Sr. Director - Product Management (Choose)

About the Role

The Sr. Director, Product Management – Choose is a strategic leader responsible for shaping how customers evaluate, compare, and select products across digital and in-store environments. This role oversees three core domains — Product Merchandising, Size & Fit, and Upsell & Cross-Sell — that collectively drive product understanding, confidence, and purchase intent.

This leader defines the strategy and execution framework that delivers engaging, data-informed merchandising experiences; builds trust and accuracy in size and fit decisions through AI-driven tools; and uses intelligent recommendations to elevate basket value and customer satisfaction. Partnering closely with UX, Engineering, Ecommerce, Marketing, and Merchandising teams, this leader ensures the Choose experience is seamless, personalized, and aligned to brand identity across all touch points.
What You'll Do

• Define and execute a unified Choose strategy across Product Merchandising, Size & Fit, and Upsell & Cross-Sell to improve product clarity, confidence, and conversion. 

• Lead development of enhanced PDP experiences, inventory visibility, and promotional storytelling that blend creativity and data-driven optimization. 

• Advance the use of AI and personalization engines to support sizing guidance, virtual try-on, and real-time fit recommendations across channels. 

• Drive the roadmap for upsell and cross-sell capabilities, leveraging predictive data and customer insights to increase basket size and engagement. 

• Partner cross-functionally with Content Supply Chain, Purchase, and Customer Lifecycle teams to ensure seamless integration of content, pricing, and loyalty strategies within the Choose journey. 

• Foster a culture of experimentation, using A/B testing and analytics to validate customer behavior insights and optimize product discovery and decision-making. 

• Build and lead a high-performing team of up to 8–12, providing coaching, accountability, and development opportunities consistent with Gap Inc.’s leadership framework. 

Who You Are

• 10+ years of product management experience in retail or e-commerce, including 5+ years in a senior leadership capacity overseeing cross-functional digital experiences. 

• Proven track record of delivering measurable improvements in conversion, customer satisfaction, and revenue growth through product innovation. 

• Strong technical acumen with experience in recommendation engines, personalization platforms, and commerce systems. 

• Ability to lead and influence cross-functional teams, balancing creativity, data insights, and brand alignment. 

• Excellent communication skills with the ability to articulate product vision and outcomes to executive and technical audiences. 

• Experience with agile product development and enterprise-level commerce platforms. 

• Familiarity with AI-based recommendation systems, AR/VR fit tools, and advanced analytics frameworks. 

• Demonstrated ability to interpret behavioral and transactional data to guide roadmap decisions. 

• Passion for user-centered design, innovation, and continuous improvement in the retail customer experience. 

• Proven success building and developing high-performing, collaborative product teams.