Director, Enterprise Retail Sales — Remote-First Leader

Affirm, Inc.; Chicago (IL); Remote; USD 328,000 - 490,000; Full time

Benefits offered by this job

Health coverage

Tech stipends

Generous time off

ESPP

Job summary

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a senior AE team across fashion, beauty, apparel, and lifestyle categories. You will mentor AEs, shape complex deals, and partner with cross-functional teams to drive merchant growth.

The role is remote-first with leadership exposure to C-level partners. Ideal candidates bring 10+ years in enterprise sales, proven経験 leading senior sales talent, and a strategic mindset to navigate large-scale retail negotiations.

Qualifications

• Ten-plus years in enterprise sales or commercial leadership.
• ,
• Experience leading senior sales teams in complex, high-growth environments.
• Experience selling to large retail merchants and managing executive stakeholders.

Responsibilities

• Lead a team of senior Account Executives, setting expectations and driving accountability and results.
• Where appropriate edges trimmed to fit length
• Own pipeline health, forecast accuracy, deal progress, merchant growth, and revenue outcomes.
• Coach AEs on complex deals, build business cases, navigate stakeholders, negotiate effectively.
• Build relationships with senior retail merchants and pursue high-priority opportunities.
• Shape GTM strategy with leadership: planning, territory, pipeline reviews.
• Partner with Product, Client Success, Marketing, Finance, Legal, RevOps to hit milestones and resolve escalations.
• Travel as needed for merchant meetings, deals, events, and team gatherings.

Skills

Enterprise sales leadership

Senior AE coaching

Executive stakeholder management

Data-driven selling

Strategic partnerships

Job description

Affirm, Inc. is seeking a Director, Enterprise Retail Sales to lead a senior AE team across fashion, beauty, apparel, and lifestyle categories. You will mentor AEs, shape complex deals, and partner with cross-functional teams to drive merchant growth.

The role is remote-first with leadership exposure to C-level partners. Ideal candidates bring 10+ years in enterprise sales, proven経験 leading senior sales talent, and a strategic mindset to navigate large-scale retail negotiations.