Enterprise Sales Director – Strategic, Retail

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🔥 0 minutes ago

🇺🇸 United States – Remote

💵 $315k - $370k / year

⏰ Full Time

🔴 Lead

🤑 Sales

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Sierra

WebsiteLinkedInAll Job Openings

51 - 200 employees

🤖 Artificial Intelligence

🤝 B2B

☁️ SaaS

Artificial Intelligence • B2B • SaaS

Sierra is a company that specializes in transforming customer experiences through the power of conversational AI. Their platform enables businesses to deploy AI agents that are empathetic, always available, and aligned with the brand's tone and voice. Sierra offers capabilities for real-time support, seamless integration into existing technology stacks, and the capacity to solve complex issues while continuously improving the customer experience. Trusted by leading brands, Sierra's AI platform is designed with a strong commitment to security and privacy, ensuring safe and secure interactions. The platform allows for personalization, enabling companies to imbue their AI agents with their own identity and processes, ensuring consistency and reliability across all customer interactions.

📋 Description

• Lead the largest and most complex multi-business-unit, multi-geography opportunities • Design sophisticated deal structures and manage deal risk • Build trusted relationships across customer C-suites and working teams • Regularly engage Sierra’s co-founders in front of customers • Deliver precise messaging, positioning, and timing across interactions • Influence strategy for Sierra’s most important accounts • Set standards for the broader sales organization • Use AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution • Continuously adopt and experiment with new sales tools

🎯 Requirements

• 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 • Experience running end-to-end complex six- and seven-figure ACV deals • Deep, sustained C-suite relationships • Gravitas to be treated as a peer by executive buyers • Mastery of complex deal structuring, risk navigation, and pricing • Exceptional executive communication • Reputation for precision and trust • Deep familiarity with the AI landscape is advantageous • Ability to speak credibly to technical and business stakeholders • Experience operating alongside founders/executives in front of strategic customers is advantageous

🏖️ 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 • Lunch, as well as delicious snacks and coffee • Discretionary benefit stipend • Free alphorn lessons • Equity plans for eligible full-time employees • Commission • Offers equity