Director, Enterprise Sales

WinsAbove; United States; Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

100% health coverage for employee and

Monthly tech and wellness stipends

ESPP stock purchase plan

Generous holiday calendar

Job summary

Affirm seeks a Director of Enterprise Retail Sales to lead a seniorAE team across fashion, beauty, apparel, and lifestyle categories. You will shape the GTM strategy, coach experienced AEs, and navigate complex deals with senior merchant executives.

You will partner with cross‑functional leaders to drive growth, forecast accuracy, and successful implementations while traveling as needed to close strategic opportunities.

Qualifications

• 10+ years of experience in enterprise sales or related leadership.
• Experience managing senior Account Executives.
• Proven success in large, complex sales cycles with executive stakeholders.
• Experience selling to large retail merchants and complex solutions.
• Strong judgment and executive presence with cross‑functional influence.
• Proficiency with data, AI, and modern sales tools to improve effectiveness.

Responsibilities

• Lead, coach, and develop a team of senior Account Executives, setting expectations and driving accountability.
• Own team performance across pipeline health, forecast accuracy, deal progression, and revenue outcomes.
• Coach through complex opportunities, helping AEs build cases and negotiate.
• Build trusted relationships with senior leaders at major retail merchants.
• Shape and evolve Enterprise Retail GTM strategy with senior leadership.
• Drive cross‑functional collaboration across Product, Client Success, Marketing, Finance, Legal, and RevOps.
• Enhance sales operations with data, AI, and modern tools for planning and forecasting.
• Travel as needed for merchant meetings, deal support, and events.

Skills

Senior sales leadership

Enterprise sales

Executive stakeholder management

GTM strategy

Forecasting & analytics

Job description

At Affir, 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 Affirms 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 Affirms products.

About the Role:

We’re looking for a Director, Enterprise Retail Sales to lead a team of Account Executives responsible for some of Affirms 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 Affirms mission and a clear understanding of the value Affirms 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 Affirms typically come in at the start of the pay range. Affirms 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.

#LI-Remote

Remote-first with flexibility built inAffirm 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 youOur 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 Affirms 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: Affirms considers qualified applicants with arrest and conviction records, as required by law.