Enterprise Sales Director – Majors

About the role

We are looking for an Enterprise Sales Director – Majors to lead complex, high‑value enterprise deals for Sierra, the leading platform for customer‑facing AI agents. The role is fully remote within Canada and reports to senior leadership, driving 6‑ and 7‑figure sales cycles from prospecting to close.

Key responsibilities

• Own end‑to‑end enterprise deals, managing a broad book of 6‑ and 7‑figure opportunities with strong autonomy.
• Lead VP‑level conversations, build durable C‑suite relationships, and earn credibility quickly with new stakeholders.
• Identify and mitigate deal risk early, creating rigorous stakeholder maps for each account.
• Partner with managers on pricing, escalation timing, executive alignment, and deal strategy, presenting clear points of view.
• Engage Sierra’s co‑founders for executive involvement when it advances the deal.
• Act as a visible leader on deal teams, continuously raising standards and performance.
• Leverage AI tools throughout the sales cycle for research, outreach, call summarization, pipeline forecasting, and deal execution.

Required profile

• 8–10 years of enterprise, customer‑facing sales experience with a proven track record of closing large accounts.
• Experience managing a $1M+ quota and executing complex 6‑ and 7‑figure ACV deals.
• Demonstrated ability to multi‑thread and build trusted relationships across C‑suite stakeholders.
• Exceptional verbal and written communication skills.
• Analytical mindset with data‑driven decision making.
• Familiarity with the AI landscape and emerging trends is a plus.

What we offer

• Unlimited paid time off.
• Medical, dental, and vision benefits for you and your family.
• Life insurance, disability coverage, and retirement plan (where applicable).
• Parental leave and fertility/family‑building benefits.
• Lunch, snacks, coffee, and a discretionary benefit stipend.
• Equity participation for eligible full‑time employees.
• Free alphorn lessons.