Director, Enterprise Retail Sales

Location: Remote US.

On-target earnings: $370,000–$490,000 per year in California, Washington, New York, New Jersey, and Connecticut; $328,000–$448,000 per year in all other US states. Visa sponsorship is not available.

Company

Affirm provides consumers with a clear and predictable way to pay over time and helps merchants acquire, retain, and expand customer relationships through its products.

What you will do

• Lead, coach, and develop a team of senior Account Executives, setting expectations and driving accountability, performance, and consistent execution.
• Own team performance across pipeline health, forecast accuracy, deal progression, merchant acquisition and expansion, and revenue outcomes.
• Coach complex strategic opportunities, including business cases, stakeholder management, commercial structuring, and negotiations.
• Build relationships with senior leaders at major retail merchants and participate directly in high-priority opportunities.
• Shape Enterprise Retail go-to-market strategy through account planning, territory management, pipeline reviews, sales planning, and operating discipline.
• Partner with Product, Client Success, Marketing, Finance, Legal, and RevOps; use data, AI, automation, and modern sales tools to improve sales effectiveness.

Requirements

• 10+ years of experience in enterprise sales, strategic partnerships, or commercial leadership, including significant experience leading senior sales teams in complex, high-growth environments.
• Direct experience managing and developing senior, quota-carrying Account Executives.
• Proven success leading teams through large, complex sales cycles involving executive stakeholders, commercial negotiations, and significant cross-functional coordination.
• Strong alignment with Affirm’s mission and understanding of the value Affirm delivers to merchants and consumers.
• Experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment.
• Strong judgment, communication, and executive presence, with the ability to build trust and influence C-level merchant stakeholders and senior internal partners.
• Track record of developing high-performing sales talent, improving performance, and creating consistent operating discipline.
• Proficiency with data, AI, automation, and modern sales tools to improve sales effectiveness and decision-making.

Culture & Benefits

• Remote-first work model with flexibility within the country of employment; occasional in-person work, team gatherings, and onboarding may be required.
• Medical coverage with 100% of premiums covered for employees and dependents, plus dental and vision coverage.
• Monthly stipends for technology, health, and wellness spending.
• Flexible time off and generous holiday calendars.
• Employee stock purchase plan with a discounted opportunity to buy Affirm stock.
• Inclusive interview process with accommodations available for candidates with disabilities.