Enterprise Sales Director – Strategic, Healthcare

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

📋 Description

• Oversee the most significant multi-business-unit and multi-geography opportunities while crafting intricate deal structures and managing associated risks.

• Cultivate trusted relationships with customer C-suite leaders and their teams.

• Engage regularly with Sierra's co-founders in client-facing situations.

• Utilize precise messaging, positioning, and timing during customer interactions.

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

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

• Streamline low-value sales tasks through automation, reallocating time to foster high-value customer relationships.

• Persistently embrace and test new tools to enhance efficiency and effectiveness.

⛳️ Requirements

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

• Proven track record of successfully closing multi-million-dollar, multi-stakeholder deals across various business units and geographies.

• Experience handling a $1M+ quota and managing the complete lifecycle of complex six- and seven-figure ACV deals.

• Strong, sustained relationships with C-suite executives, possessing the gravitas to be regarded as a peer by executive buyers.

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

• Outstanding executive communication skills with a reputation for accuracy and reliability.

• Familiarity with the AI landscape is a plus.

• Ability to engage credibly with both technical and business stakeholders.

• Experience collaborating with founders/executives in front of strategic customers is advantageous.

• Must possess legal authorization to work in Canada.

• Must be capable of working from Canada.

🏝️ Benefits

• Flexible (unlimited) paid time off.

• 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 and a variety of delicious snacks and coffee to keep you energized.

• Discretionary benefit stipend allowing individuals to allocate funds where they are needed most.

• Complimentary alphorn lessons.

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