Senior Director, Key & Enterprise Sales
WFA Digital Insight
As the demand for digital payment solutions grew 25% in 2025, companies like Affirm are at the forefront of this trend. With 15+ years of experience in enterprise sales, you can leverage your skills to drive top-line growth in the retail sector. Affirm's commitment to honest and flexible credit options sets it apart in the fintech industry, making this role an attractive opportunity for those looking to make a real impact.
Job Description
About the Role
The Senior Director, Key & Enterprise Sales will lead Affirm's retail sales organization, overseeing a team of sales leaders and account executives. This role is crucial in driving top-line growth through strategic partnerships and commerce solutions. You will report to the VP of Global Sales and work closely with cross-functional partners to deliver value-added solutions and drive adoption.The ideal candidate will have a deep understanding of the retail industry and experience selling to large retail merchants. You will be responsible for building executive relationships, guiding complex commercial opportunities, and turning strategy into measurable business results.
What You Will Do
- Set the vision, strategy, and operating direction for Affirm's Key & Enterprise Retail Sales organization
- 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
- Shape and scale the go-to-market approach through territory design, account planning, sales planning, pipeline reviews, and operating discipline
- Apply AI, automation, data, and modern sales tools to improve planning, decision-making, insight generation, and team productivity
- Lead and scale a multi-layered sales organization, creating clarity, accountability, and consistent execution across teams
- Coach and develop high-performing sales leaders and teams through training, solution selling, written communication, and consistent deal execution
- Travel as needed for merchant meetings, deal support, industry events, and team gatherings
What We Are Looking For
- 15+ years of experience in enterprise sales, strategic partnerships, or commercial leadership
- Proven success building, scaling, and leading high-performing sales organizations focused on large, strategic accounts
- 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 plans
- Experience with Salesforce, Excel, and other sales tools
Nice to Have
- Experience with AI, automation, data, and modern sales tools
- Familiarity with the fintech or commerce industry
- Certification in sales or a related field
Benefits and Perks
- Competitive salary and equity package
- Comprehensive health, dental, and vision insurance
- Generous PTO policy and remote work stipend
- Opportunities for professional growth and development
- Access to cutting-edge sales tools and technology
How to Stand Out
- Develop a strong understanding of the retail industry and the role of digital payment solutions in commerce
- Build a portfolio that showcases your experience in enterprise sales and strategic partnerships
- Practice your executive presence and communication skills to effectively build trust with C-level stakeholders
- Familiarize yourself with Salesforce, Excel, and other sales tools to improve your productivity and insight generation
- Be prepared to discuss your experience with complex commercial opportunities and your ability to turn strategy into measurable business results
- Research Affirm's products and services to understand how they can be leveraged to drive growth in the retail sector
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