Enterprise Sales Director - Strategic, Consumer Business Services

About the role

Sierra is seeking an Enterprise Sales Director to lead its most complex, multi‑business‑unit, multi‑geography opportunities within the Consumer Business Services vertical. You will partner directly with C‑suite executives, shape account strategy, and drive high‑value AI‑enabled solutions for some of the world’s largest brands.

Key responsibilities

• Architect and close the company’s largest, multi‑BU, multi‑geo deals, designing sophisticated structures and managing risk.
• Maintain trusted relationships across the customer’s C‑suite and working teams, acting as an extension of their organization.
• Engage regularly with Sierra’s co‑founders in front of customers, pitching with founder‑level conviction.
• Deliver precise messaging, positioning, and timing across all interactions.
• 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 managing the largest and most complex accounts.
• Proven success closing multi‑million‑dollar, multi‑stakeholder deals across business units and geographies.
• Experience managing a $1M+ quota and executing 6‑ and 7‑figure ACV transactions.
• Deep, sustained C‑suite relationships with the gravitas to be treated as a peer.
• Mastery of complex deal structuring, risk navigation, and pricing.
• Exceptional executive communication and a reputation for precision and trust.

What we offer

• Flexible (unlimited) paid time off.
• Medical, dental, and vision benefits for you and your family.
• Life insurance, disability coverage, and retirement plans.
• Parental leave and fertility/family‑building benefits.
• Daily lunch, snacks, coffee, and a discretionary benefit stipend.
• Free alphorn lessons and other unique perks.