Enterprise Sales Director – Majors, Retail

About the role

Sierra is seeking an experienced Enterprise Sales Director to lead major retail accounts. You will own end‑to‑end complex deals, build C‑suite relationships, and drive revenue through AI‑powered customer‑facing agents. This role is fully remote and reports to senior sales leadership.

Key responsibilities

• Independently manage a broad enterprise book, leading 6‑ and 7‑figure deal cycles from prospecting to close.
• Multi‑thread with VP‑level and C‑suite stakeholders, establishing durable executive relationships.
• Identify and mitigate deal risk early, creating rigorous stakeholder maps.
• Partner with managers on pricing, escalation, and deal strategy, presenting clear points of view.
• Leverage Sierra’s co‑founders for executive engagement when needed.
• Utilize AI tools throughout the sales cycle for research, outreach, summarization, forecasting, and execution.

Required profile

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

What we offer

• Unlimited paid time off.
• Medical, dental, and vision benefits for you and your family.
• Life insurance, disability, and retirement plans (region‑dependent).
• Parental, fertility, and family‑building benefits.
• Discretionary benefit stipend and free alphorn lessons.