Enterprise Sales Director – Strategic Consumer Business Services

About the role

As an Enterprise Sales Director for Strategic Consumer Business Services, you will own Sierra’s most complex, multi‑business‑unit and multi‑geography deals. You will work directly with C‑suite executives and Sierra’s co‑founders, shaping high‑value opportunities and driving AI‑enabled sales transformations for leading consumer‑focused enterprises.

Key responsibilities

• Lead the largest multi‑BU, multi‑geo opportunities, designing sophisticated deal structures and managing risk with precision.
• Build and maintain trusted relationships across customer C‑suite and operational teams.
• Engage regularly with Sierra’s co‑founders, pitching with founder‑level conviction.
• Craft precise messaging, positioning, and timing for every interaction.
• Influence account strategy and set standards for the broader sales organization.
• Leverage AI tools throughout the sales cycle—including account research, personalized outreach, call summarization, pipeline forecasting, and deal execution—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 track record 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 and 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.
• Bonus: familiarity with the AI landscape and experience working alongside founders or senior executives.

What we offer

• Flexible unlimited paid time off.
• Medical, dental, and vision benefits for you and your family.
• Life insurance and disability coverage.
• Retirement plan (varies by country).
• Parental leave and fertility/family‑building benefits through Carrot.
• Lunch, snacks, coffee, and a discretionary benefit stipend.
• Free alphorn lessons.