At Affirm, we exist for the moments that matter—giving people a clear, predictable way to pay over time, with no hidden fees, no surprises, and no tradeoffs on what matters most. We’re looking for a Senior Director, Key & Enterprise Retail Sales to lead this business and help shape Affirm’s long-term growth in retail. Reporting to the VP of Global Sales, this leader will oversee three sales leaders and their teams of Account Executives and work with some of Affirm’s most strategic merchants across fashion, beauty, apparel, sporting goods, electronics, furniture, and other lifestyle categories. This is a true leader-of-leaders role, requiring prior experience managing and developing senior sales leaders. This leader will build executive relationships, guide complex commercial opportunities, and turn strategy into measurable business results. They will lead a high-impact team and partner across the business to help Affirm win, launch, and grow strategic merchant relationships. What You’ll Do Set the vision, strategy, and operating direction for Affirm’s Key & Enterprise Retail Sales organization, aligning sales leadership and cross-functional partners around priorities, investment decisions, and market positioning Own business performance across pipeline health, forecast accuracy, deal progression, merchant launches, account expansion, and revenue outcomes Build trusted relationships with senior leaders at major retail merchants and lead complex commercial opportunities end to end, from business case through contract negotiation Shape and scale the go-to-market approach through territory design, account planning, sales planning, pipeline reviews, and operating discipline, partnering across Product, Partnerships, Client Success, Marketing, Finance, Legal, RevOps, and leadership to improve how Affirm wins and grows strategic accounts Apply AI, automation, data, and modern sales tools in practical ways that improve planning, decision-making, insight genera
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About us Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor and Clay Bavor . Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was
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Department · Sales
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Sierra
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