Enterprise Sales Director – Strategic

This is a fully remote position, open to applicants in California, +1 more state.

📋 Description

• Oversee Sierra's most significant opportunities spanning multiple business units and geographies while crafting intricate deal structures.

• Manage risks and implement complex strategic agreements.

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

• Frequently connect with Sierra’s co-founders in customer-facing situations.

• Ensure accuracy in messaging, positioning, timing, and customer engagement.

• Shape the strategy for Sierra’s key accounts.

• Establish benchmarks for the wider sales organization.

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

• Constantly test new tools to enhance sales productivity and customer connections.

⛳️ Requirements

• 10–12+ years of experience in enterprise or strategic sales.

• Proven track record of managing the largest and most intricate accounts.

• Demonstrated success in closing multi-million-dollar deals involving multiple stakeholders across various business units and regions.

• Experience managing a quota exceeding $1M.

• Proficient in handling end-to-end complex six- and seven-figure ACV agreements.

• Established, sustained relationships with C-suite executives.

• Possess the gravitas to be regarded as an equal by executive buyers.

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

• Superior communication skills tailored for executive audiences.

• Known for precision and trustworthiness.

• Familiarity with the AI landscape is considered an asset.

• Ability to communicate effectively with both technical and business stakeholders.

• Experience collaborating with founders or executives in front of strategic customers is a plus.

• Legal authorization to work in the United States is required as part of the application process.

🏝️ Benefits

• Flexible (unlimited) paid time off.

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

• Life insurance and disability benefits.

• Retirement plan options based on the country of employment.

• Parental leave provisions.

• Fertility and family planning benefits provided through Carrot.

• Lunch, along with tasty snacks and coffee.

• Discretionary benefit stipend.

• Complimentary alphorn lessons.

• Equity plans available for eligible full-time employees.

• Option for remote work.