Director, Enterprise Retail Sales – Remote-First

Affirm, Inc.; St. Louis (MO); Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

100% medical coverage for you and your

Monthly tech stipends

Flexible time off

Employee stock purchase plan (ESPP)

Job summary

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

You will coach, shape deals, and engage senior merchant executives while collaborating with cross-functional partners to drive growth. The role emphasizes building relationships with top retailers, guiding strategy, and maintaining accountability for pipeline and revenue.

Qualifications

• 10+ years in enterprise sales or strategic leadership
• Experience leading senior sales teams
• Proven track record in complex, cross-functional deals
• Strong executive presence and negotiation skills

Responsibilities

• Lead and develop a team of senior Account Executives.
• Own pipeline health, forecast accuracy, and revenue outcomes.
• Coach on complex, strategic opportunities and build business cases.
• Build relationships with senior leaders at major retailers.
• Shape and evolve Enterprise Retail GTM strategy with leadership.
• Collaborate with Product, Client Success, Marketing, Finance, Legal, RevOps.
• Leverage data and AI to improve planning, forecasting, and deal strategy.
• Travel for merchant meetings, deal support, and events.

Job description

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

You will coach, shape deals, and engage senior merchant executives while collaborating with cross-functional partners to drive growth. The role emphasizes building relationships with top retailers, guiding strategy, and maintaining accountability for pipeline and revenue.