Director, Enterprise Sales

Affirm

3d • $328,000 - $490,000 • Remote

About The Position

Affirm is seeking a Director, Enterprise Retail Sales to lead a team of Account Executives pursuing strategic retail opportunities across fashion, beauty, apparel, sporting goods, electronics, furniture, and other lifestyle categories. Reporting to the Senior Director of Enterprise Retail Sales, this leader will manage a senior sales team while remaining hands-on in complex commercial opportunities. The Director will coach and develop experienced Account Executives, guide complex deals, build relationships with senior merchant executives, and partner across functions to support strategic merchant growth.

The role is part of Affirm’s Revenue team, which drives top-line growth through strategic partnerships, pricing, and go-to-market execution. The team acquires, retains, and expands merchant relationships across eCommerce, in-store, telesales, and the Affirm app, and supports merchant onboarding, relationship management, performance optimization, and long-term growth.

This is a remote-first role with flexibility within the country of employment. Travel may be needed for merchant meetings, deal support, industry events, and team gatherings; new hires are invited to attend an in-person onboarding experience. Visa sponsorship is not available.

Requirements

• 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.

Nice To Haves

• 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 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 Account Executives through complex strategic opportunities, including business cases, stakeholder dynamics, commercial solutions, and negotiations.
• Build trusted relationships with senior leaders at major retail merchants and engage directly in high-priority opportunities.
• Shape and evolve Enterprise Retail go-to-market strategy and objectives with senior leadership, including account planning, territory management, pipeline reviews, sales planning, and operating discipline.
• Partner with Product, Client Success, Marketing, Finance, Legal, and RevOps to drive commercial and operational outcomes, maintain shared accountability for milestones, resolve escalations, and influence company-level initiatives.
• Leverage data, AI, automation, and modern tools to improve planning, pipeline management, forecasting, deal strategy, and sales effectiveness.
• Travel as needed for merchant meetings, deal support, industry events, and team gatherings.

Benefits

• 100% subsidized medical coverage for employees and dependents.
• Dental and vision coverage for employees and dependents.
• Monthly stipends for technology setup, health, and wellness spending.
• Flexible time off and generous holiday calendars.
• Employee stock purchase plan (ESPP) allowing employees to buy Affirm stock at a discount.
• Equity rewards may be part of the total compensation package.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed