Senior Director, Product Management — AI-Driven Choose

SupportFinity™; San Francisco (CA); On-site; USD 227,000 - 306,000; Full time

Benefits offered by this job

Merchandise discount

Generous PTO

Volunteer hours

401(k) with company matching

Employee stock purchase plan

Health, dental, vision, life insurance

Job summary

Gap Inc. is seeking a Sr. Director of Product Management for the Choose domain to shape how customers evaluate and select products across online and in-store experiences.

You will oversee Product Merchandising, Size & Fit, and Upsell & Cross-Sell, defining strategy and a data-informed execution framework that enhances clarity, trust in sizing, and basket value. Lead AI-powered sizing guidance, virtual try-on, and personalized recommendations, collaborating with UX, Engineering, Ecommerce,

Qualifications

• 10+ years of product management experience in retail or e-commerce.
• 5+ years in a senior leadership capacity overseeing cross-functional digital experiences.
• Proven track record of delivering improvements in conversion and revenue through product innovation.
• Strong technical acumen with experience in recommendation engines and personalization.
• Experience with agile product development and enterprise-level commerce platforms.

Responsibilities

• Define and execute a unified Choose strategy across Product Merchandising, Size & Fit, and Upsell & Cross-Sell to improve clarity, confidence, and conversion.
• Lead development of enhanced PDP experiences, inventory visibility, and promotional storytelling with data-driven optimization.
• Advance AI and personalization engines to support sizing guidance, virtual try-on, and real-time fit recommendations.
• Drive roadmap for upsell and cross-sell capabilities using predictive data and customer insights.
• Partner with Content Supply Chain, Purchase, and Customer Lifecycle teams to align content, pricing, and loyalty strategies.
• Foster a culture of experimentation with A/B testing and analytics to optimize product discovery.
• Build and lead a high-performing team of up to 8–12.

Skills

Product management

Leadership

Cross-functional collaboration

Agile methodologies

Data analytics

Tools

Recommendation engines

Personalization platforms

Commerce systems

AR/VR fit tools

Job description

Gap Inc. is seeking a Sr. Director of Product Management for the Choose domain to shape how customers evaluate and select products across online and in-store experiences.

You will oversee Product Merchandising, Size & Fit, and Upsell & Cross-Sell, defining strategy and a data-informed execution framework that enhances clarity, trust in sizing, and basket value. Lead AI-powered sizing guidance, virtual try-on, and personalized recommendations, collaborating with UX, Engineering, Ecommerce,