Sierra
Enterprise Sales Director - Strategic, Retail
US - Remote. Posted 3 months ago
The role
The Enterprise Sales Director will architect complex, large-scale deals and manage multi-BU, multi-geo opportunities. This person will hold C-suite relationships and engage with co-founders to drive revenue for retail brands using AI agents.
What you will do
- Architect Sierra's most complex deals
- Lead largest multi-BU, multi-geo opportunities
- Design sophisticated deal structures and manage risk
- Hold trusted relationships across customer C-suite and working teams
- Engage and manage Sierra's co-founders in front of customers
- Influence how Sierra approaches its most important accounts
- Set the standard for the broader sales org
- Leverage AI tools across the full sales cycle
Required qualifications
- 10-12+ years of enterprise/strategic sales experience
- Experience owning the largest and most complex accounts
- Demonstrated success closing multi-million-dollar, multi-stakeholder deals
- Experience managing a $1M+ quota
- Experience running end-to-end complex 6- and 7-figure ACV deals
- Deep, sustained C-suite relationships
- Mastery of complex deal structuring, risk navigation, and pricing
- Exceptional executive communication
Nice to have
- Deep familiarity with the AI landscape
- Ability to speak credibly to technical and business stakeholders
- Experience operating alongside founders/executives in front of strategic customers
Benefits
- Flexible (unlimited) paid time off
- Medical, dental, and vision benefits for you and your family
- Life insurance and disability benefits
- Retirement plan dependent on country of employment
- Parental leave
- Fertility and family building benefits
- Lunch, delicious snacks and coffee when working onsite
- Discretionary benefit stipend
- Free alphorn lessons
- Equity plans for eligible full-time employees
About the company
Sierra is a platform for customer-facing AI agents working with large brands to transform customer service and growth. The company is primarily in-person based in San Francisco and was co-founded by Bret Taylor and Clay Bavor.