Enterprise Sales Leader – Retail

About the role

Lead Sierra’s retail sales organization, driving AI‑powered customer experiences for some of the world’s most‑loved consumer brands. You will build and scale a high‑performing team that turns AI agents into revenue generators across apparel, beauty, grocery, and more.

Key responsibilities

• Lead and develop a high‑performing retail sales team, hiring, onboarding and coaching Account Executives across the region.
• Own regional performance metrics, forecast accuracy and pipeline health, partnering with RevOps to ensure clean data.
• Participate in strategic customer conversations, guide complex buying committees, and support pricing, negotiation and closing strategies.

Required profile

• 10‑15+ years of enterprise sales experience, consistently closing large ($1M+) accounts.
• 5+ years of people leadership, mentoring and developing high‑performing sales teams.
• Proven track record managing end‑to‑end complex deals and driving revenue growth.
• Exceptional verbal and written communication abilities.
• Analytical mindset with data‑driven decision‑making skills.

What we offer

• Unlimited paid time off and flexible work policies.
• Comprehensive medical, dental and vision coverage for employees and families.
• Life insurance, disability benefits and a retirement plan (where applicable).
• Parental leave and fertility/family‑building benefits.
• Daily lunch, snacks, coffee and a discretionary benefit stipend.
• Unique perks such as free alphorn lessons.