Senior Director, Key & Enterprise Sales at Affirm
- Remote.
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 generation, and team productivity, including Salesforce, Gong, Google Workspace, Notion, Spekit, and generative AI tools such as ChatGPT and Claude Lead and scale a multi-layered sales organization, creating clarity, accountability, and consistent execution across teams supporting Key and Enterprise Retail Sales Coach and develop high-performing sales leaders and teams through training, solution selling, written communication, and consistent deal execution, and travel as needed for merchant meetings, deal support, industry events, and team gatherings What We Look For 15+ years of experience in enterprise sales, strategic partnerships, or commercial leadership, including meaningful experience leading leaders in complex, high-growth environments Demonstrated experience leading through managers is required, including coaching and developing sales leaders who oversee their own teams Proven success building, scaling, and leading high-performing sales organizations focused on large, strategic accounts across both new business and expansion Deep experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment Executive presence, clear written and verbal communication, and the ability to build trust and influence with C-level external stakeholders and senior internal partners Ability to navigate ambiguity, build business cases, and turn strategy into clear execution and measurable results Track record of coaching and developing talent, improving performance, building collaborative teams, and driving consistency through clear processes Practical fluency with modern sales tools, data, and AI, and the ability to apply them in ways that improve team effectiveness and merchant outcomes and inform cross-functional and executive decisions related to strategy, resource allocation, and market expansion Qualities of All Affirmers We look for people who connect their work to Affirm’s strategy and customer impact, bring excellence to …