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Salary: USD 328,000 - 490,000 / annual
Affirm is seeking a Director of Enterprise Retail Sales to lead a team of senior Account Executives responsible for strategic retail partnerships across fashion, beauty, apparel, sporting goods, electronics, furniture, and lifestyle categories. This is a hands-on leadership role reporting to the Senior Director of Enterprise Retail Sales.
In this position, you will lead, coach, and develop a team of experienced Account Executives while remaining actively involved in complex commercial opportunities. You'll set clear expectations, drive accountability, and ensure consistent execution against team goals. Your responsibilities include owning team performance across pipeline health, forecast accuracy, deal progression, merchant acquisition and expansion, and revenue outcomes.
You will coach your team through strategic, complex opportunities—helping Account Executives build business cases, navigate stakeholder dynamics, structure commercial solutions, and negotiate effectively. You'll build trusted relationships with senior leaders at major retail merchants and engage directly in high-priority deals where executive involvement can accelerate progress.
Working cross-functionally with Product, Client Success, Marketing, Finance, Legal, and RevOps, you'll drive commercial and operational outcomes, maintain shared accountability for key milestones, resolve escalations, and influence company-level initiatives. You'll also shape and evolve Enterprise Retail go-to-market strategy and objectives with senior leadership, including account planning, territory management, pipeline reviews, and sales planning.
Driving operational excellence is key—you'll leverage data, AI, and modern sales 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.
Affirm's mission is to give people a clear, predictable way to pay over time with no hidden fees or surprises. The Revenue team drives top-line growth through strategic partnerships, pricing, and go-to-market execution across eCommerce, in-store, telesales, and the Affirm app.
REQUIREMENTS:
- 10+ years of enterprise sales, strategic partnerships, or commercial leadership experience, 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 clear understanding of value delivered to merchants and consumers
- Experience selling to large retail merchants, ideally in payments, fintech, commerce, or complex solution-selling environments
- Strong judgment, communication, and executive presence with 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
- Proficiency with data, AI, automation, and modern sales tools to improve sales effectiveness and decision-making
- Visa sponsorship not available for this position
