Enterprise Sales Director – Strategic Retail

About the role

Lead Sierra’s most complex enterprise deals for strategic retail customers, shaping multi‑business, multi‑geography opportunities and driving revenue growth.

Key responsibilities

• Architect and close the largest multi‑BU, multi‑geo deals, designing sophisticated structures and managing risk.
• Maintain trusted relationships across the customer C‑suite and working teams, acting as part of the customer’s team.
• Engage directly with Sierra’s co‑founders, pitching with founder‑level conviction.
• Deliver precise messaging, positioning and timing in every interaction.
• Influence account strategy and set standards for the broader sales organization.
• Leverage AI tools throughout the sales cycle to automate low‑value tasks and focus on high‑value relationships.

Required profile

• 10‑12+ years of enterprise/strategic sales experience handling the largest and most complex accounts.
• Proven track record of closing multi‑million‑dollar, multi‑stakeholder deals across business units and geographies.
• Experience managing a $1M+ quota and leading end‑to‑end 6‑ and 7‑figure ACV transactions.
• Deep, sustained C‑suite relationships with the gravitas to be treated as a peer by executive buyers.
• Mastery of complex deal structuring, risk navigation and pricing.
• Exceptional executive communication with a reputation for precision and trust.

What we offer

• Unlimited paid time off.
• Medical, dental and vision benefits for you and your family.
• Life insurance, disability and retirement plans (depending on country).
• Parental and fertility benefits.
• Discretionary stipend for personal expenses.
• Free lunch, snacks and coffee.
• Equity participation for eligible full‑time employees.