Senior Director, Key & Enterprise Sales

Affirm seeks a Senior Director of Key & Enterprise Retail Sales to lead strategic merchant relationships and oversee three sales teams operating across eCommerce, in-store, and direct channels. Based remotely in the US and reporting to the VP of Global Sales, you will manage Account Executives, build executive relationships with major retailers in fashion, beauty, apparel, sporting goods, electronics, furniture, and lifestyle categories, and drive revenue growth through complex commercial negotiations and account expansion.

Responsibilities

• Set vision, strategy, and operating direction for the Key & Enterprise Retail Sales organization; align sales leadership and cross-functional partners on priorities, investment decisions, and market positioning
• Own business performance metrics including pipeline health, forecast accuracy, deal progression, merchant launches, account expansion, and revenue outcomes
• Build and maintain trusted relationships with senior executives at major retail merchants; lead complex commercial opportunities from business case development through contract negotiation and closure
• Design and scale go-to-market strategy through territory design, account planning, sales planning, pipeline reviews, and operating discipline; partner with Product, Partnerships, Client Success, Marketing, Finance, Legal, RevOps, and leadership to improve account acquisition and growth
• Implement AI, automation, data analytics, and modern sales tools to enhance planning, decision-making, and team productivity using Salesforce, Gong, Google Workspace, Notion, Spekit, ChatGPT, Claude, and similar platforms
• Lead and scale a multi-layered sales organization; establish clarity, accountability, and consistent execution standards across teams
• Coach, develop, and mentor high-performing sales leaders and individual contributors through structured training, feedback, and career development

Requirements

• Proven experience leading enterprise or key account sales teams at scale (managing multiple sales leaders and Account Executives)
• Track record closing large, complex B2B deals with C-suite executives and managing multi-stakeholder negotiations
• Demonstrated proficiency with Salesforce, CRM systems, and sales analytics platforms
• Experience using AI and automation tools in a sales or operational context
• Experience building go-to-market strategy and scaling sales organizations

Benefits

• Remote work opportunity (US-based)