Senior Director, Enterprise Retail Sales — Remote

Affirm, Inc.; Madison (WI); Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

Health coverage

Tech stipends

Generous time off

ESPP stock purchase plan

Job summary

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a senior team targeting major retail opportunities across categories. The role partners with cross-functional teams and engages in high-stakes negotiations to drive merchant growth, adoption, and revenue.

The position is remote-first with occasional in-person work and travel within the U.S. The candidate will mentor senior AEs, shape GTM strategy, and own pipeline health, forecast accuracy, and deal progression in a

Qualifications

• 10+ years of experience in enterprise sales, strategic partnerships, or commercial leadership.
• Experience directly managing and developing senior, quota-carrying Account Executives.
• Proven success leading teams through large, complex sales cycles with executive stakeholders.
• Strong judgment, communication, and executive presence with senior merchant stakeholders.
• Experience selling to large retail merchants, ideally in payments/fintech or complex solutions.
• Track record of developing high-performing sales talent and maintaining operating discipline.
• Proficiency with data, AI, automation, and modern sales tools.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives, setting clear expectations and driving accountability.
• Own team performance across pipeline health, forecast accuracy, deal progression, and revenue outcomes.
• Coach through complex, strategic opportunities, building business cases and negotiating effectively.
• Build trusted relationships with senior leaders at major retail merchants and engage in high-priority opportunities.
• Shape and evolve Enterprise Retail GTM strategy with senior leadership including planning and territory management.
• Drive outcomes by partnering across Product, Client Success, Marketing, Finance, Legal, and RevOps.
• Drive sales excellence by leveraging data, AI, and tools to improve planning and forecasting.
• Travel as needed for merchant meetings, deal support, and industry events.

Job description

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a senior team targeting major retail opportunities across categories. The role partners with cross-functional teams and engages in high-stakes negotiations to drive merchant growth, adoption, and revenue.

The position is remote-first with occasional in-person work and travel within the U.S. The candidate will mentor senior AEs, shape GTM strategy, and own pipeline health, forecast accuracy, and deal progression in a