Senior Director, Key & Enterprise Sales (Fintech)

TL;DR

Senior Director, Key & Enterprise Sales (Fintech): Leading the Key and Enterprise Retail Sales organization to drive Affirm's growth in the retail sector with an accent on strategic merchant partnerships and executive relationship management. Focus on scaling a multi-layered sales organization, optimizing go-to-market strategies, and applying AI-driven tools to improve team productivity.

Location: Remote (Must be based in the USA)

USA On Target Earnings: $408,000 - $580,000 per year

Company

Affirm is a fintech company reinventing credit to provide honest and friendly buy-now-pay-later solutions without hidden fees.

What you will do

• Set the vision, strategy, and operating direction for the Key & Enterprise Retail Sales organization.
• Own business performance across pipeline health, forecast accuracy, and revenue outcomes.
• Build C-level relationships with major retail merchants and lead complex commercial opportunities end-to-end.
• Scale go-to-market approaches through territory design and account planning in collaboration with cross-functional teams.
• Apply AI, automation, and modern sales tools (Salesforce, Gong, ChatGPT, Claude) to improve productivity and decision-making.
• Coach and develop high-performing sales leaders and teams through training and solution selling.

Requirements

• 15+ years of experience in enterprise sales, strategic partnerships, or commercial leadership.
• Proven success leading leaders in complex, high-growth environments.
• Deep experience selling to large retail merchants, preferably in payments, fintech, or commerce.
• Must be based in the USA; visa sponsorship is not available for this position.
• Strong executive presence and ability to influence C-level external stakeholders.
• Practical fluency with modern sales tools and generative AI.

Culture & Benefits

• 100% subsidized medical, dental, and vision coverage for employees and dependents.
• Generous Flexible Spending Wallets for technology, food, lifestyle, and family-forming expenses.
• Competitive vacation and holiday schedules to ensure rest and recharge.
• Employee Stock Purchase Plan (ESPP) allowing discounted share purchases.
• Remote-first culture with flexibility to work from almost anywhere within the country of employment.