[Remote] Senior Director, Key & Enterprise Sales

Note: The job is a remote job and is open to candidates in USA. Affirm provides transparent, predictable ways for people to pay over time. The Senior Director, Key & Enterprise Retail Sales will lead the retail sales organization, oversee sales leaders and account executives, manage strategic merchant relationships, and drive pipeline, revenue, launches, and account expansion. The role also partners cross-functionally to scale go-to-market strategy, develop sales talent, and improve execution through data, AI, automation, and modern sales tools.

Responsibilities

• 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

Skills

• 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
• Please note that visa sponsorship is not available for this position

Benefits

• Remote-first work with flexibility built in; most roles can be done from almost anywhere within the country of employment.
• 100% subsidized health coverage premiums for employees and their dependents.
• Monthly stipends to support employees’ tech setup and health and wellness options.
• Flexible time off and generous holiday calendars.
• Employee stock purchase plan (ESPP) allowing employees to buy Affirm stock at a discount.

Company Overview