more things inconsistently

• Transparent Reasoning: When AI suggests changes, merchants need to understand why—"trust me" isn't enough

• Easy Reversal: If AI makes changes, undoing them should be trivial

• Gradual Autonomy: Starting with suggestions, earning trust, then gaining permissions for direct action

The Competitive Landscape

Shopify isn't alone in AI commerce:

• Amazon's Rufus: AI shopping assistant with massive scale but accuracy concerns

• Klarna's AI: Handling customer service at scale, demonstrating AI commerce viability

• Platform Wars: Every major e-commerce platform now has AI initiatives; differentiation is difficult

The Bottom Line

Shopify's Winter '26 Edition represents a genuine bet on AI commerce. The technology is impressive, the vision is coherent, and the features address real merchant needs. But the trust problem remains unsolved. Mature merchants have seen too many AI overpromises to hand over control of their businesses based on marketing materials.

The key question: Can Shopify demonstrate reliability before merchants tune out? The 150 features mean nothing if merchants won't use them. Sidekick's evolution from assistant to "co-founder" requires earning trust that hasn't been established yet.