Director, Enterprise Retail Sales — Remote-First Growth Leader

Affirm, Inc.; United States; Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

100% employee health coverage

Monthly tech & wellness stipends

Generous time off & holiday calendar

Employee stock purchase plan (ESPP)

Job summary

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a senior team of Account Executives driving strategic retail opportunities across fashion, beauty, and lifestyle categories. This leader will stay hands-on in complex deals while coaching top performers.

You will shape GTM strategy, partner across functions, and travel as needed for key opportunities, with a remote-first model and flexibility within the United States.

Qualifications

• 10+ years of enterprise sales or related leadership experience.
• Experience leading senior Account Executives in complex, high-growth environments.
• Proven track record selling to large retail merchants and managing multi-stakeholder deals.
• Strong executive presence with negotiation and influencing skills.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives and drive accountability.
• Own team performance across pipeline health, forecast accuracy, and revenue outcomes.
• Shape and execute Enterprise Retail GTM strategy with senior leadership.
• Collaborate with Product, Client Success, Marketing, Finance, Legal, and RevOps to align initiatives.
• Drive data-driven planning, pipeline management, and deal strategy.

Skills

Enterprise sales leadership

Executive stakeholder management

Coaching teams

Forecasting & pipeline management

Cross-functional collaboration

Education

Bachelor's degree or equivalent

Tools

CRM (Salesforce)

Data analytics tools

Job description

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a senior team of Account Executives driving strategic retail opportunities across fashion, beauty, and lifestyle categories. This leader will stay hands-on in complex deals while coaching top performers.

You will shape GTM strategy, partner across functions, and travel as needed for key opportunities, with a remote-first model and flexibility within the United States.