Enterprise Sales Director - Strategic, Retail

📋 Description

• Architect Sierra's most complex deals: lead large multi-BU, multi-geo opportunities with risk
• Operate as part of the customer's team: build trusted C-suite relationships.
• Engage at the founder level: collaborate with Sierra co-founders in front of customers.
• Bring precision to messaging, positioning, and timing across interactions.
• Shape strategy: influence accounts and set standards for the sales org.
• Operate as an AI-native seller: leverage AI tools across the full sales cycle to automate low-value

🎯 Requirements

• 10-12+ years of enterprise/strategic sales experience with large, complex accounts.
• Proven success closing multi-million-dollar, multi-stakeholder deals across geographies.
• Experience managing a $1M+ quota and end-to-end 6-7 figure ACV deals.
• Deep C-suite relationships and executive-level communication.
• Mastery of complex deal structuring, risk navigation, and pricing.
• Ability to speak credibly about AI with technical and business stakeholders.

🎁 Benefits

• Unlimited flexible PTO
• Medical, dental, and vision benefits for you and family
• Life insurance and disability benefits
• Retirement plan (regional variations)
• Parental leave and family-building benefits
• Catered perks and discretionary stipend to spend where it matters