Director, Enterprise Sales

Affirm is a mission-driven company dedicated to building honest financial products that improve lives. We are seeking a Director of Enterprise Sales – Retail who is passionate about our mission and the unique value our products bring to both merchants and consumers. This individual will have a proven track record of success leading mid-market or enterprise sales teams.

As the Director of Enterprise Sales – Retail, you will be a key leader within Affirm’s sales organization, driving the expansion of our rapidly growing enterprise business across a broad range of retail categories. You will lead a team of senior-level Account Executives focused on acquiring and expanding partnerships with the largest and most strategic merchants in fashion, beauty, sporting goods, apparel, electronics, bedding, furniture, auto, and other lifestyle categories. 

This role requires a dynamic, hands-on sales leader who thrives in a fast-paced, high-growth environment. You will work closely with your team to creatively generate new opportunities, advance deals through the sales cycle, and negotiate complex proposals and contracts. You will also partner closely with Affirm’s executive team to shepherd high-priority deals forward, ensuring alignment and momentum at every stage. Beyond closing new business, your team will be responsible for ensuring a seamless merchant launch in collaboration with cross-functional partners—including Client Success and Technical Account Management—and driving upsell opportunities within the first 12 months of any initial deal closing. These upsell opportunities may include cross-channel expansion, geographic growth, or additional brand integrations. This role requires regular travel to support Account Executives for onsite meetings, represent Affirm at industry conferences, and facilitate team planning sessions and offsites.

What You’ll Do:

• Lead and mentor a team of senior-level Enterprise Account Executives, helping them develop strategies to win new business and subsequently expand existing partnerships.
• Instill and uphold a strong team culture aligned with Affirm’s values and mission, ensuring a high level of collaboration, integrity, and accountability.
• Partner closely with Affirm’s leadership and executive team to move high-impact deals forward and maintain momentum throughout the sales cycle.
• Support prospecting efforts to facilitate warm leads that fuel pipeline growth for your team.
• Support your team in deal execution, providing strategic guidance from pipeline development through negotiation and close.
• Ensure newly signed merchants successfully launch with Affirm, thus ensuring strong coordination between your team and other cross-functional partners, including Client Success, Product, Technical Account Management, and other internal teams.
• Oversee expansion opportunities within the first 12 months of a deal closing, including cross-channel, cross-geography, or multi-brand growth.
• Bring structure and innovation to sales execution, pipeline management, and deal strategy, driving efficiency and effectiveness across the team.
• Hold your team accountable for performance, providing immediate and thoughtful coaching to drive continuous improvement.
• Represent Affirm at industry events and conferences, advocating for our mission representing Affirm as a senior thought leader and strengthening our position in the market.
• Travel regularly to help Account Executives accelerate their deal cycles, and facilitate team planning sessions and offsites.

What We Look For:

• A strategic and hands-on sales leader with a deep understanding of enterprise sales and complex deal structures.
• 15+ years of solution selling experience, including 5+ years of leadership experience managing high-performing enterprise sales teams.
• Proven track record of selling into large, enterprise retail merchants.
• Experience in Retail and/or the Credit and Payments landscape.
• Strong alignment with Affirm’s mission, with a passion for building financial products that improve lives. Ideally, you have used our product and understand its value to merchants and consumers.
• Strong executive presence and ability to build relationships with senior stakeholders at major brands.
• An active networker who can broker warm leads and open doors to new opportunities.
• A structured, organized leader who brings new ways of thinking and managing to the team.
• A proactive, entrepreneurial mindset with the ability to navigate ambiguity and drive initiatives forward.
• A strong coach and mentor who holds the team accountable and provides real-time, constructive feedback to improve performance.
• Willingness to travel regularly to support deal acceleration, industry events, and team collaboration.

Pay Grade - L

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: $320,000 - $420,000

USA On Target Earnings (all other U.S. states) per year: $284,000 - $384,000

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

#LI-Remote