Director, Product Management - Cart & Checkout

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.

Responsibilities

• 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.

Requirements

• 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.

Qualifications

• Experience with e-commerce platform architecture and checkout funnel analytics.
• Strong understanding of customer journey mapping and optimization.
• Proven ability to lead and mentor a team of product managers.
• Experience with data-driven experimentation and A/B testing.
• Excellent communication and presentation skills.
• Ability to work collaboratively with cross-functional teams.

Skills

• Product management expertise in e-commerce and retail technology.
• Leadership and management experience in a product-oriented role.
• Technical proficiency in e-commerce platform architecture and checkout processes.
• Data analysis and interpretation skills.
• Strategic thinking and ability to translate business objectives into actionable product strategies.
• Experience with customer journey mapping and optimization.
• Strong problem-solving and analytical skills.

Benefits

Gap Inc. offers a comprehensive benefits package including:

• Merchandise discount for our brands: 50% off regular-priced merchandise at Old Navy, Gap, Banana Republic and Athleta, and 30% off at Outlet for all employees.
• One of the most competitive Paid Time Off plans in the industry.
• Employees can take up to five “on the clock” hours each month to volunteer at a charity of their choice.
• Extensive 401(k) plan with company matching for contributions up to four percent of an employee’s base pay.
• Employee stock purchase plan.
• Medical, dental, vision and life insurance.

We will meet minimum wage or minimum of the pay range (whichever is higher) based on city, county and state requirements.

Gap Inc. is an equal-opportunity employer and is committed to providing a workplace free from harassment and discrimination. We are committed to recruiting, hiring, training and promoting qualified people of all backgrounds, and make all employment decisions without regard to any protected status. We have received numerous awards for our long-held commitment to equality and will continue to foster a diverse and inclusive environment of belonging.

In 2022, we were recognized by Forbes as one of the World's Best Employers and one of the Best Employers for Diversity.