Senior Director, Key & Enterprise Sales (Fintech)

Location: Remote within the United States

On Target Earnings: $460,000–$580,000 per year in CA, WA, NY, NJ, and CT; $408,000–$528,000 per year in other U.S. states.

Company

Affirm provides buy-now-pay-later products that let consumers pay over time without hidden fees or compounding interest.

What you will do

• Set the vision, strategy, and operating direction for Key & Enterprise Retail Sales.
• Own pipeline health, forecast accuracy, deal progression, merchant launches, account expansion, and revenue outcomes.
• Build executive relationships with major retail merchants and lead complex opportunities from business case through contract negotiation.
• Scale go-to-market operations through territory design, account planning, sales planning, pipeline reviews, and cross-functional collaboration.
• Apply AI, automation, data, Salesforce, Gong, Google Workspace, Notion, Spekit, ChatGPT, and Claude to improve planning and sales productivity.
• Lead, coach, and develop a multi-layered sales organization, traveling as needed for merchant meetings, industry events, and team gatherings.

Requirements

• 15+ years of experience in enterprise sales, strategic partnerships, or commercial leadership.
• Experience leading leaders and building high-performing sales organizations focused on strategic accounts.
• Deep experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment.
• Executive presence and strong written and verbal communication skills, including the ability to influence C-level stakeholders.
• Experience building business cases, translating strategy into execution, coaching talent, and improving performance through clear processes.
• Practical fluency with modern sales tools, data, and AI.

Culture & Benefits

• Remote-first work environment within the country of employment.
• Affirm covers medical premiums for employees and dependents, with dental and vision coverage.
• Flexible spending wallets and monthly stipends for technology, food, lifestyle, and family-forming expenses.
• Competitive vacation and holiday schedules.
• Employee stock purchase plan with discounted shares.
• Visa sponsorship is not available for this position.