Director, Enterprise Sales

Affirm, Inc.; Raleigh (NC); Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

Health coverage

Tech stipends

Flexible time off

ESPP program

Job summary

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a team of Senior Account Executives across fashion, beauty, apparel and lifestyle categories. You will coach AEs, shape complex deals, and partner with senior merchants to drive growth.

This remote-first role reports to the Senior Director and emphasizes hands-on leadership in high-stakes negotiations. You will guide strategy with cross-functional partners and influence cross-functional teams to optimize pipeline, forecasting,

Qualifications

• 10+ years of experience in enterprise sales, partnerships, or commercial leadership, including leadership of senior sales teams.
• Proven track record managing senior, quota-carrying Account Executives.
• Experience guiding large, complex deals with executive stakeholders and cross-functional coordination.
• Strong understanding of Affirm’s value to merchants and consumers.
• Experience selling to large retail merchants, ideally in payments/fintech.
• Strong judgment, communication, and executive presence with C-level stakeholders.
• Proven ability to develop high-performing sales talent and maintain operating discipline.
• Proficiency with data, AI, automation, and modern sales tools.

Responsibilities

• Lead and develop a team of senior Account Executives, setting clear expectations and accountability, driving pipeline, forecast accuracy, and revenue outcomes.
• Own team performance across pipeline health, deal progression, merchant acquisition, and revenue.
• Coach through complex opportunities, building business cases, navigating stakeholder dynamics, and negotiating solutions.
• Build relationships with senior leaders at major retail merchants and engage in high-priority opportunities.
• Shape and evolve Enterprise Retail GTM strategy with senior leadership, including territory management and sales planning.
• Collaborate with Product, Client Success, Marketing, Finance, Legal, and RevOps to ensure shared accountability and resolve escalations.
• Drive sales operations excellence using data, AI, and modern tools for planning, forecasting, and deal strategy.
• Travel as needed for merchant meetings, deal support, and events.

Skills

Enterprise sales

Senior leadership

Executive presence

Cross-functional collaboration

Strategic negotiations

Data analytics

AI tools

Job description

At *Affirm* we exist for the moments that matter—giving people a clear, predictable way to pay over time, with no hidden fees, no surprises, and no tradeoffs on what matters most.

About The Revenue Team

The Revenue team drives *Affirm*’s top-line growth through strategic partnerships, pricing, and go-to-market execution. We acquire, retain, and expand merchant relationships across eCommerce, in-store, telesales, and the *Affirm* app. The team leads onboarding, relationship management, and performance optimization to help partners succeed. We deliver value-added solutions, drive adoption, and support long-term business growth by connecting merchants and consumers through *Affirm*’s products.

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.

What You’ll Do

• 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

What We Look For

• 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

Pay Grade - M

Equity Grade - 12

Employees new to *Affirm* typically come in at the start of the pay range. *Affirm* focuses on providing a simple and transparent pay structure which is based on a variety of factors, including location, experience and job-related skills. For sales roles, the range provided is the role’s On Target Earnings ("OTE") range, which includes the annual base pay and the sales incentive target.

Base pay is part of a total compensation package that may include equity rewards, monthly stipends for health, wellness and tech spending, and benefits (including 100% subsidized medical coverage, dental and vision for you and your dependents.)

USA On Target Earnings (CA, WA, NY, NJ, CT) per year: $370,000 - $490,000

USA On Target Earnings (all other U.S. states) per year: $328,000 - $448,000

Please note that visa sponsorship is not available for this position.

Remote-first with flexibility built in

*Affirm* is proud to be a remote-first company. Most roles can be done from almost anywhere within the country of employment. Some positions may occasionally require in-person work at an *Affirm* office, and a few are office-based due to the nature of the work. All new hires will be invited to attend an in-person onboarding experience.

Benefits Designed For You

Our benefits reflect our commitment to care, transparency, and flexibility. Here are a few highlights:

• Health coverage at no cost: We cover 100% of premiums for employees and their dependents.
• Spending stipends: Monthly stipends support your tech setup, and the ability to choose health and wellness options that are right for you.
• Time off to recharge: Flexible time off and generous holiday calendars help you rest when you need to.
• Own a piece of what you build: Our employee stock purchase plan (ESPP) lets you buy *Affirm* stock at a discount.

We’re committed to providing an inclusive interview process, including accommodations for candidates with disabilities. If you need support, we’re happy to help.

For positions based in San Francisco or Los Angeles: *Affirm* considers qualified applicants with arrest and conviction records, as required by law.