[Remote] Director, Enterprise Sales

Note: The job is a remote job and is open to candidates in USA. Affirm is hiring a Director, Enterprise Retail Sales to lead a team responsible for strategic retail opportunities. The role combines coaching senior Account Executives with hands-on support for complex deals, merchant relationships, and cross-functional growth initiatives.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives, setting clear expectations and driving accountability, performance, and consistent execution against team goals
• Own team performance across pipeline health, forecast accuracy, deal progression, merchant acquisition and expansion, and revenue outcomes
• Coach through complex, strategic opportunities, helping AEs build business cases, navigate stakeholder dynamics, structure commercial solutions, and negotiate effectively
• Build trusted relationships with senior leaders at major retail merchants and engage directly in high-priority opportunities where executive involvement can help move the business forward
• Shapes and evolves Enterprise Retail GTM strategy and objectives with senior leadership including account planning, territory management, pipeline reviews, sales planning, and operating discipline
• Drive commercial and operational outcomes by partnering across Product, Client Success, Marketing, Finance, Legal, and RevOps to maintain shared accountability for key milestones, resolve escalations, and influence company-level initiatives
• Drive operational excellence and sales effectiveness by leveraging data, AI, and modern tools to bring structure and innovation to planning, pipeline management, forecasting, and deal strategy
• Travel as needed for merchant meetings, deal support, industry events, and team gatherings

Skills

• 10+ years of experience in enterprise sales, strategic partnerships, or commercial leadership, including significant experience leading senior sales teams in complex, high-growth environments
• Demonstrated experience directly managing and developing senior, quota-carrying Account Executives
• Proven success leading teams through large, complex sales cycles involving executive stakeholders, commercial negotiations, and significant cross-functional coordination
• Strong alignment with Affirm's mission and a clear understanding of the value Affirm delivers to merchants and consumers
• Strong judgment, communication, and executive presence, with the ability to build trust and influence C-level merchant stakeholders and senior internal partners
• Track record of developing high-performing sales talent, improving performance, and creating consistent operating discipline across a team
• Proficiency with data, AI, automation, and modern sales tools to improve sales effectiveness and decision-making
• Please note that visa sponsorship is not available for this position
• Experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment

Benefits

• Sales incentive target as part of OTE.
• Equity rewards may be included in the total compensation package.
• Monthly stipends for health, wellness, and tech spending.
• 100% subsidized medical, dental, and vision coverage for employees and their dependents; the company covers 100% of premiums.
• Monthly stipends support your tech setup, and you can choose health and wellness options.
• Flexible time off and generous holiday calendars.
• Employee stock purchase plan (ESPP) to buy Affirm stock at a discount.
• Remote-first work arrangement: most roles can be done from almost anywhere within the country of employment; some positions may occasionally require in-person work at an Affirm office, and a few are office-based. All new hires are invited to attend an in-person onboarding experience.

Company Overview