Enterprise Sales Director – Majors, Consumer Business Insights

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

📋 Description

• Take the initiative to drive intricate enterprise agreements from start to finish, managing a diverse portfolio and overseeing 6- and 7-figure deal cycles from initial prospecting to closure.

• Engage in conversations at the VP level and cultivate strong C-suite relationships within customer organizations.

• Proactively identify and manage potential deal risks early on, while creating comprehensive stakeholder maps for accounts.

• Collaborate with the manager on pricing strategies, timing of escalations, executive alignment, and overall deal strategy.

• Involve Sierra’s co-founders in executive interactions whenever advantageous to the deal.

• Serve as a visible and steady leader within deal teams, raising the team's performance standards.

• Utilize AI tools for account research, tailored outreach, call summaries, pipeline forecasting, and executing deals.

• Consistently explore and adopt new tools to enhance sales efficiency.

• Integrate AI agents into both consumer business and enterprise sectors, including areas such as consumer products, real estate, automotive, logistics, manufacturing, and utilities.

⛳️ Requirements

• 8–10 years of experience in enterprise customer-facing sales, with a proven track record of identifying and closing substantial accounts.

• Proven experience managing a quota exceeding $1M.

• Demonstrated ability to run complex 6- and 7-figure Annual Contract Value (ACV) deals from beginning to end.

• Established capability to nurture multiple threads and build trusted relationships across customer C-suites.

• Outstanding verbal and written communication skills.

• An analytical mindset, including the ability to analyze market trends, identify opportunities, and make decisions based on data.

• Familiarity with the AI landscape, including key players and emerging trends, is a plus.

• Must have legal authorization to work in Canada.

• Should address current or future visa sponsorship needs for employment in 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 the country of employment.

• Parental leave.

• Fertility and family building benefits through Carrot.

• Lunch, along with tasty snacks and coffee.

• Discretionary benefit stipend.

• Free alphorn lessons.

• Equity plans for eligible full-time employees.

• Commission.

• Offers Equity.