Enterprise Sales Director - Strategic

What you'll do

• Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.
• Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.
• Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.
• Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.
• Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.
• Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.

What you'll bring

• 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
• Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.
• 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.

Even better...

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