Enterprise Sales Director - Strategic

📋 Description

• Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities
• Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and
• Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in
• Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing
• Shape strategy: Influence how Sierra approaches its most important accounts and set the standard
• Operate as an AI-native seller: Leverage AI tools across the full sales cycle—account research

🎯 Requirements

• 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
• Proven success closing multi-million-dollar, multi-stakeholder deals spanning business units and
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
• Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.
• Mastery of complex deal structuring, risk navigation, and pricing.
• Exceptional executive communication and a reputation for precision and trust.

🎁 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 through Carrot