Senior Director, Enterprise Retail Sales

Affirm, Inc.; Miami (FL); Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

100% premium health coverage

Monthly stipends for tech setup

Flexible time off

Employee stock purchase plan (ESPP)

Job summary

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a senior team of Account Executives across fashion, beauty, apparel and lifestyle categories. The role focuses on high-impact opportunities, coaching, and hands-on deal shaping.

You’ll partner with cross-functional teams, influence GTM strategy, and travel as needed to advance merchant relationships. This remote-first role offers a transparent pay structure, strong equity and growth opportunities.

Qualifications

• 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
• Experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment

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

Enterprise sales

Strategic partnerships

Commercial leadership

Executive presence

Data-driven

Job description

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a senior team of Account Executives across fashion, beauty, apparel and lifestyle categories. The role focuses on high-impact opportunities, coaching, and hands-on deal shaping.

You’ll partner with cross-functional teams, influence GTM strategy, and travel as needed to advance merchant relationships. This remote-first role offers a transparent pay structure, strong equity and growth opportunities.