Enterprise Sales Director - Strategic, Retail

Highlights

• Lead Sierra's largest multi-BU, multi-geo deals for retail AI agents.
• Help top retail brands turn AI agents into revenue and delightful shopping.
• Partner with C-suite to deploy agents for orders, discovery and service.

What they offer

• Flexible (unlimited) paid time off
• Medical, dental and vision benefits for you and 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 participation

Ideal candidate

A seasoned strategic seller who thrives on complex, C-level deals and operates with precision and trust. You love partnering with iconic retail brands and using AI to deepen customer relationships and drive growth.

Requirements

• 10-12+ years of enterprise/strategic sales experience owning largest, most complex accounts
• Proven success closing multi-million-dollar, multi-stakeholder deals across BUs and geographies
• Experience managing $1M+ quota and running end-to-end 6- and 7-figure ACV deals
• Deep, sustained C-suite relationships with gravitas as 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 and credibility with technical and business stakeholders