Enterprise Sales Director – Strategic, Consumer Business Insights

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

📋 Description

• Oversee the largest and most intricate opportunities spanning multiple business units and geographical locations.

• Create advanced deal structures and manage associated risks.

• Establish and nurture trusted relationships with customer executives and operational teams.

• Involve Sierra’s co-founders in client meetings and presentations.

• Craft accurate messaging, positioning, and timing for all interactions.

• Influence Sierra’s strategy for its key accounts.

• Set benchmarks for the wider sales organization.

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

• Streamline low-value sales tasks through automation, allowing more focus on high-value client relationships.

• Persistently explore and adopt new sales tools and techniques.

⛳️ Requirements

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

• Proven track record managing the largest and most complex accounts.

• Successful history of closing multi-million-dollar, multi-stakeholder deals across various business units and regions.

• Experience managing a quota exceeding $1M.

• Skilled in handling complex 6- and 7-figure ACV deals from start to finish.

• Extensive, sustained relationships with C-suite executives.

• Gravitas 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 precision and reliability.

• In-depth knowledge of the AI landscape.

• Capable of engaging credibly with both technical and business stakeholders.

• Experience working alongside founders or executives in front of strategic clients.

• Legally authorized to work in Canada.

• Must be able to work from Canada.

🏝️ Benefits

• Flexible (unlimited) paid time off.

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

• Life insurance and disability coverage.

• Retirement plans based on the country of employment.

• Parental leave policies.

• Fertility and family-building benefits through Carrot.

• Lunch provisions, along with delicious snacks and coffee.

• Discretionary benefit stipend.

• Complimentary alphorn lessons.

• Equity plans available for eligible full-time employees.

• Commission opportunities.

• Home office or remote work arrangements.