Jen Chaffee

Background

About Jen Chaffee

Strategic retail technology leader with over 15 years of experience driving end-to-end product modernization across demand forecasting, replenishment, and merchandise planning. Proven ability to unify product and technology strategies across complex B2B SaaS portfolios—enabling platform cohesion, operational scalability, and business value realization. A trusted cross-functional influencer skilled in aligning executives, product teams, and customer stakeholders to shape future-fit roadmaps that leverage AI, orchestration, and data products. Unified Product Strategy & Orchestration: Led transformation of T-Mobile's cross-domain planning platforms, aligning supply chain and retail solutions under a unified roadmap; scaled platform to support all commerce channels and eliminate $300M+ in redundant assortment post-merger with Sprint. Customer-Centric Innovation: Technology lead at Mattress Firm, overseeing implementation of integrated demand forecasting, inventory management, replenishment, pricing, and merchandise planning technologies; partner closely with VP and C-level stakeholders to align platform capabilities with merchandising and supply chain operational strategies and goals. Created benefit over five years across improved forecast accuracy, reduced working capital and labor and optimized discount depth through promotions. Influence Without Authority: Enabled alignment across Product, R&D, Finance, and C-level stakeholders at L Brands (Victoria's Secret, Pink, Bath & Body Works, and La Senza) and Dollar Tree Stores (Family Dollar and Dollar Tree Brands)—driving investment cases, capability roadmaps, and storytelling for multi-product modernization efforts. AI & Data Product Strategy: Partnered with vendors and internal R&D to introduce hybrid forecasting engines, data modeling accelerators, and AI-powered planning features; reduced implementation complexity and increased speed across use cases. Go-To-Market and Demo Leadership: Led creation of vertical-specific capability demos during platform evaluations, improving sales alignment and accelerating time-to-value for new customers. Industry Thought Leadership: • NRF 2025 Speaker: AI Simplified – A Modern Approach to Profit-Optimized Retail Planning • PI Apparel NYC: Keynote Panel – Beyond the Hype: How Brands Use AI in Merchandise Planning • Featured Speaker: Balancing Innovation & Budget and Choosing the Right Tech for Your Business