Director, Enterprise Retail Sales — Remote-First Leader

Affirm, Inc.; San Jose (CA); Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

100% premium health coverage

Stipends for tech setup

Flexible time off

Employee stock purchase plan

Job summary

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a high-performing team of Account Executives across fashion, beauty, apparel and lifestyle categories.

You will shape GTM strategy, coach senior AEs, and drive complex, high-value opportunities with senior merchant executives. You will partner with cross-functional teams to ensure disciplined pipeline management, accurate forecasting, and sustained revenue growth, while maintaining an executive-level presence with key retail

Qualifications

• 10+ years in enterprise sales or commercial leadership with senior teams.
• Proven record managing senior, quota-carrying Account Executives.
• Experience negotiating complex deals with cross-functional stakeholders.
• Strong judgment, communication and executive presence.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives and drive accountability.
• Own pipeline health, forecast accuracy, deal progression, and revenue outcomes.
• Coach on complex opportunities, build business cases, and negotiate effectively.
• Engage senior merchants directly on high-priority opportunities to move the business forward.
• Shape Enterprise Retail GTM strategy with account planning and territory management.
• Collaborate with Product, Client Success, Marketing, Finance, Legal, and RevOps.
• Enhance sales operations using data, AI, and modern tools for planning and forecasting.
• Travel as needed for merchant meetings and industry events.

Skills

Enterprise sales

Strategic partnerships

Commercial leadership

Leading senior AEs

Forecasting & pipeline

Executive stakeholder management

Data-driven sales

Job description

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a high-performing team of Account Executives across fashion, beauty, apparel and lifestyle categories.

You will shape GTM strategy, coach senior AEs, and drive complex, high-value opportunities with senior merchant executives. You will partner with cross-functional teams to ensure disciplined pipeline management, accurate forecasting, and sustained revenue growth, while maintaining an executive-level presence with key retail