Senior Director, Key & Enterprise Sales

Affirm

Senior Director of Key & Enterprise Sales at Affirm focusing on managing strategic retail sales relationships. Leading teams and driving revenue growth across various merchant categories in a remote US setting.

Posted 5/20/2026full-timeRemote • 🇺🇸 United StatesSenior💰 $382,000 - $530,000 per yearWebsite

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

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

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

enterprise salesstrategic partnershipscommercial leadershipsolution sellingaccount planningpipeline managementforecast accuracydeal negotiationbusiness case developmentperformance improvement

Soft Skills

executive presencewritten communicationverbal communicationtrust buildinginfluencecoachingteam developmentcollaborationaccountabilityexecution consistency