What retail leaders said at eTail Boston: AI, stores, quick commerce, and loyalty

At eTail Boston, retail executives focused on concrete operational choices rather than abstract trends. Conversation clustered around four topics: how to adopt AI responsibly, why physical stores still matter, the revival of sub-30-minute delivery, and loyalty designs that change behavior.

Target's SVP of technology, Brad Thompson, described the company's early AI work as "dicey" because of hallucination risk. The practical response: build and control key systems internally. Target's e‑commerce stack is custom-built, and the teams that decide to deploy AI are the company's own software developers and data scientists. The takeaway is tactical: reduce external dependencies on black-box models when quality and factual accuracy matter.

Wayfair and Warby Parker presented opposing examples to the narrative that online-first means offline-irrelevant. Wayfair's CMO Paul Toms said the company is opening stores — noting the first physical location opened in 2024 after 23 years as an online business — because customers in home goods want to see and touch items and stores help with brand awareness.

Warby Parker's chief retail and customer officer, Sandy Gilsenan, said the company plans 50 new locations this year and is integrating services such as eye exams. She connects those services directly to customer loyalty: adding services increases the reasons for repeat visits.

Quick commerce revival led by scale players

Euromonitor's Bob Hoyler framed the delivery discussion with data: online transactions are expected to account for 31% of all retail sales by year-end and reach 36% by 2030, while offline sales will decline about 1.3% this year. He pointed to quick commerce — deliveries in 30 minutes or less — as a driver of that growth.

Hoyler argued the model collapsed in 2022 but is returning because large players like Amazon and Walmart have the resources to support dark stores and the logistics footprint required for such speed. The implication for other retailers: quick commerce requires scale or partnerships with players that already have it.

Loyalty tied to trip type and measurable behavior

Heather Bennett, president and chief customer officer at Michaels, explained why the retailer offers 9% rewards for its top-tier members. Michaels is a specialty seller, she said, so store visits are often "special trips" rather than routine grocery runs. The company A/B tested the rewards and found that those who received the benefit visited more frequently. The conclusion: reward rates and tiers should reflect both the nature of customer trips and measurable impact on visit frequency.

• Treat AI as an engineering and data problem. If accuracy and trust matter, prefer in-house control or tightly governed deployments.

• Assess quick commerce realistically: without the logistics scale of Amazon or Walmart, competing on 30-minute delivery is expensive and operationally complex.
• Design loyalty with experiments. Michaels' A/B test shows that higher rewards can shift visit behavior for specialty retailers.

Taken together, the eTail Boston discussions favored hands-on experiments, owning critical systems, and matching channel strategy to the product and customer trip type.