Director, Enterprise Retail Sales - Remote First

Resume Skip; United States; Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

Health coverage

Tech & wellness stipends

Flexible time off

Employee stock purchase plan

Job summary

Affirm is seeking a Director, Enterprise Retail Sales to lead a senior team of Account Executives across top retail sectors. You will mentor AEs, guide complex negotiations, and partner with cross‑functional leaders to drive merchant growth.

The role emphasizes executive collaboration, GTM strategy, and data‑driven sales, with a remote‑first setup nationwide and visa sponsorship not available.

Qualifications

• 10+ years of experience in enterprise sales, strategic partnerships, or commercial leadership.
• Demonstrated experience directly managing and developing senior, quota‑carrying Account Executives.
• Proven success leading teams through large, complex sales cycles with executive stakeholders and cross‑functional coordination.
• Strong alignment with the company mission and value delivered to merchants and consumers.
• Experience selling to large retail merchants, ideally in payments, fintech, or complex solution selling.
• Strong judgment, communication, and executive presence with ability to influence C‑level stakeholders.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives and ensure accountability.
• Own team performance across pipeline health, forecast accuracy, deal progression, and revenue outcomes.
• Coach through complex, strategic opportunities and help AEs build business cases and negotiate.
• Build trusted relationships with senior leaders at major retail merchants and engage in high‑priority opportunities.
• Shape Enterprise GTM strategy with senior leadership, including planning, territory management, and pipeline reviews.
• Collaborate across Product, Client Success, Marketing, Finance, Legal, and RevOps to drive milestones and resolve escalations.
• Drive sales effectiveness using data, AI, and modern tools for planning, forecasting, and deal strategy.

Skills

enterprise sales

strategic partnerships

team leadership

complex deal structuring

exec stakeholder management

data-driven selling

Job description

Affirm is seeking a Director, Enterprise Retail Sales to lead a senior team of Account Executives across top retail sectors. You will mentor AEs, guide complex negotiations, and partner with cross‑functional leaders to drive merchant growth.

The role emphasizes executive collaboration, GTM strategy, and data‑driven sales, with a remote‑first setup nationwide and visa sponsorship not available.