At a glance
- Experience
- 10+ years experience
- Workplace
- Remote
- Location
- Remote US
- Visa sponsorship
- Visa sponsorship not offered
About the role
- We're looking for a Director, Enterprise Retail Sales to lead a team of Account Executives responsible for some of Affirm's most 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 lead a senior sales team while remaining hands-on in complex commercial opportunities.
- The Director will coach and develop experienced AEs, help shape and progress complex deals, build relationships with senior merchant executives, and work closely with cross-functional partners to support strategic merchant growth.
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
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
- Experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment
- 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
Benefits
- 100% subsidized medical coverage, dental and vision for you and your dependents
- Equity rewards
- Monthly stipends for health, wellness and tech spending
- Flexible time off and generous holiday calendars
- Employee stock purchase plan (ESPP)
Workplace
- Remote-first with flexibility built in
- Some positions may occasionally require in-person work at an Affirm office
Skills
- AI
- Data
- Automation
- Modern Sales Tools
