Enterprise Sales Director - Strategic, Retail

Highlights

• Lead Sierra's largest multi-BU, multi-geo deals for top retail brands.
• Build AI agents that help millions track orders and find products.
• Turn AI agents into revenue drivers via discovery and cart recovery.

What they offer

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance and disability benefits
• Retirement plan
• Parental leave
• Fertility and family building benefits through Carrot
• Lunch, snacks and coffee
• Discretionary benefit stipend
• Equity

Ideal candidate

A seasoned strategic seller who thrives on complex C-suite deals and operates with precision and ownership. You care about craftsmanship, customer obsession, and using AI to redefine retail experiences.

Requirements

• 10-12+ years of enterprise/strategic sales experience owning large, complex accounts
• Proven success closing multi-million-dollar, multi-stakeholder deals across business units and geographies
• Experience managing a $1M+ quota and running end-to-end 6- and 7-figure ACV deals
• Deep, sustained C-suite relationships with gravitas as a peer to executive buyers
• Mastery of complex deal structuring, risk navigation, and pricing
• Exceptional executive communication with reputation for precision and trust
• Deep familiarity with AI landscape with credibility across technical and business stakeholders