About the Role
We're looking for a Senior Director, Key & Enterprise Retail Sales to lead this business and help shape Affirm's long-term growth in retail. Reporting to the VP of Global Sales, this leader will oversee three sales leaders and their teams of Account Executives and work with some of Affirm's most strategic merchants across fashion, beauty, apparel, sporting goods, electronics, furniture, and other lifestyle categories.
This leader will build executive relationships, guide complex commercial opportunities, and turn strategy into measurable business results. They will lead a high-impact team and partner across the business to help Affirm win, launch, and grow strategic merchant relationships.

What You'll Do

• Set the vision, strategy, and operating direction for Affirm's Key & Enterprise Retail Sales organization, aligning sales leadership and cross-functional partners around priorities, investment decisions, and market positioning
• Own business performance across pipeline health, forecast accuracy, deal progression, merchant launches, account expansion, and revenue outcomes
• Build trusted relationships with senior leaders at major retail merchants and lead complex commercial opportunities end to end, from business case through contract negotiation
• Shape and scale the go-to-market approach through territory design, account planning, sales planning, pipeline reviews, and operating discipline, partnering across Product, Partnerships, Client Success, Marketing, Finance, Legal, RevOps, and leadership to improve how Affirm wins and grows strategic accounts
• Apply AI, automation, data, and modern sales tools in practical ways that improve planning, decision-making, insight generation, and team productivity, including Salesforce, Gong, Google Workspace, Notion, Spekit, and generative AI tools such as ChatGPT and Claude
• Lead and scale a multi-layered sales organization, creating clarity, accountability, and consistent execution across teams supporting Key and Enterprise Retail Sales
• Coach and develop high-performing sales leaders and teams through training, solution selling, written communication, and consistent deal execution, and travel as needed for merchant meetings, deal support, industry events, and team gatherings

What We Look For

• 15+ years of experience in enterprise sales, strategic partnerships, or commercial leadership, including meaningful experience leading leaders in complex, high-growth environments
• Proven success building, scaling, and leading high-performing sales organizations focused on large, strategic accounts across both new business and expansion
• Deep experience selling to large retail merchants, ideally in payments, fintech, commerce, or another complex solution-selling environment
• Executive presence, clear written and verbal communication, and the ability to build trust and influence with C-level external stakeholders and senior internal partners
• Ability to navigate ambiguity, build business cases, and turn strategy into clear execution and measurable results
• Track record of coaching and developing talent, improving performance, building collaborative teams, and driving consistency through clear processes
• Practical fluency with modern sales tools, data, and AI, and the ability to apply them in ways that improve team effectiveness and merchant outcomes and inform cross-functional and executive decisions related to strategy, resource allocation, and market expansion

Qualities of All Affirmers
We look for people who connect their work to Affirm's strategy and customer impact, bring excellence to their craft, and operate with accountability, sound judgment, and integrity. Strong Affirmers collaborate across teams, communicate clearly, listen with humility, and help build alignment in complex environments. They keep learning, adapt quickly, and raise the bar through curiosity, initiative, and thoughtful experimentation. Leaders at Affirm also build effective teams, develop others, create clarity in times of change, and inspire confidence through transparency and high standards.

Base Pay Grade - O
Equity Grade - 16

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: $430,000 - $530,000
USA On Target Earnings (all other U.S. states) per year: $382,000 - $482,000

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

#LI-Remote

Affirm is proud to be a remote-first company! The majority of our roles are remote and you can work almost anywhere within the country of employment. Affirmers in proximal roles have the flexibility to work remotely, but will occasionally be required to work out of their assigned Affirm office. A limited number of roles remain office-based due to the nature of their job responsibilities.

We're extremely proud to offer competitive benefits that are anchored to our core value of people come first. Some key highlights of our benefits package include:

• Health care coverage - Affirm covers all premiums for all levels of coverage for you and your dependents
• Flexible Spending Wallets - generous stipends for spending on Technology, Food, various Lifestyle needs, and family forming expenses
• Time off - competitive vacation and holiday schedules allowing you to take time off to rest and recharge
• ESPP - An employee stock purchase plan enabling you to buy shares of Affirm at a discount