Senior AI-Driven Enterprise Sales Director

Sierra; United States; On-site; USD 250,000 - 450,000; Full time

Benefits offered by this job

Flexible (unlimited) paid time off

Medical, dental, and vision benefits

Life insurance and disability benefits

Retirement plan dependent on country

Parental leave

Fertility and family building benefits

Lunch, snacks and coffee

Discretionary benefit stipend

Free alphorn lessons

Job summary

Sierra is building an AI-powered platform and is seeking an accomplished enterprise sales leader to own the largest, most strategic accounts. You will lead multi-geo deals, engage with C-suite executives, and coordinate with founders as needed.

In this role you will shape deal structures, navigate risk, and drive revenue growth by leveraging AI tools across the sales cycle, aiming to deliver exceptional outcomes for retail brands and partners.

Qualifications

• 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
• Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.
• Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
• 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 and a reputation for precision and trust.

Responsibilities

• Architect Sierra's most complex deals across multiple BUs and geos with risk management.
• Maintain trusted relationships across the customer's C-suite.
• Engage founders level with co-founders in front of customers.
• Ensure precision in messaging, positioning, and timing across interactions.
• Shape strategy for key accounts and set standards for the sales org.
• Operate as an AI-native seller using AI tools across the full sales cycle.

Skills

Enterprise/strategic sales

Closing large multi-stakeholder deals

C-suite relationship management

Deal structuring & pricing

Executive communication

Job description

Sierra is building an AI-powered platform and is seeking an accomplished enterprise sales leader to own the largest, most strategic accounts. You will lead multi-geo deals, engage with C-suite executives, and coordinate with founders as needed.

In this role you will shape deal structures, navigate risk, and drive revenue growth by leveraging AI tools across the sales cycle, aiming to deliver exceptional outcomes for retail brands and partners.