Director, Enterprise Retail Sales — Remote & Equity

Affirm, Inc.; Boston (MA); Remote; USD 328,000 - 448,000; Full time

Benefits offered by this job

100% subsidized medical coverage

Monthly tech stipend

Flexible time off

Employee stock purchase plan (ESPP)

Remote-first

Job summary

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a team of Account Executives across fashion, beauty, apparel and more. You’ll coach, shape complex deals, and partner with senior merchants to grow key retail partnerships.

Reporting to Senior Director, you’ll drive GTM strategy, manage pipeline health, forecast accuracy, and negotiate in high-stakes negotiations, while staying hands-on in large opportunities.

Qualifications

• 10+ years of enterprise sales or strategic partnerships leadership.
• Experience leading senior Account Executives and complex deals.
• Proven ability to manage large-scale negotiations with C-level stakeholders.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives, setting clear expectations and driving accountability, performance, and consistent execution against team goals
• Own team performance across pipeline health, forecast accuracy, deal progression, merchant acquisition and expansion, and revenue outcomes
• Coach through complex, strategic opportunities, helping AEs build business cases, navigate stakeholder dynamics, structure commercial solutions, and negotiate effectively
• Build trusted relationships with senior leaders at major retail merchants and engage directly in high-priority opportunities where executive involvement can help move the business forward
• Shapes and evolves Enterprise Retail GTM strategy and objectives with senior leadership including account planning, territory management, pipeline reviews, sales planning, and operating discipline
• Drive commercial and operational outcomes by partnering across Product, Client Success, Marketing, Finance, Legal, and RevOps to maintain shared accountability for key milestones, resolve escalations, and influence company-level initiatives
• Drive operational excellence and sales effectiveness by leveraging data, AI, and modern tools to bring structure and innovation to planning, pipeline management, forecasting, and deal strategy
• Travel as needed for merchant meetings, deal support, industry events, and team gatherings

Skills

Enterprise sales

Senior AE management

Strategic partnerships

Cross-functional leadership

Executive stakeholder engagement

Forecasting & pipeline

Job description

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a team of Account Executives across fashion, beauty, apparel and more. You’ll coach, shape complex deals, and partner with senior merchants to grow key retail partnerships.

Reporting to Senior Director, you’ll drive GTM strategy, manage pipeline health, forecast accuracy, and negotiate in high-stakes negotiations, while staying hands-on in large opportunities.