← All roles

Director, Enterprise Sales

Affirm· US Sales
Apply on company site
Remote$370k - $490kFull-timePosted 4d ago

About the role

Director, Enterprise Retail Sales leading a senior team of Account Executives across fashion, beauty, apparel, sporting goods, electronics, furniture, and other lifestyle categories; responsible for complex commercial opportunities, pipeline, and collaborative go-to-market 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

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
  • 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

Skills

Required:People leadershipStrategic deal shapingSales forecasting & pipeline management

Benefits

  • Health coverage at no cost for employees and dependents
  • Monthly tech stipends and health/wellness options
  • Flexible time off and generous holiday calendars
  • Employee stock purchase plan (ESPP) with stock purchase at a discount
Last updated Oct 21, 2026. Interested? Apply on the company site.

About Affirm

Pay over time with flexible payment plans and no fees

Buy now pay later without the fees. Flexible payment options with longer plans, lower payments, and no fees. Pay in 4 interest-free or get more time and see your total cost upfront.

Buy now pay laterFinancial servicesPayment plansCredit
Company profileWebsite

More open roles at Affirm