Enterprise Sales Director - Majors, Retail

The role

The Enterprise Sales Director will independently drive complex enterprise deals from prospecting to close. This role involves managing a broad enterprise book, building C-suite relationships, and leveraging AI tools throughout the sales cycle.

What you will do

• Independently drive complex enterprise deals end-to-end
• Manage a broad enterprise book with strong autonomy
• Lead 6- and 7-figure deal cycles from prospecting to close
• Multi-thread to the C-suite and build durable relationships
• Identify and manage deal risk early
• Build rigorous stakeholder maps for accounts
• Partner with manager on pricing, escalation, and deal strategy
• Bring in co-founders for exec engagement
• Act as a visible, steady leader on deal teams
• Operate as an AI-native seller using AI tools for the sales cycle

Required qualifications

• 8-10 years of enterprise customer-facing sales experience
• Experience identifying and closing large accounts
• Experience managing a $1M+ quota
• Experience running end-to-end complex 6- and 7-figure ACV deals
• Ability to multi-thread and build trusted relationships across customer C-suites
• Exceptional verbal and written communication
• Analytical mindset

Nice to have

• Familiarity with the AI landscape, key players, and emerging trends

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 an in-person company based in San Francisco.