Enterprise Sales Director – Majors & Retail

About the role

Sierra is looking for an Enterprise Sales Director to lead major retail accounts. You will own complex, high‑value deals and work closely with C‑suite stakeholders to drive revenue for AI‑powered customer‑facing agents.

Key responsibilities

• Drive end‑to‑end enterprise deals, managing 6‑ and 7‑figure cycles from prospecting to close.
• Lead VP‑level conversations, build durable C‑suite relationships, and map stakeholders across accounts.
• Identify and mitigate deal risk early, creating rigorous stakeholder maps and escalation plans.
• Collaborate with senior leadership and co‑founders for executive engagement when needed.
• Leverage AI tools throughout the sales cycle to automate low‑value tasks and focus on high‑value relationships.

Required profile

• 8–10 years of enterprise, customer‑facing sales experience with a proven record of closing large accounts.
• Experience managing a $1M+ quota and handling 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 and an analytical mindset for data‑driven decisions.

What we offer

• Unlimited paid time off and flexible work arrangements.
• Medical, dental, and vision benefits for you and your family.
• Life insurance, disability coverage, and retirement plans (region‑dependent).
• Parental leave, fertility and family‑building benefits, and a discretionary stipend.
• Free lunch, snacks, coffee, and unique perks such as alphorn lessons.