Senior Director, Enterprise Retail Sales – Remote-First

Affirm, Inc.; Houston (TX); Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

Health coverage for dependents

Monthly tech stipends

Generous time off & holidays

ESPP stock purchase plan

Job summary

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a senior AE team across fashion, beauty, apparel and more. You will coach AEs, shape complex deals, and partner with cross-functional teams to drive merchant growth.

You will engage senior merchant executives, progress strategic opportunities, and influence GTM strategy while maintaining hands-on involvement in high-value deals. This role emphasizes leadership, strategic thinking, and client relationship excellence.

Qualifications

• 10+ years of enterprise sales, strategic partnerships, or commercial leadership.
• Experience coaching and developing senior Account Executives.
• Proven ability to navigate large, complex sales cycles with executive stakeholders.
• Strong alignment with Affirm’s mission and merchant value.
• Experience selling to large retail merchants in payments/fintech.

Responsibilities

• Lead and develop a team of senior Account Executives to meet goals and maintain accountability.
• Own pipeline health, forecast accuracy, deal progression, merchant acquisition and revenue outcomes.
• Coach through complex opportunities, build business cases, negotiate, and structure solutions.
• Build relationships with senior leaders at major retailers and drive high-priority opportunities.
• Shape and evolve Enterprise Retail GTM strategy with senior leadership and operating discipline.
• Collaborate across Product, Client Success, Marketing, Finance, Legal, and RevOps to ensure shared milestones.
• Leverage data, AI, and modern tools to improve planning, forecasting, and deal strategy.
• Travel as needed for merchant meetings and events.

Skills

Enterprise sales leadership

Executive stakeholder management

Team coaching

Cross-functional collaboration

Strategic partnerships

Job description

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a senior AE team across fashion, beauty, apparel and more. You will coach AEs, shape complex deals, and partner with cross-functional teams to drive merchant growth.

You will engage senior merchant executives, progress strategic opportunities, and influence GTM strategy while maintaining hands-on involvement in high-value deals. This role emphasizes leadership, strategic thinking, and client relationship excellence.