Director, Enterprise Retail Sales — Remote-First Leader

Affirm, Inc.; New York (NY); Remote; USD 370,000 - 490,000; Full time

Benefits offered by this job

Health coverage at no cost for you and

Stipends for tech setup and health/wel

Job summary

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a seasoned team driving strategic retail opportunities across fashion, beauty, and lifestyle categories. You will coach senior Account Executives, shape GTM strategy, and collaborate with cross-functional partners to accelerate merchant growth.

The role emphasizes executive engagement, complex negotiations, and data-driven sales leadership in a remote-first environment with national scope.

Qualifications

• 10+ years in enterprise sales or strategic partnerships.
• Experience managing senior quota-carrying Account Executives.
• Proven success guiding large, complex deals with executive stakeholders.
• Understanding Affirm's mission and the value delivered to merchants.
• Experience selling to large retail merchants, payments/fintech.
• Executive presence and ability to influence C-level stakeholders.
• Proficiency with data, AI, automation, and modern sales tools.

Responsibilities

• Lead and develop a team of senior Account Executives, setting clear expectations and driving accountability.
• Own pipeline health, forecast accuracy, deal progression, merchant acquisition and revenue outcomes.
• Coach through complex opportunities, helping AEs build business cases and negotiate.
• Build relationships with senior leaders at major retail merchants for high-priority opportunities.
• Shape and evolve Enterprise Retail GTM strategy with senior leadership and planning.
• Drive cross-functional collaboration across Product, Client Success, Marketing, Finance, Legal, RevOps.
• Leverage data, AI, and tools to improve planning, forecasting, and deal strategy.
• Travel as needed for merchant meetings and events.

Skills

Enterprise sales

Strategic partnerships

Commercial leadership

Leading senior sales teams

Executive presence

Cross-functional coordination

Data/AI tools

Job description

Affirm, Inc. is seeking a Director of Enterprise Retail Sales to lead a seasoned team driving strategic retail opportunities across fashion, beauty, and lifestyle categories. You will coach senior Account Executives, shape GTM strategy, and collaborate with cross-functional partners to accelerate merchant growth.

The role emphasizes executive engagement, complex negotiations, and data-driven sales leadership in a remote-first environment with national scope.