The primary obstacle for OpenAI's shopping features isn't the transaction layer, but the complex task of standardizing inconsistent product data (sizing, pricing, inventory) across millions of merchants. This foundational data problem requires deep collaboration with partners and explains the slow, deliberate rollout.

For OpenAI's commerce features to succeed, it's not enough to build one-click checkout. They must fundamentally retrain hundreds of millions of users to trust a new purchasing workflow inside a chatbot, breaking deeply ingrained habits of searching on ChatGPT then buying on Google or Amazon.

By integrating shopping into ChatGPT, OpenAI can become a massive e-commerce engine. With a potential take rate of 15-30%, similar to Amazon or Meta, capturing just 20% of the $1.2T U.S. e-commerce market would generate tens of billions in new, high-margin revenue.

Amazon's potential commerce partnership with OpenAI is fraught with risk. Allowing ChatGPT to become the starting point for product searches threatens Amazon's highly profitable on-site advertising revenue, even if Amazon gains referral traffic. It's a classic battle to avoid being aggregated by another platform.

OpenAI's partnership with Stripe to enable in-app purchases transforms ChatGPT from an information tool into a transactional platform. This creates a frictionless sales channel for e-commerce brands, directly challenging Google's established search-to-purchase business model.

Instead of traditional cost-per-click models, ChatGPT could pioneer a "verified outcome" system where advertisers pay only upon a completed transaction and user satisfaction. This would inherently favor advertisers with superior products that lead to actual conversions, improving ad quality and relevance for all users.

OpenAI is more public and aggressive with its shopping features (partnering with Shopify, DoorDash) than its ad strategy. By first attracting thousands of merchants to its e-commerce waitlist, it's establishing a foundational transaction layer. This de-risks its future ad platform by ensuring a ready base of paying customers.

While large retailers will adopt Google's in-app AI checkout, smaller D2C brands face a tough choice. Participating means ceding control of branding and the customer relationship, but sitting out risks becoming invisible as shopper behavior shifts to AI-native purchasing, making it difficult to catch up later.

While a commerce partnership with OpenAI seems logical, Amazon is hesitant. They recognize that if consumers start product searches on ChatGPT, it could disintermediate Amazon's on-site search, cannibalizing their high-margin advertising revenue and ceding aggregator power.