Director, Enterprise Retail Sales (Remote | Equity)

Affirm, Inc.; Washington (District of Columbia); Remote; USD 328,000 - 448,000; Full time

Benefits offered by this job

Health coverage

Tech stipend

Flexible time off

ESPP

Job summary

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a senior team of Account Executives across fashion, beauty, apparel, and lifestyle categories. You will drive strategic merchant relationships and shape complex deals from discovery to close.

You will coach AEs, align GTM plans with cross-functional partners, and push for revenue growth while remaining hands-on in high-impact opportunities.

Qualifications

• 10+ years in enterprise sales, partnerships, or commercial leadership.
• Direct management of senior, quota-carrying Account Executives.
• Experience leading teams through large, complex sales cycles with executive stakeholders.
• Experience selling to large retail merchants, ideally in payments/fintech.
• Strong judgment, communication, and executive presence.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives and drive accountability.
• Own team performance across pipeline health, forecast accuracy, deal progression, and revenue.
• Coach through complex deals, structure commercial solutions, and negotiate.
• Build relationships with senior leaders at major retailers and engage in high-priority opportunities.
• Shape and evolve Enterprise Retail GTM strategy with senior leadership and planning processes.
• Collaborate with Product, Client Success, Marketing, Finance, Legal, and RevOps to ensure milestones and escalations are managed.
• Drive sales operations using data, AI, and modern tools for planning and forecasting.
• Travel as needed for merchant meetings and events.

Skills

Enterprise sales leadership

Account Executives coaching

Strategic partnerships

Cross-functional collaboration

Executive stakeholder management

Data-driven sales

AI-enabled sales tools

Large retail merchant experience

Tools

CRM systems

Sales analytics

Job description

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a senior team of Account Executives across fashion, beauty, apparel, and lifestyle categories. You will drive strategic merchant relationships and shape complex deals from discovery to close.

You will coach AEs, align GTM plans with cross-functional partners, and push for revenue growth while remaining hands-on in high-impact opportunities.