Note: The job is a remote job and is open to candidates in USA. Affirm is reinventing credit to make it more honest and friendly, giving consumers the flexibility to buy now and pay later without any hidden fees or compounding interest. The Senior Director, Key & Enterprise Retail Sales will lead the business and shape Affirm’s long-term growth in retail by overseeing sales leaders and their teams, building executive relationships, and guiding complex commercial opportunities.
Responsibilities
- 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
Skills
- 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
Benefits
- Equity rewards
- Monthly stipends for health, wellness and tech spending
- Benefits (including 100% subsidized medical coverage, dental and vision for you and your dependents.)
- 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
Company Overview