Enterprise Sales Director – Strategic

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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 Sierra's largest multi-business-unit, multi-geography opportunities and design sophisticated deal structures • Manage deal risk, pricing, and execution for complex strategic accounts • Build trusted relationships across customer C-suites and working teams • Engage Sierra's co-founders in front of customers and manage founder-level customer interactions • Develop precise messaging, positioning, and timing across sales interactions • Influence Sierra's strategy for important accounts and set standards for the broader sales organization • Leverage AI tools across account research, personalized outreach, call summarization, pipeline forecasting, and deal execution • Automate low-value sales tasks and reinvest time in high-value customer relationships • Continuously adopt and experiment with new AI 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 6- and 7-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 and ability to speak credibly to technical and business stakeholders alike • Experience operating alongside founders/executives in front of strategic customers • Experience building GTM strategies, sales teams, and sales motions from scratch or during early-stage growth • Must be legally authorized to work in Canada • Must be able to work from Canada

🏖️ 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 • Eligible full-time employees can participate in Sierra's equity plans • Commission • Equity