Checkout Jobs in California (NOW HIRING)

About the Role
The Director, Product Management - Cart and Checkout is a senior product leadership role within the Purchase Value Stream, responsible for driving conversion and revenue across Gap Inc.'s digital commerce platforms. This leader owns three critical steps in the customer journey: the shopping bag (cart), the checkout flow, and order confirmation - across all four brands and all digital surfaces.
Cart and Checkout represents one of the highest-leverage surfaces in the Customer Journey: it is where customer intent converts to revenue. This Director must balance conversion optimization with a seamless customer experience - maximizing basket size, ensuring pricing and promotions transparency, and delivering a frictionless path from bag to confirmed order.
Leading a team of product managers, this Director shapes purchase strategy alongside the Sr. Director of Purchase while owning cross-product-area outcomes, performance reviews, and team development.What You'll Do
• Define and execute the product strategy for the shopping bag, checkout flow, and order confirmation across Gap Inc.'s digital commerce platforms - driving conversion, reducing abandonment, and delivering a seamless purchase journey for all customers across all four brands.
• Lead a team of product managers, owning product-area goals, delivery outcomes, and talent development across cart, checkout, and order confirmation surfaces.
• Present at Value Stream Performance Reviews with product-level goals, progress updates, and escalations for Sr. Director visibility.
• Own cross-functional dependencies - particularly with Discover and Choose (pricing and promotions transparency from browse through bag), Lifecycle & Loyalty (loyalty cardholder experience and benefits display at checkout), and Post-Purchase (order confirmation and returns initiation).
• Drive cart and bag strategy - including upsell and cross-sell recommendations, product suggestions, and cart engagement features that increase average order value and basket size.
• Advance promotions and pricing visibility within the cart - ensuring customers can understand discount application, loyalty benefits, and final pricing with confidence at every step of checkout.
• Optimize the checkout flow - including address entry, order review, and the path to order confirmation - to reduce drop-off and improve completion rates across web and app.
• Contribute substantively to the Sr. Director's quarterly strategy planning, translating checkout conversion trends, competitive intelligence, and customer behavior into strategic product direction.
• Champion data-driven experimentation through A/B testing, feature flagging, and analytics-driven iteration to optimize conversion and reduce drop-off across the purchase funnel.
• Drive Gap credit cardholder acquisition at the point of purchase - designing and optimizing card sign-up entry points within the bag and checkout experience to increase new cardholder conversion while maintaining a seamless checkout flow.
Who You Are
• Bachelor's degree in Business, Computer Science, or related field; MBA or advanced degree preferred.
• 9+ years of product management experience in e-commerce, retail technology, or digital commerce.
• 3+ years of people leadership managing product managers.
• Proven experience building and scaling cart and checkout experiences that measurably improved conversion rates, average order value, or funnel completion.
• Strong technical acumen in e-commerce platform architecture and checkout funnel analytics.
• Exceptional cross-functional influence across Engineering, UX, Data Science, and Brand partners.
• Experience with cart upsell and cross-sell strategies - including product
recommendations, add-on suggestions, and basket-building mechanics that increase average order value.
• Experience with promotions engines, discount application logic, and pricing transparency in multi-brand retail environments.
• Understanding of checkout flow optimization including address validation, order review design, and accelerated checkout patterns.
• Familiarity with loyalty program integration at the bag and checkout level - including benefit visibility, member pricing, and earning mechanics.
• Experience designing or optimizing co-branded credit card sign-up flows within e-commerce checkout - balancing cardholder acquisition goals with conversion rate and customer experience.
• Experience with checkout analytics platforms and funnel instrumentation.