Enterprise Sales Director – Strategic

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

📋 Description

• Spearhead Sierra's most extensive multi-business-unit and multi-geography projects while crafting intricate deal structures.

• Oversee deal risk, pricing, and execution for intricate strategic accounts.

• Foster trusted relationships within customer C-suites and operational teams.

• Involve Sierra's co-founders in customer engagements and handle interactions at the founder level.

• Create clear messaging, positioning, and timing for all sales interactions.

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

• Utilize AI tools for account research, tailored outreach, call summarization, pipeline forecasting, and deal execution.

• Streamline low-value sales tasks through automation, allowing for a focus on high-value customer relationships.

• Persistently explore and test new AI tools.

⛳️ Requirements

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

• Proven track record in closing multi-million-dollar, multi-stakeholder deals across various business units and regions.

• Experience managing a quota exceeding $1M.

• Proficient in managing complex 6- and 7-figure ACV deals from start to finish.

• Established, enduring relationships with C-suite executives.

• Ability to command respect and be regarded as an equal by executive buyers.

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

• Outstanding communication skills at the executive level.

• Known for accuracy and trustworthiness.

• Thorough understanding of the AI landscape and capability to engage with both technical and business stakeholders effectively.

• Experience collaborating with founders/executives in strategic customer settings.

• Demonstrated success in creating go-to-market strategies, assembling sales teams, and developing sales motions from the ground up or during early-stage growth.

• Must have legal authorization 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 based on your country of employment.

• Parental leave.

• Fertility and family-building benefits through Carrot.

• Lunch, along with tasty snacks and coffee.

• Discretionary benefit stipend.

• Complimentary alphorn lessons.

• Eligible full-time employees can participate in Sierra's equity plans.

• Commission.

• Equity.