Enterprise Sales Director - Strategic

About the role

As the Enterprise Sales Director – Strategic you will own Sierra’s most complex, multi‑business‑unit and multi‑geography deals. You will act as a trusted advisor to C‑suite stakeholders and collaborate directly with Sierra’s co‑founders to close high‑value opportunities.

Key responsibilities

• Lead the largest multi‑BU, multi‑geo opportunities, designing sophisticated deal structures and managing risk with precision.
• Maintain trusted relationships across the customer’s C‑suite and working teams, operating as an extension of the client’s organization.
• Engage regularly with Sierra’s co‑founders in front of customers, delivering pitches with founder‑level conviction.
• Ensure precision in messaging, positioning, and timing across every interaction.
• Shape account strategy, influencing how Sierra approaches its most important customers and setting standards for the broader sales organization.

Required profile

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

What we offer

• Flexible (unlimited) paid time off.
• Medical, dental, and vision benefits for you and your family.
• Life insurance, disability benefits, and a retirement plan (depending on country of employment).
• Parental leave and fertility/family‑building benefits through Carrot.
• Discretionary benefit stipend, free lunch, snacks, coffee, and even free alphorn lessons.