Enterprise Sales Director – Strategic, Retail

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

📋 Description

• Oversee the largest and most intricate opportunities across multiple business units and geographies.

• Create advanced deal structures and manage associated risks.

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

• Frequently collaborate with Sierra’s co-founders during customer interactions.

• Provide clear messaging, positioning, and timing throughout all communications.

• Shape the strategy for Sierra’s key accounts.

• Establish benchmarks for the wider sales organization.

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

• Persistently embrace and test new sales tools.

⛳️ Requirements

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

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

• Experience overseeing a quota of $1M or more.

• Proficient in managing complex six- and seven-figure ACV deals from start to finish.

• Strong, lasting relationships with C-suite executives.

• Presence and credibility to be regarded as an equal by executive buyers.

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

• Outstanding executive communication skills.

• Known for accuracy and reliability.

• Familiarity with the AI landscape is a plus.

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

• Experience working alongside founders and executives in front of strategic clients is advantageous.

🏝️ Benefits

• Flexible (unlimited) paid time off.

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

• Life insurance and disability coverage.

• Retirement plans based on the country of employment.

• Parental leave policy.

• Fertility and family planning benefits provided through Carrot.

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

• Discretionary stipend for benefits.

• Complimentary alphorn lessons.

• Equity plans available for eligible full-time employees.

• Commission opportunities.

• Offers include equity.