Director, Enterprise Sales

About This Role

This role is for a Director of Enterprise Retail Sales to lead a team of Account Executives focusing on strategic retail opportunities across various lifestyle categories. The Director will coach and develop experienced AEs, help shape complex deals, build relationships with senior merchant executives, and collaborate with cross-functional partners to support strategic merchant growth.

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
• Shape and evolve Enterprise Retail Go-to-Market 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

Requirements

• 10+ years of experience in enterprise sales, strategic partnerships, or commercial leadership, including significant experience leading senior sales teams in complex, high-growth environments
• Demonstrated experience directly managing and developing senior, quota-carrying Account Executives
• Proven success leading teams through large, complex sales cycles involving executive stakeholders, commercial negotiations, and significant cross-functional coordination
• Strong alignment with Affirm’s mission and a clear understanding of the value Affirm delivers to merchants and consumers
• Experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment
• Strong judgment, communication, and executive presence, with the ability to build trust and influence C-level merchant stakeholders and senior internal partners
• Track record of developing high-performing sales talent, improving performance, and creating consistent operating discipline across a team