Enterprise Sales Director – Strategic, Retail

This is a fully remote position, open to applicants in Canada.

📋 Description

• Oversee Sierra's largest multi-business unit and multi-geographic opportunities, crafting intricate deal structures and managing associated risks.

• Cultivate reliable relationships with customer C-suite executives and operational teams.

• Frequently engage with and manage Sierra's co-founders during customer interactions.

• Utilize precise messaging, positioning, and timing throughout all engagements.

• Shape Sierra's strategy for key accounts and establish benchmarks for the wider sales team.

• Employ AI tools throughout the sales process, including account research, tailored outreach, call summarization, pipeline forecasting, and deal execution.

• Revolutionize customer engagement for leading consumer brands using Sierra's AI-driven customer experience platform.

⛳️ Requirements

• 10–12+ years of experience in enterprise or strategic sales, managing the largest and most intricate accounts.

• Proven track record of closing multi-million-dollar deals involving multiple stakeholders across various business units and regions.

• Experience overseeing a $1M+ quota and managing complex 6- and 7-figure annual contract value transactions from start to finish.

• Established, long-term relationships with C-suite executives and credibility with executive buyers.

• Expertise in complex deal structuring, risk management, and pricing strategies.

• Outstanding executive-level communication skills with a reputation for accuracy and dependability.

• In-depth understanding of the AI landscape is a plus.

• Experience collaborating with founders or executives in front of key strategic clients is advantageous.

• Must be legally authorized to work in Canada.

• Must be able to work from Canada.

🏝️ Benefits

• Flexible (unlimited) paid time off.

• Comprehensive medical, dental, and vision coverage for you and your family.

• Life insurance and disability coverage.

• Retirement plan based on the country of employment.

• Parental leave.

• Fertility and family-building benefits through Carrot.

• Lunch provided, along with a variety of snacks and coffee.

• Discretionary benefit stipend.

• Complimentary alphorn lessons.

• Equity plans available for eligible full-time employees.

• Commission structure.