Director, Enterprise Retail Sales — Remote-First + Equity

Affirm, Inc.; Portland (OR); Remote; USD 328,000 - 448,000; Full time

Benefits offered by this job

Health coverage for you and dependents

Monthly tech and health stipends

Flexible time off

Employee stock purchase plan (ESPP)

Job summary

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a team of Account Executives responsible for strategic retail opportunities across fashion, beauty, apparel, electronics, and other lifestyle categories.

Reporting to the Senior Director of Enterprise Retail Sales, this leader will lead a senior sales team while remaining hands-on in complex commercial opportunities. You’ll coach AEs, shape GTM strategy, build executive relationships with merchant leaders, and partner with

Qualifications

• 10+ years of experience in enterprise sales or commercial leadership.
• Experience leading senior Account Executives with quotas.
• Proven track record in large, complex sales cycles with executive stakeholders.
• Strong alignment with affirms mission and value to merchants.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives, driving accountability and execution against goals.
• Own team performance across pipeline, forecast accuracy, deal progression, and revenue outcomes.
• Coach through complex, strategic opportunities, building business cases and negotiating effectively.
• Build relationships with senior leaders at major retail merchants and engage in high-priority opportunities.
• Shape and evolve Enterprise Retail GTM strategy with senior leadership.
• Drive cross-functional collaboration with Product, Client Success, Marketing, Finance, Legal, and RevOps.
• Utilize data, AI, and modern tools to improve planning, pipeline management, forecasting, and deal strategy.
• Travel as needed for merchant meetings and events.

Skills

Enterprise sales leadership

Account Executive coaching

Strategic partnerships

Cross-functional collaboration

Data-driven approach

Negotiation

Executive presence

Job description

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a team of Account Executives responsible for strategic retail opportunities across fashion, beauty, apparel, electronics, and other lifestyle categories.

Reporting to the Senior Director of Enterprise Retail Sales, this leader will lead a senior sales team while remaining hands-on in complex commercial opportunities. You’ll coach AEs, shape GTM strategy, build executive relationships with merchant leaders, and partner with