Enterprise Sales Director – Strategic, Consumer Business Insights

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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 risk • Build and maintain trusted relationships across customer C-suites and working teams • Engage Sierra’s co-founders in customer meetings and pitches • Develop precise messaging, positioning, and timing across interactions • Shape Sierra’s strategy for its most important accounts • Set the standard for the broader sales organization • Use 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 sales tools and methods

🎯 Requirements

• 10–12+ years of enterprise/strategic sales experience • Experience owning the largest and most complex accounts • Demonstrated success closing multi-million-dollar, multi-stakeholder deals across 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 • Ability to speak credibly to technical and business stakeholders • Experience operating alongside founders/executives in front of strategic customers • Legally authorized to work in Canada • 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 • Equity plans for eligible full-time employees • Commission • Home office/remote work arrangement