Senior Director, Key & Enterprise Sales

United StatesRemotesenior

OtherDirectorEnterprise Sales

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Overview

At Affirm, 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.

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OtherDirectorEnterprise Sales

At Affirm, 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.

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 is a true leader-of-leaders role, requiring prior experience managing and developing senior sales leaders.

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
Demonstrated experience leading through managers is required, including coaching and developing sales leaders who oversee their own teams
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.

What We Offer

~2 min read

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

#LI-Remote

Remote-first with flexibility built in
Affirm 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 you
Our 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 Affirm stock at a discount.