Enterprise Sales Director - Majors

About the role

Sierra is seeking an experienced Enterprise Sales Director to own and close large‑scale deals with major accounts. You will operate as an AI‑native seller, leveraging cutting‑edge tools to accelerate the full sales cycle and build lasting C‑suite relationships.

Key responsibilities

• Drive complex enterprise deals end‑to‑end, managing 6‑ and 7‑figure ACV cycles from prospecting through close.
• Multi‑thread with VP‑level and C‑suite stakeholders, building durable relationships across customer organizations.
• Proactively identify and mitigate deal risk, creating rigorous stakeholder maps and escalation plans.
• Partner with senior leadership and co‑founders for executive engagement and strategic pricing decisions.
• Utilize AI tools for account research, personalized outreach, call summarization, pipeline forecasting, and deal execution.

Required profile

• 8‑10 years of enterprise, customer‑facing sales experience with a proven $1M+ quota.
• Demonstrated ability to close large, complex 6‑ and 7‑figure deals and build trusted C‑suite relationships.
• Strong analytical mindset with data‑driven decision making.
• Exceptional verbal and written communication skills.

Required skills

• Proficiency with AI‑driven sales tools for account research and outreach.
• Experience using AI for pipeline forecasting and deal execution.

What we offer

• Unlimited paid time off and flexible work arrangements.
• Comprehensive medical, dental, vision, life, and disability benefits for you and your family.
• Retirement plan, parental leave, and fertility benefits.
• Equity participation for eligible full‑time employees.
• Free lunch, snacks, coffee, and discretionary benefit stipend.