Enterprise Sales Director - Strategic, Retail

The role

The Enterprise Sales Director will architect complex, large-scale deals and manage multi-BU, multi-geo opportunities. This person will hold C-suite relationships and engage with co-founders to drive revenue for retail brands using AI agents.

What you will do

• Architect Sierra's most complex deals
• Lead largest multi-BU, multi-geo opportunities
• Design sophisticated deal structures and manage risk
• Hold trusted relationships across customer C-suite and working teams
• Engage and manage Sierra's co-founders in front of customers
• Influence how Sierra approaches its most important accounts
• Set the standard for the broader sales org
• Leverage AI tools across the full sales cycle

Required qualifications

• 10-12+ years of enterprise/strategic sales experience
• Experience owning the largest and most complex accounts
• Demonstrated success closing multi-million-dollar, multi-stakeholder deals
• Experience managing a $1M+ quota
• Experience running end-to-end complex 6- and 7-figure ACV deals
• Deep, sustained C-suite relationships
• Mastery of complex deal structuring, risk navigation, and pricing
• Exceptional executive communication

Nice to have

• Deep familiarity with the AI landscape
• Ability to speak credibly to technical and business stakeholders
• Experience operating alongside founders/executives in front of strategic customers

Benefits

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance and disability benefits
• Retirement plan dependent on country of employment
• Parental leave
• Fertility and family building benefits
• Lunch, as well as delicious snacks and coffee when working onsite
• Discretionary benefit stipend
• Free alphorn lessons
• Equity plans for eligible full-time employees

About the company

Sierra is a platform for customer-facing AI agents working with large brands to transform customer service and growth. It was co-founded by Bret Taylor and Clay Bavor.