Enterprise Sales Director – Strategic, Retail

Job not on LinkedIn

🕒 August 5

🇨🇦 Canada – Remote

💵 CA$375k - CA$430k / year

⏰ Full Time

🔴 Lead

🤑 Sales

👻 Ghost score 29%

What it means: the chance that no one is really hiring for this job.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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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-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk • Build trusted relationships across customer C-suites and working teams • Regularly engage and manage Sierra's co-founders in front of customers • Apply precise messaging, positioning, and timing across interactions • Influence Sierra's strategy for important accounts and set standards for the broader sales organization • Use AI tools throughout the sales cycle, including account research, personalized outreach, call summarization, pipeline forecasting, and deal execution • Transform customer engagement for major consumer brands through Sierra's AI customer-experience platform

🎯 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 across 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 executive-buyer credibility • Mastery of complex deal structuring, risk navigation, and pricing • Exceptional executive communication and a reputation for precision and trust • Deep familiarity with the AI landscape is an advantage • Experience operating alongside founders/executives in front of strategic customers is an advantage • 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

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