In this episode of Brilliant Commerce, I sit down with Jason Bertrand, VP of E-commerce at Purple, to unpack lessons from his journey scaling D2C operations from Under Armour’s early $20M online business to Purple’s $450M empire. Jason shares refreshingly honest takes on why chasing complex tech can derail growth, how to build premium positioning in discount-heavy categories, and his team’s specific AI SEO implementation that drove measurable traffic growth from Perplexity and ChatGPT in just six months. Topics discussed: - Why headless commerce created Purple’s biggest tech debt: Jason’s candid assessment of how their post-COVID headless implementation overcomplicated their limited SKU catalog, and his framework for evaluating when architectural complexity actually hinders growth for brands without dedicated engineering teams. - Premium pricing discipline in discount-conditioned markets: Purple’s operational approach to maintaining MAP pricing across wholesale partners with 90-day advance promotional planning, using web-exclusive products like the Purple Flex ($1,000 queen) as their only promotional lever while avoiding the industry’s ”fool’s pricing” trap. - Multi-channel parity enforcement at $450M scale: Purple’s specific guardrails for maintaining pricing consistency across D2C, 55 owned retail stores, and thousands of wholesale doors while protecting their $30-40M Amazon revenue stream and preventing internal channel conflict. - AI implementation beyond automation: How Purple deploys AI to analyze customer service conversations (chats, emails, calls) for actionable product development insights, moving beyond surface-level sentiment analysis to extract feature requests that inform their R&D roadmap. - Natural language SEO for AI search engines: Purple’s tactical shift from keyword-focused optimization to conversational query optimization, resulting in measurable traffic growth from Perplexity and ChatGPT by restructuring content around customer questions rather than traditional search terms. - Progressive profiling through product quizzes: How Purple’s mattress quiz captures behavioral intelligence (sleep position, partner preferences, temperature sensitivity) for personalized email sequences while building the data foundation for AI-powered product recommendations. - Team architecture for nine-figure operations: Jason’s 20-person team structure spanning UI/UX, analytics, merchandising, Amazon, CRM, and SEO, with scaling insights from Under Armour’s growth from $20M to $150M online and the critical handoff points between functions. - Brand positioning through messaging constraints: Purple’s ”less pain, better sleep” logo treatment addresses the challenge of high brand recognition with unclear brand meaning, using consistent messaging guardrails to convert awareness into purchase intent across all touchpoints.