Director, Enterprise Retail Sales

About this role

Lead a team of senior Account Executives pursuing strategic retail merchants and deliver growth through merchant acquisition and expansion. The role combines sales-team leadership with hands-on involvement in complex deals, executive relationships, and enterprise retail go-to-market strategy.

About the company

Affirm offers buy now, pay later financing that lets consumers split purchases into transparent installment payments at checkout. It partners with merchants to provide flexible credit options without late fees.

The team

Enterprise Retail Sales, within the Revenue team; reports to the Senior Director of Enterprise Retail Sales.

What you'll do

• Lead, coach, and develop senior Account Executives while setting performance expectations and accountability.
• Own team pipeline health, forecast accuracy, deal progression, merchant acquisition and expansion, and revenue outcomes.
• Coach complex sales opportunities, including business cases, stakeholder navigation, commercial solutions, and negotiations.
• Build senior merchant relationships and participate directly in priority opportunities.
• Shape enterprise retail go-to-market strategy, account planning, territory management, and sales operations.
• Partner cross-functionally to coordinate milestones, resolve escalations, and support strategic growth.
• Use data, AI, automation, and modern sales tools to improve planning, forecasting, and deal strategy.

What we're looking for

• 10+ years in enterprise sales, strategic partnerships, or commercial leadership, including leadership of senior sales teams.
• Experience directly managing and developing senior quota-carrying Account Executives.
• Success leading complex sales cycles with executive stakeholders, commercial negotiations, and cross-functional coordination.
• Experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment.
• Strong executive presence, communication, judgment, and ability to influence senior stakeholders.
• Track record of developing sales talent and establishing operating discipline.
• Proficiency with data, AI, automation, and modern sales tools.
• Alignment with Affirm’s mission and understanding of its value to merchants and consumers.

Nice to have

• Experience in payments, fintech, or commerce.

Benefits

• 100% subsidized medical, dental, and vision coverage for employees and dependents.
• Monthly technology, health, and wellness spending stipends.
• Flexible time off and generous holiday calendars.
• Employee stock purchase plan with a discount.
• Equity rewards may be included in total compensation.

Hiring process

1. In-person onboarding experience for new hires.